7926. Psilocybin

Nomenclature

CAS number: 520-52-5
3-[2-(Dimethylamino)ethyl]-1H-indol-4-ol dihydrogen phosphate ester; O-phosphoryl-4-hydroxy-N,N-dimethyltryptamine; Indocybin (Sandoz).
C12H17N2O4P; mol wt 284.25.
C 50.70%, H 6.03%, N 9.86%, O 22.51%, P 10.90%.

Description and 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).

Chemical structure

Properties

Crystals from boiling water, mp 220-228°; from boiling methanol, mp 185-195°. uv max (methanol): 220, 267, 290 nm (log ε 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): 21 CFR, 1308.11.

Therapeutic Category

Psychomimetic.