PSILOCYBINE

Investigational

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26841800 | https://clinicaltrials.gov/ct2/show/NCT03341689 | http://onlinelibrary.wiley.com/doi/10.1002/hlca.19590420518/abstract | https://clinicaltrials.gov/ct2/show/NCT02061293 | https://clinicaltrials.gov/ct2/show/NCT03181529

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 In the 1960's psilocybin was marketed for use as a treatment for various psychoses, however, it was withdrawn from the market when the regulatory environment changed.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 Target	Pharmacology	Condition	Potency
5-hydroxytryptamine receptor 2A 68 Target ID: P28223 Gene ID: 3356.0 Gene Symbol: HTR2A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26841800	Agonist 2470

Conditions

Condition	Modality	Highest Phase	Product
Migraine headache 2 Sources: https://clinicaltrials.gov/ct2/show/NCT03341689	Primary	Phase II 1101	Unknown Approved Use Unknown
Obsessive-compulsive disorder 26 Sources: https://clinicaltrials.gov/ct2/show/NCT03300947	Primary	Phase II 1101	Unknown Approved Use Unknown
Major depressive disorder 170 Sources: https://clinicaltrials.gov/ct2/show/NCT03181529	Primary	Phase II 1101	Unknown Approved Use Unknown
Alcohol addiction 17 Sources: https://clinicaltrials.gov/ct2/show/NCT02061293	Primary	Phase II 1101	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
16 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28353056	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28353056	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28353056	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

Value	Dose	Analyte	Population
140 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28353056	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28353056	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28353056	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

T_1/2

Value	Dose	Analyte	Population
3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28353056	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28353056	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28353056	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

Sourcing

Vendor/Aggregator	ID	URL
BioSynth	P-7825	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/P-7825
Cayman Chemical	14041	http://www.caymanchem.com/app/template/Product.vm/catalog/14041
Compound Cloud	10624
Toronto Research Chemicals	P839650	https://www.trc-canada.com/product-detail/?CatNum=P839650

PubMed

Title	Date	PubMed
Brain mechanisms of hallucinogens and entactogens.	2001 Dec	22033605
[Psychoactive mushrooms - an update].	2001 Dec	11753749
The detection of psilocin in human urine.	2001 May	11373000
Persistent psychosis after a single ingestion of 'ecstasy'.	2001 Nov-Dec	11815690
Possible mechanisms of panic attack and schizophrenia via APUD system.	2002 Feb	11812187
Synthetic studies of psilocin analogs having either a formyl group or bromine atom at the 5- or 7-position.	2002 Jan	11824592
Mismatch negativity predicts psychotic experiences induced by NMDA receptor antagonist in healthy volunteers.	2002 Mar 1	11904134
Synthesis of a psilocin hapten and a protein-hapten conjugate.	2002 Sep	12356281
Renal excretion profiles of psilocin following oral administration of psilocybin: a controlled study in man.	2002 Sep 5	12191719
[Discrimination of psychoactive fungi (commonly called "magic mushrooms") based on the DNA sequence of the internal transcribed spacer region].	2003 Feb	12749196
Concise large-scale synthesis of psilocin and psilocybin, principal hallucinogenic constituents of "magic mushroom".	2003 Jun	12828485
Poly(dimethylsiloxane) electrospray devices fabricated with diamond-like carbon-poly(dimethylsiloxane) coated SU-8 masters.	2003 May	15100784
Optimized glucuronide hydrolysis for the detection of psilocin in human urine samples.	2003 Nov 5	14581081
Mushrooms: toxins right in your own backyard.	2003 Oct	14583729
Development of a psilocin immunoassay for serum and blood samples.	2004 Dec	15526212
Acute psychological and physiological effects of psilocybin in healthy humans: a double-blind, placebo-controlled dose-effect study.	2004 Mar	14615876
Poisonings resulting from the ingestion of magic mushrooms in Kraków.	2005	16225077
Hallucinogen persisting perception disorder after psilocybin consumption: a case study.	2005 Aug	15963699
Investigation into the temporal stability of aqueous standard solutions of psilocin and psilocybin using high performance liquid chromatography.	2006 Apr-Jun	17002211
Psilocybin can occasion mystical-type experiences having substantial and sustained personal meaning and spiritual significance.	2006 Aug	16826400
Not imagining it. Research into hallucinogens cautiously resumes.	2006 Nov	17076078
Psilocybin links binocular rivalry switch rate to attention and subjective arousal levels in humans.	2007 Dec	17874073
[Hallucinogenic fungi (psilocybe). Part II. Identification of Psilocybe semilanceata by PCR].	2007 Jul-Sep	17907620
[Prof. Günther Hole on his self-experiments. "What did I actually endure?"].	2007 Mar 15	20104696
The effects of the preferential 5-HT2A agonist psilocybin on prepulse inhibition of startle in healthy human volunteers depend on interstimulus interval.	2007 Sep	17299516
Albert Hofmann, the father of LSD (1906-2008).	2008	18799895
Mystical-type experiences occasioned by psilocybin mediate the attribution of personal meaning and spiritual significance 14 months later.	2008 Aug	18593735
[Hallucinogen-induced psychological disorders].	2008 Jun	18512184
Apical regional wall motion abnormalities reminiscent to Tako-Tsubo cardiomyopathy following consumption of psychoactive fungi.	2009 May 1	18378018
Availability of websites offering to sell psilocybin spores and psilocybin.	2009 Sep	19999684
Hallucinogens as medicine.	2010 Dec	21141361
Forensic analysis of hallucinogenic mushrooms and khat (Catha edulis Forsk) using cation-exchange liquid chromatography.	2010 Feb 25	20047807
The hallucinogenic world of tryptamines: an updated review.	2015 Aug	25877327

Patents

Sample Use Guides

In Vivo Use Guide

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

Official Name

English

CY 39

Code

English

TEONANACATL

Common Name

English

PSILOCYBIN [MI]

Common Name

English

PSILOCYBINE [INN]

Common Name

English

PSILOCYBIN

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