Erowid
 
 
Plants - Drugs Mind - Spirit Freedom - Law Arts - Culture Library  
Matching Challenge during Erowid's Support Drive!
We still need 567 donations by September 30th to meet our goal.
Donate during Erowid's September Public Support Drive.
and get your donation of $10-500 doubled by a matching challenge!
Psilocybin & Psilocin Chemistry
by Erowid



NAME :Psilocybin
CHEMICAL NAME :3-[2-(Dimethylamino)ethyl]-1H-indol-4-ol dihydrogen phosphate ester
ALTERNATE CHEMICAL NAMES :O-phosphoryl-4-hydroxy-N,N-dimethyltryptamine; Indocybin
CHEMICAL FORMULAC12H17N2O4P
MOLECULAR WEIGHT284.25
MELTING POINT220-228° C (Crystals from boiling water)
MELTING POINT185-195° C (Crystals from methanol)
pH5.2 (in 50% aq ethanol)
LD50285 mg/kg i.v.(mice)
LD50280 mg/kg i.v. (rats)
LD5012.5 mg/kg i.v.(rabbits)
From the Merck Index 12th Edition


3D Psilocybin Molecule


NAME :Psilocin
CHEMICAL NAME :3-[2-(Dimethylamino)ethyl]-1H-indol-4-ol
ALTERNATE CHEMICAL NAMES :4-hydroxy-N,N-dimethyltryptamine; psilocyn
CHEMICAL FORMULAC12H16N2O
MOLECULAR WEIGHT204.27
MELTING POINT173-176° C (plates from methanol)
From the Merck Index 12th Edition


3D Psilocin Molecule




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).

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


TiHKAL 18: Psilocybin / Psilocin