N,N-dimethyl-2-{5-[(methylsulfamoyl)methyl]-1H-indol-3-yl}ethanamine oxide

• ChemBase ID: 178032
• Molecular Formular: C14H21N3O3S
• Molecular Mass: 311.39984
• Monoisotopic Mass: 311.13036255
• SMILES: c1cc(cc2c1[nH]cc2CC[N+]([O-])(C)C)CS(=O)(=O)NC
• Canonical SMILES: CNS(=O)(=O)Cc1ccc2c(c1)c(c[nH]2)CC[N+](C)(C)[O-]
• InChI: InChI=1S/C14H21N3O3S/c1-15-21(19,20)10-11-4-5-14-13(8-11)12(9-16-14)6-7-17(2,3)18/h4-5,8-9,15-16H,6-7,10H2,1-3H3
• InChIKey: GRHYJEBKFWDYFD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N,N-dimethyl-2-{5-[(methylsulfamoyl)methyl]-1H-indol-3-yl}ethanamine oxide
• IUPAC Traditional name: N,N-dimethyl-2-{5-[(methylsulfamoyl)methyl]-1H-indol-3-yl}ethanamine oxide
• Synonyms: 3-[2-(Dimethyloxidoamino)ethyl]-N-methyl-1H-indole-5-methanesulfonamide; GR 112504; Sumatriptan N-Oxide

Database IDs

• CAS Number: 212069-94-8
• PubChem SID: 164233942
• PubChem CID: 57903461

CALCULATED PROPERTIES

• Acid pKa: 11.236052
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.23292759
• LogD (pH = 7.4): -0.23055434
• Log P: -0.23046634
• Molar Refractivity: 84.1291 cm^3
• Polarizability: 33.539204 Å^3
• Polar Surface Area: 88.84 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - S810010

A degradation product of the antimigraine drug Sumatriptan (S810000).

REFERENCES

• Xu, X. et al.: J. Pharmac. Biomed. Anal., 26, 367 (2001)
• Cheng, K.N. et al.: J. Pharmac. Biomed. Anal., 17, 399 (2001)