Clomacran
Antipsychotic medication
From Wikipedia, the free encyclopedia
Clomacran is an antipsychotic drug of the dihydroacridine class, developed in the 1970s[2] by the pharmaceutical company Smith, Kline & French (now GlaxoSmithKline) under the brand names Devryl and Olaxin.[1]
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| Trade names | Devryl, Olaxin,[1] Develar[2][3] |
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| Formula | C18H21ClN2 |
| Molar mass | 300.83 g·mol−1 |
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| Density | 1.120 g/cm3 g/cm3 [1] |
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It was used to treat schizophrenia in the 1970s.[6] It was withdrawn from the market in the UK, due to liver toxicity, in 1982.[5][7][8]
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).[9][10][11][12] Dehydration by means of acid or simply heat gives the corresponding olefin (4). Catalytic reduction completes the synthesis of clomacran (5).
