(2S)-N-(2,6-dimethylphenyl)-1-methylpiperidine-2-carboxamide hydrochloride

• ChemBase ID: 172675
• Molecular Formular: C15H23ClN2O
• Molecular Mass: 282.80892
• Monoisotopic Mass: 282.14989105
• SMILES: C1CCN([C@@H](C1)C(=O)Nc1c(cccc1C)C)C.Cl
• Canonical SMILES: CN1CCCC[C@H]1C(=O)Nc1c(C)cccc1C.Cl
• InChI: InChI=1S/C15H22N2O.ClH/c1-11-7-6-8-12(2)14(11)16-15(18)13-9-4-5-10-17(13)3;/h6-8,13H,4-5,9-10H2,1-3H3,(H,16,18);1H/t13-;/m0./s1
• InChIKey: RETIMRUQNCDCQB-ZOWNYOTGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-N-(2,6-dimethylphenyl)-1-methylpiperidine-2-carboxamide hydrochloride
• IUPAC Traditional name: (2S)-N-(2,6-dimethylphenyl)-1-methylpiperidine-2-carboxamide hydrochloride
• Synonyms: (2S)-N-(2,6-Dimethylphenyl)-1-methyl-2-piperidinecarboxamide Hydrochloride; (+)-Mepivacaine Hydrochloride; (+)-1-Methyl-2',6'-pipecoloxylidide, MonoHydrochloride; (S)-N-(2,6-Dimethylphenyl)-1-methyl-2-piperidinecarboxamide Hydrochloride; (S)-(+)-Mepivacaine Hydrochloride

Database IDs

• CAS Number: 34333-71-6
• PubChem SID: 164228585
• PubChem CID: 66586222

CALCULATED PROPERTIES

• Acid pKa: 13.623901
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.4378594
• LogD (pH = 7.4): 2.9576306
• Log P: 3.1916199
• Molar Refractivity: 76.3197 cm^3
• Polarizability: 28.751305 Å^3
• Polar Surface Area: 32.34 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M225075

An optical isomer of the local anesthetic Mepivacaine (M225060) that is slightly less active than its (-)-isomer.

REFERENCES

• Luduena, F.P. et al.: Arch. Int. Pharmacodyn. Ther., 200, 359 (1972)
• Jeske, A.H. et al.: Meth. Find. Exp. Clin. Pharmacol., 3, 33 (1972)