Erowid Psilocybin Mushroom Vault : Chemistry

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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 FORMULA	C12H17N2O4P
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-(Dimethylamino)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 :	Baeocystin
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

Psilocybin Mushroom 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 FORMULA C12H17N2O4P

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-(Dimethylamino)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 : Baeocystin

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

Brief Baeocystin Info
Psilocybin Extraction Notes

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).

Last Modified - Thu, Jul 19, 2007

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