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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:
520-53-6
Molecular Weight:
204.27
EC Number:
208-296-5
MDL number:
MFCD00079228
UNSPSC Code:
12352200
PubChem Substance ID:
24898305
NACRES:
NA.77

form

powder

Quality Level

200

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

human ... HTR1A(3350)
rat ... Htr2a(29595) , Htr2c(25187)

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Biochem/physiol Actions

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

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Tryptamine ≥97%

Sigma-Aldrich

193747

Tryptamine

Picrylsulfonic acid solution 5 % (w/v) in H2O, BioReagent, suitable for determination of primary amines

Sigma-Aldrich

P2297

Picrylsulfonic acid solution

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
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
Tooru Kamata et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 796(2), 421-427 (2003-10-29)
In order to develop a sensitive and reliable analytical method for psilocin (PC) in urine samples, the hydrolysis conditions including the acid, alkaline and enzymatic hydrolyses have been investigated by monitoring not only PC but also psilocin glucuronide (PCG) by
A Koçak et al.
Forensic science international, 195(1-3), 36-41 (2009-12-09)
This paper compares the use of ATR and transflection spectroscopic techniques for the qualitative analysis of psilocin extracted from hallucinogenic mushrooms and control spiked mushrooms. Both techniques gave comparable results and agreed with prior GC/MS analysis of the actual case
Kimberly G Nugent et al.
Forensic science international, 140(2-3), 147-157 (2004-03-24)
Hallucinogenic fungi synthesize two controlled substances, psilocin and psilocybin. Possession of the fungal species that contain these compounds is a criminal offence in North America. Some related species that are morphologically similar, do not contain the controlled substances. Therefore, unambiguous
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