5859. Mepivacaine

Nomenclature

CAS number: 96-88-8
N-(2,6-Dimethylphenyl)-1-methyl-2-piperidinecarboxamide; 1-methyl-2′,6′-pipecoloxylidide; dl-N-methylpipecolic acid 2,6-dimethylanilide; dl-N-methylhexahydropicolinic acid 2,6-dimethylanilide.
C15H22N2O; mol wt 246.35.
C 73.13%, H 9.00%, N 11.37%, O 6.49%.

Description and references

Prepn: Ekenstam et al., Acta Chem. Scand. 11, 1183 (1957); US 2799679 (1957 to A. B. Bofors). Prepn of other salts: Rinderknecht, Helv. Chim. Acta 42, 1324 (1959); GB 826668 (1960 to Crookes Labs.). Resolution of isomers: Tullar, J. Med. Chem. 14, 891 (1971); Friberger, Aberg, Acta Pharm. Suec. 8, 361 (1971). Pharmacology: Helmy et al., J. Egypt. Med. Assoc. 50, 688 (1967). Metabolism: Reynolds, Br. J. Anaesth. 43, 33 (1971). Toxicity data: G. Aberg, Acta Pharmacol. Toxicol. 31, 273 (1972).

Chemical structure

Properties

Crystals from ether, mp 150-151°.

Derivative

Hydrochloride.

Nomenclature

CAS number: 1722-62-9
Carbocaina (Astra); Carbocaine hydrochloride (Winthrop); Chlorocain (Pharm. Mfg.); Meaverin (Woelm); Mepicaton (Pharmaton); Mepident (Parke-Davis); Mepivastesin (Espe); Optocain (Bayer); Scandicain (Bofors).
C15H22N2O.HCl; mol wt 282.81.
C 63.70%, H 8.20%, N 9.91%, O 5.66%, Cl 12.54%.

Properties

mp 262-264°. Sol in water. LD50 in mice, rats (mg/kg): 280, 500 s.c. (Aberg).

Derivative

(+)-Form.

Nomenclature

Dexivacaine.

Therapeutic Category

Anesthetic (local).

Therapeutic Category (Veterinary)

Anesthetic (local).

Keywords

Anesthetic (Local)