84-04-8

Mornidine ,Searle ,US ,1959

Pipamazine is a drug od the phenothiazine class which used to be used as an antiemetic.

ChEBI: Pipamazine is a member of phenothiazines.

To a stirred and refluxing suspension of 4.95 parts of 4piperidinecarboxamide, 1 part of sodium iodide and 8.4 parts of potassium carbonate in 40 parts of butanone there are added in the course of 30 minutes 9.3 parts of 2-chloro-10-(γ-chloropropyl)phenothiazine in 40 parts ofbutanone. Stirring and refluxing are continued for 12 hours after which the mixture is cooled and filtered. The filtrate is concentrated under vacuum to give a residue which is recrystallized from a mixture of 2-propanol and petroleum ether. The 1-[γ-(2'-chloro-10'-phenothiazine)propyl]piperidine-4carboxamide thus obtained melts at approximately 139°C.
This base is dissolved in a small amount of 2-propanol and treated with a 25% solution of hydrogen chloride in 2-propanol. Upon treatment of this solution with anhydrous ether a hydrochloride precipitates as a white solid melting at about 196°C to 197°C with formation of bubbles.

Normetine;.

Antiemetic

Pipamazine, which is pharmacologically similar to chlorpromazine, was introduced in 1959 for the treatment of nausea and vomiting. Although it was withdrawn in 1969 by the United States FDA on grounds of lack of proof of efficacy and safety, it remains available in some countries.