1086. Benzocaine

Nomenclature

CAS number: 94-09-7
4-Aminobenzoic acid ethyl ester; ethyl aminobenzoate; Americaine (Medeva); Anaesthesin (Ritsert); Flavamed (Berlin-Chemie); Subcutin (Ritsert).
C9H11NO2; mol wt 165.19.
C 65.44%, H 6.71%, N 8.48%, O 19.37%.

Description and references

Prepd by the esterification of p-aminobenzoic acid: Salkowski, Ber. 28, 1921 (1895); Vorlnder, Meyer, Ann. 320, 135 (1902); by the reduction of ethyl p-nitrobenzoate: Limpricht, ibid. 303, 278 (1898); R. Adams, F. L. Cohen, Org. Synth. coll. vol. I, 240 (2nd ed., 1941). In industrial practice the reducing agent is usually iron and water in the presence of a little acid. Comprehensive description: S. L. Ali, Anal. Profiles Drug Subs. 12, 73-104 (1983).

Chemical structure

Properties

Rhombohedra from ether, mp 88-90°. Stable in air. One gram dissolves in about 2500 ml water, 5 ml alcohol, 2 ml chloroform, in about 4 ml ether, and in 30 to 50 ml of expressed almond oil or olive oil. Also sol in dil acids. pKa 2.5.

Therapeutic Category

Anesthetic (local).

Therapeutic Category (Veterinary)

Local (usually surface) anesthetic.

Keywords

Anesthetic (Local)