(2S)-N-(4-hydroxy-2,6-dimethylphenyl)piperidine-2-carboxamide

• ChemBase ID: 170409
• Molecular Formular: C14H20N2O2
• Molecular Mass: 248.3208
• Monoisotopic Mass: 248.15247789
• SMILES: C1CCN[C@@H](C1)C(=O)Nc1c(cc(cc1C)O)C
• Canonical SMILES: O=C([C@@H]1CCCCN1)Nc1c(C)cc(cc1C)O
• InChI: InChI=1S/C14H20N2O2/c1-9-7-11(17)8-10(2)13(9)16-14(18)12-5-3-4-6-15-12/h7-8,12,15,17H,3-6H2,1-2H3,(H,16,18)/t12-/m0/s1
• InChIKey: PNGZGTQKSFXTPA-LBPRGKRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-N-(4-hydroxy-2,6-dimethylphenyl)piperidine-2-carboxamide
• IUPAC Traditional name: (2S)-N-(4-hydroxy-2,6-dimethylphenyl)piperidine-2-carboxamide
• Synonyms: (2S)-N-(4-Hydroxy-2,6-dimethylphenyl)-2-piperidinecarboxamide; 4-Hydroxy-N-despropyl Ropivacaine

Database IDs

• CAS Number: 243989-47-1
• PubChem SID: 164226319
• PubChem CID: 71748964

CALCULATED PROPERTIES

• Acid pKa: 9.720533
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -0.3507149
• LogD (pH = 7.4): 1.2941262
• Log P: 2.2819173
• Molar Refractivity: 73.0059 cm^3
• Polarizability: 27.503609 Å^3
• Polar Surface Area: 61.36 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Crystals

DETAILS

Toronto Research Chemicals - H941690

Ropivacaine (R675000) metabolite.

REFERENCES

• Arvidsson, T. et al.; Biomed. Chromatogr., 13, 286 (1999)