Benzocaine

Title: Benzocaine
CAS Registry Number: 94-09-7
CAS Name: 4-Aminobenzoic acid ethyl ester
Additional Names: ethyl aminobenzoate
Trademarks: Americaine (Medeva); Anaesthesin (Ritsert); Flavamed (Berlin-Chemie); Subcutin (Ritsert)
Molecular Formula: C9H11NO2
Molecular Weight: 165.19
Percent Composition: C 65.44%, H 6.71%, N 8.48%, O 19.37%
Literature References: Prepd by the esterification of p-aminobenzoic acid: Salkowski, Ber. 28, 1921 (1895); Vorländer, 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).
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.
Melting point: mp 88-90°
pKa: pKa 2.5
Therap-Cat: Anesthetic (local).
Therap-Cat-Vet: Local (usually surface) anesthetic.
Keywords: Anesthetic (Local).
Benzoctamine Benzodepa Benzofuran Benzoguanamine Benzohydrol

Benzocaine
Benzocaine.svg
Benzocaine-from-xtal-3D-balls.png
Systematic (IUPAC) name
Ethyl 4-aminobenzoate
Clinical data
Trade names Anbesol, Cepacol, Lanacane
AHFS/Drugs.com monograph
Pregnancy cat. C (US)
Legal status OTC (US)
Routes Topical
Identifiers
CAS number 94-09-7 YesY
ATC code C05AD03 D04AB04, QN01AX92, N01BA05, R02AD01
PubChem CID 2337
DrugBank DB01086
ChemSpider 13854242 YesY
UNII U3RSY48JW5 YesY
KEGG D00552 YesY
ChEBI CHEBI:116735 YesY
ChEMBL CHEMBL278172 YesY
Chemical data
Formula C9H11NO2 
Mol. mass 165.189 g/mol
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Benzocaine is a local anesthetic commonly used as a topical pain reliever or in cough drops. It is the active ingredient in many over-the-counter anesthetic ointments such as products for oral ulcers. It is also combined with antipyrine to form A/B Otic Drops to relieve ear pain and remove earwax.