Hexylcainc

Toxicity

Symptoms of anesthetic overdose include headache, tinnitus, circumoral and tongue paresthesias, restlessness, talkativeness, facial twitching, convulsions, respiratory arrest, and cardiac depression

Originator

Cyclaine,MSD,US,1952

The Uses of Hexylcainc

Hexylcaine is an intermediate in the synthesis of Hexylcaine Hydrochloride which is used in pain management in as an antifungal agent. Anaesthetic.

Background

Hexylcaine hydrochloride is also known as cyclaine and osmocaine. It is a short acting local anesthetic that acts through inhibition of sodium channels. Patients experience an overdose may present with headache, tinnitus, numbness and tingling around the mouth and tongue, convulsions, inability to breathe, and decreased heart function. Hexylcaine has been discontinued in the US market.

Indications

Used as a local anesthetic for surface application, infiltration or nerve block

Definition

ChEBI: Hexylcaine is a benzoate ester.

Manufacturing Process

A solution of 0.1 mol of 1-cyclohexylamino-2-propanol in 30 grams of chloroform was saturated with dry hydrogen chloride gas, with cooling. A solution of 0.1 mol of benzoyl chloride in 30 grams of chloroform was added and the solution was heated in a bath at 50° to 55°C for four days under a reflux condenser protected from atmospheric moisture. Then the solvent was removed by vacuum distillation while the mixture was warmed on a water bath. Benzene was then added to the syrupy residue and the reaction product crystallized out after the benzene was removed by vacuum distillation.
The crystallized solid residue was washed with anhydrous ether to remove any unreacted benzoyl chloride. The 1-cyclohexylamino-2-propyl benzoate hydrochloride obtained was purified by two recrystallizations from absolute alcohol. It melted at 177° to 178.5°C.

Therapeutic Function

Local anesthetic

Pharmacokinetics

Hexylcaine is a local ester-class anesthetic. Local anesthetics produce a transient block of nerve conduction by interfering with sodium channels. This effect of the anesthetic interferes with the development of an action potential across the nerve.

Safety Profile

Human systemic effects. When heated to decomposition it emits toxic vapors of NOx.

Metabolism

Hydrolyzed by plasma esterases to benzoic acid and other derivatives