3-[2-(dimethylamino)(2H4)ethyl]-1H-indol-5-ol

• ChemBase ID: 163086
• Molecular Formular: C12H16N2O
• Molecular Mass: 204.26824
• Monoisotopic Mass: 204.12626314
• SMILES: c1c(cc2c(c1)[nH]cc2CCN(C)C)O
• Canonical SMILES: CN(CCc1c[nH]c2c1cc(O)cc2)C
• InChI: InChI=1S/C12H16N2O/c1-14(2)6-5-9-8-13-12-4-3-10(15)7-11(9)12/h3-4,7-8,13,15H,5-6H2,1-2H3
• InChIKey: VTTONGPRPXSUTJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[2-(dimethylamino)(^2H₄)ethyl]-1H-indol-5-ol
• IUPAC Traditional name: 3-[2-(dimethylamino)(^2H₄)ethyl]-1H-indol-5-ol
• Synonyms: 3-[2-(Dimethylamino)ethyl-d4]-1H-indol-5-ol; 3-(β-Dimethylaminoethyl-d4)-5-hydroxyindole; 5-Hydroxy-N,N-dimethyltryptamine-d4; Bufotenin-d4; Cinobufotenine-d4; Dimethylserotonin-d4; Mappin-d4; Mappine-d4; N,N-Dimethyl-5-hydroxytryptamine-d4; N,N-Dimethylserotonin-d4; NSC 89593-d4; Bufotenine-d4

Database IDs

• PubChem SID: 162257221
• PubChem CID: 71314292

CALCULATED PROPERTIES

• Acid pKa: 9.232412
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -1.3982623
• LogD (pH = 7.4): -0.15401816
• Log P: 1.2922695
• Molar Refractivity: 62.4231 cm^3
• Polarizability: 25.078705 Å^3
• Polar Surface Area: 39.26 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Low Melting Pale Brown Solid

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - B689527

Labelled Bufotenine. Controlled substance (hallucinogen).

REFERENCES

• Stoll, et al.: Helv. Chim. Acta, 38, 1452 (1955)
• Bhattacharya, S., et al.: Indian. J. Physiol. Pharmacol., 15, 133 (1955)
• Falkenberg, G., et al.: Acta Crystallogr., 28B, 3219 (1955)