Mushroom Chemistry
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).