1-[(1S,2S)-2-hydroxy-2-(3-methoxyphenyl)cyclohexyl]-N,N-dimethylmethanamine oxide

• ChemBase ID: 178797
• Molecular Formular: C16H25NO3
• Molecular Mass: 279.3746
• Monoisotopic Mass: 279.18344367
• SMILES: c1c(cccc1[C@@]1(CCCC[C@H]1C[N+]([O-])(C)C)O)OC
• Canonical SMILES: COc1cccc(c1)[C@]1(O)CCCC[C@H]1C[N+](C)(C)[O-]
• InChI: InChI=1S/C16H25NO3/c1-17(2,19)12-14-7-4-5-10-16(14,18)13-8-6-9-15(11-13)20-3/h6,8-9,11,14,18H,4-5,7,10,12H2,1-3H3/t14-,16+/m0/s1
• InChIKey: HBXKSXMNNGHBEA-GOEBONIOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(1S,2S)-2-hydroxy-2-(3-methoxyphenyl)cyclohexyl]-N,N-dimethylmethanamine oxide
• IUPAC Traditional name: 1-[(1S,2S)-2-hydroxy-2-(3-methoxyphenyl)cyclohexyl]-N,N-dimethylmethanamine oxide
• Synonyms: (1R,2R)-rel-2-[(Dimethyloxidoamino)methyl]-1-(3-methoxyphenyl)-cyclohexanol; RWJ 38705; Tramadol N-Oxide

Database IDs

• CAS Number: 147441-56-3
• PubChem SID: 164234707
• PubChem CID: 25271934

CALCULATED PROPERTIES

• Acid pKa: 13.777869
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.3233564
• LogD (pH = 7.4): 1.3254586
• Log P: 1.3254863
• Molar Refractivity: 80.3141 cm^3
• Polarizability: 30.96107 Å^3
• Polar Surface Area: 56.34 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid
• Melting Point: 168-170°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - T712530

A metabolite of Tramadol.

REFERENCES

• Lave, T., et al.: J. Pharm. Sci., 86, 584 (1997)
• Trapnell, C., et al.: Antimicrob. Agents Chemother., 42, 1592 (1997)
• Wu, W., et al.: Xenobiotica, 31, 423 (1997)
• Yuan, R., et al.: Drug Metab. Dispos., 30, 1311 (1997)