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Occurrence and use of hallucinogenic mushrooms containing psilocybin alkaloids

January 2008

January 2008

Publisher: Nordic Counsil of Ministers
ISBN: 978-92-893-1836-5

Authors:

Jakob Kristinsson

University of Iceland

. Occurrence of psilocybin, psilocin and baeocystin and neo-baeocystin mg/kg dry weight if not otherwise stated) in hallucinogenic mushrooms. An empty square im- plies that this compound was not analysed for.

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Occurrence and use of

hallucinogenic mushrooms

containing psilocybin

alkaloids

Christer Andersson – National Food Administration, Uppsala,

Sweden.

Jakob Kristinsson – Department of Pharmacology, University of

Iceland.

Jørn Gry – National Food Institute, Technical University of

Denmark

TemaNord 2008:606

Occurrence and use of hallucinogenic mushrooms containing psilocybin alkaloids

TemaNord 2008:606

ISBN 978-92-893-1836-5

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Content

Preface................................................................................................................................ 7

Summary ............................................................................................................................ 9

1. Background .................................................................................................................. 13

1.1 A historical perspective........................................................................................ 13

2. Identity, physical and chemical properties.................................................................... 17

2.1 Identity ................................................................................................................. 17

2.2. Physical and chemical properties ........................................................................ 19

2.2.1. Chemical synthesis of psilocybin and psilocin................................................. 19

2.3. Analytical methods.............................................................................................. 21

3. Biosynthesis.................................................................................................................. 31

4. Occurrence.................................................................................................................... 33

4.1. Content of psilocybin and related compounds in various mushroom species...... 33

4.2. Influence of cultivation, storage and processing.................................................. 56

4.3. Wild mushrooms in the Nordic countries that contain psilocybin and/or related

compounds...................................................................................................... 58

4.4. Cultivation of psilocybin-containing mushrooms................................................ 59

5. Exposure....................................................................................................................... 61

5.1. The habit of consuming hallucinogenic mushrooms ........................................... 61

5.2. Legal aspects of hallucinogenic mushrooms and/or psilocybin and related

compounds...................................................................................................... 70

5.3. Market................................................................................................................. 73

6. Summary of biological effects of psilocybin and psilocin............................................ 75

6.1. Pharmacokinetic.................................................................................................. 75

6.2 Pharmacological effects in humans...................................................................... 76

6.3. Hallucinogenic experience and potential toxicity................................................ 78

6.4. Hallucinogenic mushroom use in the Nordic countries....................................... 88

6.5. Treatment of psilocybin-intoxication .................................................................. 89

6.6. Medical uses of psilocybin and psilocin.............................................................. 90

7. References.................................................................................................................... 91

Sammanfattning.............................................................................................................. 119

Preface

The Nordic Committee of Senior Officials for Food Issues is an advisory

body of the Nordic Council of Ministers which co-ordinates Nordic work

in the field of food and nutrition. The Nordic Working Group on Food

Toxicology and Risk Evaluation (NNT) was until 2006 given the responsi-

bility by the Committee to promote co-operation and co-ordination among

Nordic countries in matters relating to food toxicology and risk assessment.

Assessment of health risk connected with naturally occurring toxicants

in foodstuffs has become an important area for NNT. A series of Nordic

reports based on the work performed by the Nordic project group on inher-

ent natural toxicants in food plants and mushrooms has been published:

Gry, J. and Pilegaard, K. (1991) Hydrazines in the Cultivated Mushroom (Agari-

cus bisporus). Vår Föda 43;Supplement 1

Uggla, A. and Busk, L. (1992) Ethyl carbamate (urethane) in alcoholic beverages

and foodstuffs - A Nordic View. Nordiske Seminar- og Arbejdsrapporter 1992:570.

Størmer, F.C., Reistad, R. and Alexander, J. (1993) Adverse health effects of gly-

cyrrhizic acid in licorice. A risk assessment. Nordiske Seminar- og Arbejdsrap-

porter 1993:526.

Andersson, C., Slanina, P. And Koponen, A. (1995) Hydrazones in the false mo-

rel. TemaNord 1995:561.

Søborg, I., Andersson, C. and Gry, J. (1996) Furocoumarins in Plant Food - exposure,

biological properties, risk assessment and recommendations. TemaNord 1996:600.

Gry, J. and Andersson, H.C. (1998) Nordic seminar on phenylhydrazines in the

Cultivated Mushroom (Agaricus bisporus). TemaNord 1998:539.

Andersson, H.C. (2002) Calystegine alkaloids in Solanaceous food plants. Te-

maNord 2002:513.

Andersson, C., Wennström, P. and Gry, J. (2003) Nicotine in Solanaceous food

plants. TemaNord 2003:531.

Andersson, H.C. and Gry, J. (2004) Phenylhydrazines in the cultivated mushroom

(Agaricus bisporus) – occurrence, biological properties, risk assessment and rec-

ommendations. TemaNord 2004:558.

Gry, J., Søborg, I. and Andersson, H:C: (2006) Cucurbitacins in plant food. Te-

maNord 2006:556.

Beckman Sundh, U., Rosén, J. and Andersson, H.C. (2007) Analysis, occurrence,

and toxicity of -methylaminoalanine (BMAA). TemaNord 2007:561.

Pilegaard, K. and Gry, J. (2008) Alkaloids in edible lupin seeds. A toxicological

review and recommendations. TemaNord 2008 (in press)

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

Mushrooms containing psilocybin and related hallucinogenic compounds

have been used in the Nordic countries for recreational purposes since the

1970´s. During the last decade Internet has given both an easy assess to

information about hallucinogenic mushrooms and possibilities to pur-

chase mushroom products. At the end of the 1990’s the number of phone

calls to National Poison Information centres and the number of epicrises

from hospitals related to hallucinogenic mushrooms increased signifi-

cantly. It was decided to initiate a risk assessment of hallucinogenic

mushrooms as at the time mushrooms of this type were defined as food in

some Nordic countries. As subsequently national legislations have been

introduced, defining hallucinogenic mushrooms as illegal products, it was

decided to instead review the ‘Occurrence and use of hallucinogenic

mushrooms’.

The literature reviewed in this report has been found in searches on

Medline, Toxline and FSTA (- August 2007), and not least in the refer-

ence lists of the publications found in the searches.

The Nordic Project Group on Natural Toxins consisting of members of

the NNT has reviewed and accepted the present document in January 2008.

The Project Group consisted of the following members:

Jørn Gry (co-ordinator) Fødevareinstituttet. Danmarks Tekniske Universitet,

Denmark

Christer Andersson National Food Administration, Sweden

Jan Alexander National Institute of Public Health, Norway

Anja Hallikainen EVIRA, Finland

Jakob Kristinsson Department of Pharmacology University of Iceland,

Iceland

The Project Group and NNT like to acknowledge the contribution of

Henning Knudsen, Natural History Museum of Denmark, University of

Copenhagen, for the momenclature of psilocybin/psilocin-containing

mushrooms growing in the Nordic countries.

Summary

From having been used in ritual religious ceremonies over thousands of

years, hallucinogenic mushrooms started to be used as a recreational drug

late in the 1960´s. Which the hallucinogenic mushrooms used in religious

ceremonies by Indian tribes in Mexico were, became known from ethono-

mycological investigations in the 1930s and 1940s, but the first list of

hallucinogenic mushrooms of Mexico was not published until 1961. At

that time, chemists working for the Swiss pharmaceutical company San-

doz had already identified the compound in the mushroom responsible for

the effect. It was a phosphorylated alkaloid, given the name psilocybin (a

phosphoric acid ester of 4-dihydroxymethyltryptamine) after the mush-

room species from which it was originally isolated, Psilocybe mexicana.

Subsequent studies showed that the real hallucinogenic compound is psi-

locin, which is formed from psilocybin by dephosphorylation. The

dephosphorylation can take place in the mushroom after harvest or when

damaged, or in the body of the consumer.

Mycological investigations have identified a large number of mush-

rooms able to produce psilocybin. The compound has been chemically

identified in about 90 different mushrooms belonging to the genera Agro-

cybe, Conocybe, Copelandia*, Gymnopilus*, Hypholoma, Inocybe, (Pan-

aeolina), Panaeolus*, Pluteus, Psathyrella*, Psilocybe, and Stropharia

(*most species do not contain psilocybin/psilocin). In addition, several

other species have been reported to be hallucinogenic. The studies on the

mushroom chemistry has also identified that psilocybin/psilocin is not the

only hallucinogenic compound of this type in the mushrooms. Three

other phosphoric acid ester of 4-hydroxytryptamine with one, zero or

three methyl groups on the tryptamine side chain – baeocystin, nor-

baeocystin, and aeruginascin – also have hallucinogenic properties. How-

ever, these compounds occur at lower levels and in a much more limited

set of mushroom species.

Critical steps in the chemical analysis of psilocybin and related sub-

stances in mushrooms are the method of extraction, the chromatographic

method used to separate compounds, and the method used to identifying

the hallucinogens. GC-MS and LC-MS are common methods used in

human biological samples to identify psilocybin/psilocin.

The chemical analysis of hallucinogenic mushrooms has identified

modest levels in the mycelium, and higher levels in the fruit bodies. In

the latter, caps contain higher amounts than the stalk. No correlation be-

tween psilocybin level and size of fruit bodies has been found.

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

Species with high psilocybin/psilocin content include Agrocybe prae-

cox (Pers.) Fayod., Copelandia cambodginiensis (Ola´h et Heim) Singer

and Weeks, Inocybe aeruginascens Babos, Panaeolus cyanescens (Berk.

& Br.) Sacc., Panaelous subbalteatus (Berk. & Br.) Sacc., Pluteus

salicinus (Pers. Ex Fr.) Kummer, Psilocybe arcana Bor et Hlav., Psilo-

cybe azurescens Stamets and Gartz, Psilocybe baeocystis Singer and

Smith, Psilocybe bohemica Sebek, Psilocybe cubensis (Earle) Singer,

Psilocybe cyanescens Wakefield, Psilocybe liniformans Guzmán & Bas

var. americana Guzmán & Stamets, Psilocybe pelliculosa (Smith) Singer

and Smith, Psilocybe samuiensis Guzmán, Bandala and Allen, Psilocybe

semilanceata (Fr.) Kummer, Psilocybe semperviva Heim and Cailleux,

and Psilocybe subcubensis Guzmán. The highest levels, more than 15 000

mg/kg dry weight, have been identified in Pluteus salicinus (Pers. Ex Fr.)

Kummer, Psilocybe cyanescens Wakefield, and Psilocybe semilanceata

(Fr. Ex Secr.) Kummer.

Baeocystin is found only in some of the species synthesizing psilocy-

bin, usually at levels bellow 1000 mg/kg dry weight. High levels, up to

more than 5 000 mg/kg dry weight have been found in Inocybe aerugi-

nascens Babos. The same species contains up to 3 500 mg/kg dry weight

aeruginascin.

Of the about 90 psilocybin and/or psilocin-containing mushrooms

identifyied, about 30 have been found in the Nordic countries. Among

these are 6 Psilocybe species, 6 Panaeolus species, 3 Gymnopilus species,

2 Conocybe species, 2 Inocybe species, 2 Pluteus species and one

Psathyrella species. Many of them are rare but some can be found in

considerable quantities.

Collecting hallucinogenic mushrooms requires substantial mycologi-

cal knowledge as there are many look-a-likes. Some of these look-a-likes

are toxic. Only experienced mushroom pickers should therefore collect

these types of mushrooms. An alternative way to get hands on hallucino-

genic mushrooms is to cultivate them at home or buy samples over inter-

net. Most of the latter types of mushroom are dried. Being hard to chew,

dried mushrooms are frequently prepared in a drink, eg. tea, coffee or

Coca Cola. Another way of using dried hallucinogenic mushrooms is to

smoke them like a cigarette. As psilocybin may be extracted by heating,

but is not degraded, the total amount of psilocybin in the cooking water

and in the mushroom corresponds to the level in the mushroom before

household processing.

Hallucinogenic mushrooms are most frequently used by young people,

mainly men, and particularly users of other drugs. However, such use of

mushrooms is infrequent. In the Nordic countries, use of hallucinogenic

mushrooms has mainly been studied in Denmark. Three percent of high-

school students had used psilocybin-containing mushrooms (1% had tried

LSD) in a recreational atmosphere, whereas the corresponding figure in

university students and pupils at a school for journalists was nine percent.

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

This suggests that mushrooms are the most commonly used hallucino-

genic substance in Denmark.

Although it has been difficult to demonstrate toxic effects of hallu-

cinogenic mushroom use, it is well established that such use can induce

uncontrolled action in the user. In rare cases, when the intake of such

mushrooms has been substantial, flash-backs of adverse experiences have

been reported. For these reasons, and perhaps due to the fact that the use

of hallucinogenic mushrooms is not uncommon in users of other drugs,

many countries, including the Nordic countries, have wished to restrict

the use of these mushrooms.

1. Background

1.1 A historical perspective

It is no longer possible to view mankind’s contacts with mushrooms

solely in terms of food gathering and food production. Historical texts,

anthropological literature, and present day drug culture shows that mush-

rooms have been used, and still are used to allow the human mind to tran-

sit natural borders. This is discussed by Stamets (1978) in the book “Psi-

locybe Mushrooms and their Allies”, where he splits the history of the

hallucinogenic fungi into four periods of time. The first phase, constitut-

ing the historic era, corresponds the period when hallucinogenic mush-

rooms were used in traditional and cultural settings by various popula-

tions around the world - most notably the indigenous tribes in Mexico.

The second phase was a time of confusion, before the mushrooms men-

tioned in the early texts were identified. This period lasted from the early

1900s to the 1950s. The third phase consisted of mycological and ethno-

mycological expeditions proposing to taxonomically identify the hallu-

cinogenic mushrooms and to become acquainted with the indigenous

groups who used them. Also the elucidation of the chemistry of the active

compounds and their role in medicine belongs to this period, which there-

fore makes this period the gold era of hallucinogenic mushroom research.

Finally, the last phase, still ongoing, is characterised by making use of the

mushrooms in recreational settings.

Botanical and anthropological literature contains many references to

mushrooms, which have been employed to link the earthly life to the

divine state by some of the Indian tribes of Mexico in ritual ceremonies.

The Aztecs and the Chichimecas were the earliest recorded users of such

mushrooms, which they called ‘teonanacatl’. This Middle American cult

of divine mushrooms can be traced back to about B.C. 1500 (Wasson,

1961), but is first mentioned in Andrés de Olmos' work "Antigüedades

Mexicanas" from 1453. The Spaniards returning from Mexico after the

conquest during the early part of the 16th century, described the effect of

using ‘teonanacatl’, and spread the knowledge about the mushroom use in

sacred rituals. In most users the mushrooms gave rise to altered percep-

tion of time and space, and a sense of elation and joy or bliss, whereas

other users responded with anxiety and depression and even deep uncon-

sciousness (e.g. de Sahagun, 16th century). The effects described by the

Spanish conquerors are comparable to those experienced today after in-

take of lysergic acid dimethylamide, LSD (Subramanian, 1995).

It is possible that the mushroom-formed stones found in Guatemala,

and to some extent also in El Salvador and Mexico, have had a role in

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

this type of ritual a long time ago. Some of these stones seems to have

been produced as early as 2 000 BC but the habit of forming stones to

mushrooms reached its zenith in Central America some time between 200

BC and 300 AD. Since miniature metates (grinding stones) have been

found in the vicinity of such mushroom stones, it has been suggested that

they have been used to crush and prepare mushrooms (Wasson, 1966).

For several centuries, however, the identity of ‘teonanacatl’ remained

obscure. Recurring references to it have mystified biological and anthro-

pological investigators, inasmuch as careful search had failed to reveal

any Mexican fungus possessing properties used to induce a narcosis. It

was suggested that the reports which associate ‘teonanacatl’ with a mush-

room are misleading or erroneous, although the sources from which they

come are in other respects dependable and credible (Schultes, 1939).

During the end of the 1930s and the1940s Dr Schultes of Harvard

University, USA, and colleagues began ethno-botanical investigations

among the Mazatec Indians of north-eastern Oaxaca and brought back

mushrooms claimed to be narcotic from Mexico to USA (Schultes, 1939).

This material stimulated the pioneering and exciting studies of Gordon

Wasson and his wife Valentina, mycologist Roger Heim of the Museum

Cryptogamie in Paris, and Dr. Albert Hofmann, biochemist with Sandoz

in Basel to focus their scientific studies on the ritual use, taxonomy and

chemistry of these mushrooms (Wasson, 1957; Hofmann et al., 1959).

In 1952 the Wasson couple learnt from the documents of Spanish con-

querors and priests that a 16th century mushroom cult had existed in

Mexico and spent several seasons there searching for surviving traces of

this cult. During these studies Gordon Wasson and one of his colleagues,

along with 18 Mayan Indians, in 1955 participated in a ritual ceremony in

Huautla de Jiménez in Mexico where the Mexican sacred mushroom,

‘teonanacatl’, was consumed. The ceremony was lead by a shaman.

Wasson received six pairs of mushrooms which he consumed and the

shaman kept 13 pairs for herself. After a while the lights were extin-

guished and about half an hour later Wasson and his colleague Richard-

son started having harmonious visions (vivid in colour) which became

quite intense late in the night and remained for around four hours. It is not

known whether this cult was a surviving relic from the mushroom cult

that occurred in Guatemala centuries ago.

It was early recognised that more than one mushroom species were

used in the rituals. The mushroom brought back to USA from Mexico by

Dr. Schultes (1939) and co-workers was identified as Panaeolus cam-

panulatus L. var. sphinctrinus (Fr.) Bresadola by Dr. David Linder, Har-

vard University. Subsequent studies of Roger Heim identified Wasson´s

collections of hallucinogenic mushrooms from Mexico as various species

belonging to the genus Psilocybe, e.g. Psilocybe mexicana. Later on also

other hallucinogenic mushrooms have been identified.

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

In 1961 Gordon Wasson published the first list on the hallucinogenic

mushrooms of Mexico. The list appeared as an appendix to a lecture of

the Mycological Society of America, published in the Botanical Museum

Leaflets of the Harvard University, and was one of the earliest compre-

hensive catalogue of hallucinogenic mushrooms in the scientific litera-

ture. It was soon to be followed by similar types of information aimed for

the non-scientific audience. Magic mushroom is the most common term

applied to psychoactive fungi. It was invented by a Life magazine editor

in 1957.

2. Identity, physical and chemical

properties

2.1 Identity

The original successful isolation and identification of hallucinogenic com-

pounds from Psilocybe mexicana became possible when large quantities of

fruit bodies, sclerotia and mycelium of the mushroom could be produced in

laboratory cultures (Heim and Hofmann, 1958a, b). The dried fruit bodies,

sclerotia and mycelium of P. mexicana were in self-tests shown to possess

the same psychoactive activity as fresh fruit bodies.

The psychoactive principle of Psilocybe mexicana was isolated in

crystalline form in 1958 by Hofmann and co-workers, and identified as

the phosphoric acid ester of 4-hydroxy-dimethyltryptamine (Fig. 1a),

which was given the name psilocybin (Hofmann et al., 1958a, b: Heim et

al., 1958). It is the first natural phosphorylated indole-compound de-

tected. A second substance closely related to psilocybin but found only in

traces was isolated and identified in parallel with psilocybin (Hofmann et

al., 1956a). This compound was 4-hydroxy-dimethyltryptamine, which

was given the trivial name psilocin (Fig. 1b). Subsequently these com-

pounds were identified also in other mushroom species (see section 5.1.).

The structure of psilocybin was confirmed by total chemical synthesis

(Hofmann et al., 1958b). Using the oxalylchloride method (Speeter and

Anthony, 1954), 4-hydroxy-dimethyltryptamine was produced from 4-

benzyloxy-indole. The phenolic hydroxyl group of 4-hydroxy-

dimethyltryptamine was subsequently esterified with dibenzylphos-

phorylchloride, after which reductive debenzylation produced psilocybin

(Hofmann et al., 1958b, 1958c).

In 1968 Leung and Paul isolated two new compounds from methanol-

extracts of submerged cultures of Psilocybe baeocystis. The structures of

these compounds were determined as the monomethyl and demethyl ana-

logues of psilocybin by thin layer chromatography characteristics, colour

reactions, UV, IR, and mass spectral analysis (Leung and Paul, 1967;

1968). They were given the names baeocystin (monomethyl) and nor-

baeocystin (demethyl), respectively. Their chemical structure is shown in

Fig. 1c and 1d, respectively. Both compounds have subsequently been

identified in various hallucinogenic mushrooms.

The latest analogue of psilocybin identified is aeruginascin, the trimethyl

analogue of psilocybin (Fig. 1e). Also this compound obtained its name

from the mushroom species were it was identified Inocybe aeruginascens

after extraction with polar solvents (Gartz, 1989a; Jensen et al., 2006).

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

Although the molecule contains a quarternary ammonium group, aerugi-

nascin (N,N,N- trimethyl-4-phosphoryloxytryptamine) seems to be stable

in dried mushrooms at room temperature for years. The authors speculate

that aeruginascin is likely to be enzymatically dephosphorylated in vivo

when aeruginascin- containing mushrooms are consumed. Due to the

quaternary ammonium group aeruginacin as such is unlikely to pass the

blood-brain barrier, a requirement for centrally mediated hallucinogenic

effects. Aeruginascin is structurally related to the frog skin toxin bufo-

tenidine (N,N,N-trimethylserotonin).

a) psilocybin

POHO

CH2CH2N(CH3)2

POHO

CH2CH2NCH3

POHO

CH2CH2N

POHO

CH2CH2N(CH3)3

b) psilocin

c) baeocystin d) nor-baeocystin

e) aeruginascin

Figure 1. Chemical structure of a) psilocybin; b) psilocin; c) baeocystin; d)nor-baeocystin;

and e) aeruginascin occurring in various hallucinogenic mushrooms.

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

2.2. Physical and chemical properties

Psilocybin, re-crystallised from water, is made up of white, soft, crystal-

water containing needles that melts at 220-228oC. From boiling methanol,

psilocybin produces massive prisms that contain crystal-methanol and

melts at 185–195oC. Psilocybin is soluble in 20 parts boiling water or in

120 parts methanol, but is poorly soluble in ethanol. The compound is

practically insoluble in chloroform and benzene. A 1% solution of psilo-

cybin dissolved in 50% ethanol has a pH of 5.2 (Hofmann et al., 1959).

The degradation product psilocin forms white crystals in methanol (m.p.

173–176oC) and is quite insoluble in water but dissolves in most organic

solvents. However, it is unstable in solution (Shulgin, 1980). The chemi-

cal and physical properties of psilocybin and psilocin are summarised in

Table 1.

Isolated and chromatographically separated psilocybin and psilocin

were visualised by coupling the compounds with Keller-Reagent (iron

chloride in concentrated acetic acid and sulphuric acid) or Van-Urk Re-

agent (p-dimethylbenzaldehyde). Reagent- coupled psilocybin produced a

violet colour-reaction and reagent-coupled psilocin a blue one (Hofmann

et al., 1958a, 1959).

Since psilocybin has similar pharmacological effects to LSD, the pos-

sibility of psilocybin forming a hydrogen bond between the ammonium

nitrogen atom and an oxygen atom of the 4-phosphoryloxy group of the

indole ring, to form a ring analogous to ring C of LSD, has been investi-

gated. X-ray crystallographic studies have revealed that such a hydrogen

bond neither is formed in psilocybin, nor in any of the other tested tryp-

tamine derivatives (Baker et al., 1973).

2.2.1. Chemical synthesis of psilocybin and psilocin

To be able to analyse for the occurrence of hallucinogenic compounds in

mushrooms, as well as in experimental animals and humans that have

ingested such mushrooms, chemical standards are required for the ana-

lytical methods. The compounds were originally synthesized by chemists

at the Sandoz laboratories in Switzerland (Hofmann et al., 1958; Troxler

et al., 1959). Several investigators have subsequently reported on the

chemical

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

Table 1. Chemical and physical properties of psilocybin and psilocin.

Psilocybin

Synonyms: 3–[2-(dimethylamino)ethyl]-1H-indol-4-ol-dihydrogen phosphate

ester; O-phosphoryl-4-hydroxy-N,N- dimethyltryptamine; indocybin

IUPAC System. Name:

Chem. Abst. Name:

CAS reg. No.: 520–52–5

Molecular formula: C12H17N2O4P

Chemical structure: See, figure 1a.

Molecular weight: 284.27

Chemico-physical

characteristics: A water/ethanol solution of psilocybin has a pH of 5.2.

Density: D20 = 0o

Solubility: Soluble in 20 parts boiling water, 120 parts boiling methanol; only

slightly soluble in ethanol. Practically insoluble in chloroform, benzene.

Melting point: 185–195oC

Boiling point:

Psilocin

Synonyms: 3–[2-(dimethylamino)ethyl]-1H-indol-4-ol; 4-hydroxy-N,N-

dimethyltryptamine; psilocin

IUPAC System. Name:

Chem. Abst. Name:

CAS reg. No.: 520–53–6

Molecular formula: C12H16N2O

Chemical structure: See, figure 1b.

Molecular weight: 204.27

Chemico-physical

characteristics: Plates from methanol, mp 173–176oC. Amphoteric substance.

Unstable in solution, especially alkaline solutions.

Density:

Solubility: Very slightly soluble in water.

Melting point:

Boiling point:

synthesis of psilocybin (Ono et al., 1973; Repke et al., 1981; Ametamey et

al., 1998; Yamada et al., 1998; Nichols and Frescas, 1999; Sakagami and

Ogasawara, 1999; Yamada, 2000; Shirota et al., 2003), but only a few on

the synthesis of psilocin (Nichols and Frescas, 1999; Shirota et al., 2003).

In 1998, Yamada and co-workers suggested a method that in five steps

synthesizes psilocin from indole-3-carbaldehyde. The starting point for this

synthesis is indole-3-carbaldehyde (Yamada et al., 1998; Yamada, 2000).

Gathergood and Scammelis (2003) suggested an alternative method to

synthesise psilocin. They prepared the mushroom hallucinogen via palla-

dium-catalysed cyclization of protected N-tert-butoxycarbonyl-2-iodo-3-

methoxyaniline and appropriately substituted silyl acetylene. Subsequent

removal of the protecting groups gave good yields of psilocin.

Shirota et al. (2003) recently reported on a concise large-scale synthe-

sis of both psilocybin and psilocin. The synthesis started with protection

of the hydroxyl group of commercially available 4-hydroxyindole by

addition of an acetyl group. The 4-acetylindole formed was allowed to

react with oxalyl chloride to yield yellow crystals of the oxalyl-group

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

coupled to the 4-acetylindole at the 3-position. A subsequent amidation

step produced 3-dimethylaminooxalyl-4-acetylindole, which could be

converted to psilocin in high yields by reduction. Psilocybin was pro-

duced in high yields from psilocin via a zwitterionic N,O-dibenzyl phos-

phate intermediate. The newly described method allows gram scale syn-

thesis of psilocybin and psilocin.

2.3. Analytical methods

2.3.1 Extraction methods

When Hofmann and co-workers isolated psilocybin from Psilocybe mexi-

cana they observed that the substance was only extracted by very polar

solvents like methanol or mixtures of ethanol and water (Hofmann et al.,

1958a, Hofmann et al., 1959). Due to the polar properties of the phos-

phate group (Figure 1) the substance is soluble in water and methanol but

not in less polar solvents. Psilocin on the other hand is less polar and

readily soluble in less polar solvents like 1-chlorobutane (Lee, 1985).

As shown in Table 2 most investigators have used methanol for the quantita-

tive extraction of psilocybin and psilocin from mushroom samples. Most of

the methods involve some kind of mechanical mixing of the finely ground

mushroom material with the solvent (Table 2). Extraction times have ranged

from 2 minutes to 24 hours. Only a few studies have investigated the effect

of the extraction conditions on recovery. Perkal et al. (1980) found that ho-

mogenization of finely ground samples of Psilocybe subaeruginosa with 30

parts of methanol for no more than 2 minutes gave maximum yield of the

alkaloids. Christiansen et al. (1981a) found this method inadequate when

analysing samples of Norwegian Psilocybe semilanceata. They extracted the

samples twice with 10% 1 N ammonium nitrate in methanol in a centrifuge

tube by rotating the tubes in a rotary mixer for 30 minutes. Almost quantita-

tive (98%) yield of psilocybin was obtained by this method. The role or ef-

fect of ammonium nitrate in the extraction solvent was not discussed.

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

Table 2. Analytical methods used for the isolation and quantitative determination of psilocybin and/or psilocin in mushroom material.

Extraction solvent and method Separation* Detection** Comments References

Methanol, stirring for ½ h, repeated three

times. LC, cellulose Keller´s reaction Preparative isolation of psilocybin and psilocin and

weighing of the compounds Hofmann et al., 1958a, 1959

Methanol, according to Hofmann et al., 1958a LC, cellulose UV McCawley et al., 1962

Methanol, shaking for 8 h, repeated two times PC Acidified DMAB Semiquantitative results. Catalfomo & Tyler, 1964

Methanol, shaking for 5 h. TLC, silica gel UV Psilocybin was eluted from the TLC plate and deter-

mined by UV-spectrophotometry Heim et al., 1966b

Methanol, shaking for 1 h. TLC, silica gel Acidified DMAB Semiquantitative results. Neal et al., 1968

Methanol, shaking for 24 h. TLC, silica gel Acidified DMAB Semiquantitative results. Robbers et al., 1969

Methanol, shaking for 24 h. GC, packed col., SE-30 & OV-101 FID, MS Analyzed as trimethylsilyl derivatives. Repke et al., 1977

Methanol, homogenization for 2 min. HPLC, ion exchange col. UV, FLD Perkal et al., 1980

Methanol, mixing for 24 h. HPLC, C18 col. with ion par reag. UV Thomson, 1980

Methanol, macerating for 1 day HPLC, amino-bonded col. UV Extracts purified by ion-exchange chromatography. Koike et al., 1981

Methanol with ammonium nitrate, mixing twice

for 30 min. HPLC, silica col. UV, FLD Christiansen et al., 1981a, 1981b,

1982

Methanol, stirring for 12 h. HPLC, C18 col. with ion-pair reag. UV Stamets et al., 1980, Beug and

Bigwood, 1981, 1982.

