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

• ChemBase ID: 155684
• Molecular Formular: C15H23ClN2O
• Molecular Mass: 282.80892
• Monoisotopic Mass: 282.14989105
• SMILES: Cc1cccc(c1NC(=O)C1CCCCN1C)C.Cl
• Canonical SMILES: CN1CCCCC1C(=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
• InChIKey: RETIMRUQNCDCQB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(2,6-dimethylphenyl)-1-methylpiperidine-2-carboxamide hydrochloride
• IUPAC Traditional name: mepivacaine hydrochloride
• Synonyms: Carbocaina; Chlorocain; Meaverin; Mepicaton; Mepident; Mepivacaine Hydrochloride; Mepivastesin; Optocain; Polocaine; Scandicain; Scandonest; Mepivacaine Hydrochloride; 1-Methyl-2′,6′-pipecoloxylidine hydrochloride; N-(2,6-Dimethylphenyl)-1-methyl-2-piperidinecarboxamide hydrochloride; Mepivacaine hydrochloride; Mepivacaine HCl; N-(2,6-Dimethylphenyl)-1-methylpiperidine-2-carboxamide hydrochloride

Database IDs

• CAS Number: 1722-62-9
• EC Number: 217-023-9
• MDL Number: MFCD00144738
• PubChem SID: 162249822; 24896810
• PubChem CID: 66070

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

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: White Solid
• Melting Point: 255-257°C (dec.)

Safety Information

• Storage Condition: Refrigerator
• RTECS: TK6475000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Pharmacology Properties

• Target: Others

Product Information

• Purity: 95+%; 98.0-102.0%
• Salt Data: HCl
• Suitability: meets USP testing specifications
• Empirical Formula (Hill Notation): C15H22N2O · HCl

DETAILS

Sigma Aldrich - M3189

Biochem/physiol Actions
Local anesthetic. Reversibly blocks transient Na+ inward current, as well as the steady-state K+ outward current. Blocks tandem pore (TASK) and Kv1.5, potassium channels in model systems.

Toronto Research Chemicals - M225060

An anti-inflammatory and analgesic agent. Anesthetic (local).

REFERENCES

• Reynolds, et al.: Br. J. Anaesth., 43, 33 (1971)
• Tullar, et al.: J. Med. Chem., 14, 891 (1971)
• Aberg, G., et al.: Acta Pharmacol. Toxicol., 31, 273 (1971)