Psilocybin

Psilocybin

Names
Preferred IUPAC name 3-[2-(Dimethylamino)ethyl]-1H-indol-4-yl dihydrogen phosphate
Identifiers
CAS Number	520-52-5 Y
3D model (JSmol)	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 CID	10624
RTECS number	NM3150000
UNII	2RV7212BP0 Y
CompTox Dashboard (EPA)	DTXSID0048898
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[1]
Excretion	Renal
Legal status	AU: S9/S8 (Controlled Drug) BR: Class F2 (Prohibited psychotropics)[2] CA: Schedule III UK: Class A US: Schedule I
Properties
Chemical formula	C12H17N2O4P
Molar mass	284.252 g·mol−1
Melting point	220–228 °C (428–442 °F)[3]
Solubility in water	Soluble
Solubility	Soluble in boiling methanol and water slightly soluble in ethanol insoluble in chloroform, benzene[4]
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.)[3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Psilocybin^[a] (/ˌsaɪləˈsaɪbɪn/ sy-lə-SY-bin, /ˌsɪl-/) is a naturally occurring psychedelic prodrug compound produced by more than 200 species of fungi. The most potent are members of genus Psilocybe, such as P. azurescens, P. semilanceata, and P. cyanescens, but psilocybin has also been isolated from about a dozen other genera. Psilocybin is itself biologically inactive but is quickly converted by the body to psilocin, which has mind-altering effects similar, in some aspects, to those of lysergic acid diethylamide (LSD), mescaline, and dimethyltryptamine (DMT). In general, the effects include euphoria, visual and mental hallucinations, changes in perception, distorted sense of time, and perceived spiritual experiences. It can also cause adverse reactions such as nausea and panic attacks.

Imagery found on cave paintings and rock art of modern-day Spain and Algeria suggests that human use of psilocybin mushrooms predates recorded history. In Mesoamerica, the mushrooms had long been consumed in spiritual and divinatory ceremonies before Spanish chroniclers first documented their use in the sixteenth century. In 1958, the Swiss chemist Albert Hofmann isolated psilocybin and psilocin from the mushroom Psilocybe mexicana. Hofmann's employer Sandoz marketed and sold pure psilocybin to physicians and clinicians worldwide for use in psychedelic therapy. Although the increasingly restrictive drug laws of the 1960s and the 1970s curbed scientific research into the effects of psilocybin and other hallucinogens, its popularity as an entheogen (spirituality-enhancing agent) grew in the next decade, owing largely to the increased availability of information on how to cultivate psilocybin mushrooms.

The intensity and duration of the effects of psilocybin are variable, depending on species or cultivar of mushrooms, dosage, individual physiology, and set and setting, as was shown in experiments led by Timothy Leary at Harvard University in the early 1960s. Once ingested, psilocybin is rapidly metabolized to psilocin, which then acts on serotonin receptors in the brain. The mind-altering effects of psilocybin typically last from two to six hours, although to individuals under the influence of psilocybin, the effects may seem to last much longer, since the drug can distort the perception of time. Possession of psilocybin-containing mushrooms has been outlawed in most countries, and psilocybin has been classified as a Schedule I controlled substance under the 1971 United Nations Convention on Psychotropic Substances.

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