3-[2-(dimethylamino)(2H4)ethyl]-1H-indol-4-ol

• ChemBase ID: 177101
• Molecular Formular: C12H16N2O
• Molecular Mass: 204.26824
• Monoisotopic Mass: 204.12626314
• SMILES: c1cc(c2c(c1)[nH]cc2CCN(C)C)O
• 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)(^2H₄)ethyl]-1H-indol-4-ol
• IUPAC Traditional name: 3-[2-(dimethylamino)(^2H₄)ethyl]-1H-indol-4-ol
• Synonyms: 3-[2-(Dimethylamino)ethyl]-1H-indol-4-ol-d4; 4-Hydroxy-N,N-dimethyltryptamine-d4; Psilocyn-d4; Psilocin-d4

Database IDs

• PubChem SID: 164233011
• PubChem CID: 71751873

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: 25.082687 Å^3
• Polar Surface Area: 39.26 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Methanol, Tetrahydrofuran

DETAILS

Toronto Research Chemicals - P839632

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)