Chloroprocaine hydrochloride

Chemical properties

crystalline solid

Originator

Nesacaine,Astra,US,1956

The Uses of Chloroprocaine hydrochloride

Chloroprocaine Hydrochloride is a local anaesthetic compound showing similar effects to Lidocaine.

The Uses of Chloroprocaine hydrochloride

Anesthetic (local).

Definition

ChEBI: The monohydrochloride salt of chloroprocaine. Used as a local anaesthetic, particularly for oral surgery, it has the advantage over lidocaine of constricting blood vessels, so reducing bleeding.

Manufacturing Process

In the first step, 2-chloro-4-aminobenzoyl chloride hydrochloride is prepared by refluxing a mixture of 25 cc of purified thionyl chloride and 10 g of 2- chloro-4-aminobenzoic acid until all of the solid has gone into solution. To the cooled solution is added 150 cc of dry ethyl ether. A brisk stream of dry hydrogen chloride is passed into the solution until the precipitation of 2- chloro-4-aminobenzoylchloride hydrochloride is complete. The acyl halide is removed by filtration and dried in a vacuum desiccator.
In the second step, the diethylaminoethyl 2-chloro-4-aminobenzoate hydrochloride is prepared by refluxing equimolar proportions of the hydrochloride of beta-diethylaminoethanol in a suitable inert solvent such as a mixture of dry toluene and tetrachloroethane and the hydrochloride of 2- chloro-4-aminobenzoyl chloride until the reaction as indicated by the cessation of hydrogen chloride evolution is complete. The supernatant solvents are decanted from the reaction product which can be conveniently purified by crystallization from absolute ethanol.
An alternative purification can be effected by dissolving the reaction product in water. The ester base is liberated by rendering the clarified aqueous solution alkaline. Removal of the base from the alkaline solution is achieved by extraction with a suitable solvent such as benzene or ether. The pure hydrochloride of diethylaminoethyl 2-chloro-4-aminobenzoate is then precipitated from the dried extract by the addition of dry hydrogen chloride. After removal by filtration and recrystallization from ethanol it is found to have a melting point of 173° to 174°C.

brand name

Nesacaine (Abraxis).

Therapeutic Function

Local anesthetic