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Substance Name: Psilocybine [INN:BAN:DCF]
RN: 520-52-5
UNII: 2RV7212BP0
InChIKey: QVDSEJDULKLHCG-UHFFFAOYSA-N

Note

  • The major of two hallucinogenic components of Teonanacatl, the sacred mushroom of Mexico, the other component being psilocin. (From Merck Index, 11th ed)

Molecular Formula

  • C12-H17-N2-O4-P

Molecular Weight

  • 284.2503
 

Classification Codes

Classification Codes

  • Central Nervous System Agents
  • Drug / Therapeutic Agent
  • Hallucinogens
  • Human Data
  • Mutation Data
  • Psychotropic Drugs

Superlist Classification Code

  • DEA Schedule I
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Names and Synonyms

Name of Substance

  • Psilocybine
  • Psilocybine [INN:BAN:DCF]

MeSH Heading

  • Psilocybin

Synonyms

  • 3-(2-(Dimethylamino)ethyl)-1H-indol-4-ol dihydrogen phosphate ester
  • 3-(2-Dimethylaminoethyl)indol-4-yl dihydrogen phosphate
  • 3-2'-Dimethylaminoethylindol-4-phosphate
  • 4-22-00-05665 (Beilstein Handbook Reference)
  • 4-Phosphoryloxy-omega-N,N-dimethyltryptamine
  • BRN 0273158
  • CY 39
  • CY-39
  • EINECS 208-294-4
  • HSDB 7365
  • Indocybin
  • O-Phosphoryl-4-hydroxy-N,N-dimethyltryptamine
  • Psilocibin
  • Psilocibina
  • Psilocibina [INN-Spanish]
  • Psilocin phosphate ester
  • Psilocybine
  • Psilocybinum
  • Psilocybinum [INN-Latin]
  • Psilotsibin
  • Teonanacatl
  • UNII-2RV7212BP0

Systematic Names

  • 1H-Indol-4-ol, 3-(2-(dimethylamino)ethyl)-, dihydrogen phosphate (ester)
  • 3-(2-Dimethylaminoethyl)indol-4-yl dihydrogen phosphate
  • Indol-4-ol, 3-(2-(dimethylamino)ethyl)-, dihydrogen phosphate
  • Psilocybine

Superlist Names

  • Constituent of Magic mushrooms
  • DEA No. 7437
  • Psilocybin

Mixture Name

  • Magic mushrooms

Registry Numbers

CAS Registry Number

  • 520-52-5

FDA UNII

  • 2RV7212BP0

System Generated Number

  • 0000520525

Structure Descriptors

InChI

1S/C12H17N2O4P/c1-14(2)7-6-9-8-13-10-4-3-5-11(12(9)10)18-19(15,16)17/h3-5,8,13H,6-7H2,1-2H3,(H2,15,16,17)

InChIKey

QVDSEJDULKLHCG-UHFFFAOYSA-N

Smiles

CN(C)CCc1c[nH]c2c1c(ccc2)OP(=O)(O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TDLo intramuscular 75ug/kg (0.075mg/kg) BEHAVIORAL: EUPHORIA

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
Psychopharmacologia Vol. 3, Pg. 219, 1962.
human TDLo intramuscular 130ug/kg (0.13mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: TOXIC PSYCHOSIS
Proceedings of the European Society for the Study of Drug Toxicity. Vol. 8, Pg. 59, 1967.
human TDLo intraperitoneal 37ug/kg (0.037mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE

BEHAVIORAL: MUSCLE WEAKNESS
Journal of Nervous and Mental Disease. Vol. 131, Pg. 428, 1960.
human TDLo oral 60ug/kg (0.06mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE

BEHAVIORAL: MUSCLE WEAKNESS
Journal of Nervous and Mental Disease. Vol. 131, Pg. 428, 1960.
mouse LD50 intraperitoneal 420mg/kg (420mg/kg) SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS
Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 64, Pg. 159, 1968.
mouse LD50 intravenous 275mg/kg (275mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS
Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 64, Pg. 159, 1968.
rabbit LD50 intravenous 13mg/kg (13mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 138, 1972.
rat LD50 intravenous 280mg/kg (280mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 138, 1972.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 224 deg C   EXP
log P (octanol-water) 1.000 (none)   EST
Atmospheric OH Rate Constant 2.81E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.