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Benzocaine

Structure

  • Benzocaine is a simple amino benzoic acid derivative with a diethylamino group attached to the benzene ring, enhancing its lipophilicity and anesthetic properties.

  • Chemical Formula: C₇H₉NO₂

    formula of Benzocaine


Structure of Benzocaine
Structure of Benzocaine

Mode of Action

  • Sodium Channel Blockade: Inhibits voltage-gated sodium channels, preventing nerve impulse conduction.

  • Membrane Stabilization: Alters nerve membrane permeability, reducing excitability.

Uses

  • Topical Anesthesia: Applied to mucous membranes, skin, and minor cuts for numbing.

  • Oral Preparations: Used in throat lozenges and sprays to alleviate sore throat pain.

  • Dental Anesthesia: Utilized in gels and creams for minor dental procedures.

Structure-Activity Relationship (SAR)

  • Diethylamino Group: Increases lipophilicity, enhancing membrane permeability and anesthetic potency.

  • Ester Group: Facilitates rapid hydrolysis and onset of action.

  • Benzene Ring Substitution: Modifications can affect duration and potency of anesthesia.

Synthesis

  • Benzocaine is synthesized through the esterification of p-aminobenzoic acid with ethanol in the presence of an acid catalyst.

Synthetic Route Overview:

  • p-Aminobenzoic Acid + Ethanol → Benzocaine


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