Psilocybin

Psilocybin
Names


IUPAC name [3-(2-Dimethylaminoethyl)-1H-indol-4-yl] dihydrogen phosphate
Identifiers
CAS Number	520-52-5^Y
3D model (Jmol)	Interactive image
Beilstein Reference	273158
ChEBI	CHEBI:8614^Y
ChEMBL	ChEMBL194378^Y
ChemSpider	10178^Y
ECHA InfoCard	100.007.542
EC Number	208-294-4
KEGG	C07576^Y
MeSH	Psilocybine
PubChem	10624
RTECS number	NM3150000
InChI 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)^Y Key: QVDSEJDULKLHCG-UHFFFAOYSA-N^Y InChI=1/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)
SMILES CN(C)CCC1=CNC2=C1C(=CC=C2)OP(=O)(O)O
Pharmacology
Dependence liability	Low
Routes of administration	Oral, intravenous
Pharmacokinetics:
Metabolism	Hepatic
Biological half-life	oral: 163±64 min intravenous: 74.1±19.6 min
Excretion	Renal
Legal status	AU: S9 (Prohibited) CA: Schedule III UK: Class A US: Schedule I
Properties
Chemical formula	C₁₂H₁₇N₂O₄P
Molar mass	284.25 g·mol⁻¹
Melting point	220–228 °C (428–442 °F)
Solubility in water	soluble
Solubility	soluble in methanol slightly soluble in ethanol negligible in chloroform, benzene
Hazards
Lethal dose or concentration (LD, LC):
LD₅₀ (median dose)	285 mg/kg (mouse, i.v.) 280 mg/kg (rat, i.v.) 12.5 mg/kg (rabbit, i.v.)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y (what is ^YN ?)
Infobox references

Psilocybin (/ˌsɪləˈsaɪbɪn/ SIL-ə-SY-bin) is a naturally occurring psychedelic compound produced by more than 200 species of mushrooms, collectively known as psilocybin mushrooms. The most potent are members of the genus Psilocybe, such as P. azurescens, P. semilanceata, and P. cyanescens, but psilocybin has also been isolated from about a dozen other genera. As a prodrug, psilocybin is quickly converted by the body to psilocin, which has mind-altering effects similar, in some aspects, to those of LSD, mescaline, and DMT. In general, the effects include euphoria, visual and mental hallucinations, changes in perception, a distorted sense of time, and spiritual experiences, and can include possible adverse reactions such as nausea and panic attacks.