Carfenazine (

INN Inns are generally establishments or buildings where travelers can seek lodging, and usually, food and drink. Inns are typically located in the country or along a highway. Before the advent of motorized transportation, they also provided accomm ...

; former development code WY-2445; BAN carphenazine;

USAN 280px, "Samguk Sagi" Book 04. Silla's Records. In 512, Usan-guk（于山國）was Ulleungdo（鬱陵島） Usan-guk, or the State of Usan, occupied Ulleung-do and the adjacent islands during the Korean Three Kingdoms period. According to t ...

carphenazine maleate; brand name Proketazine; former development code NSC-71755) is an

antipsychotic Antipsychotics, previously known as neuroleptics and major tranquilizers, are a class of Psychiatric medication, psychotropic medication primarily used to manage psychosis (including delusions, hallucinations, paranoia or disordered thought), p ...

and

tranquilizer A sedative or tranquilliser is a substance that induces sedation by reducing irritability or excitement. They are central nervous system (CNS) depressants and interact with brain activity, causing its deceleration. Various kinds of sedatives c ...

of the

phenothiazine Phenothiazine, abbreviated PTZ, is an organic compound that has the formula S(C6H4)2NH and is related to the thiazine-class of heterocyclic compounds. Derivatives of phenothiazine are highly bioactive and have widespread use and rich history. ...

group that was withdrawn from the market.

Synthesis

The alkylation reaction between 2-propionyl phenothiazine (1) and

1-bromo-3-chloropropane 1-Bromo-3-chloropropane is an organohalogen compound with the formula Br(CH2)3Cl. It is a colorless liquid, produced by free-radical addition of hydrogen bromide to allyl chloride. It is used as an alkylating agent Alkylation is a chemical react ...

(2) gives 1- 0-(3-chloropropyl)phenothiazin-2-ylropan-1-one (3). A second alkylation step, this time with 2-(1-Piperazinyl)ethanol (4), completes the synthesis of carfenazine (5). Although above procedure is proof-of-concept, bear in mind no

protecting group A protecting group or protective group is introduced into a molecule by chemical modification of a functional group to obtain chemoselectivity in a subsequent chemical reaction. It plays an important role in multistep organic synthesis. In man ...

. Other patent uses ketalization technique.

Analogs

* Butaperazine, uses butanoyl and not propanoyl group *

Fluphenazine Fluphenazine, sold under the brand name Prolixin among others, is a high-potency typical antipsychotic medication. It is used in the treatment of chronic psychoses such as schizophrenia, and appears to be about equal in effectiveness to low-pot ...

, analog with

trifluoromethyl The trifluoromethyl group is a functional group that has the formula . The naming of is group is derived from the methyl group (which has the formula ), by replacing each hydrogen atom by a fluorine atom. Some common examples are trifluoromethane ...

on position 2 of the

ring.

References

{{Tricyclics Phenothiazines Typical antipsychotics Withdrawn drugs Hydroxyethyl compounds