It was used to treat schizophrenia in the 1970s.[6] It was withdrawn from the market in the UK, due to liver toxicity, in 1982.[4][7][8]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).
^Pecknold JC, Ban TA, Lehmann HE, Climan M (June 1975). "Clomacran in the treatment of schizophrenic patients: a comparison of two assessment methods". International Journal of Clinical Pharmacology and Biopharmacy. 11 (4): 299–303. PMID1099021.
^"Clomacran". PubChem. U.S. National Library of Medicine. Retrieved 2023-08-25.
^Elvin L Anderson & Harold Graboyes, U.S. patent 3,692,834 (1972 to Smith Kline and French Laboratories Ltd, GlaxoSmithKline LLC SmithKline Beecham Corp).
^Elvin L Anderson & Harold Graboyes, U.S. patent 3,919,312 (1975 to SmithKline Beecham Corp).