Methanol with ammonium nitrate, mixing twice

for 30 min. HPLC, silica col. UV+FLD+ED Christiansen & Rasmussen, 1983

Methanol, ultrasonication for 50 min. HPLC, cyano-amino bonded col. UV Sottolano & Lurie, 1983

Methanol, macerating overnight. HPLC, C18 col. UV Stijve et al., 1984*, 1985*

Methanol with ammonium nitrate, mixing twice

for 30 min. HPLC, silica col. UV The method of Christiansen et al. 1981a with minor

modifications. Jokiranta et al., 1984

Methanol, homogenization for 2 min., shaking

for 16 h. HPLC, C18 col. UV, FLD, ED Wurst et al., 1984, Semerdžieva et

al., 1986, Gartz, 1989b, Gartz &

Müller, 1989

Ethanol-water (1:1) with 1-heptanesulphonic

acid (0,05 M), 2 h. in a micropercolator. HPLC, alkylphenyl bonded col. with ion-pair

reag. UV Ion-pair extraction Vanhaelen-Fastré & Vanhaelen,

1984

Methanol, shaking for 24 h HPLC, C18 col. UV+FLD Kysilka et al. 1985

Methanol, macerating for ½ h. Liquid-liquid extraction with butyl chloride. UV Only psilocin is quantified by this method. Lee, 1985

Methanol, mixing for 24 h TLC, silica gel VIS after reaction with DMAB Substances isolated from the TLC-plate by extraction. Gartz, 1986a

Methanol, ultrasonication for 15 min. HPLC, C18 col. UV Borner & Brenneisen, 1987

Methanol, shaking for 60 min. HPLC, C18 col. with ion-pair reagent. UV Ohenoja et al. 1987

Not reported HPLC, C18 col. ED+UV Kysilka & Wurst, 1989

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

Table 2 cont. Analytical methods used for the isolation and quantitative determination of psilocybin and/or psilocin in mushroom material.

Extraction solvent and method Separation* Detection** Comments References

75% methanol saturated with KNO3, shaking

for 10 min. HPLC, C18 col. ED+UV Kysilka & Wurst, 1990, Wurst et

al. 1992

Methanol, magnetic stirring for 12 h. HPLC, C18 col. UV Gartz, 1994

Methanol, ultrasonication for 15 min. CZE, 57 cm×50 µm fused silica capillary UV Pedersen-Bjergaard et al., 1997,

1998

Methanol, grinding and storage over night HPLC, C12 col. Chemolumine-scence Anastos et al., 2006a

Methanol, homogenization HPLC, C18 col. FLD Beck et al. 1998

Methanol, method not specified HPLC, C18 col. MS Only psilocin quantified. Bogusz et al., 1998

Chloroform, ultrasonication for 1 h. GC, fused silica capillary col. (HP-5) MS Analyzed as trimethylsilyl derivatives. Keller et al., 1999a

Methanol, soaking 22 h LC, OD col. MS or MS-MS Kamata et al., 2005

* LC= gravity flow liquid chromatography, LC-MS = liquid chromatography-mass spectrometry, TLC = thin layer chromatography, GC = gas chromatography, HPLC = high-performance liquid chromatography, CZE = capillary zone electrophoresis, C18 = octade-

cyl silica bonded stationary phase.

** DMAB = 4-(dimethylamino)-benzaldehyde, FID = flame ionization detection, MS = mass spectrometry, UV = ultra violet spectrophotometric detection, VIS = visible spectrophotometry, FLD = fluorescence spectrophotometric detection, ED = electrochemical

detection.

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

Beug and Bigwood (1981) obtained quantitative extraction of psilocybin

and psilocin from powdered freeze-dried mushrooms by magnetic stirring

for 12 hours in methanol. Recoveries were tested by adding known

amounts of psilocin and psilocybin to Psathyrella foenisecii and

Psathyrella baeocystis. The effectiveness of this method was later con-

firmed by Gartz (1994). He studied the time course of the extraction in six

different mushroom species and found that the time to maximal yield dif-

fered between the species. None was completely extracted in 30 minutes

and two needed more than six hours. Maximum yield was obtained for all

species in 12 hours.

Sottolano and Lurie (1983) investigated the effect of ultrasonication

on the extraction yield of psilocybin. They found that treatment of finely

powdered mushroom material with methanol, in an ultrasonic water bath

breaks up the mushroom tissue matrix sufficiently to allow over 95%

extraction yield in less than 1 hour. The mushroom species used in this

experiment was not specified.

Vanhaelen-Fastré and Vanhaelen (1984) extracted psilocin, psilocybin

and baeocystin as ion pairs with 1-heptanesulphonic acid in a mixture of

ethanol and water. Finely ground dried specimens of Psilocybe semi-

lanceata were allowed to macerate for 2 hours in a micropercolator. After

percolation of the first solvent fraction, the percolation was repeated with

a fresh solvent. The yield of psilocybin by this method was 99%.

Kysilka and Wurst (1990) reported a new extraction method for psilo-

cybin and psilocin in mushroom samples (Psilocybe bohemica). They

investigated the influence of the composition of the extraction solvent on

the extraction yield and found that these compounds are best extracted

separately. The optimal solvent for the extraction of psilocybin was 75%

methanol saturated with potassium nitrate and 75% ethanol for psilocin.

They stated that conventional extraction with methanol would only ex-

tract 76% of the psilocybin content and 8% of the psilocin content as

compared to the new method. The study was criticized by Gartz (1994),

who was unable to confirm their findings. He found that more psilocin

but less psilocybin was constantly extracted with aqueous mixtures of

methanol or ethanol compared to pure methanol. At the same time he

found high phosphatase activity in the aqueous extracts but not in extracts

from pure methanol. It has previously been demonstrated that psilocybin

is readily hydrolysed to psilocin by phosphatases (Horita and Weber,

1961, 1961a). Although he did not confirm it by experiments he ascribed

the high yield of psilocybin reported by Kysilka and Wurst (1990) to

hydrolytic cleavage of psilocybin to psilocin by phosphatases extracted

from the mushrooms. Unfortunately Kysilka and Wurst (1990) did not

investigate whether extraction of psilocin from the samples had any effect

on the psilocybin content of the same samples.

Anastos et al. (2006a) extracted psilocybin and psilocin with metha-

nol, separated the compounds on a C12 column using a methanol/ ammo-

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

nium formate mixture as mobile phase, and detected the compounds

through a dual reagent chemiluminescence detection system of acidic

potassium permanganate and tris(2,2´- bipyridyl)ruthenium (II). During

these studies it was observed that the aquous chemical standards of psilo-

cybin and psilocin are prone to be degraded by light. However, taking

care of protecting the standards from light, they are stable for at least one

week (Anastos et al., 2006b).

From these studies it can be seen that the extraction of psilocybin and

psilocin from mushroom samples deserves further investigation. It still

remains unclear whether the high psilocin content reported by Kysilka

and Wurst (1990) and Wurst et al. (1992) in some species is an artefact.

Moreover the time course of the extraction under different experimental

conditions needs to be thoroughly studied.

2.3.2 Quantitative determination of psilocybin and psilocin in mushroom

samples

As shown in Table 2 almost all published methods for the quantitative

determination psilocybin and psilocin have utilized some kind of chroma-

tography to separate them from other co-extracted compounds. In their

original identification of psilocybin and psilocin in Psilocybe mexicana,

Hofmann and co-workers (1958a) used chromatography on a cellulose

column. After a further purification and crystallization procedure, the

isolated substances were quantitated by weighing. McCawley et al.

(1962) adopted this method when analysing samples of Psilocybe baeo-

cystis. Instead of weighing the isolated substances they quantified them

by ultraviolet spectrophotometry.

Although paper and thin-layer chromatography have mostly been used

for the qualitative analysis of these substances, some authors have used

them quantitatively. Catalfomo and Tyler (1964) used a serial dilution

procedure to quantify psilocybin on paper chromatograms after reaction

with 4-dimethylaminobenzaldehyde. Robbers et al. (1969) used the same

method to quantify psilocybin on thin-layer chromatograms and a similar

approach was used by Neal et al. (1968). Gartz (1986a) extracted psilo-

cybin and baeocystin from thin-layer chromatograms and quantified them

by measuring the colour formed after reaction with 4-(dimethylamino)-

benzaldehyde.

Due to its versatility high-performance liquid chromatography is the

most popular method for the determination of psilocybin and psilocin in

mushroom samples. Normal phase chromatography on a silica column is

the simplest form of this technique. It was used qualitatively by White

(1979) and for quantitative analysis by Christiansen et al. (1981a, 1981b,

1982), Christiansen and Rasmussen (1983) and Jokiranta et al. (1984). By

this method Christiansen and Rasmussen obtained an excellent separation

of the indole alkaloids present in Norwegian Psilocybe semilanceata. It

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

has been stated that silica columns are susceptible to contamination from

polar materials that shorten column life and are less reproducible than

bonded columns (Thomson, 1980; Lindsay, 1987). This may explain why

they have not gained popularity in the analysis of these substances.

The most versatile bonded columns are those with non-polar groups like

octyl (C8) or octadecyl (C18) hydrocarbon chains attached. As can be seen

in table 2 C18 is the most widely used column for these purposes. Because

of the hydrophobic nature of the stationary phase psilocybin is only weakly

retained on this type of column and therefore prone to interference from co-

extracted, water soluble impurities. Another disadvantage of using these

columns is that the different polarity of psilocybin and psilocin makes si-

multaneous analysis difficult. The problem may be solved, at least in part,

by using a mobile phase gradient (Borner and Brenneisen, 1987) or by

using two different solvent systems for these two compounds (Kysilka and

Wurst 1990). In none of the published methods using C18 columns under

isocratic conditions was it confirmed whether these systems were able to

separate psilocibin and its demethylated analogue, baeocystin (Stijve et al.,

1984, 1985; Wurst et al. 1984; Semerdžieva et al., 1986; Gartz, 1987a,

1989b; Kysilka et al., 1985; Kysilka and Wurst 1989; Gartz & Müller,

1989; Kysilka & Wurst, 1990; Wurst et al. 1992).

Several authors (Thomson, 1980; Stamets et al., 1980; Beug and Big-

wood, 1981, 1982; Vanhaelen-Fastré and Vanhaelen, 1984; Ohenoja et

al., 1987) have separated these substances as ion-pairs with ion-pair re-

agents on hydrocarbon bonded phase columns. However, it should be

kept in mind that it is virtually impossible to remove completely an ion-

pair reagent from such columns and they are therefore not reusable with

other mobile phases (Gill 1986).

Psilocybin and psilocin have excellent absorption characteristics in the

ultraviolet region, both exhibit native fluorescence and they are electro-

chemically active. These features have all been used to monitor the efflu-

ent from the chromatographic column. Although ultraviolet spectropho-

tometry is the most commonly used method (Table 2) greater sensitivity

may be obtained by other methods (Perkal et al., 1980; Wurst et al.,

1992). Increased specificity has been obtained by connecting two or more

of these detectors in series (Christiansen and Rasmussen, 1983; Wurst et

al., 1992).

Only three authors have described gas chromatographic methods to

quantify psilocybin and psilocin in mushroom samples (Repke et al., 1977;

Keller et al., 1999a, 1999b; Kikura-Hanajiri et al., 2005). The reason is,

without doubt, the low volatility of psilocybin, which makes derivatization

necessary prior to analysis. This technique is therefore rather impractical as

compared to high-performance liquid chromatography. Both authors used

silylation, where psilocybin was converted to its tris-(trimethylsilyl) deriva-

tive and psilocin to its bis-(trimethylsilyl) derivative.

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

Recently Pedersen-Bjergaard et al. (1997, 1998) developed a capillary

zone electrophoretic method to determine psilocybin and other indole

alkaloids in Psilocybe semilanceata. Although this method seems to be a

promising alternative to high-performance liquid chromatography it did

not allow a simultaneous determination of psilocybin and psilocin.

This review shows that none of the published methods seems to offer

a totally satisfactory solution to the analysis of psilocybin and psilocin in

mushroom samples. Further research in this field is therefore needed.

2.3.3 Qualitative analysis of psilocybin and psilocin in mushroom samples

Although the aforementioned instrumental chromatographic techniques are

all usable for screening of mushroom samples for psilocybin and related

substances, most authors have used thin-layer chromatography. It offers the

possibility of using more or less group specific detection reagents, which

makes it even more versatile and specific than most of the quantitative

methods. In Table 3 are listed the thin-layer chromatographic systems re-

ported for the identification of psilocybin and closely related substances.

The most commonly used system is n-butanol-acetic acid-water (2:1:1). It

has the disadvantage that psilocybin and baeocystin are not well separated.

A mixture of these solvents in the proportions 12:3:5 gives a better separa-

tion of these two substances. However, the systems cyclohex-

ane:chloroform (1:1) (Leung et al., 1965) and n- propanol-acetic-acid-

water (10:3:3) (Vanhaelen-Fastré and Vanhaelen, 1984) seem to give the

best overall separation of psilocybin, psilocin and baeocystin.

Paper chromatography, the forerunner of thin-layer chromatography,

was the most commonly used screening method in the first years after the

discovery of psilocybin and psilocin (Hofmann et al. 1958a, 1958b). Ty-

ler (1961) used paper chromatography with three different solvent sys-

tems to identify indole derivatives in certain North American mushrooms.

He identified psilocybin in Psilocybe pelliculosa on a filter paper buff-

ered to pH 5. The mobile phase was n-butanol saturated with water. This

same system was later used by Benedict et al. (1962a, 1962b, 1967),

Picker and Rickards (1970), and Ott and Guzmán (1976). The other sys-

tems described by Tyler (1961) were the upper phase of n-butanol-acetic

acid-water (4:1:5) and n-propanol-ammonia (5:1) (see also Benedict et al.

(1962a, 1962b, 1967)). Other solvent systems that have been used for

these purposes are n-butanol-acetic acid-water (12:3:5) (Ott and Guzmán,

1976) and n-butanol-acetic acid-water-isopropanol (8:2:5:3) (Michaelis,

1977).

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

Table 3. Thin-layer chromatographic systems used for the identification of psilocybin, psilocin and baeocystin in mushroom samples. Systems, where no Rf-values are reported or

where any of these substances is not retained, or stays at the origin are excluded from the table. The Rf-values cited are from the first reference in which they appear.

Mobile phase Stationary phase* Rf. **

PSB

Rf.**

PSI

Rf.** BAE References

n-Butanol-acetic acid-water (2:1:1) SG 0.33 0.54 0.38 Heim et al., 1966b; Høiland , 1978; Hatfield and Valdes,

1978; White, 1979; Beug and Bigwood, 1981; Gartz, 1985c

n-Butanol-acetic acid-water (2:1:1) SG+KG 2:1 0.15 0.76 0.16 Leung et al., 1965; Leung and Paul 1968

n-Butanol-acetic acid-water (12:3:5) CE 0.48 0.78 n.r. Beug and Bigwood, 1981

n-Butanol-acetic acid-water (12:3:5) SG 0.18-0.26 0.42 0.31 Stamets et al., 1980; Beug and Bigwood, 1981, 1982; Stijve

et al., 1984, Marcano et al., 1994

n-Butanol-acetic acid-water (24:10:10) SG 0.19 0.50-

0.54 n.r. Picker and Rickards, 1970; Wurst et al., 1984; Semerdžieva

et al., 1986; Wurst et al., 1992.

n-Butanol-acetic acid-isopropanol-water (8:2:3:5) SG 0.21 n.r. 0.25 Gartz, 1985b,c

n-Butanol-pyridine-acetic acid-water (15:10:3:10) SG n.r. 0.55 n.r. Hatfield et al., 1978

Cyclohexane-chloroform (1:1) SG 0.15 0.55 0.46 Leung et al., 1965; Leung and Paul 1968

Methanol-acetic acid-water (75:10:15) SG 0.25 0.55 0.51 Mantle and Waight, 1969; Stijve et al., 1984

Methanol-concentrated ammonia (98.5:1.5) SG 0.14 0.45 n.r. Beug and Bigwood, 1981

Methanol-benzene-5% ammonia (10:15:2) SG 0.04 0.54 n.r. Heim et al., 1966b

n-Propanol-concentrated ammonia-water (500:12:188) SG 0.11 0.58 n.r. Beug and Bigwood, 1981

n-Propanol-5% ammonia (2:1) SG 0.14 0.73 n.r. Heim et al., 1966b

n-Propanol-5% ammonia (5:1) CE 0.03 0.9 0.02 Stijve et al., 1984

n-Propanol-5% ammonia (5:2) SG+KG 2:1 0.19 0.79 n.r. Neal et al., 1968

n-Propanol-5% ammonia (5:2) SG 0.27 n.r. 0.22 Repke and Leslie, 1977a, 1977b; Repke et al., 1977, Hatfield and

Valdes, 1978; Koike et al., 1981

n-Propanol-6% ammonia (5:2) SG 0.16 n.r. 0.13 Gartz, 1985a

n-Propanol-acetic acid-water (10:3:3) SG 0.30 0.53 0.40 Vanhaelen-Fastré and Vanhaelen, 1984

n-Propanol-concentrated ammonia-water (150:10:50) SG 0.16 0.82 n.r. Beug and Bigwood, 1981

n-Propanol-concentrated ammonia-wate (500:12:188) SG 0.11 0.58 n.r. Beug and Bigwood, 1981

* SG = Silica gel, CE = Cellulose, KG = Kieselguhr.

* * PSB = Psilocybin, PSI = Psilocin, BAE = Baeocystin, n.r. = not reported.

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

The most commonly used reagent to detect indole alkaloides on paper or

thin-layer chromatograms is 4-(dimethylamino)-benzaldehyde (DMAB). It

is usually applied in a mixture with strong hydrochloric acid (Ehrlich´s

reagent) or followed by exposition to hydrogen chloride fumes. DMAB

reacts at position 3 in the indole ring to form a coloured derivative (Jork et

al., 1994). An alternative to this reagent is 4-(dimethylamino)-cinnamalde-

hyde in a mixture with strong hydrochloric acid. This reagent was found

more sensitive than the Ehrlich´s reagent and gave more varied colours

(Stijve et al., 1984, 1985). Among other reagents that have been reported

for the localisation of psilocybin and related alkaloids are diazotized sulfa-

nilic acid (Pauly´s reagent) (Tyler, 1961; Benedict et al., 1962a, 1967),

ceric sulphate and an alkaline solution of Fast Blue B (Heim et al., 1966b).

Finally it should be mentioned that non-chromatographic techniques

have also been used to identify psilocybin and other indole alkaloids in

mushroom samples. Unger and Cooks (1979) used mass spectrome-

try/mass spectrometry (MS/MS) to identify psilocybin in powdered

mushrooms and mushroom extracts. Lee (1985) isolated and identified

psilocin from psilocin/psilocybin containing mushrooms by UV and IR-

spectrophotometry. The method is based on the hydrolysis of psilocybin

to psilocin and a selective extraction of psilocin from the extracts by 1-

chlorobutane. Recently Keller et al. (1999a, 1999b, 2006) used ion mobil-

ity spectrometry to identify psilocybin and psilocin in finely cut samples

of Psilocybe subcubensis. The method is highly sensitive but not entirely

specific since psilocybin is thermally degraded to psilocin during analy-

sis. In line with developments in analytical methodology also liquid

chromatography-mass spectrometry (LC-MS) and liquid chromatogra-

phy-tandem mass spectrometry (LC-MS-MS) have been used to deter-

mine psilocybin and psilocin in samples of ‘magic mushrooms’ (Kamata

et al., 2005). In particular the tandem mass spectrometry provided im-

proved specificity and accuracy.

2.3.4. Analysis of psilocybin and psilocin in human fluids and tissues

Moeller and Kraemer (2002) described procedures for detection of drugs

of abuse in whole blood, plasma, and serum. Reviewing what is known

about psilocybin/psilocin they identify Sticht and Käferstein (2000) to be

first to report the identification of psilocin in serum in a subject after

magic mushroom intake. However, the amount was to low to be quanti-

fied by common analytical methods.

Psilocybin can not be detected with GC-MS because of its phosphoric

acid structure. The analysis has to focus on psilocin but as psilocin is

thermally labile, it requires derivatization before being analysed by GC-

MS (Ondra et al., 2006; Tiscione and Miller, 2006). To quantify the in-

ternal dose of mushroom hallucinogens, psilocin conjugates should be

cleaved enzymatically, extracted and, if required, derivatized (silylated)

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

before being determined by suitable instrumentation. Sticht and Käfer-

stein (2000) found 18 ng/ml free psilocin in serum, but the total psilocin

content was 52 ng/ml.. It is to be expected that LC-MS will be a suitable

technique for determination of psilocybin and psilocin in various bioma-

trices (Drummer, 1999; Polettini, 1999; Bogusz, 2000). For example,

Bogusz et al. (2000) reported a limit of detection of 1 g psilocin/L se-

rum using a LC-electrospray ionization (ESI)-MS system.

Exposure to psilocybin-containing mushrooms or drugs can also be

documented by urinary analysis. As psilocin glucuronide is an important

excretion product in urine, Kamata et al. (2003) developed an optimized

glucuronide hydrolysis method for the detection of psilocin by LC-MS-

MS in human urine. Recently, Ramirez Fernandez et al. (2007) reported a

validated LC-MS-MS method for the simultaneous analysis of multiple

hallucinogens, including psilocin, in urine of subjects that have ingested

hallucinogenic mushrooms.

In addition to the GC-MS and LC-MS methods developed, a single

immunoassay for analysis of psilocin in serum and blood samples has

been published (Albers et al., 2004). This method makes use of a poly-

clonal rabbit antisera developed against a psilocin hapten conjugate

(Albers et al., 2002). Cross-reactivity of structurally related compounds

were usually limited but reached close to 20% for tricyclic neuropeptics

with a (dimethylamino)ethyl side-chain. This method is, however,

unlikely to become important in the analysis of forensic samples poten-

tially containing psilocybin/psilocin.

3. Biosynthesis

Experimental evidence regarding the biosynthesis of psilocybin and psi-

locin is limited. The structural similarity between these compounds and

tryptophan indicate they might be derived from that amino acid. In 1961

Brack and co-workers showed that labelled tryptophan was incorporated

into psilocybin by cultured mycelium of Psilocybe semperviva. Subse-

quently, labelled tryptophan was found to be incorporated into psilocybin

also in submerged cultures of Psilocybe cubensis (Agurell et al., 1966).

Separate studies showed that addition of tryptophan to the culture me-

dium had no influence on the biosynthesis of psilocybin in Psilocybe

cubensis and Psilocybe baeocystis (Catalfomo and Tyler, 1964; Leung

and Paul, 1969). It is not known to what extent the data obtained from

studies on mycelial cultures are representative for the biosynthesis in fruit

bodies grown in the wild.

To produce psilocybin, the tryptophan molecule has to be modified by

decarboxylation, methylation of the amino group, hydroxylation of the 4-

position of the indole moiety, and phosphorylation of the 4-hydroxy-

indole moiety; although not necessarily in the above order. Since tryp-

tamine functioned as a better precursor for psilocybin synthesis than tryp-

tophan in cultured Psilocybe cubensis, it seems probable that decarboxy-

lation of tryptophan to tryptamine is the first step in the biosynthesis of

psilocybin (Agurell et al., 1966). In agreement with this observation, 4-

hydroxytryptophan was found to be a very poor precursor to psilocybin

(Agurell and Nilsson, 1968a).

The biosynthetic route from tryptamine to psilocybin is much more

controversial. Available data (Agurell and Nilsson, 1968a; 1968b; Chil-

ton et al., 1979) from studies on Psilocybe cubensis are consistent with

the psilocybin biosynthes shown in Figure 2.

Using mini-cultures of Psilocybe cubensis and deuterium-labelled

precursor solutions, Chilton et al. (1979) found that a wide range of tryp-

tamines were readily absorbed by mycelia and translocated into develop-

ing mushrooms. Deuterated tryptamine was incorporated more efficiently

into psilocin and psilocybin than were monomethyltryptamine and di-

methyltryptamine. Both of the latter two compounds were incorporated,

however, without prior demethylation to tryptamine. These data suggests

that the hydroxylation enzyme operates normally on tryptamine, but may

be sufficiently flexible to oxidise dimethyltryptamine or other natural

substrates forced on it at high concentration. The hydroxylation of di-

methyltryptamine in mini-cultures to give psilocin was observed to occur

with NIH shift. Thus a tryptamine-4,5-epoxide is the probable intermedi-

ate between tryptamine and psilocin.

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

In studies on mycelial cultures of Psilocybe cubensis, which are capable

of forming psilocybin and psilocin de novo, german investigators, in

agreement with the above referred findings, observed a high capacity for

hydroxylation of tryptamine and tryptamine derivatives at the 4-position.

Although no data was shown on the hydroxylation of N,N-

dimethyltryptamine to psilocin, the mushroom efficiently hydroxylated

tryptamine to psilocin (and much less efficiently to psilocybin) (Gartz,

1989c), and N,N- diethyltryptamine to 4-hydroxy-N,N-diethyltryptamine

(up to 33 000 mg/kg dry weight) (Gartz, 1989b). Parallel investigations

with mycelial cultures of Psilocybe semilanceata revealed that also this

mushroom was able to biotransform N-methyltryptamine to 4-

phosphoryloxy-N-methyltryptamine (baeocystin). Comparatively little

psilocin was produced. These observations indicate that surface cultures

of Psilocybe semilanceata have a high hydroxylation and phosphoryla-

tion capacity, although the ability to methylate tryptamine derivatives is

low. Thus, the latter observation agree with the finding of Agurell and

Nilsson (1968b) that psilocybin may be formed from 4-hydroxytryptamine

(in cultures of Psilocybe cubensis), were this compound to be formed in the

mushrooms.

tryptophan tryptamine

N-methyltryptamine N,N-dimethyltryptamine

psilocin psilocybin

CH2CHCOOH

NH2N

CH2CH2NH2

CH2CH2NHCH3

CH2CH2NCH3

CH3

CH2CH2NCH3

CH3

CH2CH2NCH3

CH3

POO

Fig. 2.A tentative pathway for the biosynthesis of psilocybin from tryptophan. The model

is based on data obtained in studies on submerged cultures of Psilocybe cubensis (Agurell

and Nilsson, 1968a, 1968b; Chilton et al., 1979).

4. Occurrence

The first identification of ritual 'teonanácatl' samples took place in 1939

and revealed that more than one mushroom species was used by the sha-

mans. The identified mushrooms were Panaeolus campanulatus var.

sphinctrinus, Panaeolus acuminatus, Psilocybe cubensis and Psilocybe

caerulescens (Guzmán, 1983). After psilocybin, psilocin, baeocystin, nor-

baeocystin and aeruginacin initially being identified in Psilocybe mexi-

can, Psilocybe baeocystis and Inocybe aeruginascens (Hofmann et al.,

1958a; Leung and Paul, 1968; Gartz, 1989a), respectively, the hallucino-

genic compounds were also detected in other mushrooms growing in

various parts of the world.

4.1. Content of psilocybin and related compounds in

various mushroom species

Table 4 tabulates the analytical data on psilocybin, psilocin and/or baeo-

cystin content in various mushrooms available in the litterature. Lists of

this type require correct identification of the mushrooms. In practise, this

is unlikely due to the sometimes poorly developed and often progressivly

developing taxonomy, and the difficulties in accurately identifying the

various mushroom species. The present authors have not changed the

information of the original author unless this is obviously motivated, e.g.

when it is commonly accepted that a mushroom has been transferred from

one genus to another.

Psilocybin, psilocin and/or baeocystin have been identified in the gen-

era Agrocybe, Conocybe, Copelandia, Geerronema, Gymnopilus, Hygro-

cybe, Hypholoma, Inocybe, (Panaeolina), Panaeolus, Pluteus, Psathyrella,

Psilocybe and Stropharia. Of the about 190 different mushrooms which

have been analysed for psilocybin, psilocin or beaocystin, about 90 have

been identified to contain at least one of these hallucinogenic compounds

and in more than 60 of the cases the levels have been quantified. In the

genus Psilocybe 41 out of 55 species(or varieties) contain psilocybin or

related compounds, whereas the corresponding figures for the genus Pan-

aeolus are 9 out of 26 species. Hallucinogenic compounds also seem to be

common in the genus Gymnophilus.

The table also states which analytical techniques have been used to

identify and quantify the hallucinogens. Additional information available

in Table 4 is a statement on whether the analysed mushrooms material

were harvested from cultures in the laboratory as fruit bodies (C), scle-

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

rotia (Sc), submerged mycelium culture (S) or mycelium (M). When col-

lected in the wild, the country of origin is given. It should be noted that

partial degradation of psilocybin, psilocin and/or baeocystin may have

taken place in the dried materials from herbarial collections.

It has been argued that the ability to synthesise psilocybin and related

compounds can be used as a toxonomic criterion. The background for this

suggestion is that all mushroom samples of a species collected from dif-

ferent areas of the world contain the investigated compounds. For exam-

ple, fruit bodies of Psilocybe cubensis grown from spores obtained from

such different places as Mexico, Thailand and Cambodia all contained

appreciable amounts of psilocybin and traces of psilocin (Heim and Hof-

mann, 1958a). However, in some species this character seems not to be

stable. For these species there are both reports on the absence and the

presence of psilocybin. Although it is clear that the ability to produce

psilocybin and related compounds has a genetic background, not only

genetic factors determine the level of these compounds in the mush-

rooms.

The complicated relationship between genetic closeness of different

mushroom species and their ability to synthesise psilocybin has been

explored for the genus Gymnophilus, since Gymnopilus spectabilis has

been implicated in intoxications with hallucinogenic episodes (Hatfield et

al., 1978; Walters, 1965; Buck, 1967; Romagnesi, 1964). The material in

this investigation was 13 collections of mushrooms. In one toxiconomic

treatment of Gymnopilus, the genus is divided into two subgenera (Annu-

lati and Gymnopilus) based on the presence or absence of a persistent

annulus. Of the 16 species in the Annulati group, five were screened for

psilocybin. Whereas G. luteus, G. spectabilis and G. validipes contained

psilocybin, it was absent from G. subspectabilis and G. ventricosus. The

subgenus Gymnopilus has been subdivided into two sections - Microspori

and Gymnopilus. Four of the 22 species found in section Microspori were

screened and none contained psilocybin. The section Gymnopilus of sub-

genus Gymnopilus contains 33 species of which 10 were screened. Two

of these, G. aeruginosus and G. viridans contained psilocybin, whereas

the rest (G. aurantiophyllus, G. flavidellus, G. liquiritae, G. luteofolius,

G. mitis, G. penetrans, G. picreus and G. sapineus) did not (Hatfield et

al., 1978). The age of some of the collections (up to 21 years old) is likely

in part responsible for the variability in psilocybin content measured in

the various samples. However, this is probably not the only factor in-

volved since psilocybin has been found to be quite stable in some dried

herbarium samples. Another explanation of these results is that two or

more subspecies exists in some of the Gymnopilus species (Hatfield et al.,

1978).

