Psilocybin

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H17N2O4P
Molecular Weight	284.2481
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

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	284.2481
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/25342005 | https://www.ncbi.nlm.nih.gov/pubmed/23851905 | https://www.ncbi.nlm.nih.gov/pubmed/21148021 | https://www.ncbi.nlm.nih.gov/pubmed/11101361https://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 In the 1960's psilocybin was marketed for use as a treatment for various psychoses, however, it was withdrawn from the market when the regulatory environment changed.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	Potency
5-hydroxytryptamine receptor 2A 73 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 2752
5-hydroxytryptamine receptor 1A 58 Target ID: Q64264 Gene ID: 15550.0 Gene Symbol: Htr1a Target Organism: Mus musculus (Mouse) Sources: https://www.ncbi.nlm.nih.gov/pubmed/21148021	Agonist 2752	49.0 nM [Ki]
5-hydroxytryptamine receptor 2A 73 Target ID: P35363 Gene ID: 15558.0 Gene Symbol: Htr2a Target Organism: Mus musculus (Mouse) Sources: https://www.ncbi.nlm.nih.gov/pubmed/21148021	Agonist 2752	25.0 nM [Ki]
5-hydroxytryptamine receptor 2C 29 Target ID: P34968 Gene ID: 15560.0 Gene Symbol: Htr2c Target Organism: Mus musculus (Mouse) Sources: https://www.ncbi.nlm.nih.gov/pubmed/21148021	Agonist 2752	10.0 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Migraine headache 5 Sources: https://clinicaltrials.gov/ct2/show/NCT03341689	Primary	Phase II 1147	Unknown Approved Use Unknown
Obsessive-compulsive disorder 33 Sources: https://clinicaltrials.gov/ct2/show/NCT03300947	Primary	Phase II 1147	Unknown Approved Use Unknown
Major depressive disorder 179 Sources: https://clinicaltrials.gov/ct2/show/NCT03181529	Primary	Phase II 1147	Unknown Approved Use Unknown
Alcohol addiction 24 Sources: https://clinicaltrials.gov/ct2/show/NCT02061293	Primary	Phase II 1147	Unknown Approved Use Unknown
Unknown 2596

