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<td valign="top" width="50%"><strong>Other Names</strong>

Psilocybin: CY-39, indocybin, 0-phosphoryl-4hydroxy-

N,N-dimethyltryptamine, 3(2-dimethylamino)

ethylindol-4-01 dihydrogenphosphatester

Psilocin: 4-hydroxy-N,N-dimethyltryptamine,

psilocine, psilocyn (misspelling in the legal literature),

3- [2-(dimethylamino)ethyl]-1H-indole-4-01

Empirical formula: C12H17N204P (psilocybin),

C12H16N20 (psilocin)

Substance type: tryptamines, indole amines (indole

alkaloids)

Psilocybin was first isolated from Psilocybe mexicana

and identified by Albert Hofmann in 1955

(Hofmann et al. 1958, 1959). The phosphorylated

indole amine psilocybin is transformed into

psilocin by splitting off the phosphoric acid group

(Hofmann and Troxler 1959). Because the

protection the phosphoric acid would provide is

lacking, psilocin easily oxidizes with the phenolic hydroxyl group, resulting in blue quinonoid products.

This explains why psilocybin mushrooms

turn blue after they have been squeezed and

harvested (cf. Panaeolus cyanescens, Psilocybe cyanescens).

In the body, psilocybin is immediately

metabolized into psilocin, which is the actual

psychoactive constituent.

Psilocybin and psilocin are closely related to

baeocystin (= 0-phosphoryl-4-hydroxy-N-methyltryptamine,

norpsilocybin), which probably represents

the biogenic precursor of psilocybin (Repke

et al. 1977; cf. also Brack et al. 1961 and Chilton et

al. 1979). Baeocystin may be a derivative of tryptophan

(Brack et al. 1961).

The usual psychedelic dosage of psilocybin is

10 mg. When psilocybin is taken orally, the effects

typically become apparent in about twenty

minutes504 (Shulgin 1980). Rudolf Gelpke (19281972)

took between 6 and 20 mg during his selfexperiments;

with 10 mg, he made his historic

"journey to the outer space of the soul": This inebriation was a space flight not into the

outer realm, but into the inner person, and for

a moment I experienced reality from a

position located somewhere beyond the

gravity of time. (Gelpke 1962,395)

With very high dosages, it is common to perceive

voices (Beach 1997). This could explain why

Indians say that the mushroom talks to them.

Toxic dosages are unknown!

Walter Pahnke's "Good Friday experiment," in

which theology students were administered psilocybin

in a church on Good Friday, has become

renowned. Pahnke applied the theory of dosage,

set, and setting as part of the test to see whether

mystical revelations would occur, which was

indeed the case (Pahnke 1972; Pahnke and

Richards 1970; cf. Doblin 1991).

Timothy Leary and his colleagues at Harvard

experimented with psilocybin on prisoners. Their

experiments were aimed at determining whether

the psychedelic constituent was suitable for use in

therapy with inmates. It was hoped that the drug

experience would enable the prisoners to attain

insights into their behavior that would then enable

them to change themselves on their own. Although

these experiments showed great promise, they had

to be terminated (Clark 1970; Forcier and Doblin

1994; Riedlinger and Leary 1994).

Both psilocybin and two synthetic derivatives

(CZ-74, CY-19) have been used with success in

psychedelic and psycholytic therapy (Leuner 1963;

Leuner and Baer 1965; Passie 1995, 1996). Psilocybin

can release, stimulate, and inspire creativity

(Fischer et al. 1972), as an increasing number of

studies have shown (Baggott 1997; Spitzer et al.

1996), and "archetypal art therapy" is making use

of this effect (Allen 1995).

Today, psilocybin is playing a central role in

neurochemical research into brain activity, in

which it is being studied with the very elaborate

and costly positron-emission tomography (PET)

method (Vollenweider 1996).

Jochen Gartz has discovered that fungal

enzymes synthesize the "synthetic" psilocin analog

CZ-74 (diethyl-4-hydroxytryptamine, 4-0H-DET)

from diethyltryptamine when it is added to a

Psilocybe spp. substrate 0. Gartz, pers. comm.). It

is possible that the "synthetic" CY-19 (= diethyl-4phosphoryloxytryptramine)

can be produced in

the same fashion.

