3-[2-(dimethylamino)ethyl]-1H-indol-4-ol

• ChemBase ID: 130311
• Molecular Formular: C12H16N2O
• Molecular Mass: 204.26824
• Monoisotopic Mass: 204.12626314
• SMILES: Oc1cccc2c1c(c[nH]2)CCN(C)C
• Canonical SMILES: CN(CCc1c[nH]c2c1c(O)ccc2)C
• InChI: 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
• InChIKey: SPCIYGNTAMCTRO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[2-(dimethylamino)ethyl]-1H-indol-4-ol
• IUPAC Traditional name: psilocin
• Synonyms: 3-[2-(Dimethylamino)ethyl]-1H-indol-4-ol; Psilocyn; Psilocin solution; 4-hydroxy-''N'',''N''-dimethyltryptamine; Psilocin; 4-Hydroxy-N,N-dimethyltryptamine; Psilocin; 4-羟基-N,N-二甲基色胺 溶液; 4-羟基-N,N-二甲基色胺

Database IDs

• CAS Number: 520-53-6
• EC Number: 200-659-6; 208-296-5
• MDL Number: MFCD00079228
• PubChem SID: 162224590; 24898489; 24898305
• PubChem CID: 4980
• CHEBI ID: 8613
• CHEMBL: 65547
• Chemspider ID: 4807
• KEGG ID: C08312
• Wikipedia Title: Psilocin

CALCULATED PROPERTIES

• Acid pKa: 8.971079
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -1.3831663
• LogD (pH = 7.4): -0.095287494
• Log P: 1.1496978
• Molar Refractivity: 62.4231 cm^3
• Polarizability: 25.000689 Å^3
• Polar Surface Area: 39.26 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 173-176 °C (343.4-348.8°F)
• Flash Point: 11 °C; 51.8 °F

Safety Information

• RTECS: NM2625000
• European Hazard Symbols: Flammable (F); Toxic (T); Harmful (Xn)
• UN Number: 1230
• German water hazard class: 1; 3
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-23/24/25-39/23/24/25; 22
• Safety Statements: 36/37/39; 7-16-36/37-45
• GHS Pictograms: GHS02; GHS06; GHS07; GHS08
• GHS Signal Word: Danger; Warning
• GHS Hazard statements: H225-H301-H311-H331-H370; H302
• GHS Precautionary statements: P210-P260-P280-P301 + P310-P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1230 3/PG 2
• Drug Control: Home Office Schedule 1; stupéfiant; kontrollierte Droge in Deutschland; USDEA Schedule I; Home Office Schedule 1; stupéfiant; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: -20°C

Pharmacology Properties

• Admin Routes: Oral, IV
• Excretion: Kidneys/Urine
• Half Life: 2–3 hours
• Metabolism: Liver
• Legal Status: Class A(NZ); Class A(UK); S9 (Australia); Schedule I (US); Schedule III (Canada)
• Gene Information: human ... HTR1A(3350)rat ... Htr2a(29595), Htr2c(25187)

Product Information

• Concentration: 100 μg/mL in methanol
• Grade: drug standard

DETAILS

Sigma Aldrich - P2279

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

Toronto Research Chemicals - P839630

The minor hallucinogenic component of the Teonanacatl mushroom. Psilocin is the 4-hydroxy analog of Psilocybin, formed by metabolic dephosphorylation of Psilocybin and is an active neurochemical. Psychomimetic. Controlled substance (hallucinogen).

REFERENCES

• Hofmann, et al.: Experientia, 14, 397 (1958)
• Callahan, P., et al.: J. Pharmacol. Exp. Ther., 246, 866 (1958)
• Appel, J., et al.: Eur. J. Pharmacol., 159, 41 (1958)
• Blair, J., et al.: J. Med. Chem., 43, 4701 (1958)