N-(4-hydroxy-2,6-dimethylphenyl)-1-propylpiperidine-2-carboxamide

• ChemBase ID: 171291
• Molecular Formular: C17H26N2O2
• Molecular Mass: 290.40054
• Monoisotopic Mass: 290.19942808
• SMILES: c1(cc(c(c(c1)C)NC(=O)C1N(CCCC1)CCC)C)O
• Canonical SMILES: CCCN1CCCCC1C(=O)Nc1c(C)cc(cc1C)O
• InChI: InChI=1S/C17H26N2O2/c1-4-8-19-9-6-5-7-15(19)17(21)18-16-12(2)10-14(20)11-13(16)3/h10-11,15,20H,4-9H2,1-3H3,(H,18,21)
• InChIKey: BWDXZCNWLNJBBI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(4-hydroxy-2,6-dimethylphenyl)-1-propylpiperidine-2-carboxamide
• IUPAC Traditional name: N-(4-hydroxy-2,6-dimethylphenyl)-1-propylpiperidine-2-carboxamide
• Synonyms: (2S)-N-(4-Hydroxy-2,6-dimethylphenyl)-1-propyl-2-piperidinecarboxamide; (-)-4'-Hydroxyropivacaine; 4'-Hydroxyropivacaine; 4-Hydroxy Ropivacaine

Database IDs

• CAS Number: 163589-31-9
• PubChem SID: 164227201
• PubChem CID: 10424332

CALCULATED PROPERTIES

• Acid pKa: 9.688869
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.5328473
• LogD (pH = 7.4): 3.2507224
• Log P: 3.6616893
• Molar Refractivity: 87.5732 cm^3
• Polarizability: 33.029392 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: White Solid
• Melting Point: 172-175°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - H953425

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)