<strong>Commercial Forms and Regulations</strong>

Both psilocybin and psilocin are classified as

Schedule I drugs in the United States (Shulgin

1980). They are internationally regarded as illegal

"narcotics." The analog substances psilocin-(eth)

and psilocybin-(eth) are also illegal (Korner 1994,

40).</td>
<td valign="top" width="53%"><strong>Literature</strong>

See also the entries for Psilocybe mexicana and

Psilocybe spp.

Allen, Tamara D. 1994. Research in archetypal art

therapy with psilocybin. Maps 5 (1): 39-40.

---.1995. Archetypal art therapy: Hearing

psilocybin in the art & metaphor work of

volunteer no. 31. Maps 6 (1): 23-26.

Baggot, Matthew. 1997. Psilocybin's effects on

cognition: Recent research and its implications

for enhancing creativity. Maps 7 (1): 10-11.

Beach, Horace. 1997. Listening for the logos: Study

of reports of audible voices at high doses of

psilocybin. Maps 7 (1): 12-17.

Bocks, S. M. 1968. The metabolism of psilocin and

psilocybin by fungal enzymes. Biochemical

Journal 106:12-13.

Borner, Stefan, and Rudolf Brenneisen. 1987.

Determination of tryptamines in hallucinogenic

mushrooms using high-performance liquid

chromatography with photodiode array

detection. Journal ofChromatography 408:402-8.

Brack, A., Albert Hofmann. F. Kalberer, H. Kobel,

and J. Rutschmann. 1961. Tryptophan als

biogenetische Vorstufe des Psilocybins. Archiv der

Pharmazie 294/66 (4): 230-34.

Chilton, W. Scott, Jeremy Bigwood, and Robert E.

Jensen. 1979. Psilocin, bufotenine, and serotonin:

Historical and biosynthetic observations. Journal

ofPsychedelic Drugs 11 (1-2): 61-69.

Clark, Jonathan. 1970. Psilocybin: The use of

psilocybin in a prison. In Psychedelics, ed.

Bernard Aaronson and Humphry Osmond,

40-44. Garden City, N.Y.: Anchor Books.

Doblin, Rick. 1991. Pahnke's (Good Friday

experiment': Along-term follow-up and

methodological critique. The Journal of

Transpersonal Psychology 23 (1): 1-28.

Fischer, Roland, Ronald Fox, and Mary Ralstin. 1972.

Creative performance and the hallucinogenic

drug-induced creative experience. Journal of

Psychedelic Drugs 5 (1): 29-36. (On psilocybin

and creativity research.)

Forcier, Michael W., and Rick Doblin. 1994. Longterm

follow-up to Leary's Concord Prison

psilocybin study. Maps 4 (4): 20-21.

Gelpke, Rudolf. 1962. Von Fahrten in den Weltraum

der Seele: Berichte tiber Selbstversuche mit

Delysid (LSD) und Psilocybin (CY). Antaios

3:393-411.

---. [1997]. Von Fahrten in den Weltraum der

Seele: Berichte uber Selbstversuche mit LSD und

Psilocybin. Lohrbach: Werner Pieper's

MedienXperimente and Edition Rauschkunde.

Gnirss, Fritz. 1959. Untersuchung mit Psilocybin,

einem Phantastikum aus dem mexikanischen

Rauschpilz Psilocybe mexicana. Schweizer Archiv

fur Neurologie, Neurochirurgie und Psychiatrie

84:346-48.

Hofmann, Albert, A. Frey, H. Ott, Th. Petrzilka, and

F. Troxler. 1958. Konstitutionsautklarung und

Synthese von Psilocybin. Experientia 14 (11):

397-401.

Hofmann, Albert, Roger Heim, A. Brack, and H.

Kobel. 1958. Psilocybin, ein psychotroper

Wirkstoff aus dem mexikanischen Rauschpilz

Psilocybe mexicana Heim. Experientia 14 (3):

107-12.

