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

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 In the 1960's psilocybin was marketed for use as a treatment for various psychoses, however, it was withdrawn from the market when the regulatory environment changed.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
Effect of ring fluorination on the pharmacology of hallucinogenic tryptamines.	2000 Nov 30	11101361
Brain mechanisms of hallucinogens and entactogens.	2001 Dec	22033605
[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
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
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
Psilocin identified in a DUID investigation.	2006 Jun	16839473
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
Not imagining it. Research into hallucinogens cautiously resumes.	2006 Nov	17076078
[Chronic cluster headache: Response to psilocybin].	2006 Nov 1-15	17072817
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
Reviving the study of hallucinogens.	2006 Oct	17183740
Application of ion mobility spectrometry in cases of forensic interest.	2006 Sep 12	16831529
[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
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
Timothy Leary, Richard Alpert (Ram Dass) and the changing definition of psilocybin.	2010 May	19744846
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
Differential contributions of serotonin receptors to the behavioral effects of indoleamine hallucinogens in mice.	2011 Nov	21148021
Fungal hallucinogens psilocin, ibotenic acid, and muscimol: analytical methods and biologic activities.	2013 Aug	23851905
Effect of psilocin on extracellular dopamine and serotonin levels in the mesoaccumbens and mesocortical pathway in awake rats.	2015	25342005
The hallucinogenic world of tryptamines: an updated review.	2015 Aug	25877327

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

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