Another illustration of the complicated relationship between genetic

closeness and the ability to produce psilocybin is given by the taxa be-

longing to the genus Panaeolus, which are difficult to exactly identify.

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

Differential anatomic criteria commonly used for identification do not

permit a precise differentiation between the various species. Therefore, it

is easy to understand that results of chemical studies on this genus are

contradictory as they are done on poorly identified material (Ola´h,

1968). In order to confirm the presence or absence of psilocybin and re-

lated compounds, chemical analyses were performed with wild fruit bod-

ies, with fruit bodies from in vitro cultures, and with the dry matter of

mycelial cultures (Ola´h, 1968). The results of these analyses indicate

that the genus Panaeolus may be subdivided into three distinct groups, as

far as their psychodysleptic power is concerned: the psilocybian species,

the latent psilocybian species and the non-psilocybian species. The obvi-

ous problem here is the latent psilocybian species.

Genetic techniques based on polymerase chain reactions (PCR) of

specific regions of the genomes have been developed to identify species

and strains of various mushrooms (Lee et al., 2000a; Maruyama et al.,

2003b). Using this approach, studies of ribosomal RNA genes (the large

subunit) in Psilocybe and Panaeolus mushrooms have recently allowed

the differentiation between psilocybin-producing and non-psilocybin-

producing species, particularly of the genus Psilocybe (Moncalvo et al.,

2002; Maruyama et al., 2003a, 2003b, 2006). The tested hallucinogenic

mushrooms were classified into six groups (Maruyama et al., 2003b). The

identification of psilocybin-producing and non-psilocybin-producing

groups within Psilocybe might indicate that sometime during evolution an

event such as loss of psilocybin biosynthetic enzymes or their transcrip-

tion control factors might have occurred (Maruyama et al., 2003a). As

DNA samples may be obtained from nearly all types of material, includ-

ing forensic material, the method is useful with samples that do not allow

identification of mushrooms by morphological methods. However, the

fluorescence signal given in the TaqMan assay was influenced by the

preservation time after harvest (Maruyama et al., 2003a). Lee et al.

(2000b) have reported on another DNA-based test to identify hallucino-

genic fungi. This test used the technique of amplified fragment length

polymorphisms in combination with using a suitable set of different

primers. Similarly, Nugent and Saville (2004) amplified and sequenced

the internal transcribed spacer region of the rDNA (ITS-1) and a 5´ por-

tion of the nuclear large ribosomal subunit of rRNA (nSLU rRNA) in 35

mushroom species belonging to hallucinogenic and non-hallucinogenic

genera. Whereas the ITS-1 locus sequence data was highly variable and

produced a phylogenetic resolution that was not consistent with morpho-

logical identification, the nLSU rRNA data clustred isolates from the

same species and separated hallucinogen-containing and non-

hallucinogen containing isolates into distinct clades.

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

Table 4. Occurrence of psilocybin, psilocin and baeocystin and neo-baeocystin (mg/kg dry weight if not otherwise stated) in hallucinogenic mushrooms. An empty square implies

that this compound was not analysed for.

Species, geographical region where it was collected Analytical method* Psilocybin Psilocin Baeocystin Comments** Reference

Agrocybe farinacea Hongo, Japan LC, HPLC n.d.-4 000 Koike et al., 1981

Agrocybe praecox (Pers.) Fayod, Austria IMS/GC-MS 8 000 – 8 600 Keller et al., 1998

Agrocybe semiorbicularis (Bull.) Fayod, Japan LC, HPLC n.d. Koike et al., 1981

Agrocybe sp., Finland HPLC/HPLC 30 n.d. Ohenoja et al., 1987

Amanita muscaria (L.: Fr.) Hooker, Brazil, n=4 HPLC n.d. n.d. n.d. Stijve and de Meijer, 1993

Conocybe antipus (Lasch) Kühner, Japan LC, HPLC n.d. Koike et al., 1981

Conocybe brunneola (Kühn.) Wall., Brazil HPLC n.d. n.d. n.d. Stijve and de Meijer, 1993

Conocybe cyanopus (Atk.) Kühner, Finland HPLC/HPLC 4 500^ 700^ Ohenoja et al., 1987

Conocybe cyanopus (Atk.) Kühner, Norge, n=1 HPLC 3 000–6 000 Repke et al., 1977b

Conocybe cyanopus (Atk.) Kühner, Canada, n=1 TLC 300–1 000 Repke et al., 1977b

Conocybe cyanopus (Atk.) Kühner, USA PC + n.d. Benedict et al., 1962a

Conocybe cyanopus (Atk.) Kühner, USA PC + n.d. Benedict et al., 1967

Conocybe cyanopus (Atk.) Kühner, USA HPLC/TLC 9 300 n.d. Beug and Bigwood, 1982

Conocybe cyanopus (Atk.) Kühner, USA, n=1 TLC 500 Repke et al., 1977b

Conocybe cyanopus (Atk.) Kühner, Norge, n=1 HPLC 3 300 – 5 500 40–70 Christiansen et al., 1984

Conocybe kuehneriana (Sing.) Kühner, Finland HPLC/HPLC n.d. 40 Ohenoja et al., 1987

Conocybe mesospora Kühn. & Wall., Brazil HPLC n.d. n.d. n.d. Stijve and de Meijer, 1993

Conocybe plicatella (Peck) Kühn, Brazil HPLC n.d. n.d. n.d. Stijve and de Meijer, 1993

Conocybe smithii Watling, USA, n=2 TLC n.d.-800 Repke et al., 1977b

Conocybe smithii Watling, USA PC + n.d. Benedict et al., 1967

Conocybe tenera (Schaeff.) Fayod, Italy PC n.d. n.d. Fiussello and Ceruti Scurti, 1972b

Conocybe tenera (Schaeff.) Fayod, USA HPLC/TLC n.d. n.d. Beug and Bigwood, 1982

Conocybe tenera (Schaeff.) Fayod, Norge HPLC n.d. n.d. Christiansen et al., 1984

Conocybe sp., USA HPLC/TLC n.d. n.d. Beug and Bigwood, 1982

Copelandia anomala Murrill, Hawaii (USA) TLC/HPTLC + Merlin and Allen, 1993

Copelandia bispora (Malencon & Bertault) Singer and Weeks, Hawaii (USA) TLC/HPTLC + Merlin and Allen, 1993

Copelandia cambodginiensis (Ola´h & Heim) Singer and Weeks, Hawaii

(USA) TLC/HPTLC 3 000–6 000 1 300–5 500 n.d.–200 Merlin and Allen, 1993

The abbreviation n.d. = non detectable level. + = detected, but not quantified; ( ) = not always detected; ^ = mg/kg fresh weight. Note the footnote directly after the table.

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

Table 4 cont. Occurrence of psilocybin, psilocin and baeocystin and neo-baeocystin (mg/kg dry weight if not otherwise stated) in hallucinogenic mushrooms. An empty square im-

plies that this compound was not analysed for.

Species, geographical region where it was collected Analytical method* Psilocybin Psilocin Baeocystin Comments** Reference

Copelandia chlorocystis sp. nov. Singer & Weeks, Brazil, n=2 Dry column C 4 600 2 900 Weeks et al., 1979

Copelandia cyanescens (Berk. & Br.) Singer, Italy, n=2 PC + + Fiussello and Ceruti Scurti, 1972b

Copelandia cyanescens (Berk. & Br.) Singer, Hawaii, USA TLC/HPTLC + Merlin and Allen, 1993

Copelandia tropicalis (Ola´h) Singer & Weeks, Hawaii TLC/HPTLC + Merlin and Allen, 1993

Copelandia sp., Japan, n=2 HPLC 800 –2 200 4 300 – 7 600 Tsujikawa et al., 2003

Coprinus comatus (O.F. Müll.), Japan LC, HPLC n.d. Koike et al., 1981

Coprinus plicatilis (Curtis) Fr., Norway HPLC n.d. n.d. Christiansen et al., 1984

Entoloma caesiocinctum, Switzerland, n=1 HPLC; TLC n.d. n.d. Stijve and Bonnard, 1986

Entoloma catalaunicum, Switzerland, n=1 HPLC; TLC n.d. n.d. Stijve and Bonnard, 1986

Entoloma incanum, Switzerland, n=1 HPLC; TLC n.d. n.d. Stijve and Bonnard, 1986

Entoloma lazulinum, Switzerland, n=1 HPLC; TLC n.d. n.d. Stijve and Bonnard, 1986

Entoloma mougeotii, Switzerland, n=1 HPLC; TLC n.d. n.d. Stijve and Bonnard, 1986

Entoloma nitidum, Switzerland, n=1 HPLC; TLC n.d. n.d. Stijve and Bonnard, 1986

Entoloma serrulatum, Switzerland, n=1 HPLC; TLC n.d. n.d. Stijve and Bonnard, 1986

Entoloma versatilis, Switzerland, n=1 HPLC; TLC n.d. n.d. Stijve and Bonnard, 1986

Galerina steglichii Besl spec. nov., Germany HPLC + + + Besl, 1993

Gerronema fibula (Bull) Singer, Germany TLC + n.d. n.d. Gartz, 1986d

Gerronema swarrtzii (Fr.) Kreisel, Germany TLC + n.d. n.d. Gartz, 1986d

Gymnopilus aeruginosus (Peck) Sing., Japan LC, HPLC n.d. Koike et al., 1981

Gymnopilus aeruginosus (Peck) Sing., USA TLC + Hatfield et al., 1978

Gymnopilus aurantiophyllus Hesler, USA TLC n.d. Hatfield et al., 1978

Gymnopilus chrysopellus (Berk. & Curt.) Murr., Brazil HPLC n.d. n.d. n.d. Stijve and de Meijer, 1993

Gymnopilus flavidellus Murr., USA TLC n.d. Hatfield et al., 1978

Gymnopilus liquiritiae (Pers.) P. Karst, Japan LC, HPLC 120–290 Koike et al., 1981

Gymnopilus liquiritiae (Pers.) P. Karst., USA TLC n.d. Hatfield et al., 1978

Gymnopilus luteofolius (Peck) Hesler, USA TLC n.d. Hatfield et al., 1978

Gymnopilus luteus (Peck) Hesler, USA TLC + Hatfield et al., 1978

Gymnopilus mitis Hesler, USA TLC n.d. Hatfield et al., 1978

Gymnopilus pampaenus (Speg.) Sing., Brazil HPLC n.d. n.d. n.d. Stijve and de Meijer, 1993

The abbreviation n.d. = non detectable level. + = detected, but not quantified; ( ) = not always detected; ^ = mg/kg fresh weight. Note the footnote directly after the table.

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

Table 4 cont. Occurrence of psilocybin, psilocin and baeocystin and neo-baeocystin (mg/kg dry weight if not otherwise stated) in hallucinogenic mushrooms. An empty square im-

plies that this compound was not analysed for.

Species, geographical region where it was collected Analytical method* Psilocybin Psilocin Baeocystin Comments** Reference

Gymnopilus peliolepsis (Speg.) Sing., Brazil HPLC n.d. n.d. n.d. Stijve and de Meijer, 1993

Gymnopilus penetrans (Fr.) Murr., USA TLC n.d. Hatfield et al., 1978

Gymnopilus picreus (Fr.) P. Karst., USA TLC n.d. Hatfield et al., 1978

Gymnopilus punctifolius (Peck) Sing., USA TLC n.d. Hatfield et al., 1978

Gymnopilus purpuratus (Cooke & Mass.) Sing., Germany TLC + Kreisel and Lindequist, 1988

Gymnopilus purpuratus (Cooke & Mass.) Sing. HPLC, TLC 3 400 2 900 500 C Gartz, 1994

Gymnopilus sapineus (Fr.) Marie., USA TLC + Hatfield et al., 1978

Gymnopilus sordidostipes Hesler, USA TLC n.d. Hatfield et al., 1978

Gymnopilus spectabilis (Fr.) A.H. Sm., Japan LC, HPLC n.d. Koike et al., 1981

Gymnopilus spectabilis (Fr.) A.H. Sm., USA TLC + Hatfield et al., 1978

Gymnopilus spectabilis (Fr.) A.H. Sm., Norge HPLC n.d. n.d. Christiansen et al., 1984

Gymnopilus subspectabilis Hesler, USA TLC n.d. Hatfield et al., 1978

Gymnopilus subtropicus Hesler, USA TLC n.d. Hatfield et al., 1978

Gymnopilus terrestris Hesler, USA TLC n.d. Hatfield et al., 1978

Gymnopilus validipes (Peck) Hesler, USA TLC + Hatfield et al., 1978

Gymnopilus ventricosus (Earle) Hesler, USA TLC n.d. Hatfield et al., 1978

Gymnopilus ventricosus (Earle) Hesler, USA HPLC/TLC n.d. n.d. Beug and Bigwood, 1982

Gymnopilus viridans Murr., USA TLC + Hatfield et al., 1978

Hygrocybe psittacina (Schff. ex Fr.) Wünsche (f. optima R.

Schultz), Germany TLC + + Gartz, 1986d

Hypholoma aurantiaca, Australia HPLC 9 700 – 9 900 Anastos et al., 2006a

Inocybe aeruginascens Babos, Germany n=20 TLC + Gartz, 1985d

Inocybe aeruginascens Babos, Germany HPLC, TLC 4 000 n.d. 2 100 museium coll. Gartz, 1994

Inocybe aeruginascens Babos, Germany, n=10 HPLC, TLC 2 600–5 200 traces 1 800–4 900 Aeruginascin: 1 400–3

500 Gartz, 1989a

Inocybe aeruginascens Babos, Germany, n=28 HPLC, TLC 1 600 – 8 400 0 - traces 800 – 5 300 'Aeruginascin' Gartz, 1987c

Inocybe aeruginascens Babos, Germany, n=4 HPLC, TLC 1 100 – 3 800 Semerdzieva et al., 1986

Inocybe aeruginascens Babos, Germany, n=4 HPLC 300 – 3 800 200 Wurst et al., 1992

The abbreviation n.d. = non detectable level. + = detected, but not quantified; ( ) = not always detected; ^ = mg/kg fresh weight. Note the footnote directly after the table.

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

Table 4 cont. Occurrence of psilocybin, psilocin and baeocystin and neo-baeocystin (mg/kg dry weight if not otherwise stated) in hallucinogenic mushrooms. An empty square im-

plies that this compound was not analysed for.

Species, geographical region where it was collected Analytical method* Psilocybin Psilocin Baeocystin Comments** Reference

Inocybe aeruginascens Babos, Germany, n=4 TLC n.d. – 1 000 n.d. n.d. M Gartz, 1986b

Inocybe aeruginascens Babos, Hungary HPLC, TLC 1 200 Semerdzieva et al., 1986

Inocybe aeruginascens Babos, Germany, n=9 HPLC 400 ~400 Haeselbarth et al., 1985

Inocybe aeruginascens Babos, Switzerland, n=2 HPLC; TLC 850 – 2 800 n.d. - 80 200 – 800 Stijve and Kuyper, 1985

Inocybe calamistrata Gillet, Germany TLC + + + Gartz, 1986d

Inocybe corydalina Quel. var. corydalina, Switzerland, n=2 HPLC; TLC 110 – 320 n.d. 70–340 Stijve and Kuyper, 1985

Inocybe corydalina Quel., Germany TLC + n.d. + Gartz, 1986d

Inocybe corydalina Quel., Switzerland HPLC 300 n.d. 600 Stijve and de Meijer, 1993

Inocybe corydalina Quel. var. erinaceomorpha (Stangl &

Veselsky) Kuyp., Switzerland, n=1 HPLC; TLC 1 000 n.d. 400 Stijve and Kuyper, 1985

Inocybe coelestium Kuyp., Switzerland n=1 HPLC; TLC 350 n.d. 250 Stijve and Kuyper, 1985

Inocybe curvipes Karst., Brazil HPLC n.d. n.d. n.d. Stijve and de Meijer, 1993

Inocybe haemica (Berk. et Cooke.) Sacc.,, Germany TLC + + + Gartz, 1986d

Inocybe haemica (Berk. et Cooke.) Sacc., Switzerland n=1 HPLC; TLC 1 700 n.d. 340 Stijve and Kuyper, 1985

Inocybe haemica (Berk. et Cooke.) Sacc.,, Switzerland HPLC 420 n.d. 80 Stijve and de Meijer, 1993

Inocybe haemica (Berk. et Cke.) Sacc., Czech Republic GC-MS + + Stříbrny et al., 2003

Marasmius oreades (Bolton) Fr. HPLC n.d. n.d. Christiansen et al., 1984

Naematoloma fasciculare (Fr.) Karst., Japan LC, HPLC n.d. Koike et al., 1981

Panaeolina foenisecii (Pers. ex. Fr.), Finland HPLC/HPLC 300 n.d. Ohenoja et al., 1987

Panaeolina foenisecii (Pers. ex Fr.), United Kingdom TLC n.d. n.d. Mantle and Waight, 1969

Panaeolina foenisecii (Pers. ex Fr.), Australia, n=1 HPLC 680–730 n.d. Anastos et al., 2006a

Panaeolina foenisecii (Pers. ex Fr.), Europe, USA, Australien HPLC n.d. n.d. n.d. Stijve et al., 1984., 1984

Panaeolina foenisecii (Pers. ex Fr.), n=20 HPLC n.d. n.d. Stijve, 1987

Panaeolina foenisecii, (Pers. ex Fr.), Norge HPLC n.d. n.d. Christiansen et al., 1984

Panaeolopsis nirimbii Watling & Young, n=2 HPLC n.d. n.d. Stijve, 1987

Panaeolus acuminatus (Schaeff.) Gillet not specified n.d. n.d. Ola´h, 1968

The abbreviation n.d. = non detectable level. + = detected, but not quantified; ( ) = not always detected; ^ = mg/kg fresh weight. Note the footnote directly after the table.

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

Table 4 cont. Occurrence of psilocybin, psilocin and baeocystin and neo-baeocystin (mg/kg dry weight if not otherwise stated) in hallucinogenic mushrooms. An empty square im-

plies that this compound was not analysed for.

Species, geographical region where it was collected Analytical method* Psilocybin Psilocin Baeocystin Comments** Reference

Panaeolus acuminatus (Sec.) Quel., USA, n=2 HPLC/TLC n.d. n.d. Beug and Bigwood, 1982

Panaeolus acuminatus (Schaeff.) Gillet, Czech republic GC-MS n.d. n.d. Stříbrny et al., 2003

Panaeolus acuminatus (Schaeff.) Gillets, n=1 HPLC n.d. n.d. Stijve, 1987

Panaeolus africanus Ola´h not specified (+) (+) Ola´h, 1968

Panaelous antillarum, Thailand See Stijve et al., 1984 n.d. (100) n.d. (100) n.d. (100) Allen and Merlin, 1992

Panaeolus antillarum Dennis, n=3 HPLC n.d. n.d. Stijve, 1987

Panaelous antillarum (Fr.) Dennis, Brazil, n=1 See Stijve et al., 1984 n.d. n.d. n.d. Stijve and de Meijer, 1993

Panaeolus ater (J.E. Lange) Bon, India not specified + + Ola´h, 1968

Panaeolus ater (J.E. Lange) Bon, Russia TLC n.d. n.d. Gurevich, 1993

Panaeolus ater (J.E. Lange) Bon, n=3 HPLC n.d. n.d. Stijve, 1987

Panaeolus cambodginiensis Ola´h & Heim not specified + Ola´h, 1968

Panaeolus cambodginiensis, Ola´h & Heim, USA PC + n.d. Ott and Guzmán, 1976

Panaeolus campanulatus (Fr.) Gillet not specified n.d. n.d. Ola´h, 1968

Panaeolus campanulatus (Fr.) Gillet, Italy PC (+) n.d. Fiussello and Ceruti Scurti, 1972b

Panaeolus campanulatus (Fr.) Gillet, USA, n=3 HPLC/TLC n.d. n.d. Beug and Bigwood, 1982

Panaeolus castaneifolius (Murr.) Ola´h, Canada and France not specified (+) (+) Ola´h, 1968

Panaeolus cyanescens (Berk. & Broome) Sacc., Germany, n=6 HPLC 200 – 11 500 1 400 – 9 000 dried confis-cated

material Musshoff et al., 2000

Panaeolus cyanescens (Berk. & Broome) Sacc. not specified + + Ola´h, 1968

Panaeolus cyanescens (Berk. & Broome) Sacc., USA (Hawaii) HPLC 900 3 300 n.d. Stijve and de Meijer, 1993

Panaeolus cyanescens (Berk. & Broome) Sacc., Hawaii (USA) HPLC, TLC 3 200 5 100 200 Gartz, 1994

Panaeolus cyanescens (Berk. & Broome) Sacc., Thailand HPLC n.d. (250)

n.d. (250) 4 000

10 500 n.d. (250)

n.d. (250) Allen and Merlin, 1992

Panaeolus fimicola (Pers.) Gillet not specified (+) (+) Ola´h, 1968

Panaeolus fimicola (Pers.) Gillet, n=3 HPLC n.d. n.d. Stijve, 1987

Panaeolus foenisecii (Pers.) J. Schröt., Canada and France not specified (+) (+) Ola´h, 1968

Panaeolus foenisecii (Pers.) J. Schröt TLC + Robbers et al., 1969

Panaeolus foenisecii (Pers.) J. Schröt, Italy, n=2 PC (+) n.d. Fiussello and Ceruti Scurti, 1972b

The abbreviation n.d. = non detectable level. + = detected, but not quantified; ( ) = not always detected; ^ = mg/kg fresh weight. Note the footnote directly after the table.

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

Table 4 cont. Occurrence of psilocybin, psilocin and baeocystin and neo-baeocystin (mg/kg dry weight if not otherwise stated) in hallucinogenic mushrooms. An empty square im-

plies that this compound was not analysed for.

Species, geographical region where it was collected Analytical method* Psilocybin Psilocin Baeocystin Comments** Reference

Panaeolus foenisecii (Pers.) J. Schröt, Germany, n=100 TLC n.d. n.d. Gartz, 1985f

Panaeolus foenisecii (Pers.) J. Schröt, Mexico PC n.d. n.d. Ott and Guzmán, 1976

Panaeolus foenisecii (Pers.) Schroet., Switzerland HPLC n.d. n.d. n.d Stijve and de Meijer, 1993

Panaeolus foenisecii (Pers.) Schroet., Brazil, n=1 HPLC n.d. n.d. n.d Stijve and de Meijer, 1993

Panaeolus foenisecii (Pers.) J. Schröt, Norway HPLC n.d. n.d. Christiansen et al., 1984

Panaeolus fontinalis A. H. Sm. not specified n.d. Ola´h, 1968

Panaeolus fraxinophilus A.H. Sm. not specified n.d. Ola´h, 1968

Panaeolus goosensiae Ola´h, Hawaii TLC/HPTLC n.d. n.d. Merlin and Allen, 1993

Panaeolus guttulatus Bres. not specified n.d. Ola´h, 1968

Panaeolus guttulatus Bres., Italy PC n.d. n.d. Fiussello and Ceruti Scurti, 1972b

Panaeolus guttulatus Bres., n=1 HPLC n.d. n.d. Stijve, 1987

Panaeolus leucophanes not specified n.d. n.d. Ola´h, 1968

Panaeolus microsporus Ola´h et Cailleux not specified n.d. (+) Ola´h, 1968

Panaeolus olivaceus F.H. Möller, Finland HPLC/HPLC 50 n.d. Ohenoja et al., 1987

Panaeolus olivaceus F.H. Möller, n=2 HPLC n.d. n.d. Stijve, 1987

Panaeolus papilionaceus (Bull. Ex Fr.) Quel., Russia TLC n.d. n.d. Gurevich, 1993

Panaeouls phalaenarum (Fr.) Quel. not specified n.d. Ola´h, 1968

Panaeolus phalaenarum (Fr.) Quel., USA HPLC/TLC n.d. n.d. Beug and Bigwood, 1982

Panaeolus phalaenarum (Fr.) Quel., USA HPLC/TLC n.d. n.d. C Beug and Bigwood, 1982

Panaeolus phalaenarum, (Fr.) Quel., n=2 HPLC n.d. n.d. Stijve, 1987

Panaeolus rickenii Hora HPLC n.d. n.d. Christiansen et al., 1984

Panaeolus rickenii Hora HPLC/TLC n.d. n.d. Stijve, 1987

Panaeolus rickenii Hora, Latvia TLC n.d. n.d. Gurevich, 1993

Panaeolus retirugis (Fr.) Gillet not specified n.d. n.d. Ola´h, 1968

Panaeolus retirugis (Fr.) Gillet, Italy PC + n.d. Fiussello and Ceruti Scurti, 1972b

Panaeolus semiovatus (Fr.) Lundell & Nanfeldt, USA, n=3 HPLC/TLC n.d. n.d. Beug and Bigwood, 1982

Panaeolus semiovatus (Fr.) Lundell, n=3 HPLC n.d. n.d. Stijve, 1987

Panaeolus semiovatus (Fr.) Quél., not specified n.d. n.d. Ola´h, 1968

Panaeolus sphinctrinus (Fr.) Quél., Argentina PC n.d. n.d. Tyler and Groger, 1964a

Panaeolus sphinctrinus, Canada not specified (+) (+) Ola´h, 1968

Panaeolus sphinctrinus Fr., Italy PC n.d. n.d. Fiussello and Ceruti Scurti, 1972b

The abbreviation n.d. = non detectable level. + = detected, but not quantified; ( ) = not always detected; ^ = mg/kg fresh weight. Note the footnote directly after the table.

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

Table 4 cont. Occurrence of psilocybin, psilocin and baeocystin and neo-baeocystin (mg/kg dry weight if not otherwise stated) in hallucinogenic mushrooms. An empty square im-

plies that this compound was not analysed for.

Species, geographical region where it was collected Analytical method* Psilocybin Psilocin Baeocystin Comments** Reference

Panaeolus sphinctrinus (Fr.) Quel., n=23 HPLC n.d. n.d. Stijve, 1987

Panaeolus subbalteatus (Berk. & Br.) Sacc., cultivated PC + C, M Ceruti Scurti et al., 1972

Panaeolus subbalteatus (Berk. & Br.) Sacc., Finland, n=3 HPLC/HPLC 600–1 400 n.d.-40 Ohenoja et al., 1987

Panaeolus subbalteatus (Berk. & Br.) Sacc., Finland, n=1 HPLC/HPLC 100^ n.d.^ Ohenoja et al., 1987

Panaeolus subbalteatus (Berk. & Br.) Sacc,., Italy PC + n.d. Fiussello and Ceruti Scurti, 1972b

Panaeolus subbalteatus (Berk. & Br.) Sacc., Mexico PC + n.d. Ott and Guzmán, 1976

Panaeolus subbalteatus (Berk. & Br.) Sacc.,, Canada not specified (+) (+) Ola´h, 1968

Panaeolus subbalteatus (Berk. & Br.) Sacc., USA, n=6 TLC n.d.-50 Repke et al., 1977b

Panaeolus subbalteatus (Berk. & Br.) Sacc., USA, n=3 HPLC/TLC 1 600–6 500 n.d. Beug and Bigwood, 1982

Panaeolus subbalteatus (Berk. & Br.) Sacc., n=6 HPLC;TLC 800–1 400 n.d. 80 – 330 Stijve and Kuyper, 1985

Panaeolus subbalteatus (Berk. & Br.) Sacc., Brazil, n=3 HPLC 330–800 n.d. n.d. Stijve and de Meijer, 1993

Panaeolus subbalteatus (Berk. & Br.) Sacc., Russia TLC 500–3 600 n.d.-1 100 Gurevich, 1993

Panaeolus tropicalis Ola´h not specified + + Ola´h, 1968

Panaeolus uliginosus J. Schäff., Italy PC n.d. n.d. Fiussello and Ceruti Scurti, 1972b

Pholiotina filaris (Fr.) Singer, USA HPLC/TLC n.d. n.d. Beug and Bigwood, 1982

Pholiota squarrose (Fr.) Quel., Japan LC, HPLC n.d. Koike et al., 1981

Pluteus cf aibostipitatus (Dennis) Sing., Brazil HPLC n.d. n.d. n.d. Stijve and de Meijer, 1993

Pluteus atricapillus Singer, Finland, n=2 HPLC/HPLC 40–50 n.d. Ohenoja et al., 1987

Pluteus atricapillus (Batsch) Fayod, Germany, n=1 HPLC; TLC n.d. n.d. Stijve and Bonnard, 1986

Pluteus beniensis Sing., Brazil HPLC n.d. n.d. n.d. Stijve and de Meijer, 1993

Pluteus chrysophlebius (Berk. & Rav.) Sacc. Subsp. bruchii

(Speg.) Sing. Var bruchii., Brazil HP HPLC LC n.d. n.d. n.d. Stijve and de Meijer, 1993

Pluteus cinereofuscus J. Lange, The Netherlands, n=1 HPLC; TLC n.d. n.d. Stijve and Bonnard, 1986

Pluteus cubensis (Murr.) Dennis, Brazil HPLC n.d. n.d. n.d. Stijve and de Meijer, 1993

Pluteus ephebeus (Fr.;Fr.) Gill, The Netherlands/Switzerland,

n=4 HPLC; TLC n.d. n.d. Stijve and Bonnard, 1986

The abbreviation n.d. = non detectable level. + = detected, but not quantified; ( ) = not always detected; ^ = mg/kg fresh weight. Note the footnote directly after the table.

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

Table 4 cont. Occurrence of psilocybin, psilocin and baeocystin and neo-baeocystin (mg/kg dry weight if not otherwise stated) in hallucinogenic mushrooms. An empty square im-

plies that this compound was not analysed for.

