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Details

Stereochemistry ACHIRAL
Molecular Formula C12H17N2O4P
Molecular Weight 284.2486
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PSILOCYBINE

SMILES

CN(C)CCc1c[nH]c2cccc(c12)OP(=O)(O)O

InChI

InChIKey=QVDSEJDULKLHCG-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C12H17N2O4P
Molecular Weight 284.2486
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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 In the 1960's psilocybin was marketed for use as a treatment for various psychoses, however, it was withdrawn from the market when the regulatory environment changed.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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P28223
Gene ID: 3356.0
Gene Symbol: HTR2A
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
16 μg/L
0.3 mg/kg single, oral
dose: 0.3 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
PSILOCIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
26 μg/L
0.45 mg/kg single, oral
dose: 0.45 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
PSILOCIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
37.6 μg/L
0.6 mg/kg single, oral
dose: 0.6 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
PSILOCIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
140 μg × h/L
0.3 mg/kg single, oral
dose: 0.3 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
PSILOCIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
213 μg × h/L
0.45 mg/kg single, oral
dose: 0.45 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
PSILOCIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
267 μg × h/L
0.6 mg/kg single, oral
dose: 0.6 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
PSILOCIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3 h
0.3 mg/kg single, oral
dose: 0.3 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
PSILOCIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
3 h
0.45 mg/kg single, oral
dose: 0.45 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
PSILOCIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
3 h
0.6 mg/kg single, oral
dose: 0.6 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
PSILOCIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
PubMed

PubMed

TitleDatePubMed
Brain mechanisms of hallucinogens and entactogens.
2001 Dec
[Psychoactive mushrooms - an update].
2001 Dec
The detection of psilocin in human urine.
2001 May
Persistent psychosis after a single ingestion of 'ecstasy'.
2001 Nov-Dec
Possible mechanisms of panic attack and schizophrenia via APUD system.
2002 Feb
Synthetic studies of psilocin analogs having either a formyl group or bromine atom at the 5- or 7-position.
2002 Jan
Mismatch negativity predicts psychotic experiences induced by NMDA receptor antagonist in healthy volunteers.
2002 Mar 1
Synthesis of a psilocin hapten and a protein-hapten conjugate.
2002 Sep
Renal excretion profiles of psilocin following oral administration of psilocybin: a controlled study in man.
2002 Sep 5
[Discrimination of psychoactive fungi (commonly called "magic mushrooms") based on the DNA sequence of the internal transcribed spacer region].
2003 Feb
Concise large-scale synthesis of psilocin and psilocybin, principal hallucinogenic constituents of "magic mushroom".
2003 Jun
Poly(dimethylsiloxane) electrospray devices fabricated with diamond-like carbon-poly(dimethylsiloxane) coated SU-8 masters.
2003 May
Optimized glucuronide hydrolysis for the detection of psilocin in human urine samples.
2003 Nov 5
Mushrooms: toxins right in your own backyard.
2003 Oct
Development of a psilocin immunoassay for serum and blood samples.
2004 Dec
Acute psychological and physiological effects of psilocybin in healthy humans: a double-blind, placebo-controlled dose-effect study.
2004 Mar
Poisonings resulting from the ingestion of magic mushrooms in Kraków.
2005
Hallucinogen persisting perception disorder after psilocybin consumption: a case study.
2005 Aug
Investigation into the temporal stability of aqueous standard solutions of psilocin and psilocybin using high performance liquid chromatography.
2006 Apr-Jun
Psilocybin can occasion mystical-type experiences having substantial and sustained personal meaning and spiritual significance.
2006 Aug
Not imagining it. Research into hallucinogens cautiously resumes.
2006 Nov
Psilocybin links binocular rivalry switch rate to attention and subjective arousal levels in humans.
2007 Dec
[Hallucinogenic fungi (psilocybe). Part II. Identification of Psilocybe semilanceata by PCR].
2007 Jul-Sep
[Prof. Günther Hole on his self-experiments. "What did I actually endure?"].
2007 Mar 15
The effects of the preferential 5-HT2A agonist psilocybin on prepulse inhibition of startle in healthy human volunteers depend on interstimulus interval.
2007 Sep
Albert Hofmann, the father of LSD (1906-2008).
2008
Mystical-type experiences occasioned by psilocybin mediate the attribution of personal meaning and spiritual significance 14 months later.
2008 Aug
[Hallucinogen-induced psychological disorders].
2008 Jun
Apical regional wall motion abnormalities reminiscent to Tako-Tsubo cardiomyopathy following consumption of psychoactive fungi.
2009 May 1
Availability of websites offering to sell psilocybin spores and psilocybin.
2009 Sep
Hallucinogens as medicine.
2010 Dec
Forensic analysis of hallucinogenic mushrooms and khat (Catha edulis Forsk) using cation-exchange liquid chromatography.
2010 Feb 25
The hallucinogenic world of tryptamines: an updated review.
2015 Aug
Patents

