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Key Documents

P2279

Sigma-Aldrich

Psilocin

Synonym(s):

4-Hydroxy-N,N-dimethyltryptamine

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About This Item

Empirical Formula (Hill Notation):
C12H16N2O
CAS Number:
Molecular Weight:
204.27
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

form

powder

Quality Level

drug control

USDEA Schedule I; Home Office Schedule 1; stupéfiant (France); kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada; psicótropo (Spain); Decreto Lei 15/93: Tabela IIA (Portugal)

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

forensics and toxicology
pharmaceutical (small molecule)
veterinary

storage temp.

−20°C

SMILES string

CN(C)CCc1c[nH]c2cccc(O)c12

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

InChI key

SPCIYGNTAMCTRO-UHFFFAOYSA-N

Gene Information

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Biochem/physiol Actions

Hallucinogen originally isolated from the mushroom, Psilocybe mexicana, non-selective serotonin receptor agonist.
Hallucinogen; non-selective serotonin receptor agonist.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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N Almaula et al.
Molecular pharmacology, 50(1), 34-42 (1996-07-01)
An important determinant of the neurobehavioral responses induced by a drug is its relative receptor selectivity. The molecular basis of ligand selectivity of hallucinogenic and nonhallucinogenic compounds of varying structural classes for the human 5-hydroxytryptamine (5-HT)2A and 5-HT2C receptors was
N Milne et al.
Metabolic engineering, 60, 25-36 (2020-04-01)
Psilocybin is a tryptamine-derived psychoactive alkaloid found mainly in the fungal genus Psilocybe, among others, and is the active ingredient in so-called "magic mushrooms". Although its notoriety originates from its psychotropic properties and popular use as a recreational drug, clinical
Tehila Mishraki-Berkowitz et al.
Journal of forensic sciences, 65(5), 1450-1457 (2020-05-07)
Psilocin (4-hydroxy-N,N-dimethyltryptamine, 4-HO-DMT) and bufotenine (5-hydroxy-N,N-dimethyltryptamine, 5-HO-DMT), which are both naturally occurring compounds, are classified as controlled substances in numerous countries due to their pharmacological activities and recreational usage. There are two other benzene ring regioisomers, 6-hydroxy-N,N-dimethyltryptamine (6-HO-DMT) and 7-hydroxy-N,N-dimethyltryptamine
Howard Sard et al.
Bioorganic & medicinal chemistry letters, 15(20), 4555-4559 (2005-08-03)
An SAR study of psilocybin and psilocin derivatives reveals that 1-methylpsilocin is a selective agonist at the h5-HT(2C) receptor. The corresponding phosphate derivative, 1-methylpsilocybin, shows efficacy in an animal model for obsessive-compulsive disorder, as does 4-fluoro-N,N-dimethyltryptamine. These results suggest a
Aisling Spain et al.
Neuropharmacology, 99, 210-220 (2015-07-21)
The development of pharmacological magnetic resonance imaging (phMRI) has presented the opportunity for investigation of the neurophysiological effects of drugs in vivo. Psilocin, a hallucinogen metabolised from psilocybin, was recently reported to evoke brain region-specific, phMRI signal changes in humans.

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