(2R)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide hydrochloride

• ChemBase ID: 163089
• Molecular Formular: C18H29ClN2O
• Molecular Mass: 324.88866
• Monoisotopic Mass: 324.19684124
• SMILES: c1ccc(c(c1C)NC(=O)[C@@H]1N(CCCC1)CCCC)C.Cl
• Canonical SMILES: CCCCN1CCCC[C@@H]1C(=O)Nc1c(C)cccc1C.Cl
• InChI: InChI=1S/C18H28N2O.ClH/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17-14(2)9-8-10-15(17)3;/h8-10,16H,4-7,11-13H2,1-3H3,(H,19,21);1H/t16-;/m1./s1
• InChIKey: SIEYLFHKZGLBNX-PKLMIRHRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide hydrochloride
• IUPAC Traditional name: (+)-bupivacaine hydrochloride
• Synonyms: 1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide Monohydrochloride; 1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide Hydrochloride; 1-Butyl-2',6'-pipecoloxylidide Monohydrochloride; (R)-(+)-Bupivacaine Hydrochloride

Database IDs

• CAS Number: 27262-46-0
• PubChem SID: 162257224
• PubChem CID: 117964

CALCULATED PROPERTIES

• Acid pKa: 13.623539
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.0522962
• LogD (pH = 7.4): 3.8159845
• Log P: 4.5155187
• Molar Refractivity: 90.1933 cm^3
• Polarizability: 34.286346 Å^3
• Polar Surface Area: 32.34 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B689545

Local anaesthetic used for epidural and intrathecal anaesthesia.

REFERENCES

• Tullar, B., et al.: J. Med. Chem., 14, 891 (1971)
• Schmidt, A., et al.: Pharm. Res., 22, 2121 (1971)