Patents

Sample Use Guides

In a clinical trial for the treatment of migraines patients where given either 0.0143 mg/kg or 0.143 mg/kg of psilocybin in capsule form.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Jun 26 04:37:00 UTC 2021
Edited
by admin
on Sat Jun 26 04:37:00 UTC 2021
Record UNII
2RV7212BP0
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PSILOCYBINE
HSDB   INN   MART.   WHO-DD  
INN  
Official Name English
CY 39
Code English
TEONANACATL
Common Name English
PSILOCYBIN [MI]
Common Name English
PSILOCYBINE [INN]
Common Name English
PSILOCYBIN
MI  
Common Name English
3-(2-DIMETHYLAMINOETHYL)INDOL-4-YL DIHYDROGEN PHOSPHATE
Systematic Name English
PSILOCYBINE [HSDB]
Common Name English
PSILOCYBINE [MART.]
Common Name English
CY-39
Code English
PSILOCYBINE [WHO-DD]
Common Name English
INDOCYBIN
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C47794
Created by admin on Sat Jun 26 04:37:00 UTC 2021 , Edited by admin on Sat Jun 26 04:37:00 UTC 2021
NCI_THESAURUS C221
Created by admin on Sat Jun 26 04:37:00 UTC 2021 , Edited by admin on Sat Jun 26 04:37:00 UTC 2021
DEA NO. 7437
Created by admin on Sat Jun 26 04:37:00 UTC 2021 , Edited by admin on Sat Jun 26 04:37:00 UTC 2021
Code System Code Type Description
MESH
D011562
Created by admin on Sat Jun 26 04:37:00 UTC 2021 , Edited by admin on Sat Jun 26 04:37:00 UTC 2021
PRIMARY
ECHA (EC/EINECS)
208-294-4
Created by admin on Sat Jun 26 04:37:00 UTC 2021 , Edited by admin on Sat Jun 26 04:37:00 UTC 2021
PRIMARY
WIKIPEDIA
PSILOCYBIN
Created by admin on Sat Jun 26 04:37:00 UTC 2021 , Edited by admin on Sat Jun 26 04:37:00 UTC 2021
PRIMARY
EVMPD
SUB10158MIG
Created by admin on Sat Jun 26 04:37:00 UTC 2021 , Edited by admin on Sat Jun 26 04:37:00 UTC 2021
PRIMARY
NCI_THESAURUS
C62529
Created by admin on Sat Jun 26 04:37:00 UTC 2021 , Edited by admin on Sat Jun 26 04:37:00 UTC 2021
PRIMARY
ChEMBL
CHEMBL194378
Created by admin on Sat Jun 26 04:37:00 UTC 2021 , Edited by admin on Sat Jun 26 04:37:00 UTC 2021
PRIMARY
DRUG BANK
DB11664
Created by admin on Sat Jun 26 04:37:00 UTC 2021 , Edited by admin on Sat Jun 26 04:37:00 UTC 2021
PRIMARY
FDA UNII
2RV7212BP0
Created by admin on Sat Jun 26 04:37:00 UTC 2021 , Edited by admin on Sat Jun 26 04:37:00 UTC 2021
PRIMARY
HSDB
7365
Created by admin on Sat Jun 26 04:37:00 UTC 2021 , Edited by admin on Sat Jun 26 04:37:00 UTC 2021
PRIMARY
EPA CompTox
520-52-5
Created by admin on Sat Jun 26 04:37:00 UTC 2021 , Edited by admin on Sat Jun 26 04:37:00 UTC 2021
PRIMARY
MERCK INDEX
M9305
Created by admin on Sat Jun 26 04:37:00 UTC 2021 , Edited by admin on Sat Jun 26 04:37:00 UTC 2021
PRIMARY Merck Index
INN
1218
Created by admin on Sat Jun 26 04:37:00 UTC 2021 , Edited by admin on Sat Jun 26 04:37:00 UTC 2021
PRIMARY
CAS
520-52-5
Created by admin on Sat Jun 26 04:37:00 UTC 2021 , Edited by admin on Sat Jun 26 04:37:00 UTC 2021
PRIMARY
PUBCHEM
10624
Created by admin on Sat Jun 26 04:37:00 UTC 2021 , Edited by admin on Sat Jun 26 04:37:00 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> AGONIST
Related Record Type Details
METABOLITE ACTIVE -> PRODRUG