MERCK INDEX ENTRIES
8111. Psilocybin. 3-[2-(Dimethylamino)ethyq-1 H-indol-4-oI; O-phosphoryl-4-hydroxy-N,Ndimethyltryptamine;
Indocybin. C12H17N202P; moi 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 ai., Experientia 14, 107 (1958); Heim et ai., Helv. Chim. Acto 42,1557 (1959);
Heim et ai., Ger pato 1,087,321 (1960 to Sandoz). Structure: Hofmann et ai., Experientia 14, 397 (1958).
Synthesis: Hofmann, Troxler, U.S. pato 3,075,992 (1963 to Sandoz). Crystal structure: H.P. Weber, T.J.
Petcher, J. Chem. Soe., Perkin Trans." 1974, 942. Converted to psilocin in vivo. Toxicity data: E.
Usdin, D.H.Efron, Psychotropic Drugs and Related Compounds (Nationallnstitute 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, Buli. Narcotics 23, 3 (1971).
Crystals from Boiling water, mp 220-228°; from boiling methanol, mp 185-195°. uv max (methanol):
220,267,290 nm (Iog 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,
Tttle 21 Part 1308.11(1995).
THERAPCAT: Psychomimetic
8110. Psilocin. 3-[2-(Diumethylamino)ethyl]-1 H-indol-4-ol; 4-hydroxy-N,N-dimethyltryptamine;
psilocyn. C12H16N20;moi wt 204.27.C 70.56%,H7.89%,N13.71%07.83%. 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 ai., Experientia 14, 107 (1948);
Heim et ai., Helv. Chim. Acta 42, 1557 (1959). Prepn: Heim et aI., Ger. pat 1,087,321 (1960 to Sandoz).
Synthetic precursor of psilocybin: Hofmann, Troxler, U.S. pato 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. Pharmaco/. 4, 730 (1962).
Crystal structure: T.J. Petcher, H.P. Weber, 730 (1962). Crystal structure: T.J. Petcher, H.P. Weber, J.
Chem Soe. Perkin Trans. li 1974,946. Review Hofmann, Buli. 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 (Iog E 4.6, 3.7, 3.8, 3.7, 3.6).
http://www.erowid.org/plants/mushrooms/mushrooms_chemistIy.shtml 23/3/2004