Title: Psilocybin
CAS Registry Number: 520-52-5
CAS Name: 3-[2-(Dimethylamino)ethyl]-1H-indol-4-ol dihydrogen phosphate ester
Additional Names: O-phosphoryl-4-hydroxy-N,N-dimethyltryptamine
Trademarks: Indocybin (Sandoz)
Molecular Formula: C12H17N2O4P
Molecular Weight: 284.25
Percent Composition: C 50.70%, H 6.03%, N 9.86%, O 22.51%, P 10.90%
Literature References: The major of two hallucinogenic components of Teonanácatl, 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. Acta 42, 1557 (1959); Heim et al., DE 1087321 (1960 to Sandoz). Structure: Hofmann et al., Experientia 14, 397 (1958). Synthesis: Hofmann, Troxler, US 3075992 (1963 to Sandoz). Crystal structure: H. P. Weber, T. J. Petcher, J. Chem. Soc. Perkin Trans. 2 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-Pharmacol. 1958, 446; Cerletti, Dtsch. Med. Wochenschr. 84, 2317 (1959); Hofmann, Bull. Narc. 23, 3 (1971).
Properties: 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).
Melting point: mp 220-228°; mp 185-195°
Absorption maximum: uv max (methanol): 220, 267, 290 nm (log e 4.6, 3.8, 3.6)
Toxicity data: LD50 in mice, rats, rabbits (mg/kg): 285, 280, 12.5 i.v. (Usdin, Efron)
NOTE: This is a controlled substance (hallucinogen): 21 CFR, 1308.11.
Therap-Cat: Psychomimetic. |