Mushroom Chemistry


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The psilometric scale of potency of selected Psilocybe mushrooms:

SPECIES % PSILOCYBIN % PSILOCIN % BAEOCYSTIN REFERENCE
P. azurenscens 1.78 .38 .35 Stamets and Gartz 1995
P. bohemica 1.34 .11 .02 Gartz and Muller 1989; Gartz (1994)
P. semilanceata .98 .02 .36 Gartz 1994
P. baeocystis .85 .59 .10 Repke et al. 1977; Beug and Bigwood 1982(b)
P. cyanescens .85 .36 .03 Stijve and Kuyper 1985; Repke et al. 1977
P. tampanensis .68 .32 n/a Gartz 1994
P. cubensis .63 .60 .025 Gartz 1994; Stijve and de Meijer 1993
P. weilii .61 .27 .05  
P. hoogshagenii .60 .10 n/a Heim and Hofmann 1958
P. stuntzii .36 .12 .02 Beug and Bigwood 1982(b); Repke et al. 1977
P. cyanofibrillosa .21 .04 n/a Stamets et al. 1980
P. liniformans .16 n/d .005 Stijve and Kuyper

Psilocybin Mushrooms of the World, Paul Stamets


LD50 and Chemistry

NAME : Psilocybin
CHEMICAL NAME : 3-[2-(Dimethylamino)ethyl]-1H-indol-4-ol
ALTERNATE CHEMICAL NAMES : O-phosphoryl-4-hydroxy-N,N-dimethyltryptamine; Indocybin
CHEMICAL FORMULA C12H17N2O2P
MOLECULAR WEIGHT 284.25
MELTING POINT 220-228 C (Crystals from boiling water)
MELTING POINT 185-195 C (Crystals from methanol)
pH 5.2 (in 50% aq ethanol)
LD50 285 mg/kg i.v.(mice)
LD50 280 mg/kg i.v. (rats)
LD50 12.5 mg/kg i.v.(rabbits)
From the Merck Index 12th Edition
.
NAME : Psilocin
CHEMICAL NAME : 3-[2-(Diumethylamino)ethyl]-1H-indol-4-ol
ALTERNATE CHEMICAL NAMES : 4-hydroxy-N,N-dimethyltryptamine; psilocyn
CHEMICAL FORMULA C12H16N2O
MOLECULAR WEIGHT 204.27
MELTING POINT 173-176 C (plates from methanol)
From the Merck Index 12th Edition
.
NAME : Baeocystine
CHEMICAL NAME : 3-[2-(methylamino)ethyl]-1H-indol-4-ol dihydrogen phosphate ester
ALTERNATE CHEMICAL NAMES : desmethyl psilocybine; 4-phosphoryloxy-N-methyltryptamine; baeocystin
CHEMICAL FORMULA C11H15N2O4P
MOLECULAR WEIGHT 270.28
MELTING POINT 254-258 C (crystals from methanol)
From Pharmacotheon

MERCK INDEX ENTRIES
8111. Psilocybin. 3-[2-(Dimethylamino)ethyl]-1H-indol-4-ol; O-phosphoryl-4-hydroxy-N,N-dimethyltryptamine; Indocybin. C12H17N2O2P; mol wt 284.25. C 50.71%, H 6.03%, N 9.86%, O 22.51%, P 10.90%. The major of two hallucinogenic compounds in Teonanacatl, the sacred mushroom of Mexico, the other component being psilocin, q.v. from the fruiting bodies of Psilocybe mexicana Heim, Agaricaceae: Hofmann et al., Experientia 14, 107 (1958); Heim et al., Helv. Chim. Acto 42, 1557 (1959); Heim et al., Ger pat. 1,087,321 (1960 to Sandoz). Structure: Hofmann et al., Experientia 14, 397 (1958). Synthesis: Hofmann, Troxler, U.S. pat. 3,075,992 (1963 to Sandoz). Crystal structure: H.P. Weber, T.J. Petcher, J. Chem. Soc., Perkin Trans. II 1974, 942. Converted to psilocin in vivo. Toxicity data: E. Usdin, D.H. Efron, Psychotropic Drugs and Related Compounds (National Institute of Mental Health, Rockville, Md., 2nd ed., 1972) p 138. Reviews: Hofmann, Proc. 1st Int. Congr. Neuro-Pharm., Rome 1958, 446; Cerletti, Deut. Med Wochenschr. 84, 2317 (1959); Hofmann, Bull. Narcotics 23, 3 (1971).

Crystals from Boiling water, mp 220-228; from boiling methanol, mp 185-195. uv max (methanol): 220, 267, 290 nm (log E 4.6, 3.8, 3.6). pH 5.2 in 50% aq ethanol. Sol in 20 parts boiling water, 120 parts boiling methanol; difficultly sol. in ethanol. Practically insol in chloroform, benzene. LD50 in mice, rats, rabbits (mg/kg): 285, 280, 12.5 i.v. (Usdin, Efron).

Note: This is a controlled substance (hallucinogen) listed in the U.S. Code of Federal Regulations, Title 21 Part 1308.11(1995).
THERAP CAT: Psychomimetic

8110. Psilocin. 3-[2-(Diumethylamino)ethyl]-1H-indol-4-ol; 4-hydroxy-N,N-dimethyltryptamine; psilocyn. C12H16N2O; mol wt 204.27. C 70.56%, H 7.89%, N 13.71% O 7.83%. The minor hallucinogenic component of Teonanacatl, the sacred mushroom of Mexico. Isolated in trace amounts from the fruiting bodies of Psilocybe mexicana Heim, Agaricaceae: Hofmann et al., Experientia 14, 107 (1948); Heim et al., Helv. Chim. Acta 42, 1557 (1959). Prepn: Heim et al., Ger. pat 1,087,321 (1960 to Sandoz). Synthetic precursor of psilocybin: Hofmann, Troxler, U.S. pat. 3,075,992 (1963 to Sandoz). Psilocin, the 4-hydroxy analog of psilocybin, is formed by metabolic dephosphoylation of psilocybin and is the active species in thh central nervous system: Hoita, Weber, Toxicol Appl. Pharmacol. 4, 730 (1962). Crystal structure: T.J. Petcher, H.P. Weber, 730 (1962). Crystal structure: T.J. Petcher, H.P. Weber, J. Chem Soc. Perkin Trans. II 1974, 946. Review Hofmann, Bull. Narcotics 23, 3 (1971)

Plates from methanol, mp 173-176. Amphoteric substance. Unstable in soln, esp. akaline soln. Very slightly sol in water. uv max: 222, 260, 267, 283, 293nm (log E 4.6, 3.7, 3.8, 3.7, 3.6).


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