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Details

Stereochemistry ACHIRAL
Molecular Formula C12H16N2O
Molecular Weight 204.2682
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PSILOCIN

SMILES

CN(C)CCC1=CNC2=C1C(O)=CC=C2

InChI

InChIKey=SPCIYGNTAMCTRO-UHFFFAOYSA-N
InChI=1S/C12H16N2O/c1-14(2)7-6-9-8-13-10-4-3-5-11(15)12(9)10/h3-5,8,13,15H,6-7H2,1-2H3

HIDE SMILES / InChI

Molecular Formula C12H16N2O
Molecular Weight 204.2682
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Psilocybin is a naturally occurring psychedelic prodrug compound produced by more than 200 species of mushrooms, collectively known as psilocybin mushrooms. Once ingested, psilocybin is rapidly metabolized to the psilocin, which then acts on serotonin receptors in the brain. Psilocybin was identified as the active hallucinogenic compound in magic mushrooms in 1959, but humans have used assorted psilocybin mushrooms in religious ceremonies since prehistoric times. In the 1960's psilocybin was marketed for use as a treatment for various psychoses, however, it was withdrawn from the market when the regulatory environment changed. Recently there has been as renewed interest in studying the medicinal uses of psilocybin for treatment of anxiety, depression, migraine headaches, addictions, and other neuropsychiatric conditions.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
49.0 nM [Ki]
25.0 nM [Ki]
10.0 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
16 μg/L
0.3 mg/kg single, oral
PSILOCIN plasma
Homo sapiens
26 μg/L
0.45 mg/kg single, oral
PSILOCIN plasma
Homo sapiens
37.6 μg/L
0.6 mg/kg single, oral
PSILOCIN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
140 μg × h/L
0.3 mg/kg single, oral
PSILOCIN plasma
Homo sapiens
213 μg × h/L
0.45 mg/kg single, oral
PSILOCIN plasma
Homo sapiens
267 μg × h/L
0.6 mg/kg single, oral
PSILOCIN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
3 h
0.3 mg/kg single, oral
PSILOCIN plasma
Homo sapiens
3 h
0.45 mg/kg single, oral
PSILOCIN plasma
Homo sapiens
3 h
0.6 mg/kg single, oral
PSILOCIN plasma
Homo sapiens

PubMed

Sample Use Guides

In Vivo Use Guide
Rats were administered 5 and 10 mg/kg of Psilocin as an intraperitoneal injection. Following the dosing protocol, extracellular dopamine levels were increased in the nucleus accumbens. Psilocin did not affect the extracellular 5-HT level in the nucleus accumbens. However, systemic administration of 10 mg/kg of psilocin significantly increased extracellular 5-HT levels in the ventral tegmental area, but decreased dopamine in this area. Behaviorally, psilocin significantly increased the number of head twitches.
Route of Administration: Intraperitoneal
In Vitro Use Guide
Unknown
Substance Class Chemical
Record UNII
CMS88KUW0G
Record Status Validated (UNII)
Record Version