PSILOCIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H16N2O
Molecular Weight	204.2682
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=SPCIYGNTAMCTRO-UHFFFAOYSA-N

InChI=1S/C12H16N2O/c1-14(2)7-6-9-8-13-10-4-3-5-11(15)12(9)10/h3-5,8,13,15H,6-7H2,1-2H3

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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/11101361

Psilocin is a serotonergic psychedelic substance found in most psychedelic mushrooms along with its phosphorylated counterpart psilocybin. Psilocin is the pharmacologically active agent in the body after ingestion of psilocybin. Psilocybin rapidly dephosphorylates to psilocin which acts as a 5-HT2A, 5-HT2C, and 5-HT1A agonist or partial agonist.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
5-hydroxytryptamine receptor 1A 54 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 2678	49.0 nM [Ki]
5-hydroxytryptamine receptor 2A 69 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 2678	25.0 nM [Ki]
5-hydroxytryptamine receptor 2C 26 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 2678	10.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Effect of ring fluorination on the pharmacology of hallucinogenic tryptamines.	2000 Nov 30	11101361
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

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

PSILOCIN

Common Name

English

3-(2-(DIMETHYLAMINO)ETHYL)-1H-INDOL-4-OL

Systematic Name

English

PSILOCIN [MART.]

Common Name

English

Psilocin [WHO-DD]

Common Name

English

PSILOCYN

Common Name

English

4-HO-DMT

Common Name

English

PSILOCIN [MI]

Common Name

English

4-HYDROXY-N,N-DIMETHYLTRYPTAMINE

Systematic Name

English

Classification Tree Code System Code

DEA NO.

7438