3-{2-[(2H3)methylamino]ethyl}-1H-indol-5-ol

• ChemBase ID: 174254
• Molecular Formular: C11H14N2O
• Molecular Mass: 190.24166
• Monoisotopic Mass: 190.11061308
• SMILES: c1(ccc2c(c1)c(c[nH]2)CCNC)O
• Canonical SMILES: CNCCc1c[nH]c2c1cc(O)cc2
• InChI: InChI=1S/C11H14N2O/c1-12-5-4-8-7-13-11-3-2-9(14)6-10(8)11/h2-3,6-7,12-14H,4-5H2,1H3
• InChIKey: ASUSBMNYRHGZIG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{2-[(^2H₃)methylamino]ethyl}-1H-indol-5-ol
• IUPAC Traditional name: 3-{2-[(^2H₃)methylamino]ethyl}-1H-indol-5-ol
• Synonyms: 3-[2-[Methyl-d3)amino]ethyl]-1H-indol-5-ol; 3-[2-[(Methyl-d3)amino]ethyl]indol-5-ol; 5-Hydroxy-N-(methyl-d3)tryptamine; 5-Hydroxy-Nω-(methyl-d3)tryptamine; N-(Methyl-d3)-5-hydroxytryptamine; N-(Methyl-d3)serotonin; N-Methyl Serotonin-d3

Database IDs

• PubChem SID: 164230164
• PubChem CID: 71750556

CALCULATED PROPERTIES

• Acid pKa: 9.450406
• H Acceptors: 2
• H Donor: 3
• LogD (pH = 5.5): -1.610599
• LogD (pH = 7.4): -1.0300375
• Log P: 0.6882991
• Molar Refractivity: 57.1284 cm^3
• Polarizability: 23.14951 Å^3
• Polar Surface Area: 48.05 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M326597

Labelled N-Methylserotonin, the N-methylated derivative of serotonin with similar activity. Studies have identified N-Methylserotonin as a potential active constituent that contributes to the serotonergic activity of black cohosh.

REFERENCES

• Powell, S.L. et al.: J. Agric. Food Chem., 56, 11718 (2008)
• Mais, D.E. et al.: J. Chrom. Biomed. Appl., 225, 27 (2008)