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
The hallucinogenic world of tryptamines: an updated review.	2015-08	25877327
Effect of psilocin on extracellular dopamine and serotonin levels in the mesoaccumbens and mesocortical pathway in awake rats.	2015	25342005
Fungal hallucinogens psilocin, ibotenic acid, and muscimol: analytical methods and biologic activities.	2013-08	23851905
Differential contributions of serotonin receptors to the behavioral effects of indoleamine hallucinogens in mice.	2011-11	21148021
Hallucinogens as medicine.	2010-12	21141361
Turn on, tune in, but don't drop out: The impact of neo-liberalism on magic mushroom users' (in)ability to imagine collectivist social worlds.	2010-11	20810266
Psychometric evaluation of the altered states of consciousness rating scale (OAV).	2010-08-31	20824211
Micro-solid phase extraction coupled with high-performance liquid chromatography-tandem mass spectrometry for the determination of stimulants, hallucinogens, ketamine and phencyclidine in oral fluids.	2010-08-24	20800724
Timothy Leary, Richard Alpert (Ram Dass) and the changing definition of psilocybin.	2010-05	19744846
Glucuronidation of psilocin and 4-hydroxyindole by the human UDP-glucuronosyltransferases.	2010-03	20007669
Forensic analysis of hallucinogenic mushrooms and khat (Catha edulis Forsk) using cation-exchange liquid chromatography.	2010-02-25	20047807
Comparative study of ATR and transflection IR spectroscopic techniques for the analysis of hallucinogenic mushrooms.	2010-02-25	19969433
Return of a problem child.	2009-10	19780439
Unifying electron transfer mechanism for psilocybin and psilocin.	2009-10	19604649
Sensorimotor gating depends on polymorphisms of the serotonin-2A receptor and catechol-O-methyltransferase, but not on neuregulin-1 Arg38Gln genotype: a replication study.	2009-09-15	19545856
Availability of websites offering to sell psilocybin spores and psilocybin.	2009-09	19999684
Analysis of mushroom exposures in Texas requiring hospitalization, 2005-2006.	2009-06	19415588
Apical regional wall motion abnormalities reminiscent to Tako-Tsubo cardiomyopathy following consumption of psychoactive fungi.	2009-05-01	18378018
Unrecognized magic mushroom abuse in a 28-year-old man.	2008-10	18926381
Mystical-type experiences occasioned by psilocybin mediate the attribution of personal meaning and spiritual significance 14 months later.	2008-08	18593735
The structure of human serotonin 2c G-protein-coupled receptor bound to agonists and antagonists.	2008-08	18499489
[Hallucinogen-induced psychological disorders].	2008-06	18512184
Effects of varied doses of psilocybin on time interval reproduction in human subjects.	2008-04-11	18325673
Hallucinogen-like effects of N,N-dipropyltryptamine (DPT): possible mediation by serotonin 5-HT1A and 5-HT2A receptors in rodents.	2008-01	17905422
Albert Hofmann, the father of LSD (1906-2008).	2008	18799895
Between prohibitions: patterns and meanings of magic mushroom use in the UK.	2008	18189205
[Automutilation after consumption of hallucinogenic mushrooms].	2007-12-29	18257429
Psilocybin links binocular rivalry switch rate to attention and subjective arousal levels in humans.	2007-12	17874073
[Hallucinogenic fungi (psilocybe). Part II. Identification of Psilocybe semilanceata by PCR].	2007-10-03	17907620
Psilocybin-induced stimulus control in the rat.	2007-10	17688928
The effects of the preferential 5-HT2A agonist psilocybin on prepulse inhibition of startle in healthy human volunteers depend on interstimulus interval.	2007-09	17299516
[Prof. Günther Hole on his self-experiments. "What did I actually endure?"].	2007-03-15	20104696
Effects of psilocybin on time perception and temporal control of behaviour in humans.	2007-01	16714323
[Concentration of selected microelements in blood serum of rats exposed to the action of psilocin and phenylethylamine].	2007	20143700
5-Year trends in use of hallucinogens and other adjunct drugs among UK dance drug users.	2007	17172780
Phylogenetic relationship of psychoactive fungi based on rRNA gene for a large subunit and their identification using the TaqMan assay (II).	2006-11-10	16343833
Safety, tolerability, and efficacy of psilocybin in 9 patients with obsessive-compulsive disorder.	2006-11	17196053
Not imagining it. Research into hallucinogens cautiously resumes.	2006-11	17076078
[Chronic cluster headache: Response to psilocybin].	2006-10-31	17072817
Reviving the study of hallucinogens.	2006-10	17183740
Investigation into the temporal stability of aqueous standard solutions of psilocin and psilocybin using high performance liquid chromatography.	2006-09-28	17002211
Application of ion mobility spectrometry in cases of forensic interest.	2006-09-12	16831529
Psilocybin can occasion mystical-type experiences having substantial and sustained personal meaning and spiritual significance.	2006-08	16826400
Response of cluster headache to psilocybin and LSD.	2006-06-27	16801660
Psilocin identified in a DUID investigation.	2006-06	16839473
The determination of psilocin and psilocybin in hallucinogenic mushrooms by HPLC utilizing a dual reagent acidic potassium permanganate and tris(2,2'-bipyridyl)ruthenium(II) chemiluminescence detection system.	2006-01	16423222
[Hallucinogenic fungi (Psylocibe). Part I. Characteristics, results of consumption, recognition].	2005-12-03	16320771
[Hallucinogenic mushrooms].	2005	16401965
Brain mechanisms of hallucinogens and entactogens.	2001-12	22033605
Effect of ring fluorination on the pharmacology of hallucinogenic tryptamines.	2000-11-30	11101361

Patents

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 Created by `admin` on `Wed Apr 02 08:28:43 GMT 2025` Edited by `admin` on `Wed Apr 02 08:28:43 GMT 2025`
Record UNII	2RV7212BP0
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

Psilocybine

Preferred Name

English

Psilocybin

Official Name

English

CY39

Code

English

1H-Indol-4-ol, 3-[2-(dimethylamino)ethyl]-, 4-(dihydrogen phosphate)

Systematic Name

English

TEONANACATL

Common Name

English

COMP360

Code

English

PSILOCYBIN [MI]

Common Name

English

Psilocybine [WHO-DD]

Common Name

English

psilocybine [INN]

Common Name

English

PSILOCYBIN [USAN]

Common Name

English

PSILOCYBINE [HSDB]

Common Name

English

PSILOCYBINE [MART.]

Common Name

English

3-[2-(dimethylamino)ethyl]-1H-indol-4-yl dihydrogen phosphate

Systematic Name

English

CY-39

Code

English

INDOCYBIN

Common Name

English

COMP-360

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C47794