N,N-bis(2H3)methyl-2-(5-{[(4S)-2-oxo-1,3-oxazolidin-4-yl]methyl}-1H-indol-3-yl)ethanamine oxide

• ChemBase ID: 179659
• Molecular Formular: C16H21N3O3
• Molecular Mass: 303.35624
• Monoisotopic Mass: 303.15829155
• SMILES: c1cc(cc2c1[nH]cc2CC[N+]([O-])(C)C)C[C@@H]1NC(=O)OC1
• Canonical SMILES: O=C1OC[C@@H](N1)Cc1ccc2c(c1)c(CC[N+](C)(C)[O-])c[nH]2
• InChI: InChI=1S/C16H21N3O3/c1-19(2,21)6-5-12-9-17-15-4-3-11(8-14(12)15)7-13-10-22-16(20)18-13/h3-4,8-9,13,17H,5-7,10H2,1-2H3,(H,18,20)/t13-/m0/s1
• InChIKey: GZYCQRZFJIZOKU-ZDUSSCGKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N,N-bis(^2H₃)methyl-2-(5-{[(4S)-2-oxo-1,3-oxazolidin-4-yl]methyl}-1H-indol-3-yl)ethanamine oxide
• IUPAC Traditional name: N,N-bis(^2H₃)methyl-2-(5-{[(4S)-2-oxo-1,3-oxazolidin-4-yl]methyl}-1H-indol-3-yl)ethanamine oxide
• Synonyms: (4S)-4-[[3-[2-(Dimethyl-d6-oxidoamino)ethyl]-1H-indol-5-yl]methyl-2-oxazolidinone; Zolmitriptan-d6 N-Oxide

Database IDs

• PubChem SID: 164235569
• PubChem CID: 46783279

CALCULATED PROPERTIES

• Acid pKa: 12.522525
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 0.9160395
• LogD (pH = 7.4): 0.9184653
• Log P: 0.9185001
• Molar Refractivity: 84.4841 cm^3
• Polarizability: 33.084927 Å^3
• Polar Surface Area: 81.0 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - Z639012

A labelled metabolite of Zolmitriptan.

REFERENCES

• Forrester, L., et al.: Biochem. J., 281, 359 (1992)
• Newton, D., et al.: Drug Metab. Dis., 23, 154 (1992)
• Dixon, R., et al.: Clin. Drug Invest., 15, 515 (1992)
• Whale, R., et al.: Psychopharmacology, 145, 223 (1992)
• Wild, M., et al.: Xenobiotica, 29, 84