Homofenazine is an

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

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. ...

s class. It was synthesized by

Wilhelm Schuler Wilhelm Alfons Schuler (27 December 1914 in Ulm, Germany – 5 June 2010 in Bad Homburg vor der Höhe, Germany) was a chemist, inventor and entrepreneur in the second half of the 20th century. Biography Schuler studied chemistry at the Königlic ...

and colleagues at Degussa.. In 1966, it was released in

Belgium Belgium, officially the Kingdom of Belgium, is a country in Northwestern Europe. Situated in a coastal lowland region known as the Low Countries, it is bordered by the Netherlands to the north, Germany to the east, Luxembourg to the southeas ...

under the brand name Pasaden. At some point, it was quietly discontinued and is no longer marketed.

Synthesis

The alkylation between 2-(Trifluoromethyl)Phenothiazine 2-30-8(1) and 1-(3-bromopropyl)-1,4-diazepane (2) led to 10- -(1,4-diazepan-1-yl)propyl2-(trifluoromethyl)phenothiazine
CID:110174391
(3). Further alkylation with

2-Chloroethanol 2-Chloroethanol (also called ethylene chlorohydrin or glycol chlorohydrin) is an organic chemical compound with the chemical formula HOCH2CH2Cl and the ''simplest'' beta-halohydrin (chlorohydrin). This colorless liquid has a pleasant ether-like od ...

07-07-3(4) completed the synthesis of homofenazine (5).

References

{{reflist Typical antipsychotics Phenothiazines Diazepanes Trifluoromethyl compounds Ethanolamines