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 accommo ...
) (former developmental code name WY-2445), or carphenazine (
BAN), also known as carphenazine maleate (
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 th ...
) (brand name Proketazine; former developmental code name NSC-71755), is an
antipsychotic
Antipsychotics, also known as neuroleptics, are a class of Psychiatric medication, psychotropic medication primarily used to manage psychosis (including delusions, hallucinations, paranoia or disordered thought), principally in schizophrenia but ...
and
tranquilizer
A tranquilizer is a drug that is designed for the treatment of anxiety, fear, tension, agitation, and disturbances of the mind, specifically to reduce states of anxiety and tension.
Etymology
Tranquilizer, as a term, was first used by F.F. Yonk ...
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. T ...
group that was withdrawn from the market.
Synthesis
The alkylation reaction between 2-Propionyl Phenothiazine
2-33-1(1) and
1-Bromo-3-chloropropane (2) gives 1-
0-(3-chloropropyl)phenothiazin-2-ylropan-1-one
5157-45-2(3). A second alkylation step, this time with 2-(1-Piperazinyl)ethanol
03-76-4(4) completes the synthesis of ''Carfenazine'' (5).
NB: 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 many ...
Analogues
*
Butaperazine uses
butanoyl (
Butyryl) 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-pote ...
selfsame but
trifluoromethyl
The trifluoromethyl group is a functional group that has the formula -CF3. The naming of is group is derived from the methyl group (which has the formula -CH3), by replacing each hydrogen atom by a fluorine atom. Some common examples are trifluoro ...
on position 2 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. T ...
ring.
References
Phenothiazines
Typical antipsychotics
Withdrawn drugs
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