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Clomacran 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 dihydroacridine
Acridine is an organic compound and a nitrogen heterocycle with the formula C13H9N. Acridines are substituted derivatives of the parent ring. It is a planar molecule that is structurally related to anthracene with one of the central CH groups ...
class, developed in the 1970s by the pharmaceutical company Smith, Kline & French
Smith, Kline & French (SKF) was an American pharmaceutical company that is now a part of the British group GSK plc.
History
In 1830, John K. Smith opened a drugstore in Philadelphia, and his younger brother, George, joined him in 1841 to form ...
(now GlaxoSmithKline
GSK plc (an acronym from its former name GlaxoSmithKline plc) is a British Multinational corporation, multinational Pharmaceutics, pharmaceutical and biotechnology company with headquarters in London. It was established in 2000 by a Mergers an ...
) under the brand names Devryl and Olaxin.
It was used to treat schizophrenia in the 1970s. It was withdrawn from the market in the UK, due to liver toxicity, in 1982.
Synthesis
Clomacran can be synthesized beginning with 2-chloroacridone (1) which is reacted with aGrignard reagent
Grignard reagents or Grignard compounds are chemical compounds with the general formula , where X is a halogen and R is an organic group, normally an alkyl or aryl. Two typical examples are methylmagnesium chloride and phenylmagnesium bromi ...
derived from 3-chloro-''N'',''N''-dimethylpropylamine (2) to afford the tertiary carbinol (3).Elvin L Anderson & Harold Graboyes, (1975 to SmithKline Beecham Corp). Dehydration
In physiology, dehydration is a lack of total body water that disrupts metabolic processes. It occurs when free water loss exceeds intake, often resulting from excessive sweating, health conditions, or inadequate consumption of water. Mild deh ...
by means of acid or simply heat gives the corresponding olefin (4). Catalytic reduction completes the synthesis of clomacran (5).
References
{{Tricyclics Typical antipsychotics Acridines Chloroarenes Dimethylamino compounds Tertiary amines