Species, geographical region where it was collected Analytical method* Psilocybin Psilocin Baeocystin Comments** Reference

Pluteus fibulatus Sing. Sing.& Digilio, Brazil HPLC n.d. n.d. n.d. Stijve and de Meijer, 1993

Pluteus fluminensis Sing., Brazil HPLC n.d. n.d. n.d. Stijve and de Meijer, 1993

Pluteus glaucus Singer, Brazil n=2 HPLC 1 500–2 800 1 000–1 200 n.d. Stijve and de Meijer, 1993

Pluteus nanus (Pers.;Fr) Kumm. The Netherlands, n=1 HPLC; TLC n.d. n.d. Stijve and Bonnard, 1986

Pluteus nigroviridis Babos, Switzerland, n=1 HPLC; TLC 350 n.d. Stijve and Bonnard, 1986

Pluteus pellitus (Pers.:Fr.) Kumm., Germany, n=1 HPLC; TLC n.d. n.d. Stijve and Bonnard, 1986

Pluteus phlebophorus (Ditm.;Fr.) Kumm., Germany, n=1 HPLC; TLC n.d. n.d. Stijve and Bonnard, 1986

Pluteus plautus (Weinm.) Gillet, The Netherlands, n=2 HPLC; TLC n.d. n.d. Stijve and Bonnard, 1986

Pluteus pulverulentus Murr., var. pseudonanus Sing.,

Brazil HPLC n.d. n.d. n.d. Stijve and de Meijer, 1993

Pluteus romellii (Britz.) Sacc., Germany, n=1 HPLC; TLC n.d. n.d. Stijve and Bonnard, 1986

Pluteus salicinus (Pers.), P. Kumm., USA, n=1 PC, TLC + + Saupe, 1981

Pluteus salicinus (Pers.), P. Kumm., Finland, n=2 HPLC/HPLC 2 100–3 000 n.d.-500 Ohenoja et al., 1987

Pluteus salicinus (Pers.), P. Kumm., Germany, n=5 HPLC; TLC 12 000 - 15 700

4 800–11 400 n.d.

n.d. +

n.d. hat

stipe Gartz, 1987b

Pluteus salicinus (Pers.), P. Kumm., n=5 HPLC 3 500 110 Christiansen et al., 1984

Pluteus salicinus (Pers.), P. Kumm, Switzerland, n=2 HPLC; TLC 500–2 500 n.d. n.d. - 80 Stijve and Kuyper, 1985

Pluteus salicinus (Pers.), P. Kumm.,, Switzerland, n=25 HPLC; TLC 400–6 000 n.d. - 250 Stijve and Bonnard, 1986

Pluteus salicinus (Pers.), P. Kumm.,, Czech Republic GC-MS + + Stříbrny et al., 2003

Pluteus salicinus (Pers.), P. Kumm.,, Norge HPLC 3 000–6 000 Høiland et al., 1984

Pluteus umbrosus (Pers.;Fr.) Kumm., The Nether-

lands/Switzerland, n=4 HPLC; TLC n.d. n.d. Stijve and Bonnard, 1986

Pluteus xylophilus (Speg.) Sing. var. tucumanensis (Sing.)

Sing. Ditto var. xylophilus, Brazil HPLC n.d. n.d. n.d. Stijve and de Meijer, 1993

Psathyra obtusata Fr., Italy PC n.d. n.d. Fiussello and Ceruti Scurti, 1972b

Psathyra spadiceo-grisea (Schaeff.) Fr., Italy PC n.d. n.d. Fiussello and Ceruti Scurti, 1972b

Psathyrella candolleana (Fr.) Maire, Finland HPLC/HPLC 40 50 Ohenoja et al., 1987

The abbreviation n.d. = non detectable level. + = detected, but not quantified; ( ) = not always detected; ^ = mg/kg fresh weight. Note the footnote directly after the table.

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

Table 4 cont. Occurrence of psilocybin, psilocin and baeocystin and neo-baeocystin (mg/kg dry weight if not otherwise stated) in hallucinogenic mushrooms. An empty square im-

plies that this compound was not analysed for.

Species, geographical region where it was collected Analytical method* Psilocybin Psilocin Baeocystin Comments** Reference

Psathyrella candolleana (Fr.) Maire, Italy PC n.d. n.d. Fiussello and Ceruti Scurti, 1972b

Psathyrella condolleana (Fr.) Maire, Japan LC, HPLC 800–1 500 Koike et al., 1981

Psathyrella condolleana (Fr.) Maire, Germany TLC 500 + Gartz, 1986d

Psathyrella foenisecii (Fr.) Smith, USA, n=2 HPLC/TLC n.d. n.d. Beug and Bigwood, 1982

Psathyrella hydrophila (Bull.) Maire, Italy PC n.d. n.d. Fiussello & Ceruti Scurti, 1972b

Psathyrella multipedata (Peck) A.H. Sm., Norway HPLC n.d. n.d. Christiansen et al., 1984

Psathyrella sepulchralis Singer, A.H. Sm. and Guzmán,

Mexico, n=2 PC n.d. n.d. 18 year old herbarium

sample Ott and Guzmán, 1976

Psathyrella velutina (Pers.) Konr. & Maubl., Italy PC n.d. n.d. Fiussello & Ceruti Scurti, 1972b

Psathyrella velutina (Pers.) Konr. & Maubl.,, Italy HPLC n.d. n.d. Christiansen et al., 1984

Psathyrella velutina (Pers.) Konr. & Maubl.,, Japan LC, HPLC n.d. Koike et al., 1981

Psathyrella velutina (Pers.) Konr. & Maubl.,, Norge HPLC n.d. n.d. Christiansen et al., 1984

Psilocybe sp., n=1 HPLC n.d. 2 800 Thomson, 1980

Psilocybe alnetorum Sing., Brazil HPLC n.d. n.d. n.d. Stijve and de Meijer, 1993

Psilocybe argentipes K. Yokohama, Japan, n=4 LC, HPLC 30–5 500 Koike et al., 1981

Psilocybe argentipes K. Yokohama, Japan, n=2 LC-MS-MS 3 200–3 800 600–690 Kamata et al., 2005

Psilocybe arcana Borovička & Hlaváček, Czech Republic,

n=10 GC-MS 100–11 500 100–8 500 Stříbrny et al., 2003

Psilocybe atrobrunnea (Lasch) Gillet TLC n.d. S Leung and Paul, 1967

Psilocybe atrobrunnea (Lasch) Gillet, Norway TLC + ? Høiland, 1978

Psilocybe atrobrunnea (Lasch) Gillet, USA TLC n.d. n.d. Leung et al., 1965

Psilocybe atrobrunnea (Lasch) Gillet, Norge HPLC n.d. n.d. Christiansen et al., 1984

Psilocybe aztecorum Heim var. aztecorum emend. Guz-

mán, Mexico PC 200 n.d. Heim and Hoffman, 1958a, b

Psilocybe aztecorum var. bonetii (Guzmán) Guzmán,

Mexico PC + n.d. Ott and Guzmán, 1976

Psilocybe azurescens Stamets and Gartz HPLC; TLC - 17 800 - 3 800 - 3 500 Stamets and Gartz, 1995

Psilocybe baeocystis Singer and A.H. Sm. LC + traces M Leung et al., 1965

Psilocybe baeocystis Singer and A.H. Sm. LC 435 1538 S Leung and Paul, 1967

The abbreviation n.d. = non detectable level. + = detected, but not quantified; ( ) = not always detected; ^ = mg/kg fresh weight. Note the footnote directly after the table.

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

Table 4 cont. Occurrence of psilocybin, psilocin and baeocystin and neo-baeocystin (mg/kg dry weight if not otherwise stated) in hallucinogenic mushrooms. An empty square im-

plies that this compound was not analysed for.

Species, geographical region where it was collected Analytical method* Psilocybin Psilocin Baeocystin Comments** Reference

Psilocybe baeocystis Singer and A.H. Sm., Canada, n=1 TLC 800–1 000 Repke et al., 1977b

Psilocybe baeocystis Singer and A.H. Sm., USA HPLC 2 000 (1 500–8 500) 1 900 (n.d.-5 900) Beug and Bigwood, 1981

Psilocybe baeocystis Singer and A.H. Sm., USA, n=7 HPLC/TLC 1 500–8 500 n.d.-5 900 Beug and Bigwood, 1982

Psilocybe baeocystis Singer and A.H. Sm., USA, n=7 TLC n.d.-600 Repke et al., 1977b

Psilocybe baeocystis Singer and A.H. Sm., USA TLC + n.d. Leung et al., 1965

Psilocybe baeocystis Singer and A.H. Sm., USA PC traces + Benedict et al., 1962a

Psilocybe baeocystis Singer and A.H. Sm., USA PC n.d. + tryptophan Benedict et al., 1962b

Psilocybe baeocystis Singer and A.H. Sm., USA PC, LC 4 000 – 6 300 n.d. - 1 000 Mc Cawley et al., 1962

Psilocybe bohemica Šebek HPLC 5 700 – 5 800 580–610 C Kysilka et al., 1985

Psilocybe bohemica Šebek HPLC 9 300 100 C Kysilka and Wurst, 1989

Psilocybe bohemica Šebek HPLC, TLC 9 300 400 200 C Gartz, 1994

Psilocybe bohemica Sebek, Czech Republic HPLC, TLC 8 500 200 400 Gartz, 1994

Psilocybe bohemica Sebek, Czech Republic, n=8 HPLC 2 500 – 11 500 200 – 700 Wurst et al., 1984

Psilocybe bohemica Sebak, Czech republic, n=3 HPLC 4 600 – 11 400 200 – 4 800 C Wurst et al., 1992

Psilocybe bohemica Sebak, Czech republic, n=1 HPLC 12 230±1 290 4 480±550 Kysilka and Wurst, 1990

Psilocybe bohemica Sebak, Czech republic, n=23 TLC/HPLC 1 100 – 13 400 n.d.–200 80 – 300 Gartz and Müller, 1989

Psilocybe bohemica Sebak, Czech republic, n=6 TLC/HPLC 1 500 – 2 100 n.d. n.d. M Gartz and Müller, 1989

Psilocybe bohemica Sebak, Czech republic, n=7 TLC, HPLC 2 500 – 11 400 n.d.-700 n.d. Semerdžieva et al., 1986

Psilocybe bohemica Sebak, Czech republic, n=9 GC-MS 1 000–6 300 1 700–12 700 Stříbrny et al., 2003

Psilocybe bohemica Sebak, Switzerland, n=3 TLC; HPLC 2 800 – 8 000 n.d.-200 100 – 300 Stijve and Kuyper, 1985

Psilocybe bolivarii Guzmán, Mexico PC n.d. n.d. Ott and Guzmán, 1976

Psilocybe bonetii Guzmán, Mexico PC + n.d. Ott and Guzmán, 1976

Psilocybe caeruleoannulata Sing.: Guzman, Brazil, n=2 HPLC 550–3 000 2 000–2 300 n.d. Stijve and de Meijer, 1993

Psilocybe caerulescens Murrill var caerulescens, Brazil, n=2 HPLC 1 000–2 200 n.d.-2 500 n.d. Stijve and de Meijer, 1993

Psilocybe caerulescens var. mazatecorum Murrill PC 2 000 n.d. Heim and Hofmann, 1958a, b

Psilocybe caerulipes Peck TLC n.d. C Leung and Paul, 1967

Psilocybe caerulipes Peck, USA TLC + traces Leung et al., 1965

Psilocybe callosa (Fr.) Quel. TLC n.d. Gartz, 1985d

Psilocybe candidipes Singer and A.H. Sm., Mexico PC + n.d. Ott and Guzmán, 1976

Psilocybe coprinifacies (Roll.) Pouz., Czech Republic, Slovenia TLC 1 000 Semerdzieva and Nerud, 1973

Psilocybe coprophilia (Bull. ex Fr.) Kummer, Norway TLC n.d. Høiland, 1978

Psilocybe coprophilia (Bull.) P. Kumm., USA HPLC/TLC n.d. n.d. Beug and Bigwood, 1982

Psilocybe coprophila (Bull.) P. Kumm., Brazil HPLC n.d. n.d. n.d. Stijve and de Meijer, 1993

Psilocybe cubensis (Earle) Singer HPLC/TLC 3 200–13 300 n.d. - 2 900 C Bigwood and Beug, 1982

Psilocybe cubensis (Earle) Singer HPLC, TLC 6 500 1 500 Gartz, 1987a

The abbreviation n.d. = non detectable level. + = detected, but not quantified; ( ) = not always detected; ^ = mg/kg fresh weight. Note the footnote directly after the table.

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

Table 4 cont. Occurrence of psilocybin, psilocin and baeocystin and neo-baeocystin (mg/kg dry weight if not otherwise stated) in hallucinogenic mushrooms. An empty square im-

plies that this compound was not analysed for.

Species, geographical region where it was collected Analytical method* Psilocybin Psilocin Baeocystin Comments** Reference

Psilocybe cubensis (Earle) Singer HPLC, TLC 2 500 – 5 900 n.d.-1 100 C Gartz, 1987a

Psilocybe cubensis (Earle) Singer HPLC, TLC 900 900 C-M Gartz, 1987a

Psilocybe cubensis (Earle) Singer HPLC, TLC 6 300 1 100 200 C Gartz, 1994

Psilocybe cubensis (Earle) Singer GLC-MS 4 200 1 680 freeze dried Repke et al., 1977a

Psilocybe cubensis (Earle) Singer, n=11 TLC n.d.-100 C Repke et al., 1977b

Psilocybe cubensis (Earle) Singer HPLC, TLC 2 500 – 5 900 n.d.-1 100 C Gartz, 1987a

Psilocybe cubensis (Earle) Singer HPLC, TLC 900 900 C-M Gartz, 1987a

Psilocybe cubensis (Earle) Singer HPLC, TLC 6 300 1 100 200 C Gartz, 1994

Psilocybe cubensis (Earle) Singer GLC-MS 4 200 1 680 freeze dried Repke et al., 1977a

Psilocybe cubensis (Earle) Singer, n=11 TLC n.d.-100 C Repke et al., 1977b

Psilocybe cubensis (Earle) Singer HPLC 10 700 1 800 1 100 C Borner and Brenneisen, 1987

Psilocybe cubensis (Earle) Singer, Japan, n=6 HPLC 3 700 – 13 000 1 400 – 4 200 Tsujikawa et al., 2003

Psilocybe cubensis (Earle) Singer, Brazil, n=4 HPLC 1 000–3 600 2 000–6 000 n.d.-250 Stijve and de Meijer, 1993

Psilocybe cubensis (Earle) Singer, Germany, n=18 HPLC n.d. - 10 700 100 – 2 300 dried confis-cated

material Musshoff et al., 2000

Psilocybe cyanescens (Fr.) Quél. TLC n.d. n.d. M Neal et al., 1968

Psilocybe cyanescens Wakef., n=2 TLC 40–70 C Repke et al., 1977b

Psilocybe cyanescens Wakef., Czech republic, n=8 GC-MS 1 300–18 400 2 800–18 100 Stříbrny et al., 2003

Psilocybe cyanescens Wakef., Switzerland, n=1 HPLC; TLC 1 600 n.d. 50 Stijve and Kuyper, 1985

Psilocybe cyanescens Wakef., Czech republic HPLC 1 000 4 700 Wurst et al., 1992

Psilocybe cyanescens Wakef., USA HPLC n.d. 4 500 Wurst et al., 1992

Psilocybe cyanescens Wakef., USA, n=8 TLC n.d.-400 Repke et al., 1977b

Psilocybe cyanescens Wakef., USA, n=14 HPLC/TLC 1 500–16 800 600–9 600 Beug and Bigwood, 1982

Psilocybe cyanescens Wakef., Czech republic HPLC 1 000 4 700 Wurst et al., 1992

Psilocybe cyanescens Wakef., USA HPLC n.d. 4 500 Wurst et al., 1992

Psilocybe cyanescens Wakef., USA, n=8 TLC n.d.-400 Repke et al., 1977b

Psilocybe cyanescens Wakef., USA, n=14 HPLC/TLC 1 500–16 800 600–9 600 Beug and Bigwood, 1982

Psilocybe cyanescens Wakef., USA HPLC 4 500 600 200 Krieglsteiner, 1986 1962a

Psilocybe cyanescens Wakef., USA PC + + Benedict et al., 1962a

Psilocybe cyanescens Wakef., Switzerland, n=3 HPLC; TLC 2 000 – 8 500 400 – 3 600 100 – 300 Stijve and Kuyper, 1985

Psilocybe cyanofibrillosa Guzmán and Stamets, USA HPLC, TLC 50 – 2 100 400 – 1 400 Stamets et al., 1980

Psilocybe fimetaria (P.D. Orton) Watling, United Kingdom PC + n.d. Benedict et al., 1967

Psilocybe hoogshagenii Heim, Brazil n=2 HPLC 1 500– 3 000 2 000– 3 000 n.d.-140 Stijve and de Meijer, 1993

Psilocybe inguilina (Fr.) Bres. var. inquilina, Norway TLC n.d. Høiland, 1978

The abbreviation n.d. = non detectable level. + = detected, but not quantified; ( ) = not always detected; ^ = mg/kg fresh weight. Note the footnote directly after the table.

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

Table 4 cont. Occurrence of psilocybin, psilocin and baeocystin and neo-baeocystin mg/kg dry weight if not otherwise stated) in hallucinogenic mushrooms. An empty square im-

plies that this compound was not analysed for.

Species, geographical region where it was collected Analytical method* Psilocybin Psilocin Baeocystin Comments** Reference

Psilocybe inquilina (Fr.) Bres., USA HPLC/TLC n.d. n.d. Beug and Bigwood, 1982

Psilocybe liniformans Guzmán & Bas var. americana

Guzmán & Stamets, n=7 HPLC, TLC 5 900 – 12 800 n.d. Stamets et al., 1980

Psilocybe liniformans Guzmán & Bas var. americana

Guzmán & Stamets HPLC, TLC - 1 600 n.d. 50 Stijve and Kuyper, 1985

Psilocybe merdaria (Fr.) Ricken, Norway TLC n.d. Høiland, 1978

Psilocybe mexicana Heim PC 1 000 – 2 500 500–2 000 C Heim and Hofmann, 1958b

Psilocybe mexicana Heim PC. LC 2 000 – 4 000 500 C Hofmann et al., 1959

Psilocybe mexicana Heim PC, LC 2 000 – 3 000 traces M or M+Sc Hofmann et al., 1959

Psilocybe montana (Pers.) Kumm., Norway TLC n.d. Høiland, 1978

Psilocybe montana (Pers.) Kumm, Venezuela TLC n.d. n.d. Marcano et al., 1994

Psilocybe montana (Oers. ex Fr.) Kumm., USA HPLC/TLC n.d. n.d. Beug and Bigwood, 1982

Psilocybe montana (Pers. ex Fr.) Kummer, Norway TLC n.d. Høiland, 1978

Psilocybe montana (Pers.) Kumm, Venezuela TLC n.d. n.d. Marcano et al., 1994

Psilocybe montana (Pers.) Kumm., USA HPLC/TLC n.d. n.d. Beug and Bigwood, 1982

Psilocybe muliericula Singer and A.H.Sm. PC 200 100 Heim and Hofmann, 1958a

Psilocybe paupera Sing., ss Guzman Brazil HPLC n.d. n.d. n.d. Stijve and de Meijer, 1993

Psilocybe pelliculosa (A.H. Sm.) Singer & A.H. Sm.,

Canada, n=1 TLC 200-400 Repke et al., 1977b

Psilocybe pelliculosa (A.H. Sm.) Singer & A.H. Sm., USA TLC 800 traces n.d. Repke and Leslie, 1977

Psilocybe pelliculosa (A.H. Sm.) Singer & A.H. Sm., n=5 TLC n.d.-500 Repke et al., 1977b

Psilocybe pelliculosa (A.H. Sm.) Singer & A.H. Sm., TLC n.d. S Leung and Paul, 1967

Psilocybe pelliculosa(A.H. Sm.) Singer & A.H. Sm., USA, n=3 HPLC/TLC 1 200–7 100 n.d. Beug and Bigwood, 1982

Psilocybe pelliculosa (A.H. Sm.) Singer & A.H. Sm., USA PC + n.d. Tyler, 1961

Psilocybe percevalii (Berk. & Broome) Sacc., Norway TLC n.d. Høiland, 1978

Psilocybe pseudobullacea (Petch) Pegler, Venezuela TLC + + Marcano et al., 1994

Psilocybe quebecensis Ola´h and Heim, Canada TLC + traces Ola´h and Heim, 1967

Psilocybe samuiensis Guzmán, Bandala and Allen, Thai-

land; n=15 See Gartz, 1987 2 300–9 000 500–8 100 100–5 000 Gartz et al., 1994

The abbreviation n.d. = non detectable level. + = detected, but not quantified; ( ) = not always detected; ^ = mg/kg fresh weight. Note the footnote directly after the table.

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

Table 4 cont. Occurrence of psilocybin, psilocin and baeocystin and neo-baeocystin mg/kg dry weight if not otherwise stated) in hallucinogenic mushrooms. An empty square im-

plies that this compound was not analysed for.

Species, geographical region where it was collected Analytical method* Psilocybin Psilocin Baeocystin Comments** Reference

Psilocybe samuiensis Guzmán, Bandala and Allen, Thai-

land See Gartz, 1987 3 600–7 300 2 100–5 200 200–500 C Gartz et al., 1994

Psilocybe samuiensis Guzmán, Bandala and Allen, Thai-

land, n=5 See Gartz, 1987 2 400–3 200 n.d. n.d. M Gartz et al., 1994

Psilocybe semilanceata (Fr.) Kumm. TLC + + Gartz, 1985a

Psilocybe semilanceata (Fr.) Kumm HPLC, TLC 9 800 n.d. 3 400 C Gartz, 1994

Psilocybe semilanceata (Fr.) Kumm HPLC + + + White, 1979

Psilocybe semilanceata (Fr.) Kumm., Czech Republic, n=2 TLC, HPLC 9 100 – 10 500 900 – 1 200 Semerdzieva et al., 1986

Psilocybe semilanceata (Fr.) Kumm., Czech Republic,

Slovenia TLC 2 000 + Semerdzieva and Nerud, 1973

Psilocybe semilanceata, Czech republic, n=3 HPLC 7 600 – 10 500 900 – 1 200 Wurst et al., 1992

Psilocybe semilanceata (Fr.) Kummer, Czech Republic,

n=4 HPLC 3 300 – 10 500 400 – 6 800 Wurst et al., 1984

Psilocybe semilanceata, (Fr.) Kumm., Finland, n=2 HPLC/HPLC 2 000–8 700 n.d.-40 Ohenoja et al., 1987

Psilocybe semilanceata, (Fr.) Kumm., Finland, n=3 HPLC/HPLC 1 900–8 200^ n.d.-250^ Ohenoja et al., 1987

Psilocybe semilanceata, (Fr. ex Secr.) Kumm., Finland HPLC 14 200 (6 200–23

700) n.d.-200 Jokarinta et al., 1984

Psilocybe semilanceata (Fr.) Kumm., Germany TLC, HPLC 9 600 n.d. Semerdzieva et al., 1986

Psilocybe semilanceata (Fr.) P. Kumm., n=1 TLC 50–700 C Repke et al., 1977b

Psilocybe semilanceata (Fr.) P. Kumm., n=2 HPLC 11 200

11 300 3 700

2 900 Vanhaelen-Fastré and Vanhaelen, 1984

Psilocybe semilanceata (Fr.) P. Kumm., Germany TLC 1 900 – 14 500 n.d. 300 – 3 800 Gartz, 1986b

Psilocybe semilanceata (Fr.) P. Kumm., Germany TLC + n.d. + traces of norbaeo-

cystin Michaelis, 1977

Psilocybe semilanceata (Fr.) P. Kumm., Norway, n=1 capillary zone

electrophoresis 10 400–10 500 Pedersen-Bjergaard et al., 1998

Psilocybe semilanceata (Fr.) P. Kumm., Norway, n=9 HPLC 5 500 – 10 100 (traces) Christiansen et al., 1981a

Psilocybe semilanceata (Fr.) P. Kumm., Norway, n=48 LC 1 700–19 600 d.w. Christiansen et al., 1981b

Psilocybe semilanceata (Fr.) P. Kumm., Norway, n=16 HPLC 5 500 – 19 600 500 – 3 400 Christiansen and Rasmussen, 1982

Psilocybe semilanceata (Fr.) P. Kumm., Norway TLC + n.d. + nor-baeocystin

detected Høiland, 1978

The abbreviation n.d. = non detectable level. + = detected, but not quantified; ( ) = not always detected; ^ = mg/kg fresh weight. Note the footnote directly after the table.

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

Table 4 cont. Occurrence of psilocybin, psilocin and baeocystin and neo-baeocystin mg/kg dry weight if not otherwise stated) in hallucinogenic mushrooms. An empty square im-

plies that this compound was not analysed for.

Species, geographical region where it was collected Analytical method* Psilocybin Psilocin Baeocystin Comments** Reference

Psilocybe semilanceata (Fr.) P. Kumm.,, Sweden, n=9 HPLC 1 100 – 3 500^ Beck et al., 1998

Psilocybe semilanceata (Fr.) P. Kumm.,, Sweden, n=9 HPLC 1 100 – 3 500 Beck et al., 1998

Psilocybe semilanceata (Fr.) P. Kumm., Switzerland HPLC 17 600 2 300 8 500 Borner and Brenneisen, 1987

Psilocybe semilanceata (Fr.) P. Kumm., United Kingdom TLC 1 500 n.d. Mantle and Waight, 1969

Psilocybe semilanceata (Fr.) P. Kumm., United Kingdom PC + n.d. Benedict et al., 1967

Psilocybe semilanceata var. caerulescens Cooke,

United Kingdom PC + n.d. Benedict et al., 1967

Psilocybe semilanceata (Fr.) P. Kumm., Canada, n=1 TLC 600–1 100 Repke et al., 1977b

Psilocybe semilanceata (Fr.) P. Kumm., USA TLC 3 600 traces 1 200 Repke and Leslie, 1977

Psilocybe semilanceata (Fr.) P. Kumm., USA, n=10 TLC n.d.-1 700 Repke et al., 1977b

Psilocybe semilanceata (Fr.) P. Kumm., USA, n=12 HPLC/TLC 6 200–12 800 n.d. Beug and Bigwood, 1982

Psilocybe semilanceata (Fr.) P. Kumm., Germany, n=9 HPLC 100 – 9 100 100 – 9 000 dried confis-cated

material Musshoff et al., 2000

Psilocybe semilanceata (Fr.) P. Kumm., Switzer-

land/The Netherlands/USA HPLC 3 300–19 300 800–4 300 Stijve, 1984

Psilocybe semilanceata Quel. var semilanceata, Swi-

tzerland See Stijve et al., 1984 4 700 n.d. 1 400 Stijve and de Meijer, 1993

Psilocybe semilanceata (Fr.) P. Kumm., Switzerland, n=30 HPLC; TLC 500 – 17 000 n.d. - 200 n.d. - 3 600 Stijve and Kuyper, 1985

Psilocybe semilanceata (Fr.) P. Kumm., Czech repub-

lic, n=10 GC-MS 1 200–5 100 600–2 700 Stříbrny et al., 2003

Psilocybe semperviva Heim & Cailleux 7 000 (d.w) Heim and Wasson, 1958

Psilocybe semperviva Heim & Cailleux PC 3 000–6 000 700–1 000 Heim and Hofmann, 1958b

Psilocybe serbica Mos. & Horak, Serbia PC + traces Moser and Horak, 1968

Psilocybe silvatica (Peck) Singer and Smith, USA, n=5 TLC n.d.-1 100 Repke et al., 1977b

Psilocybe spadicea (Schaeff.) Fr, Italy PC n.d. n.d. Fiussello and Ceruti Scurti, 1972b

Psilocybe squamosa (Pers.) P.D. Orton, Norway TLC n.d. Høiland, 1978

Psilocybe strictipes A.H. Sm. TLC n.d. S Leung and Paul, 1967

Psilocybe strictipes A.H. Sm., USA TLC + n.d. Leung et al., 1965

Psilocybe stuntzii Guzmán & Ott, Canada, n=1 TLC 40–90 Repke et al., 1977b

The abbreviation n.d. = non detectable level. + = detected, but not quantified; ( ) = not always detected; ^ = mg/kg fresh weight. Note the footnote directly after the table.

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

Table 4 cont. Occurrence of psilocybin, psilocin and baeocystin and neo-baeocystin (mg/kg dry weight if not otherwise stated) in hallucinogenic mushrooms. An empty square im-

plies that this compound was not analysed for.

Species, geographical region where it was collected Analytical method* Psilocybin Psilocin Baeocystin Comments** Reference

Psilocybe stuntzii Guzmán & Ott, USA, n=4 HPLC/TLC n.d.-3 600 n.d.-600 Beug and Bigwood, 1982

Psilocybe stuntzii Guzmán & Ott, USA, n=12 PC + n.d. Guzmán and Ott, 1976

Psilocybe stuntzii Guzmán & Ott, USA, n=6 TLC n.d.-200 Repke et al., 1977b

Psilocybe subaeruginosa Cleland, Australia LC 4 500 n.d. Picker and Rickards, 1970

Psilocybe subaeruginosa Cleland, Australia HPLC 100 – 2 000 Perkal et al., 1980

Psilocybe subaeruginosa Cleland, Australia HPLC 1 070 – 1 120 11 - 19 Anastos et al., 2006a

Psilocybe subaeranginascens Höhnel LC, HPLC 170–180 M Koike et al., 1981

Psilocybe subaeranginascens Höhnel LC, HPLC n.d. FC Koike et al., 1981

Psilocybe subceaerulipes Hong LC, HPLC n.d. M and FC Koike et al., 1981

Psilocybe subcoprophilia (Britzelm.) Sacc., Norge HPLC n.d. n.d. Christiansen et al., 1984

Psilocybe subcubensis Guzman TLC + Marcano et al., 1994

Psilocybe subcubensis Guzman IMS/GC-MS 8 000 – 8 600 200 – 300 Keller et al., 1999a

Psilocybe subcubensis Guzman, Japan, n=1 LC-MS-MS 1 500 1 000 Kamata et al., 2005

Psilocybe cf. subyungensis Guzman, n=1 HPLC 5 000 4 000 330 Stijve and de Meijer, 1993

Psilocybe tampanensis Guzmán & Pollock, Thailand, n=5 See Gartz, 1987 3 400–6 800 1 100–5 200 n.d. Sc Gartz et al., 1994

Psilocybe tampanensis Guzman & Pollock, Germany, n=4 HPLC n.d. - 1 900 100 – 300 dried confis-cated

material Musshoff et al., 2000

Psilocybe thailandensis Guzmán & Allen, Thaland HPLC 750 6 000 n.d. Stijve and de Meijer, 1993

Psilocybe uruguayensis Sing.; Guzman, Brazil, n=4 HPLC 850–1 400 n.d.-100 150–200 Stijve and de Meijer, 1993

Psilocybe cf. venezuelana Dennis, Brazil HPLC n.d. n.d. n.d. Stijve and de Meijer, 1993

Psilocybe weilii Guzman, Stapia and Stamets - 6 100 - 2 700 - 500 Stamets, 1996

Psilocybe zapatecorum Heim, Mexico PC 500 n.d. Hofmann et al., 1958b

Psilocybe zapatecorum Heim, Mexico PC + (+) Hofmann et al., 1959

Psilocybe zapatecorum Heim, Mexico n=5 HPLC 600–3 000 500–1 000 n.d.-200 Stijve and de Meijer, 1993

Psilocybe wassonii Heim, Mexico PC 100–200 n.d.-100 Heim and Hofmann, 1958b

Rickenella straminea (Petch) Pegler (cf. Fibyula (Bull.: Fr.)

