Psilocybin/Psilocin

Other Names 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. Commercial Forms and Regulations 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*).

Literature 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.