N-(3-hydroxy-2,6-dimethylphenyl)-1-propylpiperidine-2-carboxamide

• ChemBase ID: 171290
• Molecular Formular: C17H26N2O2
• Molecular Mass: 290.40054
• Monoisotopic Mass: 290.19942808
• SMILES: c1c(c(c(c(c1)C)NC(=O)C1N(CCCC1)CCC)C)O
• Canonical SMILES: CCCN1CCCCC1C(=O)Nc1c(C)ccc(c1C)O
• InChI: InChI=1S/C17H26N2O2/c1-4-10-19-11-6-5-7-14(19)17(21)18-16-12(2)8-9-15(20)13(16)3/h8-9,14,20H,4-7,10-11H2,1-3H3,(H,18,21)
• InChIKey: IXOVDWXTIIYVOJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(3-hydroxy-2,6-dimethylphenyl)-1-propylpiperidine-2-carboxamide
• IUPAC Traditional name: N-(3-hydroxy-2,6-dimethylphenyl)-1-propylpiperidine-2-carboxamide
• Synonyms: (2S)-N-(3-Hydroxy-2,6-dimethylphenyl)-1-propyl-2-piperidinecarboxamide; (-)-3'-Hydroxyropivacaine; 3'-Hydroxyropivacaine; 3-Hydroxy Ropivacaine

Database IDs

• CAS Number: 163589-30-8
• PubChem SID: 164227200
• PubChem CID: 10379478

CALCULATED PROPERTIES

• Acid pKa: 10.039251
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.5700012
• LogD (pH = 7.4): 3.2790253
• Log P: 3.767385
• Molar Refractivity: 87.5732 cm^3
• Polarizability: 33.03028 Å^3
• Polar Surface Area: 52.57 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White Solid
• Melting Point: 171-173°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H953420

A major metabolite of Ropivacaine (R675000).

REFERENCES

• Ekstrom, G., et al.: Drug Metab. Dispos., 24, 955 (1996)
• Arvidsson, T., et al.: Biomed. Chromatogr., 13, 286 (1996)
• Shah, V., et al.: Pharm. Res., 17, 1551 (1996)