Hofmann, Albert, Roger Heim, A. Brack, H. Kobel,

A. Frey, H. Ott, T. Petrzilka, and F. Troxler. 1959.

Psilocybin und Psilocin, zwei psychotrope

Wirkstoffe aus mexikanischen Rauschpilzen.

Helvetica Chimica Acta 42 (162): 1557-72.

Hofmann, Albert, and F. Troxler. 1959.

Identifizierung von Psilocin. Experientia 15 (3):

101-4.

Jones, Richard. 1963. "Up" on Psilocybin. The

Harvard Review 1 (4): 38-43.

Krippner, Stanley. 1970. Psilocybin: An adventure in

psilocybin. In Psychedelics, ed. Bernard Aaronson

and Humphry Osmond, 35-39, Garden City,

N.Y.: Anchor Books.

Laatsch, Hartmut. 1994. Das Fleisch der GotterVon

den Rauschpilzen zur Neurotransmission. In

Welten des Bewufitseins, ed. A. Dittrich et aI.,

3:181-95. Berlin: VWB.

---. 1996. Zur Pharmakologie von Psilocybin

und Psilocin. In Maria Sabina-Botin der heiligen

Pilze, ed. Roger Liggenstorfer and Christian

R~itsch, 193-202. Solothurn: Nachtschatten

Verlag.

Leuner, Hanscarl. 1963. Die Psycholytische Therapie:

Klinische Psychotherapie mit Hilfe von LSD-25

und verwandten Substanzen. Zeitschrijt fur

Psychotherapie und medizinische Psychologie

13:57 ff.

Leuner, Hanscarl, and G. Baer. 1965. Two shortacting

hallucinogens of the psilocybin-group. In

Neuro-pharmacology, ed. D. Bente and P. B.

Bradley. Amsterdam: Elsevier.

Ott, Jonathan, and Gaston Guzman. 1976. Detection

of psilocybin in species of Psilocybe, Panaeolus

and Psathyrella. Lloydia 39:258-60.

Pahnke, Walter N. 1972. Drogen und Mystik. In

Josuttis and Leuner, 54-76.

Pahnke, Walter N., and William A. Richards. 1970.

Implications of LSD and experimental

mysticism. Journal ofPsychedelic Drugs 3 (1):

92-108.

Passie, Torsten. 1995. Psilocybin in der westlichen

Psychotherapie. Curare 18 (1): 131-52.

---. 1996. Psilocybin in der westlichen

Psychotherapie. In Maria Sabina-Botin der

heiligen Pilze, ed. Roger Liggenstorfer and

Christian R~itsch, 211-25. Solothurn:

Nachtschatten Verlag.

Repke, David B., Dale Thomas Leslie, and Gaston

Guzman. 1977. Baeocystin in Psilocybe, Conocybe

and Panaeolus. Lloydia 40 (6): 566-78.

Riedlinger, Thomas, and Timothy Leary. 1994.

Strong medicine for prisoner reform: The

Concord Prison experiments. Maps 4 (4): 22-25.

Shulgin, Alexander T. 1980. Psilocybin. Journal of

Psychedelic Drugs 12 (1): 79.

Spitzer, M., M. Thimm, 1. HermIe, P. Holzmann, K.

A. Kovar, H. Heimann, E. Gouzoulis-Mayfrank,

U. Kischka, and F. Schneider. 1996. Increased

activation of indirect semantic associations

under psilocybin. Biological Psychiatry

39:1055-57.

Strassmann, Rick. 1992. DMT and psilocybin

research. Maps 3 (4): 8-9.

---.1995. University of New Mexico DMT and

psilocybin studies. Maps 5 (3): 14-15.

Troxler, F., F. Seemann, and Albert Hofmann. 1959.

Abwandlungsprodukte von Psilocybin und

Psilocin. Helvetica Chimica Acta 42 (226):

2073-103.

Vollenweider, Franz. 1996. Perspektiven der

BewuBtseinsforschung mit Halluzinogenen. In

Maria Sabina-Botin der heiligen Pilze, ed. Roger

Liggenstorfer and Christian R~itsch, 203-10.

Solothurn: Nachtschatten Verlag.</td>
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Psilocybin/Psilocin - Revision history

GrimReaper at 10:48, 11 March 2015