Raith., Brazil, n=1 HPLC n.d. n.d. n.d. Heim and Hofmann, 1958b

Stropharia aeruginosa (Curt.) Quel., Italy PC n.d. n.d. Fiussello and Ceruti Scurti, 1972b

Stropharia aeruginosa (Curt.) Quel.,, USA TLC n.d. n.d. Leung et al., 1965

Stropharia aeruginosa (Curt.) Quel., USA HPLC/TLC n.d. n.d. Beug and Bigwood, 1982

The abbreviation n.d. = non detectable level. + = detected, but not quantified; ( ) = not always detected; ^ = mg/kg fresh weight. Note the footnote directly after the table.

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

Table 4 cont. Occurrence of psilocybin, psilocin and baeocystin and neo-baeocystin (mg/kg dry weight if not otherwise stated) in hallucinogenic mushrooms. An empty square im-

plies that this compound was not analysed for.

Species, geographical region where it was collected Analytical method* Psilocybin Psilocin Baeocystin Comments** Reference

Stropharia aurantiaca (Cooke) Imai., Jap. LC, HPLC n.d. Koike et al., 1981

Stropharia coronilla (Bull.: Fr.) Quel., Brazil HPLC n.d. n.d. n.d. Stijve and de Meijer, 1993

Stropharia cubensis Earle, Mexico1) PC 100–4 00 200 2 500 C Heim and Hofmann, 1958a, b

Stropharia cubensis Earle, Cambodia1) PC 800–1 500 300–500 Heim and Hofmann, 1958a, b

Stropharia cubensis Earle, Thailand1) PC 800–5 000 500–1 500 Heim and Hofmann, 1958a, b

Stropharia rugosoannulata Farl.: Murr., Brazil HPLC n.d. n.d. n.d. Stijve and de Meijer, 1993

Stropharia semiglobata (Fr.) Quel., USA TLC n.d. n.d. Leung et al., 1965

Stropharia semiglobata (Fr.) Quel., Norway HPLC n.d. n.d. Christiansen et al., 1984

The abbreviation n.d. = non detectable level. + = detected, but not quantified; ( ) = not always detected; ^ = mg/kg fresh weight. Note the footnote directly after the table.

Footnote: PC = paper chromatography; LC = hydrostatic pressure chromatography on column; TLC = thin layer chromatography; HPLC = high pressure liquid chromatography; ** C = cultivated mushrooms; FC = fluid from culture; M = mycelium; S = submerged

culture; Sc = Sclerotia; 1) claimed to be identical to Psilocybe cubensis (i.e. Singer, 1978).

In the table, the names of the fungi are used as they occurred in the cited papers. However, since many of them have been synonymised, it might be helpful to the non-taxonomist to have the forthcoming overview according to Knudsen & Vesterholt (2008).

Thus, if the synonym latin name is given in Table 4, the corresponding current latin name is given in the following listing along with the synonyms (in parantheses): Copelandia cambodginiensis (Panaeolus cambodginiensis); Copelandia cyanescens (Panaeolus

cyanescens); Hypheloma fasciculare (Naematoloma fasiciculare); Panaeolus acuminatus (Panaeolus rickenii); Panaeolus cambodginiensis (Psilocybe cambodginiensis); Panaeolus cinctulus (Panaeolus subbalteatus); Panaeolus foeninisecii (Panaeolina

foeninisecii; Psatyrella foenisecii); Panaeolus olivaceus (Panaeolus castaneifolius ss. Oláh); Panaeolus reticulatus (Panaeolus fontinalis, Panaeolus; uliginosus); Panaeolus papilionaceus (Panaeolus campanulatus, Panaeolus retirugis, Panaeolus sphinctrinus);

Parasola plicatilis (Coprinus plicatilis); Pluteus atricapillus (Pluteus cervinus); Psathyrella piluliformis (Psathyrella hydrophila); Psathyrella spadiceogrisea (Psathyra spadioceo-grisea) Psilocybe aztecorum var. bonetii (Psilocybe bonetii); Psilocybe turficola

(Psilocybe atrobrunnea ss. auct.); Stropholoma aurantiaca (Stropharia aurantiaca); Stropholoma percevalii (Stropharia percevalii); Stropholoma squamosa (Psilocybe trausta, Stropharia thrausta).

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

In 1983 Guzmán made a systematic revision of the genus Psilocybe, re-

viewing the history, distribution and chemistry of the hallucinogenic spe-

cies (Guzmán, 1983). Psilocybe mushrooms are mostly small, brownish,

conic-capped, slender-stalked, gilled mushrooms that fruit on or near

dung, but can be found in wood litter, meadows, parks, and under

sparsely scattered trees (Lincoff and Mitchel, 1977). The attached gills

produce spores that on deposit are deep liliac to purple-brown. The hallu-

cinogenic species of this genus can be found around the world and are

distinguished by: i) a bluing reaction in the carpophore; ii) a farinaceous

flavour; and iii) a farinaceous odour. Some of these characterisitcs be-

come more difficult to observe, the older the sample is. Of the 144 spe-

cies of Psilocybe mentioned by Guzmán (1983), no less than 81 have

been identified as hallucinogenic. Of these, all the species of the sections

Cordisporae (26 species), Semilanceatae (13 species), Brunneocys-

tidiatae (10 species), Zapotecorum (9 species), Mexicanae (6 species),

Cyanescens (5 species), Stuntzae (5 species), Aztecorum (4 species) and

Cubensae (2 species) are hallucinogenic, but only one of the section

Subaeruginosae (1 species). All these fungi together, belong to the old

section Caerulescentes described by Singer (1958), and Singer and Smith

(1958). Some species in the Psilocybe genus contain additional toxic

compounds besides the indole derivatives.

The levels of psilocybin, psilocin and baeocystin in any one species of

hallucinogenic mushroom have been found to be highly variable between

samples. This is demonstrated by the data on some of the species belong-

ing to the genus Psilocybe. Jokiranta et al. (1984) reported a mean psilo-

cybin concentration of 14,200 mg/kg d.w. in a random sample (100

specimens) of Finnish Psilocybe semilanceata. The psilocybin concentra-

tion in the single samples varied from 6,200 to 23,700 mg/kg d.w.. Two

larger pooled unselected samples contained 16,800 and 15,300 mg/kg dry

weight, respectively. A variation in the levels of psilocybin, baeocystin

and psilocin from one sample to another has also been observed in Psilo-

cybe bohemica harvested from a single location (Gartz and Müller, 1989).

Similar observations have been done in Psilocybe cubensis (Earle) Singer

(Gartz, 1987a), Pluteus salicinus (Pers. ex. Fr.) Kumm. (Gartz, 1987b)

and Inocybe aeruginascens (Gartz, 1987c). Beug and Bigwood (1982)

reported that the observed levels of hallucinogenic compounds varied by

a factor of two to more than six. The reason for this variation is not

known, but it is surely to some extent influenced by the different condi-

tions and times of storage between collection and chemical analysis (see

section 5.2.). Other factors that might influence the content of hallucino-

genic tryptamines are the size and the part of the fruit bodies analysed.

From these observations it can be inferred that reports on the absence

of psilocybin and related compounds must be interpreted cautiously, es-

pecially when only limited amounts of material have been examined. The

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

disappearance rate of psilocybin (and related compounds) from carpo-

phores varies considerably.

No correlation between mushroom size (dry weight) and psilocybin

content was found in Pluteus salicinus and Inocybe aeruginascens (Gartz,

1987b; 1987c). However, in absolute amounts, larger fruit bodies contain

more psilocybin and baeocystin than smaller ones, showing that these

compounds are continuously produced in the mushroom. In relative

terms, small fruit bodies of P. semilanceata contain a higher percentage

of psilocybin and baeocystin than larger fruit bodies (Gartz, 1986b;

Christiansen et al., 1981b).

The part of the mushroom that has been analysed may also influence

the level of psilocybin and related compound detected. Wurst et al.

(1984) reported that caps contain more psilocybin than stems. Similar

findings have been reported by Beug and Bigwood (1982), Gartz (1987a,

1987b), Keller et al. (1998), Gartz and Müller (1989), and Gurevich

(1993). Even lower levels are found in the mycelium (Gartz, 1986b;

Kysilka and Wurst, 1989; Keller et al., 1998). Other investigators have

found marginal difference in psilocybin- and psilocin-content in the hat

and the stipe for some mushroom species (Tsujikawa et al., 2003).

Using a new technique to extract the tryptamine derivatives from the

mushroom, Kysilka and Wurst (1990) found much higher amounts of

psilocybin and psilocin in Psilocybe bohemica than had previously been

detected in this species. The original extraction procedure only extracted

76% of the psilocybin and 8% of the psilocin levels extracted by the new

technology. According to the authors these observations pose the ques-

tion whether the reported low contents of psilocin or absence of this

compound in the presence of substantially higher values of psilocybin

may not be an artefact induced by a non-proper extraction. Kysilka and

Wurst (1990) found nearly comparable content of psilocybin and psilocin

in Psilocybe bohemica, in contrast to current literature data. However, the

studies of of Kysilka and Wurst (1990) have been critizised (Gartz,

1994).

In one of the early studies on the chemistry of hallucinogenic mush-

rooms, Hofmann and co-workers (1959) reported that dried fruit bodies

of Psilocybe mexicana contained 2000-4000 mg psilocybin per kg dry

weight, whereas mycelium contained 2000-3000 mg/kg. The content of

psilocin was 500 mg/kg in dried fruit bodies but much less, if any, in the

mycelium.

Japanese workers studied the psilocybin content in cultured mycelium

of Psilocybe subaerunginascens and in the culture fluid. Mycelium con-

tained 170-180 mg psilocybin per kg dry weight, whereas no psilocybin

could be detected in the culture fluid (Koike et al., 1981). Catalfomo and

Tyler (1964) had earlier reported that psilocybin production correlated

with mycelial growth in submerged cultures of Psilocybe cubensis.

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

Maximum production of psilocybin occurred at acidic pH, and reached

levels between 2,200 and 5,200 mg/kg.

Hallucinogenic mushrooms are also found in Australia and New Zea-

land. It has been hypothesized that these mushrooms have been intro-

duced to this continent with early settlers along with their livestock,

mainly the cattle as probable dispersal mechanism (Margot and Watling,

1981). The first livestock arrived in Australia at the end of the 1700’s.

While the importation of cattle may have been responsible for introduc-

ing some hallucinogenic mushrooms, there are at least five indigenous

species (Allen et al., 1991).

The Liberty cap, Psilocybe semilanceata, is the most important hallu-

cinogenic mushroom growing in the Nordic countries. A number of stud-

ies on the occurrence of psilocybin in this species has been performed.

Of 48 mushroom samples freshly collected in Norway 1979–1980 and

dried overnight at 50oC, 70% weighed between 20 and 60 mg

(Christiansen et al., 1981b). The average weight loss during drying was

92%. The smaller mushrooms of the Norwegian samples contained

higher tissue concentrations of psilocybin than the larger ones. Mush-

rooms weighing up to 20 mg had an average tissue concentration of 12

600 mg/kg whereas the ones weighing more than 60 mg had an average

tissue concentration of 5,700 mg/kg dry weight. Even if the tissue con-

centration in percent is higher in the smaller mushrooms than in the larger

ones, the total psilocybin content is higher in the larger mushrooms, indi-

cating that psilocybin is produced during growth (Christiansen et al.,

1981b), in accordance with other studies (see above). These data have

subsequently been confirmed by Gratz (1986a).

Beck and colleagues (1998) analysed Psilocybe semilanceata samples

collected at three different locations in Sweden, together with three mush-

room samples used by patients referred to hospital due to Psilocybe semi-

lanceata intoxication. All samples contained psilocybin at levels between

1,100 and 3,500 mg/kg fresh weight.

Fresh specimens of many hallucinogenic mushrooms stain naturally

blue or blue-green at the base of the stipe and often completely blue of

the stipe apex when handled. Early studies found a good correlation be-

tween content of psilocybin and/or closely related indole derivatives and

the blueing phenomenon (Benedict et al., 1962a). Psilocybin forms blue

colour in solution. Levin (1967) suggested that the coloured compound is

produced by psilocybin first being dephosphorylated to psilocin by a

phosphatase, and then psilocin being oxidised by for example cytochrome

oxidase, copper oxidase or Fe2+. In support of this suggestion, Horita and

Weber (1961) showed that incubation of psilocybin with homogenates of

rat kidney and other mammalian tissues causes a rapid liberation of psi-

locin through the action of alkaline phosphatase. The psilocin thus

formed quickly undergoes further oxidative degradation to form a blue-

coloured product. Weber and Horita (1963) subsequently concluded that

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

cytochrome oxidase, a mitochondrial enzyme, is responsible for the rapid

oxidation of psilocin (to a dark blue product) by tissue homogenates. It is

conceivable that the blue colouring of these mushrooms result from an

identical reaction.

Recreational users of hallucinogenic mushrooms sometimes regard the

intensity of bluing as a guide to psilocybin and psilocin levels. Psilocybe

connoseurs have experimented with metol (p-methylaminophenol)

painted on the stalk or cap of a bruised mushroom as an indicator of the

presence of hallucinogenic compounds (Chilton, 1978). Metol has a low

oxidising potential and could be oxidised in the presence of any oxidases.

Therefore, it is not a surprice that a poor correlation between metol blue-

ing and psilocybin content has been found. Similarly, Beug and Bigwood

(1982) found a poor correlation between degree of natural bluing and

psilocybin or psilocin level. The variability of psilocybin and psilocin

within each species as well as the difference in average level between

species lead Beug and Bigwood (1982) to conclude that recreational users

of these mushrooms are ingesting unpredictably varying amounts of psi-

locybin and psilocin. The variability of the bluing reaction further implies

that this reaction is not a safe guide to psilocybin or psilocin levels. This

has been confirmed by Gartz (1986b).

The data summarised in this section show that the ability to synthesise

psilocybin and related compounds occurs in several mushroom genera,

but in only some of the mushrooms species in each genus. The unclear

role of tryptamine derivatives as taxonomic determinants is illustrated by

the findings of Stijve and Kuyper (1985). These investigators studied

around 100 different mushroom species, and found psilocybin, baeo-

cystin, and/or psilocin in only 10 species. For example, in 10 species of

Panaeolus, these compounds were only detected in Panaeolus subbaltea-

tus. The Panaeolus species, however, characteristically contained appre-

ciable amounts of serotonin and its precursor 5-hydroxytryptophan. Of

twenty Inocybe species analysed for the hallucinogenic compounds, these

were found in five species only. Of thirteen Pluteus species only Pluteus

salicinus was positive for psilocybin. One of these, Pluteus villosus, con-

tained tryptamine derivatives closely related to psilocybin. Too little ma-

terial was available to isolate and identify the compound. Whereas Pleu-

teus salicinus was faintly bluish green at the lower part of the stipe, Pleu-

teus villosus had a definite bluish to violet colour. Working with five

different Inocybe species containing hallucinogenic tryptamine deriva-

tives and being characterized by a bluish-green zone on the stipe, Stijve

and Kuyper (1985) concluded that although they contain high enough

concentrations of psilocybin, baecystin, and/or psilocin to render them

hallucinogenic when consumed, the likelihood this is going to happen is

very low due to the rareness of these species and the trouble to separate

them from poisonous mushrooms. Also Inocybe calamistrata had a blue-

green stipe, but this coloured zone was not influenced by bruising, and no

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

tryptamine derivatives could be detected. The investigators concluded

that psilocybin was restricted to two sections of Inocybe, viz. Lactiferae

Heim and Fibrillosae Heim. None of the psilocybin-containing species of

Inocybe contained muscarine witch is a toxic compound found in other

species of Inocybe.

4.2. Influence of cultivation, storage and processing

The formation and distribution of psilocybin and related compounds in

fruit bodies, mycelia and sklerotia have been studied in cultivated Psilo-

cybe cubensis (Gartz, 1989d).

It has been speculated that the quantity of psilocybin and related com-

pounds occurring in hallucinogenic mushrooms depends on whether it is

an early or a late flush of fruit bodies developing from the mycelium.

There is no information available on wild mushrooms to confirm this

speculation. However, an Amazonian strain of Psilocybe cubensis have

been grown in carefully controlled cultures and the variation of psilocy-

bin and psilocin levels studied with time in culture (Bigwood and Beug,

1982). The first flush (fruiting) of mushrooms occurred four to five

weeks after inoculation of the cultures. The levels of psilocybin varied

somewhat unpredictably from one flush to the next, but generally were

much the same on the last flush (5th or 6th flush) as they were on the first

flush. The levels of psilocybin were between 3,200 and 13,300 mg/kg dry

weight. Psilocin, on the other hand, generally was absent in the first one

or two flushes, reached maximum by the fourth flush, and then appeared

to start to decline. The levels of psilocin were between non-detectable

levels and 2,900 mg/kg dry weight. Were these findings with psilocin

found to be general, it would partly explain the variation in psilocin levels

observed in hallucinogenic mushrooms. Similar observations have been

made by Gartz (1987a), who, however, noted that fruit bodies from later

flushes contained somewhat higher amounts of psilocybin (and psilocin)

than fruit bodies from early flushes. When Gartz repeated his studies,

using Psilocybe semilanceata and Gymnopilus purpuratus (Cooke &

Mass.) Sing. as cultivated materials, no variation in psilocybin, psilocin

and baeocystin levels between repeated flushes from a single culture was

found (Gartz, 1991).

When Bigwood and Beug (1982) analysed five street samples of Psilo-

cybe cubensis for which the flush number or the precise growing condition

were unknown, variable levels of psilocybin (700–6 200 mg/kg dry weight)

and consistently low levels of psilocin were found (n.d.-300 mg/kg dry

weight).

Psilocybin, psilocin and related compounds cannot be expected to be

totally stable in a mushroom or a mushroom extract, particularly as they

occur mixed with many other compounds, some of which have enzymatic

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

activity. In those cases where dried ‘fresh’ mushrooms have been ana-

lysed for psilocybin and psilocin in parallel with dried stored museum

samples, it has been noted that psilocybin has been slowly degraded and

sometimes psilocin formed in the older stored samples (Semerdžieva et

al., 1986). Reports that mushrooms do not contain psilocybin and related

compounds must be interpreted cautiously, especially when only limited

amounts of material have been examined. The disappearance rate of psi-

locybin (and related compounds) from carpophores varies considerably.

Therefore, the time running between collection of mushrooms and

analysis, as well as the conditions at which the mushrooms are stored

may influence the quality and quantity of compounds analysed. For ex-

ample, the influence of the light conditions during storage has not been

studied. Many investigators have not given this experimental factor

enough consideration. Repke and co-workers (1977b), originally detected

psilocybin, psilocin and baeocystin in fresh samples of Psilocybe baeo-

cystis and Psilocybe cyanescens. However, after 66 weeks of storage at

22oC and 5–10% relative humidity, the compounds could no longer be

detected in either species. Similarly, chemical analysis of cultivated Psi-

locybe cubensis grown on horse dung showed that psilocybin, psilocin,

and baeocystin could not be detected in dried material stored at 22oC for

52 weeks (Repke et al., 1977). However, fragments of the same carpo-

phore stored under anhydrous conditions at -5oC for 52 weeks and the

freshly dried material (14 days) both contained these compounds. A simi-

lar decrease in baeocystin content related to storage was observed for

collections of Psilocybe semilanceata, Psilocybe silvatica, and Psilocybe

stuntzii. By contrast, the amount of baeocystin (and psilocin) found in one

collection of Panaeolus subbalteatus after 52 weeks storage was the same

as that detected in freshly dried specimens from the same collection. The

rate of decomposition of the studied compounds seemed to be irregular in

the investigated material. Similar observations were made by Wurst et al.

(1984). Although drying had no influence on the psilocybin level of fruit

bodies of Psilocybe mushrooms, storage of the dried mushrooms reduced

the levels significantly.

Beug and Bigwood (1982) studied how storage of mushroom samples

may influence the psilocybin and psilocin content. They noted that

freeze-dried samples showed no detectable loss of psilocybin and psilocin

when stored at -5oC or -60oC, but some freeze-dried samples lost both

psilocybin and psilocin over periods of one to two years when stored at

room temperature. Methanolic extracts were stable for over a year at -

5oC, but lost all psilocin and some psilocybin within six months when

stored at room temperature. Some dried herbarium material had lost all

psilocybin and psilocin after 1 year (Beug and Bigwood, 1981).

Ohenoja and co-workers (1987) analysed a series of dried herbarium

specimens of Psilocybe semilanceata collected in the years 1843, 1869,

1954 and 1976 in order to determine the stability of psilocybin and psilocin

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

in the dried fruit bodies. Psilocybin was found to be remarkably stable in

this study. Even the 115 year-old sample from 1869 still contained a meas-

urable amount of psilocybin, 140 mg/kg dry weight. The oldest specimen,

on the other hand, did not show any activity. Psilocin seemed to be much

less stable, and was only detected in fresh specimens or in species that

contained high concentrations of psilocybin. By comparing the psilocybin

content in fresh samples collected from nature with old herbarium samples,

Stijve and Kuyper (1985) confirmed these observations by finding 10–20

times lower psilocybin levels in the stored samples.

Also pre-treatment of samples before chemical analysis may influence

the amount of psilocybin and psilocin subsequently detected. Gartz (1994)

revealed that the relatively high amounts of psilocin detected in Psilocybe

bohemica by Kysilka and Wurst (1990) and Wurst and co-workers (1992)

was an artefact caused by enzymatic destruction of psilocybin in aqueous

solutions containing organic solvents. Extraction with pure methanol was

found to be the safest method to retain the genuine indole derivatives oc-

curring in the mushrooms. The question whether these phosphorylated

tryptamine derivatives are most efficiently extracted by pure methanol has

not been adequately settled (Kysilka and Wurst, 1990).

Stamets and co-workers (1980) pointed out that a marked variation in

psilocybin and psilocin levels from one collection to another is typical of

several species in the genus Psilocybe. The observation led the authors to

conclude that neither the level of psilocybin and/or psilocin, nor the ratio

of the two can be utilised as a chemotaxonomic tool. Further, when the

authors analysed herbarium samples of Psilocybe they found that the

samples had lost most of their psilocybin and psilocin, which made them

conclude that collections should be analysed promptly. However, activity

can be retained for at least two years by drying or freeze drying the col-

lections, sealing them in plastic and storing them frozen.

Boiling of psilocybin-containing mushrooms in water, results in a

quantitative extraction of psilocybin into the water. But no psilocybin is

degraded. A subsequent extraction of the boiled fruit bodies with metha-

nol did not yield any psilocybin (Wurst et al., 1984).

4.3. Wild mushrooms in the Nordic countries that contain

psilocybin and/or related compounds

Of the about 125 psilocybin and/or psilocin containing mushrooms identi-

fied in Table 4, no less than about 60 have been found in the Nordic

countries. Many of them are rare, but some can be found in considerable

quantities in the right biotopes (Knudsen and Vesterholt, 2008).

Twenty-two species of the genus Psilocybe have been identified in the

Nordic countries, but only 6 of these contain the hallucinogenic com-

pounds. These species are: Psilocybe atrobrunnea (Lasch) Gillet., P.

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

cyanescens Wakef., P. fimetaria (P.D. Orton) Watling, P. liniformans

Guzman & Bas var. americana Guzman & Stamets, P. semilanceata (Fr.)

Krumm., and P. silvatica (Peck) Sing. & Smith.

The next most important group of psilocybin-containing mushrooms be-

longs to the genus Panaeolus. Eleven species of this genus have been de-

scribed in the Nordic countries. Of these, the following six species have

been reported to contain psilocybin and/or psilocin: Panaeolus olivaceus

F.H. Møller, P. sphinctrinus (Fr.) Quél., P. foenisecii (Pers.) J. Schröt, P.

subbalteatus (Berk. & Broome) Sacc., P. fimicola (Pers.) Gillet, and P. ater

(J.E: Lange).

Of the four Conocybe species identified as containing psilocybin, two

have been described in the Nordic countries. These species are Conocybe

cyanopus (Atk.) Kühner and C. kuehneriana (Sing.) Kühner.

Among the nine Gymnopilus species reported to contain psilocybin,

Gymnopilus liquiritiae (Pers.) P. Karst.,.P. sapineus (Fr.) Maire, and G.

spectabilis (Fr.) A.H. Sm. have been found in the Nordic countries, and

among the three psilocybin-containing Inocybe species, the two species

Inocybe corydalina Quél. and I. haemacta (Berk. & Cooke) Sacc. occur

in the Nordic countries (Knudsen and Vesterholt, 2008).

Other mushrooms in the Nordic countries reported to contain psilocy-

bin and/or psilocin are Pluteus atricapillus (Batsch) Fayod, Pluteus

salicinus (Pers.) P. Kumm., and Psathyrella candolleana (Fr.) Maire.

4.4. Cultivation of psilocybin-containing mushrooms

The sometimes poor and season-dependent availability of hallucinogenic

mushrooms have stimulated the search for methods to cultivate these

mushrooms. Actual culturing of the mushrooms did not become common

until reports on the methodology occurred in both scientific literature and

connoisseur books (Heim and Wasson, 1958; Singer and Smith, 1958;

Brown, 1968; Enos, 1970; Oss and Oeric, 1986).

Home cultivation can be done almost everywhere with the most rudi-

mentary equipment. Cultivation kits have been commercially available on

the market for over 20 years. Home growers typically find that it is very

easy to culture the mycelium (which also contain psilocybin), but find it

hard to produce fruiting bodies in vitro. The Latin American species Psi-

locybe cubensis is an exception to this finding, apparently being very

easy to culture and fruits readily in vitro.

Home culture of mushrooms in vitro, however, requires some care and

attention. It is also feasible to induce hallucinogenic mushrooms normally

indigenous to a certain area to grow outdoors in controlled conditions in

that area. Of course, while this technique may require less care and atten-

tion than in vitro cultivation, it is seasonal; by culturing mushrooms in

vitro, users may obtain a year-round supply of mushrooms.

5. Exposure

5.1. The habit of consuming hallucinogenic mushrooms

Mind expanding or hallucinogenic drugs have been used throughout the

world from prehistoric times. Since they have often been associated with

religious rites, fortune telling and magic, they have been regarded as sa-

cred and earlier never used with levity. The habit of using hallucinogenic

mushrooms in the Western society is not older than around 30 years, and

is mainly a recreational phenomenon.

During the early period of hallucinogen use in the 1960´s, LSD was

the drug receiving most attention. As time passed, interest in other com-

pounds emerged and was stimulated by burgeoning literature as well as

the availability of the drugs. Two other illicit chemicals that became

popular at the end of the 60´s and during the 70´s were mescaline, found

in Lophophora and a few other genera of cacti, and psilocybin, found in

many mushroom species.

As is the case for many trends in society, the modern use of hallucino-

genic mushrooms emanates from the west-coast of the United States,

where it became relatively common during the middle of the 1970´s and

was sold as magic mushrooms. The epithet "magic mushroom" was in-

vented by a Life magazine editor in 1957, and is the single most common

name for the hallucingenic mushrooms (Allen et al., 1981). Some of the

specific species in addition to being called magic mushrooms have re-

ceived their own name, which varies from geographical region to geo-

graphical region or between the local drug circles. The habit of using

hallucinogenic mushrooms in Australia most probably was brought to the

island by surfers moving from America to Australia (Allen et al., 1991).

The users of hallucinogenic mushrooms can get their products from

many sources. They can collect various species of hallucinogenic mush-

rooms growing in the wild and use them fresh or after being dried, they

can grow the mushrooms themselves, or buy dried mushrooms on the

open or the black market. The habit of collecting wild mushrooms was

originally rather limited. Street samples of ”magic” mushrooms, that is

samples sold legally or not legally on the streets, were during these early

years usually found to be non-psychoactive mushrooms treated with

LSD. These findings were substantiated by reviews of street drug analysis

programs. Although true psilocybin, or magic mushroom use was negli-

gible in 1975 in the United States, the habit of using these products in-

creased thereafter.

Eastern European countries has until recently been more or less a tran-

sit zone for drugs heading to Western Europe. A remarkably fast change

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

has resulted in these countries now being more or less comparable with

other EU countries. In the Slovak Republic sniffing of fluid drugs were

previously the clearly dominating drug abuse, but now the traditional

drugs in Western Europe are the common ones. In particular, during latter

years plant drugs, including hallucinogenic mushrooms, have become

popular, probably because of their easy availability, low price and quick

spreading of information (Kresanek et al., 2005).

During the last years, Internet has become a major source of informa-

tion on where to find hallucinogenic mushrooms and how to use them.

Internet is also a forum for the enterprises selling magic mushrooms,

mushroom-growing kits and similar products (Westberg and Karlson-

Stiber, 1999). Today a large number of different mushroom species have

been claimed to have hallucinogenic properties (Table 5), assumingly due

to its content of psilocin/psilocybin (Table 4 gives mushrooms known to

contain these compounds).

Techniques for cultivation of psilocybin-containing mushrooms were

first described in a book called "The Psychedelic Guide to Preparation of

the Eucharist" (Brown, 1968). Several species of Psilocybe can be cul-

tured, but it is not easy to get all species to produce fruiting bodies. Psilo-

cybe cubensis is one of the most easy species to cultivate, whereas many

other species only produce mycelia. An increased trade of hallucinogenic

mushrooms and growing-kits over Internet has been registered by the

customs authorities in all Nordic countries.

The psilocybin-containing mushrooms may be eaten fresh in the field,

or later in the home, where they may be added to food such as soups,

salads, or omelettes, or mixed as “smoothies” with juice and fruit (Ott,

1978).

According to Zimmer (1986) chocolate or honey are sometimes mixed

with the mushroom to obtain products more easily ingested by the recrea-

tional drug users. One way of preserving the mushrooms is to freeze

them. It is also common practice to dry these mushrooms, either in the air

or in some type of drying apparatus. The mushroom so dried may be

stored for a very long time, without loosing too much of its activity, if

stored at lower temperatures (Hall, 1973).

