Procaine

Structure

• Procaine is a classic amino benzoic acid derivative with an ethyl ester group, enhancing its solubility and anesthetic duration.

• Chemical Formula: C₁₀H₂₁N₃O₂

  

Structure of Procaine

Mode of Action

• Voltage-Gated Sodium Channel Inhibition: Blocks sodium influx, preventing nerve impulse conduction.

• Membrane Stabilization: Decreases nerve excitability by altering membrane permeability.

Uses

• Local Anesthesia: Used in dental procedures, minor surgeries, and cosmetic applications.

• Topical Preparations: Applied to mucous membranes and skin for temporary numbing.

• Infiltration Anesthesia: Injected around tissues to block nerve signals in a specific area.

Structure-Activity Relationship (SAR)

• Ester Group: Facilitates rapid onset and short duration of action due to quick hydrolysis.

• Diethylamino Group: Enhances lipophilicity, improving membrane penetration and anesthetic efficacy.

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

Synthesis

• Procaine is synthesized by the esterification of p-aminobenzoic acid with diethylaminoethyl alcohol in the presence of an acid catalyst.

Synthetic Route Overview:

• p-Aminobenzoic Acid + Diethylaminoethyl Alcohol → Procaine