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

• ChemBase ID: 170214
• Molecular Formular: C15H22N2O2
• Molecular Mass: 262.34738
• Monoisotopic Mass: 262.16812795
• SMILES: C1CCN(C(C1)C(=O)Nc1c(ccc(c1C)O)C)C
• Canonical SMILES: CN1CCCCC1C(=O)Nc1c(C)ccc(c1C)O
• InChI: InChI=1S/C15H22N2O2/c1-10-7-8-13(18)11(2)14(10)16-15(19)12-6-4-5-9-17(12)3/h7-8,12,18H,4-6,9H2,1-3H3,(H,16,19)
• InChIKey: DVENKGUHBZKQPU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(3-hydroxy-2,6-dimethylphenyl)-1-methylpiperidine-2-carboxamide
• IUPAC Traditional name: N-(3-hydroxy-2,6-dimethylphenyl)-1-methylpiperidine-2-carboxamide
• Synonyms: N-(3-Hydroxy-2,6-dimethylphenyl)-1-methyl-2-piperidinecarboxamide; 1-Methyl-3'-hydroxy-2',6'-pipecoloxylidide; 1-Methyl-4'-hydroxy-2',6'-pipecoloxylidide; 1-Methylpipecolo-3'-hydroxy-2',6'-xylidide; 3-Hydroxy Mepivacaine; N-(4-Hydroxy-2,6-dimethylphenyl)-1-methyl-2-piperidinecarboxamide; 4'-hydroxy-1-methyl-2',6'-pipecoloxylidide; 1-Methylpipecolo-4'-hydroxy-2',6'-xylidide; 4-Hydroxy Mepivacaine

Database IDs

• CAS Number: 616-66-0; 37055-90-6
• PubChem SID: 164226124
• PubChem CID: 71748868

CALCULATED PROPERTIES

• Acid pKa: 10.037705
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.2309853
• LogD (pH = 7.4): 2.6920457
• Log P: 2.8880546
• Molar Refractivity: 78.3006 cm^3
• Polarizability: 29.345844 Å^3
• Polar Surface Area: 52.57 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid; White Solid
• Melting Point: >220°C (dec.); 195-197°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H825355

A metabolite of Mepivacaine (M225060).

Toronto Research Chemicals - H825360

A metabolite of Mepivacaine (M225060).

REFERENCES

• Harkins, J.D. et al.: J. Vet. Pharmacol. Therap., 22, 107 (1999)
• Cribb, A., et al.: Drug Metabol. Dispos., 19, 900 ( 1991), Brander, C., et al.: J. Immunol., 155, 2670 (1995)
• Padovan, E., et al.: Eur. J. Immunol., 27, 1303 (1995)