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

Table 5. Mushroom species reported to have hallucinogenic activity and to contain

psilocybin and/or similar compounds.

Species Reference

Conocybe siligineoides Heim and Hofmann, 1958a

Conocybe smithii Watling Guzmán et al., 1976*

Copelandia cyanescens Pollock, 1976a; Southcott, 1974; Hall, 1973; McCarthy, 1971

Gymnophilus purpuratus Allen et al., 1991

Gymnophilus spectabilis Waters, 1965

Allen et al., 1991

Inocybe aeruginascens Drewitz, 1983

Inocybe patouillardii Satora et al., 2005

Mycena pura Allen et al., 1991

Mycena cyanorrhiza Allen et al., 1991

Panaeolus antillarum Allen et al., 1991

Panaeolus cambodginiensis Pollock, 1975

Panaelous campanulatus Pollock, 1974, 1976a

Panaeolus castaneifolius Guzmán et al., 1976*, Ott, 1978

Panaeolus fimicola Ott, 1978

Panaeolus foenisecii Cooles, 1980; Pollock, 1976a; Holden, 1965; Ott, 1978

Southcott, 1974; Guzman et al., 1976*; Allen et al., 1991**

Panaelous cyanescens Lincoff and Mitchell, 1977. Allen et al., 1991**; Pollock, 1974,

1976; Ott, 1978

Panaelous papilionnaceus Pollock, 1974; Sanford, 1972

Panaeolus sphincrinus Ott, 1975; Guzmán et al., 1976*; Schultes, 1939; Pollock, 1975

Panaeolus subbalteatus Guzmán et al., 1976*; Pollock, 1976; Allen et al., 1991

Panaelous (Copelandia) subbalteatus Jacobs, 1975; Allen et al., 1991

Pluteus cyanopus Stamets, 1996

Pluteus glaucus Stijve and de Meijer. 1993

Pluteus salicinus Stamets, 1996

Pluteus villosus Stamets, 1996

Psilocybe aucklandii Guzmán et al., 1993

Psilocybe australiana Guzmán et al., 1993

Allen et al., 1991

Psilocybe aztecorum var. aztecorum Singer, 1958a; Guzmán, 1978

Psilocybe aztecorum var. bonetii Guzmán, 1978

Psilocybe baeocystis Mc Cawley et al., 1962; Benedict et al., 1962b; Guzmán et al.,

1976*

Psilocybe brasiliensis Guzman, 1983

Psilocybe brunneocystidiata Guzmán et al., 1993

Psilocybe caerulescens Guzmán and Vergerr, 1978. Singer, 1958a

Psilocybe caerulescens var. mazatecorum Wasson, 1962a, 1962b

Psilocybe campanulatus Guzmán et al., 1976*

Psilocybe caerulipes Ott, 1978

Psilocybe candidipes Singer, 1958a

Psilocybe collybiodes Pollock, 1976a; Southcott, 1974; Hall, 1973; McCarthy, 1971;

Allen et al., 1991

Psilocybe cophrophila Allen et al., 1991

Psilocybe cubensis Allen et al., 1991**; Singer, 1958a; Guzmán and Vergerr, 1978

Psilocybe cyanescens Guzmán et al., 1976*

Guzmán and Vergerr, 1978

Psilocybe cyanofibrillosa Guzmán and Vergerr, 1978

Psilocybe eucalypta Guzmán et al., 1993. Allen et al., 1991

Psilocybe fagicola Allen, 2001

Psilocybe fimentaria Guzmán and Vergerr, 1978

Psilocybe goniospora Guzman et al., 1993

Psilocybe hoogshageni Stamets, 1996

Psilocybe inconspicua Guzmán et al., 1993

Psilocybe kumaenorum Guzmán et al., 1993; Allen et al., 1991

Psilocybe lonchoporus Guzmán et al., 1993

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

Table 5 cont. Mushroom species reported to have hallucinogenic activity and to

contain psilocybin and/or similar compounds.

Species Reference

Psilocybe mammillata Guzmán et al., 1993

Psilocybe mexicana Guzmán and Vergerr, 1978

Singer, 1958a

Psilocybe muliercula Singer, 1958a

Psilocybe novae-zelandiae Allen et al., 1991

Psilocybe ochreata Guzman et al., 1993

Psilocybe papuana Guzmán et al., 1993

Psilocybe pelliculosa Guzmán et al., 1976*

Psilocybe quebecensis Ola´h and Heim, 1967

Psilocybe samuiensis Guzmán et al., 1993

Psilocybe semilanceata Guzmán and Vergerr, 1978

Allen et al., 1991; Olsen and Knudsen, 1983; Guzmán et al.,

1976*; Heim et al., 1963

Allen et al., 1991

Psilocybe semperviva Heim and Wasson, 1958

Psilocybe silvatica Guzmán and Vergerr, 1978

Psilocybe strictipes Guzmán et al., 1976*

Psilocybe stuntzii Guzmán et al., 1976*

Psilocybe subaeruginosa Allen et al., 1991

Picker and Rickards, 1970

Pollock, 1976a; Southcott,1974; Hall, 1973; McCarthy, 1971;

Guzmán et al., 1993

Allen et al., 1991

Psilocybe subaeruginascens

Höhnel var. subaeruginascens Guzmán et al., 1993

Psilocybe subcaerulipes Yokoyama, 1973

Psilocybe subcubensis Allen et al., 1991**

Psilocybe subfimetaria Stamets, 1996

Psilocybe tampanensis Guzmán and Vergerr, 1978

Psilocybe tasmaniana Guzmán et al., 1993

Psilocybe tasmaniana Allen et al., 1991

Psilocybe venenata Stamets, 1996

Psilocybe washingtonensis Stamets, 1996

Psilocybe wassonii Allen et al., 1991

Psilocybe wassoniorum Stamets, 1996

Psilocybe yungensis Allen et al., 1991

Psilocybe zapotecorum Allen et al., 1991

Stropharia cubensis (*) Singer, 1958a; Singer and Smith, 1958; Pollock, 1975

* No information on psilocybin and psilocin in this report

** Allen and Merlin, 1992

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

Being hard to chew, the dried mushrooms are often brewed into tea. This

tea is subsequently drunk, and the mushrooms are then consumed. In

Samoa, the caps of Copelandia cyanescens are steeped in boiling water to

produce a black juice which is mixed with coffee and then drunk (Cox,

1981). The hot water extracts the mushroom toxins; and it has been ob-

served that both the water and the remains of the mushrooms so prepared

have hallucinogenic activity (Ott, 1978). The hot water can also be used

to prepare foods such as rice or soups, discarding the remains of the

mushrooms. Some persons chew the caps raw, others mixed together with

Coca-cola as this method eliminates the somewhat undesirable taste of

the raw or fried mushroom (Hall, 1973).

Dried mushrooms are sometimes smoked, a practice which no doubt

comes from descriptions of this mode of ingestion in Castanedas book

"The Teaching of Don Juan".

During ethnomycological explorations of southern Thailand, Allen

and Merlin (1992) made observations of occurrence, harvesting, use, and

marketing of psychoactive fungi by local Thai natives, foreign tourists,

and German immigrants. Psychoactive fungi are prohibited plants accord-

ing to Thai law. Nonetheless, numerous restaurants on the islands of Koh

Samui and Koh Pha-ngan, in the southern part of the Gulf of Siam, served

psychoactive omelettes, stews, soups, pizzas, teas, and blended juice bev-

erages containing mind-altering, gilled fungi, referred to as 'magic mush-

rooms' (Guzmán, 1993). Purchase and use of foods containing psychoac-

tive fungi occurred primarily among tourists and West German immi-

grants living on these islands. The fungi used in these dishes were picked

from cattle dung and identified as Psilocybe cubensis, Psilocybe sub-

cubensis and Panaeolus (Copelandia) cyanescens. In addition a new spe-

cies, Psilocybe samuiensis, not growing on dung were used (Guzmán et

al., 1993)

More recently, various mushroom-containing concoctions have be-

come popular, especially grated or powdered mushrooms in chocolate.

Because of the potential for interference of ingredients of these products

in the standard analytical methods, new extraction method might be re-

quired to analyse these types of products for psilocybin and psilocin

(Sarwar and McDonald, 2003).

There are some scientific studies on the use of hallucinogenic mush-

rooms. For historical reasons, most early studies were performed in the

United States. Later on such studies have been performed also in Europe.

Thomson and colleagues in 1985 investigated the extent of hallucino-

genic mushroom use among 1507 college students in California, USA.

The major finding was that among the respondents who reported use of

hallucinogenic drugs (17%), over 85% had used hallucinogenic (psilocy-

bin) mushrooms and over half had used mushrooms but no other hallu-

cinogens. Three times as many students had used hallucinogenic mush-

rooms as had used LSD. These data indicate a high level of experimental

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

use of hallucinogenic mushrooms compared to the other hallucinogens.

The observation was substantiated by the observation that 68% of the 223

students who reported mushroom use, had tried it four times or less.

In another survey of (1 500) American college students in 1986, 15%

admitted mushroom use compared to 5% for LSD. The reported use of

hallucinogenic mushrooms among high school students were somewhat

less and ranged from 3.4% in the seventh grade (12 to 13 years old) to

8.8% in the eleventh grade (16 to 17 years old) (Schwartz and Smith,

1988). Alcohol and marijuana are the most commonly abused drugs by

students on college campuses in the United States (Rimsza and Moses,

2005).

In the study of Thomson and colleagues (1985), referred to above, the

use of hallucinogenic mushrooms or attitudes toward use of illicit drugs

in general was correlated with the number of drug-involved friends.

Mushroom users were more likely to have used each of nine other drugs

studied than were non-users. One interesting observation made by

Thompson and co-workers (1985) was that many of those who used

mushrooms claimed that they would never take LSD, which suggests that

researchers should differentiate mushrooms from other hallucinogens. It

should be stressed that this has seldom been the case. Usually, investiga-

tions on use of hallucinogenic mushrooms have been done in connection

with illicit drug use.

Not unexpectedly, use of hallucinogenic mushrooms is more common

in drug users. In a study on 174 young American drug-users 26% reported

having used hallucinogenic mushrooms, frequently in conjunction with

alcohol or other drugs (Schwartz and Smith, 1988). However, in general

the use of mushrooms was infrequent; the majority of the adolescents re-

porting psilocybin-containing mushroom ingestion only one to three times.

Ten persons had tried mushrooms at least ten times and two persons more

than 50 times. Serious adverse effects during mushroom intoxication were

reported by six (13%) of the adolescents; three cases of head trauma, two

cases of loss of consciousness, and flash-back experiences.

Trends in illicit drug use by undergraduate students has been studied

both in a private southern university in the United States and in the On-

tario Student Drug Use Survey in Canada. The American study compared

results of similar surveys performed at the same university in 1986 and

1990 (Cuomo et al., 1994). Although the validity of the data may be

questioned by the low response rate, they showed that the percentage of

students that had used mescaline/psilocybin (grouped together on the

questionnaires) increased from 8% to 24% during the five-year period of

the study (Cuomo et al., 1994). Every two years since the early 1990's,

the Addiction Research Foundation of Ontario, has sponsored the Ontario

Student Drug Use Survey. The survey is based on a questionnaire to On-

tario public school students enrolled in grades 7, 9, 11, and 13, and inves-

tigates the self-reported prevalence of use of 20 types of drugs and other

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

substances over the previous 12 months. After a substantial long-term

decline in drug use among adolescents during the 1980s, this and other

epidemiological surveys observed an increase in drug use in this segment

of the population in North America during the 1990s. In 1993 around

3.1% of the students used mescaline or psilocybin, and two years later

7.6%. The significant increase continued and were 10.1% in 1997 (Adlaf

and Ivis, 1998), and 13.6% in 1999 (Adlaf et al., 2000). The difference

between the genders was marginal. A parallel increase in "ecstasy" was

noted. None of the drugs declined in use during this period. In total, 38%

of the students had used an illicit substance during the previous year.

In a more resent Canadian study on drug-using university students

(mean age 21.7 years, 58.7% female and 78.5% Caucasian), the investi-

gators studied the simultaneous use of several drugs (Barrett et al., 2006).

Of the 149 subjects interviewed, 65% had used hallucinogenic mush-

rooms/psilocybin, starting on average at an age of 17 years. The drugs

most often combined with mushrooms/psilocybin were tobacco (61.9%),

cannabis (59.8%), and alcohol (41.2%). When alcohol was combined

with mushrooms, it was more common that the alcohol consumption oc-

curred before than after the mushroom/psilocybin intake. The mushroom

use did not influence the amount of alcohol consumed. However, tobacco

smoking increased in combination with use of mushrooms/psilocybin.

Not unexpectedly, higher rates of using hallucinogenic mushrooms

have been reported in subgroups. In a study, Schwartz and Smith (1988)

reported that 26% of 174 young American drug-users had used hallu-

cinogenic mushrooms. The use had been infrequent, but when it occurred,

it did so in conjunction with alcohol or other drugs. Similar observations

were done on young drug users from the great Los Angeles area (Siegel,

1985). Löhrer and co-workers asked 180 patients in a rehabilitation clinic

for young addicts to fill out a questionnaire regarding their regularly con-

sumed drugs (Löhrer and Kaiser, 1999) or plants (Löhrer and Albers,

1999). Of the 110 patients who answered the questionnaire, seventy-nine

were under 30 years old. Forty-nine of them stated that they regularly

(n=23) or sometimes (n=26) used Psilocybe mushrooms. Thus, hallu-

cinogenic mushrooms were one of the most used drugs in youngsters of

this age group on a rehabilitation clinic.

One of the earliest reports on the use of hallucinogenic mushrooms in

Europe is a review of 297 psilocybin-related calls to the London National

Poison Information Service between 1978 and 1981. The review revealed

peak usage in the 15 to 19 years age group, with males comprising 83%

or more of the cases (Francis and Murray, 1983).

In another study from the United Kingdom the extent of use of eight

different types of drugs by 2610 15–16 year-olds in Wales were investi-

gated (Smith and Nutbeam, 1992). Of the 86% of pupils returning the

questionnairs, the most frequently reported drugs were marijuana,

glue/solvents, and psilocybin (magic mushrooms). The current use of

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

magic mushrooms was not exceptional - 97.8% had not used it during the

last month, 1.4% had tried it 1–2 times and 0.9% at least 3 times. As

many as slightly more than 10% had ever tried magic mushrooms but of

these cases three quarters had only used it 1–2 times. The authors stated

that drug use was likely under-reported due the higher likelihood that

absentees used drugs and that some questions on drug use were not an-

swered by between 3.8 and 7.4% of the students, figures that were some-

what higher than in other studies. Past research has indicated that absen-

tees of school pupils will include a disproportionately large number of

young people who use drugs. The prevalence of drug use was higher for

pupils from single parent families, and more boys than girls reported

using psilocybin.

Webb et al. (1998) studied whether the lifestyle of medicinal students

in England was similar to those of students at other universities, and

whether their life style had changed over time. In this study of 333 men

and 417 women, 9.8% of the men and 4.6% of the women had used

magic mushrooms as a hallucinogen.

In 1989 Lassen and co-workers (1992) investigated the extent of hal-

lucinogenic mushroom consumption among students from a highschool

in the county of Aarhus, Denmark, students at the University of Aarhus

and students from the Danish school of journalism in Aarhus. Three per-

cent of the high-school students had used psilocybin-containing mush-

rooms as a hallucinogen. Only 1% had experience with LSD. Most high-

school students that had tried hallucinogenic psilocybin-containing mush-

rooms had tried it only a few times, often for the first time abroad. The

use of psilocybin-containing mushrooms in the studied group seemed to

be of a recreational nature, and did not seem to be addictive. Being a

male and above 25 years of age was significantly correlated to an in-

creased used of hallucinogenic mushrooms (Lassen et al., 1992). Of the

students at the University of Aarhus, and the Danish school of journalism

in Aarhus, 333 persons (83%) returned the anonymous questionnaire

concerning their use of mushrooms and other narcotics. Nine percent had

experience with hallucinogenic psilocybin containing mushrooms, a sur-

prisingly high fraction. Only 2% had experience with LSD. This suggests

that mushrooms are the most commonly used hallucinogenic substance in

Denmark and that the use exceeds that of LSD. Fourteen (42%) of the 33

respondents that had used hallucinogenic mushrooms had used it only

once, eleven (33%) had used it two to four times, six (18%) had used it

five to ten times, and two (6%) eleven to fifteen times. No one had tried it

more than fifteen times. Of users, 35% wanted to stop using mushrooms,

and 60% wanted to continue or had not taken a decision on this question.

Those who wanted to continue using the hallucinogenic mushrooms had

significantly more friends who used mushrooms and were themselves

more experience with marijuana than those who wanted to stop using

mushrooms. The study also showed that the intention to use mushrooms

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

is more common among persons who have friends with experience to use

hallucinogenic psilocybin-containing mushrooms, and usually in small

groups.

In February 1993, Ventegodt and Merrick (2003) investigated by

questionnaire the connection between use of psychoactive drugs and

quality of life in a representative sample of the Danish population.

Among 2 460 persons aged 18 to 88 years, randomly selected from the

Danish Central Register, and 7 222 person from the Copenhagen Perina-

tal Birth Cohort 1959–61 (31–33 years old), 61% and 64% respectively,

reported their use of ten different psychotropic drugs and quality of life.

The use of conscious-altering drugs was found to be widespread in Den-

mark. Over half the Danish population had used illegal psychotropic

drugs, most commonly cannabis (marijuana). Although other hallucino-

genic drugs were previously more common, the investigation showed that

psilocybin is now the most frequently used hallucinogenic drug in Den-

mark. 5.1% of the 31 to 33 years olds had used psilocybin compared with

1.2% of the population sample. The use was connected to a small but

significant reduction in quality of life. The study did not address the ques-

tion whether the drug use was the result of a non-optimal quality of life

(most likely), or resulted in a reduced quality of life (less likely) (Vente-

godt and Merrick, 2003).

A clear trend in drug use over the last ten to twenty years is the in-

creased consumption of hallucinogenic drugs, including psilocybin-

containing mushrooms, in the context of youth cultural and entertainment

movements (Pierrot et al., 2000). Recently performed surveys show that

close to 35% of young adults in France aged 18 to 25 years had used ille-

gal drugs. Among the participants of parties in the techno-scene the cor-

responding figure was no less than 80% (Vollenweider and Vollenwei-

der-Scherpenhuyzen, 2003).

Gross et al. (2002) recruited 210 participants from three different rave

parties in Montreal, a bilingual metropolitan Canadian city, to fill out a

self-report questionnaire on the use of drugs during the last thirty days.

The participants were between 16 and 32 years old. Average age at first

use of psilocybin was 16.5 years, which was at a later age than when first

using alcohol, nicotine, cannabis, and LSD. 70% of the participants had

ever used psilocybin-containing drugs, and 22% during the last 30 days.

On average the users had tried the mushrooms 1.7 times during the last

month.

The relationship between participating in rave parties and drug use has

been studied also in the United Kingdom. Riley et al. (2001) surveyed

122 drug-using attenders (57% males, 43% females) at three dance events

in Edinburgh to a questionnaire on recreational drug use. Ninety percent

of the participants were in employment or education (mainly higher edu-

cation), most being between 18 and 23 years old. The participants were

selected by answering yes to the question: “Have you used drugs for

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

dance events in the past year”? Fifteen participants (12.3%) reported use

of psilocybin. Eleven of these were men. Three of the fifteen reported

using psilocybin monthly or more often. Psilocybin was often used in

combination with ecstasy and/or amphetamine. The majority (85%) of the

rave party participants bought the drugs from friends (Riley et al., 2001).

More recently, McCambridge et al. (2007) in a cross-sectional survey

investigated the trend in the use of hallucinogens and other adjunct drugs

in the context of dancing parties in the UK 1999–2003. Whereas use of

LSD decreased during the period, the prevalence in psilocybin use in-

creased. However, the mean age at firt use and the number of days used

per month were unchanged.

It should be stressed that it is far from easy to study the use of hallu-

cinogenic mushrooms. The pattern of usage is known to vary within ado-

lescent subcultures, and investigators attempting to describe these pat-

terns have usually not used standardised survey techniques and data-

gathering instruments. Furthermore, they have not in depth evaluated the

response consistency in self-reporting of young adolescents’ drug use. An

Irish study has recently shown that data on use/non-use of hallucinogenic

mushrooms are particularly prone to be recanted a few years later (Percy

et al., 2005).

5.2. Legal aspects of hallucinogenic mushrooms and/or

psilocybin and related compounds

The natural tendency of human beings to use ”mind-altering” substances

is so well documented that one can easily perceive why arbitrary legisla-

tion and enforcement procedures are manifestly unsuccessful in prevent-

ing such social pharmacological behaviour in modern societies. The sanc-

tioning of some modulators of ”escape”, such as ethanol, with the disap-

proval or legal taboo of other more efficacious substances is difficult to

understand for some people.

Because the use of psilocybin-containing hallucinogenic mushrooms

possibly may result in adverse effects, or at least induce uncontrolled

action in the user, many countries have wished to restrict the use of these

mushrooms. However, the legal frame-work to reach this goal is not easy

to construct.

Three strategies of approach seem to be available to the authorities to

restrict the illicit use of hallucinogenic mushrooms. These are (i) restric-

tions based on fungal types; (ii) restrictions based on the presence of

specified chemical constituents of the fungi, or contained within extracts

of preparations of the fungi; and (iii) restrictions based on hallucinogenic

activity. All approaches have their specific merits and pitfalls. The merits

and pitfalls of these legal approaches have been extensively discussed by

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

Hall (1973) in relation to the problem of legislating against hallucino-

genic mushrooms.

From a legal point of view, it might be useful to know at what stages

of the life cycle of mushrooms psilocybin and psilocin can be detected.

To test this question scientifically, Gross (2000) cultivated Psilocybe

cyanescens mushrooms from their spores in a controlled setting, and ana-

lysed the various developmental stages of the mushroom for psilocybin

and psilocin. No hallucinogenic compounds could be found in spores and

in the early mycelium. The mycelium knot stage was the earliest point in

time when the Psilocybe culture could be shown to contain psilocybin

and psilocin. Subsequently, Gross (2002) confirmed that psilocybin and

psilocin could be identified in material of Psilocybe mushrooms at later

stages of development (mycelium, primordia, and mature fruit bodies).

These materials were confiscated by the authorities from illicit mushroom

growing operations. Although spores contain no psilocybin and psilocin,

it is evident that these mushroom tissues may produce mycelium, primor-

dial, and mature mushrooms with the hallucinogenic compounds when

cultivated.

In general, the main problems associated with attempting to produce

an effective legislation controlling the use of hallucinogenic fungi are

related either to the necessity of making exact mycological identification,

or the requirement of using chemical analytical techniques for the identi-

fication of the specific hallucinogenic compounds. Identification of

mushrooms is very difficult, and is complicated by academic controver-

sies on taxonomy. This severely complicates the situation as possession

of fungal species producing hallucinogenic mushrooms or their precur-

sors might be a criminal offence. During later years, DNA-based molecu-

lar techniques based on the polymerase chain reaction (PCR) have been

developed to identify the various species at the nucleic acid level (Nugent

and Saville, 2004; Maruyama et al., 2006). Lately, Linacre et al. (2002)

discussed the use of DNA profiling to identify presence of 'magic mush-

rooms' in forensic material. Chemical analysis requires another type of

expertise. A reasonable high degree of analytical skill is required to posi-

tively identify the presence of these compounds, particularly those pre-

sent in small concentrations (Hall, 1973). In both these cases, the authori-

ties have to consider the question of “possession” in great detail. Another

question that has to be dealt with, if the legislation is dealing with com-

pounds rather than mushrooms, is what to do with compounds capable of

being converted into a substance with hallucinogenic properties.

The problems were exemplified with the more than 60 individual Aus-

tralian drug abusers charged with offences concerning fungi containing

psilocybin or psilocin in 1972. In Australia, the non-traditional use of

psychoactive mushrooms became popular sometime between 1969 and

1975, whereas they became popular in New Zealand a few years later

(Allen et al., 1991). This development stimulated a legislative develop-

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

ment in the area, but the laws differ over the country as drug abuse legis-

lation and enforcement systems are approved for each (nine) individual

Australian State or Territory individually. The isolated compounds psilo-

cybin and psilocin were declared drugs in Tasmania already in 1965.

Only a single state in mainland Australia, Queensland, has declared a

specific fungus as being a prohibited drug (on May 8, 1971). The species

in question is Psilocybe cubensis (Hall, 1973). A few years later, Psilo-

cybe mexicana and Psilocybe cubensis were declared prohibited plants in

New Zealand by the Drug Act of 1975. Interestingly, none of these Psilo-

cybe species can be found growing in New Zealand. When it was recog-

nised that psilocybin-containing mushroom grows on the islands, an

amendment to the drug Act declared all species of the genera Psilocybe

and Panaeolus as prohibited fungi in 1988.

Although each country has a separate system for listing and classify-

ing substances classified as controlled drugs, most European countries,

including the Nordic countries, consider the isolated compounds psilocy-

bine and psilocine as such controlled substances under Schedule 1 of the

1971 UN Convention on Psychotropic Substances (European legal data-

base on drugs, 2008). At the national level, it should be noted that the

classification can be conditional.

However, the control of the mushrooms themselves is interpreted in

many different ways across Europe. In Denmark, cultivation, possession

and sale of hallucinogenic mushrooms are specifically prohibited by Dan-

ish Executive Order BEK nr 698 of 31/8/93, “Bekendtgørelse om eu-

foriserende stoffer”. In Finland, cultivation, possession and sale of the

hallucinogenic mushrooms is treated as narcotics offence according to

Decree 1603/93, with severity according to the quantity. In Norway these

mushrooms are prohibited according to the Regulation related to Narcot-

ics ("Forskrift om narkotika m.v."). There is no separate, national catego-

risation of the substances, but Norway has adopted the categorisation

used by the UN conventions. In Sweden the legal situation for hallucino-

genic mushrooms is a bit more complicated. Sweden lists its controlled

substances in the law “LVFS 1997:12 (Föreskrifter om ändring i Läke-

medelsverkets föreskrifter om förteckningar över narkotika”). According

to the Ordinance on the Control of Narcotic Drugs (1992:1554) those

parts of the fungi Psilocybe semilanceata and Psilocybe cubensis growing

above ground shall be considered to be narcotic drugs for the purposes of

the Narcotic Drug Punishment Act (1968:64). The same shall be the case

for other fungi containing psilocybin or psilocin, if the fungi have been

cultivated or if they have been dried or prepared in other ways. It could

also be noted that in Sweden, cultivation of narcotic drugs is punishable

according to the Narcotic Drugs Punishments Act (1968:64). These legis-

lations indicate that there is a potential for that some of the mushrooms

shown by Table 4 and growing in the Nordic countries may be handled

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

differently be the legal system in the Nordic countries, depending on how

the mushroom has been handled.

5.3. Market

Of the mushrooms that have been identified to contain hallucinogenic

compounds (Table 4) none is identified as a traditional edible mushroom.

Although they might not be toxic, many do not have a pleasant taste, and

others are small or rare. Hallucinogenic mushrooms might have a role in

religious ceremonies. In his extensive systematic revision of the genus

Psilocybe, Guzmán (1983) describes an episode when he in 1958 ate the

hallucinogenic. Psilocybe cubensis in an Indian religious ceremony held

in a very small town called Rancho El Cura, near Huautla de Jiménez. In

his hallucinations he saw people, friends, and relatives who talked to him

although he knew he was alone sitting on the ground in a corner of an

Indian house. He also saw a “human castle” in the corner of the room,

smiling and saying “come to me, do not be afraid”. This castle was his

mushroom dryer. The absolute majority of the hallucinogenic mushrooms

available on the market are, however, intended to be used for recreational

purposes.

According to Mace (1979) and Badham (1984), the quality of hallu-

cinogenic mushrooms on the black market is highly unreliable and a

gamble of the worst sort for the purchaser. Not only is the variation in

psilocybin concentration greater (Bigwood and Beug, 1982), but the

buyer takes the risk of purchasing adulterants. One American study from

the 1970´s reported that of 333 specimens, 25% were inert, 53% were

Agaricus bisporus (J. Lange) Pilat adulterated with LSD, 1% were Agari-

cus bisporus plus PCP, 4% were Agaricus bisporus plus LSD and PCP,

and 15% were hallucinogenic Psilocybe sp. (Ratcliffe, 1974). It is not

known whether this type of fraud is equally common today and in the

Nordic countries. Additionally, street "psilocybin" has frequently been

found to be LSD or other, mostly unidentified compounds (Johnson and

Gunn, 1972; Brown and Malone, 1973, 1976; Kok et al., 1973; Mattke

and Steinigen, 1973).

Since mushroom-growing kits can be purchased over internet or on

the black market, it should be kept in mind that many psychoactive mush-

rooms are grown in vitro and sold on the illicit market. Apart from fresh

or dried mushrooms, other unconventional preparations of Psilocybe

mushrooms on the market include crushed dried Psilocybe mushroom in

honey, "blue mead" (honey with blue Psilocybe mexicana mushrooms)

and pizza with Psilocybe mushrooms, to mention a few (Bogusz et al.,

1998). More recent description of the local mushroom market is given in

the review of Supprian et al. (2001).

6. Summary of biological effects

of psilocybin and psilocin

This section does not intend to review the extensive literature on the

pharmacological and toxicological effects available on psilocybin and

psilocin. It only aims at presenting the most characteristic properties of

the compounds in relation to effects observed in humans. Animal data

will only be mention as supporting information.

6.1. Pharmacokinetic

In the human body, psilocybin from hallucinogenic mushrooms is rapidly

metabolised to the active compound psilocin, presumably via a first pass

effect by hepatic metabolism, and then easily taken up by tissues and

exert a multitude of pharmacological effects (Hasler et al., 1997). The

absence of reliable chemical analytical methods for psilocybin in plasma

have not made it possible to show the absence of psilocybin in the blood

during the active phase of the hallucinogenic experiences, and confirm

that psilocin is the active metabolite.

Psilocybin and psilocin are stoichiometrically equivalent in potency.

