PSILOCYBINE

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=CC=CC(OP(O)(O)=O)=C12

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/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 In the 1960's psilocybin was marketed for use as a treatment for various psychoses, however, it was withdrawn from the market when the regulatory environment changed.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 69 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 2662

Conditions

Condition	Modality	Highest Phase	Product
Migraine headache 2 Sources: https://clinicaltrials.gov/ct2/show/NCT03341689	Primary	Phase II 1144	Unknown Approved Use Unknown
Obsessive-compulsive disorder 28 Sources: https://clinicaltrials.gov/ct2/show/NCT03300947	Primary	Phase II 1144	Unknown Approved Use Unknown
Major depressive disorder 172 Sources: https://clinicaltrials.gov/ct2/show/NCT03181529	Primary	Phase II 1144	Unknown Approved Use Unknown
Alcohol addiction 21 Sources: https://clinicaltrials.gov/ct2/show/NCT02061293	Primary	Phase II 1144	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
Morphological and chemical analysis of magic mushrooms in Japan.	2003 Dec 17	14642723
Effects of the 5-HT2A agonist psilocybin on mismatch negativity generation and AX-continuous performance task: implications for the neuropharmacology of cognitive deficits in schizophrenia.	2003 Jan	12496954
[Levels of psilocybin and psilocin in various types of mushrooms].	2003 Jul	14631713
Mushrooms: toxins right in your own backyard.	2003 Oct	14583729
The Meixner test in the detection of alpha-amanitin and false-positive reactions caused by psilocin and 5-substituted tryptamines.	2004 Aug	15278082
Psilocybin impairs high-level but not low-level motion perception.	2004 Aug 26	15305143
Development of a psilocin immunoassay for serum and blood samples.	2004 Dec	15526212
Transient reinforcing effects of phenylisopropylamine and indolealkylamine hallucinogens in rhesus monkeys.	2004 Mar	15096915
Acute psychological and physiological effects of psilocybin in healthy humans: a double-blind, placebo-controlled dose-effect study.	2004 Mar	14615876
Forensic analysis of hallucinogenic fungi: a DNA-based approach.	2004 Mar 10	15036436
Psychedelic drugs: the ups and downs of ecstasy.	2004 May 13	15141183
[Hallucinogenic mushrooms].	2005	16401965
Severe rhabdomyolysis, acute renal failure and posterior encephalopathy after 'magic mushroom' abuse.	2005 Dec	16276262
[Hallucinogenic fungi (Psylocibe). Part I. Characteristics, results of consumption, recognition].	2005 Jul-Sep	16320771
Liquid chromatography-mass spectrometric and liquid chromatography-tandem mass spectrometric determination of hallucinogenic indoles psilocin and psilocybin in "magic mushroom" samples.	2005 Mar	15813544
Using psilocybin to investigate the relationship between attention, working memory, and the serotonin 1A and 2A receptors.	2005 Oct	16269092
SAR of psilocybin analogs: discovery of a selective 5-HT 2C agonist.	2005 Oct 15	16061378
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 Jan	16423222
Response of cluster headache to psilocybin and LSD.	2006 Jun 27	16801660
Safety, tolerability, and efficacy of psilocybin in 9 patients with obsessive-compulsive disorder.	2006 Nov	17196053
Phylogenetic relationship of psychoactive fungi based on rRNA gene for a large subunit and their identification using the TaqMan assay (II).	2006 Nov 10	16343833
Psilocybin links binocular rivalry switch rate to attention and subjective arousal levels in humans.	2007 Dec	17874073
[Automutilation after consumption of hallucinogenic mushrooms].	2007 Dec 29	18257429
Effects of psilocybin on time perception and temporal control of behaviour in humans.	2007 Jan	16714323
[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
Psilocybin-induced stimulus control in the rat.	2007 Oct	17688928
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
Between prohibitions: patterns and meanings of magic mushroom use in the UK.	2008	18189205
Effects of varied doses of psilocybin on time interval reproduction in human subjects.	2008 Apr 11	18325673
Mystical-type experiences occasioned by psilocybin mediate the attribution of personal meaning and spiritual significance 14 months later.	2008 Aug	18593735
The structure of human serotonin 2c G-protein-coupled receptor bound to agonists and antagonists.	2008 Aug	18499489
Hallucinogen-like effects of N,N-dipropyltryptamine (DPT): possible mediation by serotonin 5-HT1A and 5-HT2A receptors in rodents.	2008 Jan	17905422
[Hallucinogen-induced psychological disorders].	2008 Jun	18512184
Unrecognized magic mushroom abuse in a 28-year-old man.	2008 Oct	18926381
Analysis of mushroom exposures in Texas requiring hospitalization, 2005-2006.	2009 Jun	19415588
Apical regional wall motion abnormalities reminiscent to Tako-Tsubo cardiomyopathy following consumption of psychoactive fungi.	2009 May 1	18378018
Return of a problem child.	2009 Oct	19780439
Availability of websites offering to sell psilocybin spores and psilocybin.	2009 Sep	19999684
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 Sep 15	19545856
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 Aug 24	20800724
Psychometric evaluation of the altered states of consciousness rating scale (OAV).	2010 Aug 31	20824211
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
Comparative study of ATR and transflection IR spectroscopic techniques for the analysis of hallucinogenic mushrooms.	2010 Feb 25	19969433
Glucuronidation of psilocin and 4-hydroxyindole by the human UDP-glucuronosyltransferases.	2010 Mar	20007669
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 Nov	20810266
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 `Thu Jul 06 22:18:39 UTC 2023` Edited by `admin` on `Thu Jul 06 22:18:39 UTC 2023`
Record UNII	2RV7212BP0
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

PSILOCYBINE

Official Name

English

CY39

Code

English

TEONANACATL

Common Name

English

PSILOCYBIN [MI]

Common Name

English

Psilocybine [WHO-DD]

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

(3-(2-(DIMETHYLAMINO)ETHYL)-1H-INDOL-4-YL) DIHYDROGEN PHOSPHATE

Common Name

English

CY-39

Code

English

INDOCYBIN

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C47794