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Benzocaine

Benzocaine
Benzocaine.svg
Benzocaine-from-xtal-3D-balls.png
Clinical data
Trade names Anbesol, Cepacol, Lanacane, Orajel
AHFS/Drugs.com Monograph
Pregnancy
category
  • US: C (Risk not ruled out)
Routes of
administration
Topical
ATC code
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ECHA InfoCard 100.002.094
Chemical and physical data
Formula C9H11NO2
Molar mass 165.189 g/mol
3D model (Jmol)
  

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.

Benzocaine is the ethyl ester of p-aminobenzoic acid (PABA). It can be prepared from PABA and ethanol by Fischer esterification or via the reduction of ethyl p-nitrobenzoate. Benzocaine is sparingly soluble in water; it is more soluble in dilute acids and very soluble in ethanol, chloroform and ethyl ether. The melting point of benzocaine is 88–90 °C, and the boiling point is about 310 °C. The density of benzocaine is 1.17 g/cm3.

Benzocaine was first synthesized in 1890 by the German chemist Eduard Ritsert (1859–1946), in the town of Eberbach and introduced to the market in 1902 under the name "Anästhesin".

Pain is caused by the stimulation of free nerve endings. When the nerve endings are stimulated, sodium enters the neuron, causing depolarization of the nerve and subsequent initiation of an action potential. The action potential is propagated down the nerve toward the central nervous system, which interprets this as pain. Benzocaine acts to inhibit the voltage-dependent sodium channels (VDSCs) on the neuron membrane, stopping the propagation of the action potential.


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