Pharmacokinetic studies have shown that slightly more than 50 percent of

orally supplied psilocin is absorbed, and its activity distributed uniformly

in the body, including the brain (Kalberer et al., 1962; Hopf and Eckert,

1969). Serum levels (Cmax commonly in the region 4–21 ng/ml) and

pharmacological activity (from 4 ng/ml in serum) peak within 2 hours

after the psilocybin intake, and then decline over the next 3 to 4 hours

(Hasler et al., 1997; Lindenblatt et al., 1998; Halpern, 2004). As the aver-

age half-life of psilocin is reported to be about 2.5–3.0 hours, the psilocin

concentration reaches the limit of quantification within around 6–7 hours

(Hasler et al., 1997; Anastos et al., 2005). Psilocin is excreted in urine,

mainly as glucuronide and unchanged psilocin (Sticht and Käferstein,

2000; Hasler et al., 2002; Kamata et al., 2003). Other metabolites found

in lower quantities include 4-hydroxyindole-3-yl-acetaldehyde, 4-

hydroxyindole-3-yl-acetic acid, and 4-hydroxytryptophol (Holzmann,

1995; Hasler et al., 1997). A possible metabolic scheme for psilocybin in

humans has been suggested by Passie et al. (2002).

Psilocin is an indoleamine that is structurally related to the neuro-

transmitter of the central nervous system serotonin (5-hydroxytryptamine;

5-HT) and the drug lysergide (LSD-25). The psychotomimetic effects

observed after exposure to psilocybin/psilocin result from stimulation of

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

5-hydroxytryptamine receptors, especially the 5-HT2a receptor (Strass-

man, 1992; Vollenweider et al., 1998). It is discussed in the scientific

community whether also other receptors are influenced by psilocy-

bin/psilocin. In contrast to LSD, psilocybin has no affinity for dopamine

receptors (Creese et al., 1975).

Using PET methodology to study brain metabolism of psilocybin,

Gouzoulis et al. (1999b) found no increase of global brain metabolism

after per oral exposure to 0.2 mg/kg psilocybin, whereas Vollenweider et

al. (1997) found a general increase of cortical metabolism in various parts

of the brain after slightly higher exposure levels (0.26 mg/kg).

6.2 Pharmacological effects in humans

Psilocybin and psilocin are stoichiometrically equivalent in potency.

Therefore, the symptoms induced by psilocybin-containing mushrooms,

psilocybin or psilocin are more or less equivalent. It is believed that the

former is dephosphorylated to psilocin in vivo. Psilocybin is an inhibitor

of serotonin, the major indolic neurotransmitter of the central nervous

system. It is also an autonomic stimulant, leading to characteristic mydri-

asis, piloerection and hyperthermia. The mono- and demethylated ana-

logues baeocystin and norbaeocystin are much less explored pharmaco-

logically.

Already in the first publication reporting the isolation of psilocybin

from hallucinogenic mushrooms, it was stated that per oral application of

the compound in man produce similar psychotropic effects to the mush-

room Psilocybe mexicana (Hofmann et al., 1958a). Depending on the

individual, an intake of 4–10 mg psilocybin/psilocin, or 1–2 g of the dried

Psilocybe mushroom, results in effects searched for. These psychic ef-

fects include stimulation, enhanced ability for introspection and altered

psychological functioning in the direction of Freudian primary processes,

also known as hypnagogic experience and dreams (Passie et al., 2002).

Especially noteworthy are generally pleasant sensation of intellectual and

bodily relaxation and detachment from the environment (perceptual

changes such as illusions, synaestesias, affective activation, and altera-

tions of thought and time sense), without producing a setback. The central

effects obtained become apparent in about 20–30 minutes and develop

with a startling rapidity over the following 20 minutes. Higher doses, at

least 6 mg, produce more profound changes associated with altered tem-

poral and spatial perception, an introspective state, and a variety of visual

effects. Illusions and hallucinations may be experienced (Cerletti and

Hofmann, 1963).

A difficulty with the hallucinogenic compounds is that the subjective

experiences produced vary considerably from person to person and within

the same person on different occasions. These experiences are markedly

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

influenced by the expectations of the user and the setting in which the

drugs are taken, as well as by the personality structure and mental status

of the user (Franz et al., 1996). There is frequently time distortion (sub-

jective slowing) under influence of psilocybin/psilocin. The activity pla-

teau rarely lasts much more than an hour and is characterized by altera-

tions in spatial and temporal perception, often with distortions in aware-

ness of body image. Positive expectations usually lead to pleasant

experiences and, conversely, larger doses in users with anxiety or uncer-

tainty may allow adverse experince. In the absence of visual and auditory

input (as with night-time isolation) the experience can be largely fantasy

and rich with hypnogogic imagery. Gradual recovery requires an addi-

tional two to three hours and there is a good recall of the phenomena

experienced (Shulgin, 1980).

There are a number of general features which are characteristic of the

psychedelic reaction. Perceptual changes include illusions, pseudo-

hallucinations, and hallucinations. Vision seems most affected. Most

common are illusions. Objects, pictures, or patterns seem to come alive,

shift, ripple, or become wavy. Depth relationships are altered so that two-

dimensional objects appear three-dimensional.

More common than true hallucinations, are pseudo-hallucinations in

which the user has a visual experience without any appropriate sensory

cue, but he knows his visions are subjective, a result of the influence of

the drug. He may se geometric figures, kaleidoscopic shapes, or flashes

of light. He may see dream-like sequences of panoramic visions related to

previous life experiences, tranquil scenes, or imagined horrors. True hal-

lucinations are rare but may assume almost any form.

Colours appear more brilliant and intense. Nuances of colours are of-

ten experienced as emotionally meaningful and exceptionally beautiful.

Changed perception in the other senses is not as dramtic, but taste, touch,

smell, and hearing all seem to become more acute.

A remarkable feature of the hallucinogenic drug reaction concerns the

translation of one type of sensory experience into another, or synesthesia.

Sounds or music may be experienced visually or as bodily vibrations. The

user may think he can feel or taste colours and images. Perception and

mood become interwoven. Colour may come to represent a particular

emotion and induce it.

When psilocybin was given to healthy volunteers, psychological

symptoms reported were emotional alterations (100%), disor-

ders/alterations of consciousness (91%), depersonalisation (84%), percep-

tual alterations (75%), disorders/alteration of volition and psychomotor

behaviour (34%), body image distortions (25%), disorders/alteration of

attention (22%), disturbances in thought processes (22%), and disorders

of memory (19%) (Parashos, 1976–1977; Spitzer et al., 1996; Vollenwei-

der et al., 1999). Similar symptom picture was noted in schizophrenic

patients consuming psilocybin, as illustrated by two case reports by

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

Nielen et al. (2004). The cases illustrate that in schizophrenic patients

hallucinogenic mushrooms may induce an acute psychotic state that ne-

cessitate hospitalisation (Nielen et al., 2004). The psychotic symptoms in

volunteers appeared within 20 to 30 minutes after oral ingestion, lasted

for about two hours and subsided completely within six hours. There are

no epidemiological on long-lasting psychiatric complications (Supprian

et al., 2001).

However, psilocybin is also an autonomic stimulant, leading to char-

acteristic mydriasis, piloerection, irregularities in heart and breathing rate,

and hyperthermia. Similar pharmacological effects have been docu-

mented in mice, rats, rabbits, cats, dogs and rhesus monkeys (Cerletti,

1958; Horibe, 1974). The mono- and demethylated analogues baeocystin

and norbaeocystin are much less explored pharmacologically.

Emotional lability, extreme mood swings, and spontaneous emotional

discharges are common. The user may become profoundly depressed,

anxious, fearful, giggly, euphoric, serene, or ecstatic during a single drug

experience. Occasionally, blunting of affect, suspiciousness, hostility, or

suicidal urges may be felt. The user can usually converse rationally when

pressed to do so and can subsequently recall much of his drug experince.

Importantly, it has not been established whether the potential benefits

of the use of psychedelic drugs justify the risk of adverse reactions. From

the users point of view, out of all mushroom users in a study 73% re-

ported some positive effects of the use and approximately 45% reported

only positive effects. Only 5% reported predominantly negative effects

(Thompson et al., 1985). In a double-blind study on hallucinogen-naïve

subjects, Griffiths et al. (2006) recently showed that psilocybin under

supportive conditions give rise to experiences similar to spontaneously

occurring mystical experiences that were rated very positively by the

volunteers. Negative effects were rare. Higher rates of adverse reactions

have been reported in habitual drug users (Schwartz and Smith, 1988).

6.3. Hallucinogenic experience and potential toxicity

The magic mushrooms are inconspicuous and are not likely to attract the

interest of anyone looking for food mushrooms. However, intoxications

due to ingestion of hallucinogenic mushrooms thought to be edible mush-

rooms have been reported. Ancient or historic evidence of cerebral my-

cetisms induced by accidental ingestion of psychoactive mushrooms in

various parts of the world has been reviewed by Allen et al. (1991). The

authors of this review article points out that outside of a few intoxications

caused by Psilocybe cubensis and Psilocybe semilanceata (Cullinan and

Henry, 1945; Charters, 1957; Stein, 1958; Wasson, 1959; Stocks, 1963;

Heim, 1971; Harries and Evans, 1981), the majority of all intoxications

that occurred before the deliberate recreational use of hallucinogenic

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

mushroom species was caused by various species of Panaeolus, with the

exception of Japan where some of the inebriations were the result of in-

gesting Gymnopilus species and some that were attributed to the ingestion

of Stropharia caerulescens. Because of some similarities with the edible

mushroom Marasmius oreades (Bolt.:Fr.) Fr., Inocybe aeruginascens has

subsequently caused accidental hallucinogenic poisonings in previous

East-Germany and Hungary (Drewitz, 1983; Gartz and Drewitz, 1985,

1986; Gartz, 1986, 1989). Other cases of miss-identification of food

mushrooms have been described by Bigwood and Beug (1982), Rold

(1986), Raff et al. (1992) and Calvino et al. (1998).

Magic mushrooms are usually collected by persons solely interested in

mushrooms containing hallucinogens. These mushroom collectors fre-

quently rely on only two identifying characteristics: a habitat on or near

dung in pastures, and stems that stain blue on handling. Since even pro-

fessional mycologists have difficulties identifying many of these small

brown mushrooms, it is no wonder that the uninformed mushroom hunter

makes mistakes. Some of these mistakes may be of low risk, others may

lead to poisoning, which sometimes may be severe.

Other risks to become intoxicated by hallucinogenic mushrooms are

usually related to natural variation in psilocybin content of the mush-

rooms (see, Table 4; differences between flushes, differences between

wild and cultivated mushrooms, etc.), miss-quantification of dose (mush-

room weight and number) or exaggerated intake (e.g., Harries and Evans,

1981), and differences in individual tolerance to hallucinogenic mush-

rooms (Beug and Bigwood, 1982; Bigwood and Beug, 1982). Stamets

(1996) has calculated the threshold for intoxication to approximately 40

g psilocybin/kg body weight, which typically would correspond to about

1–2 g of dried mushroom, or approximately 4 to 20 mg psilocybin. Allen

et al. (1991) have drawn similar conclusions, whereas others have indi-

cated that clinical doses usually require larger amounts (Stein, 1958; Lin-

coff and Mitchell, 1977; Weil, 1980).

It should be noted that several of the mushrooms mentioned in Table 4

and 5 contain other bioactive constituents in addition to the hallucino-

genic compounds. These constituents can of course influence the intoxi-

cation syndromes described. For example, the most common hallucino-

genic mushroom in the Nordic countries, Psilocybe semilanceata, con-

tains the biogenic amine phenylethylamine (Beck et al., 1998).

In Mexico, where hallucinogenic mushrooms has a natural niche in

everyday life, there are persons who have consumed hallucinogenic

mushrooms since their youth until they die over 70 years of age, without

apparent physical illness (Allen et al., 1991). The acute toxicity of psilo-

cybin/psilocin is very low (Cerletti, 1959; Hofmann, 1960; Auert et al.,

1980; Leuner, 1981; Flammer and Horak, 1983; Gartz and Drewitz, 1986;

Holm et al., 1997). In a recent double-blind, placebo-controlled dose-

effect study with psilocybin in healthy subjects, the investigators found

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

no cause for concern that psilocybin is hazardous with respect to somatic

health (Hasler et al., 2004). Damage to the body may, however, occur

when the perception of reality of an individual is influenced in such a

way by the hallucinogenic mushrooms that he or she behaves in a risky

way. For instance, Asselborn et al. (2000) describe an incident where two

girls ingested a handful of Psilocybe mushrooms (species undefined)

together with soft drinks. One of the girls tried to fly from a window on

the second floor, fell to the ground and fatally fractured the scull. Chemi-

cal analysis of the mushroom revealed around 11 000 mg psilocybin and

5 000 mg psilocin/kg mushroom. Post-mortem studies of heart blood

revealed 0.09 mg psilocin/mL, one third of which was free psilocin. The

compound was also quantified in femoral venous blood, urine, bile, liver,

kidney and lung. No psilocin, or other drugs, was found in the hair, indi-

cating that the girl had no history of drug use. It should be mentioned,

however, that there are two reports on severe toxicity, although the role

of the hallucinogenic mushrooms for these cases is not totally clear. In

one case rhabdomyolysis was reported in a hepatitis C-infected man with

a history of heroin, opiate and cannabis abuse (Bickel et al., 2005). In the

other case (Gerault and Picart, 1996), a 22-year old man used to alcohol

consumption and cannabis smoking died after first having consumed 30–

50 raw mushrooms (most likely Psilocybe semilanceata) when picking

them, another 10 raw mushrooms three hours later, and a cup of tea pre-

pared on mushrooms another two hours later, although he at this time did

not feel well. When he got unconscious and was taken to hospital, there

was no care to get. Having been transported back to his home he died. A

standard forensic analysis on body fluids and tissues were performed

without identification of any drugs and foreign substances except psi-

locin. The level of psilocin in the blood was 4 μg/mL. Four friends who

joined the victim drinking tea prepared on the mushrooms collected by

the victim showed different symptoms from only feeling drunk to having

colour vision or getting cramp.

The minimum amount of mushrooms required to promote “therapeu-

tic” doses is somewhere between two and six, assuming mushrooms of

high content of psilocybin or psilocin. Agitation and hallucinations may

be seen with 10 mushrooms in one case, whereas 200 may produce only

gastritis in another. Prolonged sympathomimetic effects and psychosis

have been seen with 50 to 60 mushrooms (Hyde et al., 1978). Hollister

and co-workers have described both the time sequence of onset of clinical

effects from psilocybin among 16 subjects exposed orally to doses be-

tween 60 and 209 g/kg, and the frequency of response among 19 sub-

jects given an oral dose of 150 g/kg (Hollister, 1961; Hollister and

Hartman, 1962; Hollister et al., 1960). The following clinical effects were

mentioned for psilocybin intoxication in humans:

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

0–30 min Slight nausea, giddiness (light headed), abdominal dis-

comfort, weakness, muscle aches and twitches, shivering,

anxiety, restlessness, and a numbness of lips.

30–60 min Visual effects (blurring, brighter colour, sharper outlines,

longer after-images, visual patterns with closed eyes). In-

creased hearing, yawning, sweating, facial flushing. De-

creased concentration and attention, slow thinking, feelings

of unreality, depersonalisation, dreamy state. Incoordina-

tion, tremulous speech.

60–120 min Increased visual effects (coloured patterns and shapes,

mostly with eyes closed). Wave-motion of viewed sur-

faces. Impaired distant perception. Euphoria, increased

perception, and slowed passage of time.

120–240 min Waning and nearly complete resolution of above effects.

Returning to normal within 4–12 hours. Other effects often

included decreased salivation and appetite; uncontrollable

laughter, transient sexual feelings and synethesis.

Similar symptoms and absence of adverse toxic effects in humans have

been observed by others (Isbell, 1959; Gouzoulis-Mayfrank et al., 1999b)

In cases of intoxication, it might be useful to distinguish between the

primary toxic effects and the secondary effects resulting due to the ex-

posed persons emotional reactions to the primary symptoms of intoxica-

tion. The primary toxicological actions of psilocybin and related com-

pounds are sympaticomimetic adrenergic symptoms and mental effects.

Sympaticomimetic adrenergic symptoms include mydriasis, flushing and

hyperreflexia, and elevated blood preassure, heart rate, frequency of res-

piration and body temperature; also tremor, dizziness, nausea, dryness of

the mouth and tiredness may occur. The mental effects include euphoria,

experiences of unreality, altered conception of time, feeling of happiness

and clearness of mind. As a consequence of the previous reactions, illu-

sions, pseudohallucinations or real hallucinations may occur. Table 6

summarizes most of the case reports on acute psychiatric symptoms after

consumption of psilocybin-containing mushrooms. It should be stressed

that most cases described in Tables 6 and 7 themselfes chose to consume

the hallucinogenic mushrooms, that is, it is a recreational activity. The

five reported cases from Japan (Musha et al., 1986), where Psilocybe

argentipes were consumed, were, however, accidental cases. None of

these consumers expected to have the type of experience they had.

Although primarily psychological effects are associated with consump-

tion of psilocybin-containing mushrooms, depressive or paranoid reactions,

mood changes, disorientation, and an inability to distinguish between real-

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

ity and fantasy may sometimes occur (Leary et al., 1963; Mills et al., 1979;

Weil, 1980; Grinspoon and Bakalar, 1981). Understandably, other routes of

exposure might be significantly more dangerous. There are case reports on

persons that have extracted Psilocybe mushrooms and experienced severe

toxic symptoms after having injected the extract intravenously (Sivyer and

Dorrington, 1984; Curry and Rose, 1985).

Fatal intoxications from the exposure to hallucinogenic mushrooms

are rare (McCawley et al., 1962; Gonmori and Yoshioka, 2003). The first

case was a 6-year-old child who developed hyperthermia and status epi-

lepticus following ingestion of Psilocybe baeocystis (McCawley et al.,

1962). In the latter case a 27-year-old man was found in an irrigation

canal. Cultivations of Psilocybe subcubensis was found in his home and

psilocybin/psilocin were detected both in the mushroom, and in body

fluids of the diseased man. It was suggested that the case had been influ-

enced by the hallucinogenic substances and died of cold temperature in

winter time.

A death of an 18-year-old male living in Hawaii, was in commercial

media declared to have died due to consumption of ten hallucinogenic

mushrooms. Later investigations into his death, however, showed that the

youngster died of an overdose of heroine. Psilocybin or psilocin were not

detected in the stomach content, nor was amatoxins (Allen, 1988).

An unexpected risk was highlighted by two young mushroom hunters

being shot in Florida when looking for their afterthought treasure (Lin-

coff and Mitchel, 1977).

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

Table 6. Case reports on acute psychiatric symptoms after eating psilocybin mushrooms.

Case Exposure Symptoms Reference

20-year-old woman The patient had smoked hasch during the last two years. She

had also injected amfetamin, tried LSD and experimented with

other drugs. As the only exposure, she had consumed 15 mush-

rooms (probably a Psilocybe sp.) a few days before the symp-

toms.

The first two to three days after the mushroom consumption the woman had a normal

behaviour. After that the got confused and tore of her clothes. She came into a delirium-

like state and could not be reached until when given electroconvulsive therapy.

Bergman and Karlsson, 1995

One women and one

man - self-test 2 500 mg dried P. semilanceata (12 mg psilocybin), 7 500 mg

dried P. mairei (150 mushrooms) (12 mg psilocybin, or 15 mg

pure psilocybin

The first symptoms of intoxication appeared already 30 min after mushroom consumption

and were a pricking sensation in the hand. The symptoms developed into intense tired-

ness, apathy, and lack of attention. After another 30 min an euphoric stage was reached,

including the experience of being easily mobile, like in a dream. During this period the

tested persons seemed to be in very good mood but started to focus on theirself and

became hungry. After another 30 min the test objects had difficulties to concentrate. Then

the persons entered a dream-like stage where optical artefacts were common - colours

became more intense and were sensitised by musik. This stage continoud until around 5–

6 hours after the intake of the test samples.

Auert et al., 1980

18-year-old man The person had consumed hallucinogenic mushrooms (Psilo-

cybe semilanceata) frequently during the last month. The patient was hospitalised efter seizures followed by cardiopulmonary arrest. Despite

resuscitation and intubation, he remained unconscious, with periodic hyperkinetic activa-

tion, dilated pupils, and massive, repeated vomiting in the first three hours. An ECG after 3

hours showed regular sinus rhythm 100/min, Wolff-Perkinson-White syndrome, early

anterolateral myocardial infarction, and hypokinesis of the para-apical segment of ven-

tricular septum

Borowiak et al., 1998

26-year-old man The patient had recently become a religious 'back-to-nature'

freak. He had heared inner voices that gave him a mission. He

had experimented with various drugs, but during the last two

years only with pot and occasional amphetamine tablets - but

neither of them during the last six months. At that time he had

started using dried P. semilanceata.

The mushroom intake resulted in heightened awareness, perceptual distortion, and visual

hallucinosis. Davies, 1979

21-year-old man The patient had tried marihuana/hasch a few times. One year

appart he consumed a pizza with 75 small hallucinogenic mush-

rooms collected in Rogaland, Norway, a pizza with 75 large

mushrooms, respectively.

A feeling of happiness but without hallusinogenic parts appeared after consumption ov the

first pizza dish.

After the second dish, he shortly felt being moved into un unrealistic world, and time

perception dissappered. He experienced that his house was on fire and was terribly afraid.

After some hours the body started to skjelva and fradga started to flow from his mouth.

Gundersen, 1979

16-year-old woman The patient had been offered unknown amounts of raw P.

semilanceate at a party. Two hours later she experienced unpleasant hallucinations. Later on she became "desori-

enterad", and her mood oscillated between apathy andhyperactivity. Pupills were dilated. Kvambe and Edenberg, 1979

35-year-old man The patient had consumed an unknown amount of raw P. semi-

lanceata together with alcohol. The patient experienced colourfull hallucinations, were unable to sit still and showed

severe signs of anxiety. He also had thoughts of suicide. Kvambe and Edenberg, 1979

27-year-old man The patient had tried LSD years earlier, but was brought into the

hospital 2½ h after consuming the cocking water of P. semi-

lanceata.

The patient was afraid and agitated, and had visual hallucinations - colours being extremly

vivid. Hyde et al., 1978

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

20-year-old man Although the patient had not used drugs for 6 months, he was

not new to drugs. He once tried 20 mushrooms with friends and

experienced pleasant effects for 6-8 hours. He continoued to

take similar doses several times during over the ensuing week,

and at the same time depriving himself of sleep and food intake.

He then took a final major dose of 50–-60 mushrooms.

He was brought into the hospital within 24 hours after the consumption in a dreamy

euphoric state. His speech was restricted. Sympatomimetic signs were present, marked

mydriasis, brisk hyperfeflexia, hypotonia, a tachycardia of 104 per minute and facial

flushing. In another 24 hourshe became fareful and aggressive. At 48 hours he showed

spasmodic stupor and excitation, and at 72 hours he showed cataleptic phenomena and

began to display episodes of agitation and fear.

Hyde et al., 1978

Young male student The patient consumed 15–25 P. semilanceata. One hour after consumption of the mushroom he first became giggly, well disposed and

talkative.This was followed by a period when he felt threathened, and later on time began

to go wrong, and colourfull hallucinations occurred.

Hyde et al., 1978

7 males (17–23 years

old) All patients were regular users of Psilocybin mushrooms. One of

the patients used also other drugs. Two patients had consumed

20–30 raw mushrooms, the rest around 100 mushrooms.

Six of the patients presented within four hours of taking the mushrooms, the remainng

patient after 2 days. The patients in general reported pleasant stimulatory effects that were

accompanied by frequent visual, auditory and tactile hallucinations. One patient was

disorientated, unco-operative and ran around naked. The presented complains were mild

and were of nausea, cramping abdominal pain, feeling of stiffness and the unpleasant

sensation of swelling in the limbs, dry mouth and tachycardia. The effects were over in 10

hours.

Mills et al., 1979

36 year-old man The man consumed 6–7 Psilocybe argentipes with soup to

supper. The man was initially dizzy, and he felt unreal. He became unable to stand up and later

experienced hallucinations. Later on the patient was impossible to contact, allthough he

was awake all the time.

Musha et al., 1986

35 year-old woman The woman consumed 3 Psilocybe argentipes with soup to

supper. The woman became dizzy, experienced mild hallucinations, and later became sleepy. Musha et al., 1986

70 year-old woman The man consumed Psilocybe argentipes with soup to supper. The women became dizzy, experienced mild hallucinations and got scared that she was

just dying. Musha et al., 1986

62 year-old man The man consumed 3 Psilocybe argentipes with soup to break-

fast. The patient experienced hallucinations and had unsteady walk. The experience was

unpleasant and he was frightened of becoming insane and of death. Musha et al., 1986

55 year-old woman The man consumed 2 Psilocybe argentipes to supper. The patient first felt dizzy and giddy, and euphoric, and later experienced hallucinations.

She felt anxiety and fear of death. Musha et al., 1986

9 women and 35 men

with a mean age of

17.6 years (11–33 y.o.)

Of 35 patients able to quantify the consumption of P. semi-

lanceata, a mean of 87 mushrooms per person were ingested

(8–300). Ten patients brewed the raw mushrooms up in boiling

water and drank the resulting tea while the remainder consumed

the raw mushrooms (in 4 cases after drying). Eight patients had

also ingested alcohol (in 1 case in large quantities) while 1 hand

smoked marijuana.

Eleven patients had vomited prior to appearing at hospital on average 3.8 h (range 1–8 h)

after mushroom consumption, while 12 others had experienced nausea and 9 patients

experienced upper abdominal pain. Eight patients exhibited flushing of the face and neck,

10 patients had tachycardia (>100 bpm), 17 patients were hypertensive (diastolic blood

preassure >100 mm Hg), and 16 patients showed hyperreflexia. Seven patients were

aggressive, 5 patients were restless and hyperkinetic, 2 patients were disoriented, 6

patients were drowsy but easily roused, 4 patients were euphoric, 4 patients appeared

fully conscious but were withdrawn, 26 patients described their experience as frighening.

Abnormalities of perception was registered by the majority of the patients, sometimes full

blown hallucinations occurred

Peden et al., 1982

21-year-old man The patient had consumed around 30 psilocybin-containing

mushrooms. The patient was excited and anxious; he vomited on arrival at the hospital. He had halluci-

nations connected to previous bad experiences, he became restless and could not be

addressed. His skin got varm and dry, blood pressure (diacystolic) was high, heart rate

was high and the body temperature high.

van Poorten et al., 1982

44 men and 5 women

of an average age of

17.5 years (12–28 y.o.)

The patients were presented to the hospital at various times

after consumption of different quantities of P. semilanceata. Four

of the patients had also ingested alcohol.

Fortyone (83.7%) of the patients had evidence of sympatomimetic stimulation including

mydriasis and tachycardia, while 47 (95.9%) had experienced or were experiencing

euphoria and/or visual hallucinations.

Young et al., 1982

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

2 individuals The patients ingested an undetermined quantity of Gymnopilus

validipes which they mistook for the an edible mushroom The patients quickly developed dysphoria, dizziness, and abnormal colour vision shortly

after consumption of the mushroom. Within an hour the individuals experienced difficulty in

expressing their thoughts, anxiety, time distortion, and vivid visual hallucinations.

Hatfield et al., 1978

3 Japanese men After dinner, two patients consumed 5 or 6 cooked Psilocybe

subaerulipes, respectively, whereas the third patient consumed

4 cooked fruitbodies and three raw. They all had the intention to

consume the selected species.

The patients experienced nausea, , became warm and sweaty, and experienced paralysis

of the limbs (maximum at 3 h after intake). Paralysis of the feet disappeared within another

1½ h but the fingers were affected for another few hours. Two of the patients had halluci-

nations and one of them felt depressed. A fourth person who ingested only one mushroom

experienced on effects. All recovered within 24 hours, but one patient was taken to hospi-

tal were a stomach wash was performed after emesis.

Yokoyama, 1973

A 56-year-old man The man consumed 2–3 fried Pholiota spectabilis (Gymnophilis

spectabilis) in the belief it was Armillaria mellea, an edible

species.

Fifteen minutes efter mushroom consumption he felt disconnected and woozy. His head

felt numb, and his vision was blurred. The size of the room changed, things became

shimmery, and appeared yellow with dark centers. The intellect was sharp, but memory

during the hallucination poor. He was unsteady on his feet and felt slight nausea and

abdominal distress. His wife who tried a small portion of mushrooms felt giggly, and

vomited. Both recovered within a few hours.

Buck, 1967

A 58-year-old woman A neighbor to the man above consumed a tablespoon of fried

Pholiota spectabilis (Gymnophilis spectabilis) in the belief it was

Armillaria mellea, an edible species.

Fifteen minutes efter mushroom consumption she felt dissy, was unable to move her joints

freely, felt chilly and then hot, and when she closed her eyes things seemd far away. She

experienced no colour sensation. She was unable to co-ordinate. On hearing her

neighbors experience she vomited. Recovery within a few hours.

Buck, 1967

4 men (16–29 years

old) Wheras three of the men had intentionally ingested 40–60

cooked or uncooked Psilocybe mushrooms, one had consumed

around 60 fruit bodies of Inocybe patouillardii.

The patients contacted the hospital because of nausea and being afraid of collaps. Symp-

toms appeared 0.3–5 hours after mushroom consumption and included increased blood

preassure, dilated pupils, blurred vision, auditory hallucinations, disorientation and anxiety.

No pathological changes were found, and patients could leave the hospital 3–6 hours

later, in some cases after given activated charcoal, laxative and fluid.

Satora et al., 2005

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

In summarising the 150 known cases of intoxication from psychoactive

mushrooms in Australia and New Zealand between 1934 and 1989, Allen

et al. (1991) pointed out that only one case required hospital care, and

that was because he had fallen and cut his head. However, three of 150

persons (2%) had suffered prolonged psychological difficulties following

their mushroom experience, two of which were flashbacks. In these cases

a predisposition was acknowledged for two of the people. Therefore, it

could be argued that certain people are psychologically at serious risk

from these substances and must be urged to avoid them (Allen et al.,

1991).

There has been continuing concern as to the long-term effects of psi-

locybin and other hallucinogenic compounds on the human body. The

most notable concerns have been the possibility or recurrent flashbacks.

