Clomacran is an antipsychotic drug of the dihydroacridine class, developed in the 1970s by the pharmaceutical company Smith, Kline & French (now GlaxoSmithKline) 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 It was withdrawn from the market in the UK, due to liver toxicity, in 1982.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 a Grignard reagent derived from 3-chloro-N,N-dimethylpropylamine (2) to afford the tertiary carbinol (3).Zirkle Charles L, (1964 to Smith Kline French Lab).E Anderson & H Graboyes, (1973 to SmithKline Beecham Corp).Elvin L Anderson & Harold Graboyes, (1972 to Smith Kline and French Laboratories Ltd, GlaxoSmithKline LLC SmithKline Beecham Corp).Elvin L Anderson & Harold Graboyes, (1975 to SmithKline Beecham Corp). Dehydration by means of acid or simply heat gives the corresponding olefin (4). Catalytic reduction completes the synthesis of clomacran (5).
See also Chlorprothixene
References