N-(2,6-dimethylphenyl)piperidine-2-carboxamide

• ChemBase ID: 66955
• Molecular Formular: C14H20N2O
• Molecular Mass: 232.3214
• Monoisotopic Mass: 232.15756327
• SMILES: N1C(CCCC1)C(=O)Nc1c(cccc1C)C
• Canonical SMILES: O=C(C1CCCCN1)Nc1c(C)cccc1C
• InChI: InChI=1S/C14H20N2O/c1-10-6-5-7-11(2)13(10)16-14(17)12-8-3-4-9-15-12/h5-7,12,15H,3-4,8-9H2,1-2H3,(H,16,17)
• InChIKey: SILRCGDPZGQJOQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(2,6-dimethylphenyl)piperidine-2-carboxamide
• IUPAC Traditional name: N-(2,6-dimethylphenyl)piperidine-2-carboxamide
• Synonyms: N-(2',6'-Dimethylphenyl)-2-piperidinecarboxamide; N-(2,6-Dimethylphenyl)-2-piperidinecarboxamide; 2’,6’-Pipecoloxylidide; 2’,6’-Pipecolylxylidine; Debutylbupivacaine; Desbutylbupivacaine; Bupivacaine Imp. B (EP); N-Desmethyl Mepivacaine; N-Desbutyl Bupivacaine; N-(2,6-Dimethylphenyl)piperidine-2-carboxamide; 2-[(2,6-Dimethylphenyl)carbamoyl]piperidine; 2-[(Piperidin-2-ylcarbonyl)amino]-m-xylene; (2S)-N-(2,6-dimethylphenyl)-2-Piperidinecarboxamide; L-Pipecolic Acid 2,6-Xylidide; (S)-N-(2,6-dimethylphenyl)-2-Piperidinecarboxamide; (+)-2',6'-Pipecoloxylidide; N-Desmethyl (S)-Mepivacaine; N-Desbutyl (S)-Bupivacaine; N-Despropyl Ropivacaine

Database IDs

• CAS Number: 15883-20-2; 27262-40-4
• MDL Number: MFCD01701244
• PubChem SID: 162032691
• PubChem CID: 115282

CALCULATED PROPERTIES

• Acid pKa: 13.6328125
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -0.038040735
• LogD (pH = 7.4): 1.6142436
• Log P: 2.8085718
• Molar Refractivity: 71.025 cm^3
• Polarizability: 26.906809 Å^3
• Polar Surface Area: 41.13 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: White Solid; White to Off-White Solid
• Melting Point: 114-117°C; 114-117°C; 131-133°C

Safety Information

• Storage Condition: -20°C Freezer; Refrigerator
• Storage Warning: Harmful/Irritant/Keep Cold; IRRITANT
• TSCA Listed: false

Product Information

• Purity: 95+%

DETAILS

Toronto Research Chemicals - D297385

A major metabolite of Levobupivacaine (B689546) and the anesthetic Ropivacaine (R675000).

Toronto Research Chemicals - D288785

A major metabolite of Bupivacaine.

REFERENCES

• Jokinen, M.J. et al.: Pharmacol. Toxicol., 88, 187 (2001)
• Fawcett, J. et al.: Chirality, 11, 50 (2001)
• Ledger, R. et al.: J. Biochem. Biophys. Meth., 57, 105 (2001)
• Bargetzi, M.J., et al.: Clin. Pharmacol. Ther., 46, 521 (1989)
• Shimada, T., et al.: J. Pharmacol. Exp. Ther., 270, 414 (1989)
• Attolini, L., et al.: Fundam. Clin. Pharmacol., 11, 152 (1989)