Flashbacks are spontaneous recurrences of a previous psilocybin experi-

ence after the immediate effect of the drug has worn off and without re-

newed intake of the compound. Table 7 summarizes cases of persistent

psychiatric symptoms described in the literature. Espiard et al. (2005)

described a 18-year old student that appeared at the clinic with perceptual

impairments. These were lasting for 8 months. The patient had a history

of social anxiety and a troubled family situation. He smoked moderate

amounts of cannabis regularly. Perceptual distortions initially appeared

after unique psilocybin consumption (40 mushrooms of the species Psilo-

cybe semilanceata in infusion). During later use of cannabis he re-

experienced the symptoms (objects’ distortions, relief’s modifications,

auditory disturbances with resonance feeling, depersonalisation, dereali-

zation, body lightness or weightiness feeling, spatiotemporal distur-

bances, and inability to distinguish illusion from reality). The flashbacks

started to weaken when the student stopped using cannabis. No somatic

lesions were identified. The flashbacks disappeared six month later after

several months on chemotherapeutica. The prevalence of flashbacks, and

its requirement for expression is difficult to estimate.

Other long-term effects investigated include potential reproductive

toxicity, teratogenicity and mutagenicity. The result of none of these has

given rise to concern. Already in 1967 Rolsten evaluated the effect of oral

administration of 25 mg psilocin per kg body weight on pregnant

C57BL/10 mice and their offspring. The psilocin treatment had no influ-

ence on fertility as determined by pregnancy rate, pregnancy length, and

weight gain. It also did not influence maternal brain weight, liver glyco-

gen, and serum cholesterol, and brain, liver, and heart organ to body

weight ratios, or mean litter weight. Neither were any influences on se-

rum and organ biochemistry of the offspring at birth found (Rolsten,

1967). An American population-based case-control study performed

1989–1991 found no increased risk for neural tube defects due to mater-

nal and paternal periconceptional use of psilocybin/mushrooms/peyote or

other recreational drugs (Shaw et al., 1996).

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

Table 7. Case reports on persistent psychiatric symptoms after eating psilocybin mushrooms.

Case Exposure Symptoms Reference

24-year-old man Two weeks before symptoms he had eaten 25

psilocybin mushrooms together with two pints

of beer

Three month history of daily attacks of tension, anxiety, fear that

something was about to befall him, depersonalisation, palpita-

tions, bounding pulses, dryness of the mouth, and "butterflies in

the stomach". Attacks sometimes accompanied by disturbed vi-

sion.

Benjamin, 1979

25-year-old man A frequent user of cannabis, LSD and 'magic

mushrooms'. He had not used LSD for several

days when he tried 200 mushrooms together

with whisky and smoked cannabis.

He felt euphoric, colours appeared more vivid, and he experi-

enced a loss of time sence. A paranoid and aggressive reaction

developed. He described his reaction as disturbed sleep rhythm,

irritability, spathy and lack of concentration. The patient followed

instructions for treatment badly. Two days later he experienced a

'flashback' accompanied by visual distortions and he became pan-

icky and aggressive. As there was no improvement after 14 days,

he was given four ECT's with beneficial results.

Dewhurst, 1980

22-year-old man Sine puberty the man had used alcohol and

marijuana. He had also tried amphetamine but

stopped using it since he lost weight. Half a

year later i tried magic mushrooms.

Shortly after having consumed 15 Psilocybe semilanceata the

man became unconsious, experienced spasms and a bad trip. Two

months later he went to the doctor for suspected epilepsy. During

the period since the bad trip with magic mushrooms, he had re-

vived som of the experiences from the bad trip. Symptoms in-

cluded heavy heart beat, blurred sight, uncontrolled muscles,

deafened ears.

Holmgaard Kristensen and

Garding Sørensen, 1988

Two cases Conditions of mushroom use not identified. Two of 150 cases of intoxication on New Zealand involved the

precipitation of a severe prolonged paranoid psychosis, eventually

requiring psychiatric treatment for a long period. In both cases

predisposing features were observed but there were clearly no

preexisting psychosis.

Allen et al., 1991

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

No micronuclei were induced in mice exposed to 4, 8 or 16 mg psilocy-

bin per kg body weight (Van Went, 1978). Tolerance to psilocybin (or

cross-tolerance with LSD) might develop, but physical dependence does

not occur (Abramson et al., 1956; Isbel et al., 1961; Abramson and Rolo,

1965; Balestrieri, 1967).

6.4. Hallucinogenic mushroom use in the Nordic

countries

In Norway the first report on the use of Psilocybe semilanceata as deliv-

ering a recreational drug appeared in 1977, and several others have ap-

peared thereafter (Nordbø, 1979, Kvambe and Edenberg, 1979). These

reports described hallucinogenic intoxications of consuming the mush-

room and stimulated investigations into the content of psilocybin and

psilocin in Norwegain mushrooms (Høiland, 1978; Høiland et al., 1984;

Christiansen et al., 1984; also see Table 4). It was concluded that Psilo-

cybe semilanceata is rich in hallucinogenic compounds, and that there is

a marked difference in psilocybin content between samples (Christiansen

et al., 1982). It was also concluded that it is a risk that mushroom pickers

looking for P. semilanceata might by mistake collect several different

toxic mushrooms with a similar structure.

Beck and his colleagues (1998) have discussed the clinical data that

had been collected from hospital case records and sent to the Swedish

Poison Information Centre concerning Psilocybe mushroom poisoning

during the period 1980–1995. The total number of patients was 25, of

which 21 were between 19 and 27 years of age. Five of the cases oc-

curred in 1995. The recorded symptoms in these hospitalized patients

included mydriasis (68%), visual hallucinations (52%), tachycardia

(44%), anxiety (40%), euphoria (24%), agitation (16%), hypertention

(16%), , hyperflexia (12%), flushing (12%), nausea (12%) and flashbacks

(8%). Thus, the symptoms in Swedish patients were the same as those

observed in patients from other countries (Malitz et al., 1960; Peden et

al., 1981, 1982).

Beck and colleagues (1998) also verified the presence of 1000–3 500

mg/kg wet weight psilocybin in Psilocybe semilanceata mushrooms that

had resulted in intoxications at three different locations in Sweden. How-

ever, these investigators also noted that these mushrooms contained the

biogenic amine phenylethylamine (1–146 mg/kg wet weight). The sample

with the highest level of phenylethylamine came from the clinical case of

hospitalization after the ingestion of magic mushrooms. The pharmacol-

ogical mode of action of phenylethylamine is not fully elucidated, but it

has been reported to exert amphetamine-like activity and to have periph-

eral sympathomimetic effects (Schwarts and Smith, 1988; Shulgin, 1980;

Mantegazza and Riva, 1963; Sabelli and Giardina, 1972). The neuro-

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

physiological effects have been related to the enhancement of catechola-

minergic activity (Sabelli and Javaid, 1995). Systemic administration of

phenylethylamine produces behavioral effects in rats and mice (Saavedra

et al., 1970). The serotonergic system is thought to mediate the neuro-

physiological responses to hallucinogens (Glennon et al., 1984; Strass-

man, 1992). It is therefore interesting to note that serotonin receptor

blockade can potentiate the behavioral effect of phenylethylamine

(Goudie and Buckland, 1982). The high amount of phenylethylamine in

the case of mushroom intoxication mentioned above suggests that

phenylethylamine may contribute to the adverese reactions. The much

higher variability in phenylethylamine content as compared with psilocy-

bin is intriguing because it could explain why adverse reactions occur

only in certain cases.

Lassen and co-workers (Lassen et al., 1990, 1992, 1993b) and Holm et

al. (1997) have summarised available information on Danish mushrooms

containing psilocybin, and the use of these mushrooms in society. Up to

1996, the Danish Poison Information center had registered 22 contacts

due to hallucinogenic mushrooms of the species P. semilanceata (Holm

et al., 1997). The reason for contacting the Poison Information center was

mainly negative secondary psychic reactions on the psychomimetic ef-

fects of psilocybin. In seven of these cases the patients experienced hallu-

cinations, showed tremendously anxiety and could not stay calm. The

other 15 cases were milder - dysfori and some anxiety - sometimes fol-

lowed by moderate sympatomimetic or gastrointestinal symptoms. One of

the cases was a young man that experienced flashback phenomena during

three months in the form of diffuse anxiety after ingestion of "magic

mushrooms" in Thailand (Holmgaard Kristensen and Harding Sørensen,

1988. In none of the cases severe somatic complications were registered.

Psilocybe semilanceata is also occacionally used as hallucinogenic

mushroom in Finland, where is grows more or less over the whole coun-

try. Jokiranta et al. (1984) reported that the psilocybin content can be

failry high, up to 23 700 mg/kg dry weight.

6.5. Treatment of psilocybin-intoxication

The major dangers associated with psilocybin are primarily psychological

in nature. Anxiety or panic states (bad trips), depressive or paranoid reac-

tions, mood changes, disorientation, and inability to distinguish between

reality and fantasy may occur (Allen et al., 1991). Recommended treat-

ment for these types of adverse reactions to hallucinogenic mushrooms is

mainly supportive and consists mostly of calming the patient's fears and

preventing him from harming himself or others (Mitchel and Rumack,

1978), but may, when indicated by symptomatic. This report does not aim

to cover the management of poisoning of psilocybin-containing mush-

Occurrence and use of psilocybin-containing hallucinogenic mushrooms

rooms. The readers interested in this area are referred to reviews available

(e.g., Leikin et al., 1989; Köppel, 1993).

In severe poisoning, restraints must be used. Diazepam (Valium), up

to 10 mg in adults, will control seizures. Chlorpromazine (Thorazine)

or equivalent phenothiazines can be used to control hallucinations (Di-

Palma, 1981). Mostly it is enough to follow the patients carefully during

the progressive decline in psychic experience. If the patient arrives at the

hospital within two hours after ingestion of the mushroom, active char-

coal may be given to the patient. Ventricular aspiration would not be the

preferred method of removing the toxins, since in this case the treatment

could be a higher risk than the exposure to the toxin. However, measures

could be taken to reduce the absorption of the toxins involved, either by

gastric lavage or emesis when it is suspected that a very poisonous mush-

room has been mistaken for a hallucinogenic mushroom (Francis and

Murray, 1983; Allen et al., 1991).

6.6. Medical uses of psilocybin and psilocin

In April 1966, Sandoz decided to withdraw its sponsorship of investga-

tions on hallucinogenic drugs such as psilocybin and LSD. The firm

transferred all of its remaining stock of these compounds to the National

Institute of Mental Health in the USA. Because the compounds are le-

gally handled in Schedule I of the Controlled Substances Act in the

United States, studies on their usefulness for society, for example, in

relation to treatment of various mental illnesses, is severly restricted.

Nontheless, psilocybin has been tested as a treatment for anxiety and

post-traumatic stress disorder, and mediator of mystical experiences.

Thus, Francisco Moreno of the University of Arizona at Tucson has

treated patients to test anecdotal reports that the drug can help patients to

manage symptoms of obsessive-compulsive disorder, and Charles Grub at

the University of California, Los Angeles, treated patients to investigate

whether psilocybin is able to relieve anxiety in terminally ill cancer pa-

tients (Check, 2004). Doctor Griffiths at John Hopkins University School

of Medicine, Baltimore, have evaluated the acute and longer-term psy-

chological effects of a high dose of psilocybin in hallucinogen-naïve

adults regularly participating in religious or spiritual activities, and re-

ported positive changes in attitudes and behaviour.

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Sammanfattning

Från att ha varit använda i rituella religiösa ceremonier under tusentals år

började hallucinogena svampar att brukas som partydroger under slutet av

1960-talet. Vilka de hallucinogena svamparna var som användes i religiö-

sa sammanhang av mexikanska indianstammar klargjordes vid etnomyko-

logiska undersökningar på 1930-och 40-talet, men den första listan över

mexikanska hullucinogena svampar publicerades först 1961. Vid den

tidpunkten hade redan kemister vid läkemedelsföretaget Sandoz identifie-

rat den beståndsdel av svampen som var orsaken till de eftersträvade ef-

fekterna. Det visade sig vara en fosforylerad alkaloid som gavs namnet

psilocybin (en fosforsyraester av 4-dihydroxymetyltryptamin) efter den

svampart från vilken den ursprungligen isolerades Psilocybe mexicana.

Senare studier visade att den hallucinogena substansen är psilocin, som

bildas från psilocybin genom defosforylering. Defosforyleringen kan ske

i svampen vid skörd eller när den skadas eller i kroppen hos den som

konsumerar svampen.

Mykologiska studier har funnit att ett stort antal svampar har förmå-

gan att bilda psilocybin. Ämnet har identifierats i mer än 90 svampar

tillhörande olika släkten: Agrocybe, Conocybe, Copelandia*, Gymnopi-

lus*, Hypholoma, Inocybe, (Panaeolina), Panaeolus*, Pluteus, Psathy-

rella*, Psilocybe, och Stropharia (*flertalet arter i detta släkte innehåller

inte psilocybin/psilocin). Dessutom har många andra arter rapporterats ha

hallucinogena egenskaper. De kemiska studierna på svamp har också

visat att psilocybin/psilocin inte är det enda hallucinogena ämnet av den-

na typ i svamp. Tre andra fosforsyraestrar av 4-hydroxytryptamin med

en, ingen eller tre metylgrupper bundna till tryptamin-sidokedjan - baeo-

cystin, nor-baeocystin, och aeruginascin - har även de hallucinogena

egenskaper. Dessa ämnen förekommer dock vid lägre nivåer och i ett

mycket mindre antal svamparter.

Viktiga steg vid den kemiska analysen av psilocybin och liknande

ämnen i svamp är den extraktionsmetod som används, den kromatogra-

fiska metod som används för att separera ämnena och metoden för att

identifiera dem. GC-MS och LC-MS är vanliga metoder vid studiet av

humanbiologiska prover för att identifiera psilocybin/psilocin.

Den kemiska analysen av hallucinogena svampar har funnit moderata

mängder i mycelet, men större mängder i fruktkropparna. Hos de senare

innehåller hatten högre nivåer än stjälken. Man har inte funnit något sam-

band mellan storleken på svampen och psilocybinhalt.

Arter med högt innehåll av psilocybin/psilocin inkluderar Agrocybe

praecox (Pers.) Fayod., Copelandia cambodginiensis (Ola´h et Heim)

Singer and Weeks, Inocybe aeruginascens Babos, Panaeolus cyanescens

120 Occurrence and use of psilocybin-containing hallucinogenic mushrooms

(Berk. & Br.) Sacc., Panaelous subbalteatus (Berk. & Br.) Sacc., Pluteus

salicinus (Pers. Ex Fr.) Kummer, Psilocybe arcana Bor et Hlav., Psilo-

cybe azurescens Stamets and Gartz, Psilocybe baeocystis Singer and

Smith, Psilocybe bohemica Sebek, Psilocybe cubensis (Earle) Singer,

Psilocybe cyanescens Wakefield, Psilocybe liniformans Guzmán & Bas

var. americana Guzmán & Stamets, Psilocybe pelliculosa (Smith) Singer

and Smith, Psilocybe samuiensis Guzmán, Bandala and Allen, Psilocybe

semilanceata (Fr.) Kummer, Psilocybe semperviva Heim and Cailleux

och Psilocybe subcubensis Guzmán. De högsta nivåerna, mer än 15 000

mg/kg torrvikt, har man funnit i Pluteus salicinus (Pers. Ex Fr.) Kummer,

Psilocybe cyanescens Wakefield och Psilocybe semilanceata (Fr. Ex

Secr.) Kummer.

Beaocystin återfinns enbart i några få av de arter som bildar psilocy-

bin, vanligtvis under 1000 mg/kg torrvikt. Högre halter, upp till mer än

5000 mg/kg torrvikt, har påvisats i Inocybe aeruginascens Babos. Samma

svampart har man funnit att kan innehålla upp till 3 500 mg/kg torrvikt av

aeruginacin.

Av de mer än 90 psilocybin- och/eller psilocin-innehållande svampar

som identifierats har cirka 30 återfunnits i Norden. Bland dessa återfinns

6 Psilocybe arter, 6 Panaeolus arter, 3 Gymnopilus arter, 2 Conocybe

arter, 2 Inocybe arter, 2 Pluteus arter och en Psathyrella art. Många av

dessa är sällsynta men somliga förekommer allmänt.

Insamlandet av hallucinogena svampar kräver stora kunskaper efter-

som det finns många förväxlingssvampar, av vilka en del är giftiga. En-

dast erfarna svampplockare bör därför ägna sig åt denna sysselsättning.

Alternativa sätt att komma över hallucinogena svampar är att odla dem

hemma eller att köpa dem över internet. Den senare typen av svamp säljs

oftast torkad. För att göra den torkade svampen mer lättförtärlig konsu-

meras den ofta i olika drycker, såsom i te, kaffe eller Coca Cola. Ett al-

ternativt sätt att använda torkad svamp på är att röka dem likt cigaretter.

Eftersom psilocybin extraheras vid upphettning i vätska och inte bryts

ned så är den totala mängden psilocybin i kokvattnet och i svampen jäm-

förbar med den mängd som ursprungligen fanns i svampen innan den

tillagades inför konsumtion.

Bruket av hallucinogen svamp är mest vanligt hos ungdomar, speciellt

bland yngre män, särskilt de som även använder andra typer av droger.

Bruket är dock inte allmänt. I de nordiska länderna har användningen av

hallucinogen svamp studerats bäst i Danmark. Tre procent av högstadie-

studenter/gymnasister har som avkoppling använt psilocybininnehållande

svamp (1% har prövat LSD). Motsvarande siffra bland universitetsstude-

rande och studenter vid en journalisthögskola var nio procent. Detta pekar

på att svamp är den vanligaste hallucinogena substansen i Danmark.

Även om man inte kunnat visa på att toxiska effekter uppträder vid

användning av hallucinogen svamp, är det välkänt att ett sådan bruk kan

föranleda okontrollerade handlingar hos brukaren. I ovanliga fall, där

Occurrence and use of psilocybin-containing hallucinogenic mushrooms 121

bruket av sådan svamp varit påtagligt, har negativa erfarenheter av den

tidigare användningen repriserats utan att sådan svamp konsumerats vid

det senare tillfället (’flash-backs’). Av den anledningen, men också därför

att bruket av hallucinogen svamp inte är ovanligt bland missbrukare av

andra droger, har många länder, däribland de nordiska, infört restriktioner

för bruket av hallucinogen svamp

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Article

Full-text available

May 2023

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Article

Full-text available

Jul 2021

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Article

Full-text available

Sep 2020
EXTREMOPHILES

Psychrophilic fungi are a critical biotic component in cold deserts that serves a central role in nutrient recycling and biogeochemical cycles. Despite their ecological significance, culture-independent studies on psychrophilic mycobiome are limited. In the present study, the fungal diversity patterns across the Drass, an Indian cold desert in the Himalaya, were indexed by targeted amplicon pyrosequencing (ITS). In the Drass dataset, Ascomycota was represented by 92 genera, while 22 genera represented Basidiomycota. The most abundant genus was Conocybe (20.46%). Most of the identified genera were reported in the literature to be prolific extracellular hydrolytic enzyme producers. To identify whether the Drass fungal assemblages share similarities to other cold deserts, these were further compared to Antarctic and Arctic cold deserts. Comparative analysis across the three cold deserts indicated the dominance of Dikarya (Ascomycota and Basidiomycota). The observed alpha diversity, Shannon index as well as Pielou's evenness was highest in the Antarctic followed by Drass and Arctic datasets. The genera Malassezia, Preussia, Pseudogymnoascus, Cadophora, Geopora, Monodictys, Tetracladium, Titaea, Mortierella, and Cladosporium were common to all the cold deserts. Furthermore, Conocybe was represented predominantly in Drass. Interestingly, the genus Conocybe has not been previously reported from any other studies on Antarctic or Arctic biomes. To the best of our knowledge, this is the first fungal metagenome study in Drass soil. Our analysis shows that despite the similarities of low temperature among the cold deserts, a significant differential abundance of fungal communities prevails in the global cold deserts.

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Article

Full-text available

Feb 2020

A new Panaeolus species was collected on a lawn at the Kunming Institute of Botany, Chinese Academy of Sciences in Southwest China and subjected to morphological and molecular analyses. Both macro- and micro-morphological features of the new species were described and compared with morphologically similar species in Panaeolus. The pileus has a distinctive reddish brown patch at the center. Phylogenetic analysis of nrITS data showed a distinct placement of the new species among the closest Panaeolus species, i.e. Panaeolus cyanescens (Berk & Broome) Sacc., Panaeolus cambodginiensis Ola’h & R. Heim, Panaeolus bisporus (Malençon & Bertault) Ew. Gerhardt and Panaeolus cyanescens var. bisporus (Malençon & Bertault) G. Moreno & Esteve-Rav. Both morphological features and phylogenetic data supported naming our taxon as a distinct new species in Panaeolus. Color photographs of basidiomata and micromorphological structures, a full description of the new species, and an updated phylogenetic tree to show the placement of the new species are provided.

Leratiomyces ceres (Strophariaceae, Basidiomycota), new to Poland

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Full-text available

Dec 2019

em>Leratiomyces ceres , an extra-European species hitherto unknown in Poland, was identified in a public park in Rybnik City (SW Poland). The first Polish collections of the fungus were studied using macroscopic and microscopic features. A brief description and illustration of the species, based on Polish specimens, are presented. The ecology and characteristics distinguishing L. ceres from related Leratiomyces species are also discussed.

Motives and Side-Effects of Microdosing With Psychedelics Among Users

Article

Full-text available

May 2019
INT J NEUROPSYCHOPH

Background: Microdosing with psychedelics has gained considerable media attention where it is portrayed as a performance enhancer, especially popular on the work floor. While reports are in general positive, scientific evidence about potential negative effects is lacking aside from the prevalence and motives for use. The present study addressed this gap by surveying psychedelic users about their experience with microdosing including their dosing schedule, motivation and potential experienced negative effects. Methods: An online questionnaire was launched on several websites and fora between March and July 2018. Respondents who had consented, were 18 years of age or older, and had experience with microdosing were included in the analyses. Results: In total, 1116 of the respondents were either currently microdosing (79.5%) or microdosed in the past (20.5%). LSD (10 mcg) and psilocybin (0.5 g) were the most commonly used psychedelics with a microdosing frequency between two-to-four times a week. The majority of users however were oblivious about the consumed dose. Performance enhancement was the main motive to microdose (37%). The most reported negative effects were of psychological nature and occurred acutely, while under the influence. Conclusion: In line with media reports and anecdotes, the majority of our respondents microdosed in order to enhance performance. Negative effects occurred mostly acutely, after substance consumption. However, the main reason to have stopped microdosing was that it was not effective. Future experimental placebo-controlled studies are needed to test whether performance enhancement can be quantified and to assess potential negative effects after longer-term microdosing.

Patterns of use, desired effects, and mental health status of a sample of natural psychoactive drug users

Article

May 2019

In recent years, the use of natural psychoactive drugs (NPDs) has grown rapidly. They are classified as new psychoactive substances (NPSs), despite the reality that they have been used for centuries. We are lacking information regarding patterns of use or characteristics of users, but some evidence suggests that NPDs substantially differ from NPSs in terms of both their safety profile and patterns of use. The aim of this study was to investigate patterns of use and user characteristics by collecting data from a sample of NPD users. We designed an online questionnaire that was shared through social media. A sample of 564 NPD users was recruited from 52 different countries, with the United States being the most common (19%), followed by Spain (14.9%). The typical user in our sample is a well-educated adult individual who uses NPDs sporadically. The most used substances were Psilocybe mushrooms (88.5%) and ayahuasca (51%). Users reported that the use of NPDs positively influenced their lives, and they showed a good mental health status. Stakeholders should consider these results particularly when deciding on legal classifications for these substances, as the study findings suggest that NPDs should not be in the same class as NPSs.

Biosynthesis of bioactive natural products from Basidiomycota

Article

Dec 2018

The Basidiomycota, also called the club fungi, comprise the large majority of fungal diversity. They are not only highly related to ecosystem functioning but also to human life. These fungi display a wide range of bioactivities and some are famous as producers of deadly toxins, hallucinogens, or used as medicinal mushrooms for thousands of years. Recently, the biosynthesis of several classes of natural products from Basidiomycota has been reported. Here, we review the recent studies of biosynthetic pathways and enzymes of bioactive natural products from Basidiomycota fungi, with focus on terpenoids, alkaloids, ribosomally synthesized and post-translationally modified peptides (RiPPs) and polyketides.

Phylogenomics of the psychoactive mushroom genus Psilocybe and evolution of the psilocybin biosynthetic gene cluster

Article

Full-text available

Jan 2024
P NATL ACAD SCI USA

Psychoactive mushrooms in the genus Psilocybe have immense cultural value and have been used for centuries in Mesoamerica. Despite the recent surge of interest in these mushrooms due to the psychotherapeutic potential of their natural alkaloid psilocybin, their phylogeny and taxonomy remain substantially incomplete. Moreover, the recent elucidation of the psilocybin biosynthetic gene cluster is known for only five of ~165 species of Psilocybe , four of which belong to only one of two major clades. We set out to improve the phylogeny of Psilocybe using shotgun sequencing of fungarium specimens, from which we obtained 71 metagenomes including from 23 types, and conducting phylogenomic analysis of 2,983 single-copy gene families to generate a fully supported phylogeny. Molecular clock analysis suggests the stem lineage of Psilocybe arose ~67 mya and diversified ~56 mya. We also show that psilocybin biosynthesis first arose in Psilocybe , with 4 to 5 possible horizontal transfers to other mushrooms between 40 and 9 mya. Moreover, predicted orthologs of the psilocybin biosynthetic genes revealed two distinct gene orders within the biosynthetic gene cluster that corresponds to a deep split within the genus, possibly a signature of two independent acquisitions of the cluster within Psilocybe .

The Psilocin (4‐hydroxy‐N,N‐dimethyltryptamine) and Bufotenine (5‐hydroxy‐N,N‐dimethyltryptamine) Case: Ensuring the Correct Isomer has Been Identified

Article

May 2020

Psilocin (4‐hydroxy‐N,N‐dimethyltryptamine, 4‐HO‐DMT) and bufotenine (5‐hydroxy‐N,N‐dimethyltryptamine, 5‐HO‐DMT), which are both naturally occurring compounds, are classified as controlled substances in numerous countries due to their pharmacological activities and recreational usage. There are two other benzene ring regioisomers, 6‐hydroxy‐N,N‐dimethyltryptamine (6‐HO‐DMT) and 7‐hydroxy‐N,N‐dimethyltryptamine (7‐HO‐DMT), which are not classified by name as controlled substances, and which were synthesized for this current work. The four isomers were analyzed using routine methodologies employed by the Israel's Police Division of Identification and Forensic Science (DIFS) Laboratory, namely thin layer chromatography (TLC), Fourier transform infrared spectroscopy (FTIR), and gas chromatography mass spectroscopy (GC‐MS). It was found possible to differentiate the four isomers. Forensic specimens that were suspected to be psilocybe mushrooms were examined, confirming that it is now possible to unequivocally identify the presence of psilocin and rule out the presence of its other isomers.

7 YEARS OF 3, 4-METHYLENEDIOXYMETHAMPHETAMINE (MDMA) TOXICITY

Article

Full-text available

Int J Med Toxicol 2000; 3(5): 28 ABSTRACT Background: The majority of published data on the clinical toxicity of 3,4-methylenedioxymethamphetamine (MDMA) consists mainly of isolated case reports. We performed the following study to record systematically our experience with MDMA toxicity.

Quantitative Bestimmung der Indolderivate von Psilocybe semilanceata (Fr.) Kumm.

Article

Dec 1986

Jochen Gartz

Psilocybe semilanceata contains psilocybin, baeocystin and other indoles in every fruit body. The content of psilocybin, the major constituent, as well as the content of the other indoles, has been investigated. In dried mushrooms the psilocybin content varied considerably, from 0.19 to 1.34%. The highest concentrations were found among mushrooms with little mass whereas the content in mg was highest in larger mushrooms. There was a correlation between the content of psilocybin and other indoles. The psilocybin content of mushrooms from the same location and with similar mass varied also considerably. Blueing of the mushrooms does not mean a variation of the psilocybin content. No destruction of the indoles and the nonindolic compounds takes place when the mushrooms are drying at their locations.

Hemmung der Entwicklung durch Psychotica

Article

Jan 1969

F. H. Kemper

Poisoning by fungi: Interesting cases

Article

Aug 1997

Roy Watling

Analysis of Aeruginascin in Fruit Bodies of the Mushroom Inocybe aeruginascens

Article

Sep 2008

J. Gartz

Analysis of ten fruit bodies of Inocybe aeruginascens Babos revealed a content of the indole derivative aeruginascin which was in the same order of magnitude as the amounts of psilocybin or baeocystin. There was a correlation between the content of psilocybin, baeocystin and aeruginascin. Aeruginascin seems to modify the pharmacological action of psilocybin to give an always euphoric mood during ingestion of the mushrooms. © 1989 Informa UK Ltd All rights reserved: reproduction in whole or part not permitted.

A New Psilocybian Species of Copelandia

Article

Jul 2004

Copelandia chlorocystis sp. nov. is described, and a key to the known species of this genus included. Psilocybin and psilocin were isolated from the new species by dry column chromatography, and the presence of baeocystin was indicated. Urea was detected by analytical tic.

The action of oxalyl chloride on indoles : A new approach to tryptamines

Article

Dec 1954

Tryptophan als biogenetische Vorstufe des Psilocybins

Article

Jan 1961
ARCH PHARM

GLC-Mass Spectral Analysis of Psilocin and Psilocybin

Article

May 1977
J PHARM SCI-US

With the combined technique of GLC-mass spectrometry, psilocin and psilocybin, two hallucinogenic indoles, were analyzed as their trimethylsilyl derivatives. The method was applied to these two components in an extract of Psilocybe cubensis (Earle) Sing.

An update on British medical students' lifestyles

Article

May 1998
MED EDUC

Information about medical students' lifestyles was obtained from 785 second-year students from seven medical schools in Great Britain by a personally administered questionnaire. Fifteen per cent of the students were non-drinkers. Among those who drank, 48% of the men and 38% of the women exceeded sensible weekly limits of alcohol consumption, and high-risk levels of consumption were reported by 12% of men and 7% of women. Cannabis had been used at least once or twice by more than half the men and 40% of the women, and 10% reported regular use (weekly or more often). Experience with other illicit drugs was also reported: amphetamines (8% of students), LSD (7%), ecstasy (4%), amyl/butyl nitrate (10%) and magic mushrooms (7%). Nineteen per cent of the students had used two or more different drugs. Experience with illicit drugs started before entering university in more than a third of those who used them. Comparison of the results with other student surveys suggests that the lifestyles of medical students differ little from those of other student groups, but that alcohol and illicit drug consumption is increasing in university students generally. Prospective studies are under way to establish whether medical students change their lifestyles at later stages of their course and after qualification.

Occurrence and use of hallucinogenic mushrooms containing psilocybin alkaloids

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