Chemistry:Clomacran
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Short description: Antipsychotic medication
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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 [1] |
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Clomacran is an antipsychotic drug of the dihydroacridine class, developed in the 1970s[2] by the pharmaceutical company Smith, Kline & French under the brand names Devryl and Olaxin.[1]
It was used to treat schizophrenia in the 70s.[5] It was withdrawn from the market in the UK, due to liver toxicity, in 1982.[4][6][7]
Synthesis
The first step involves FGI of 3-chloro-N,N-dimethylpropylamine Fb: [109-54-6] (2) into the Grignard reagent, i.e. (3-(Dimethylamino)propyl)magnesium chloride [19070-16-7] ([154034-91-0]). The Grignard reaction with 2-chloroacridone [7497-52-1] (1) affords the tertiary carbinol (3). Dehydration by means of acid or simply heat gives the corresponding olefin (4). Catalytic reduction completes the synthesis of (5).
References
- ↑ 1.0 1.1 1.2 "Clomacran | 5310-55-4" (in en). https://www.chemicalbook.com/ChemicalProductProperty_EN_CB61178346.htm.
- ↑ 2.0 2.1 (in en) Dictionary of Drugs. Boston, MA: Springer US. 1990. pp. 297. doi:10.1007/978-1-4757-2085-3. ISBN 978-1-4757-2087-7. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA297.
- ↑ "Substâncias e remédios sob controle" (in pt-br). Jornal do Brasil: pp. 14. 1986-11-05. https://memoria.bn.br/pdf/030015/per030015_1986_00211.pdf.
- ↑ 4.0 4.1 "Quantitative Structure-activity Relationship (QSAR) study of Liver Toxic Drugs". International Association of Biologicals and Computational Digest 1: 63–71. 2022-05-02. doi:10.56588/iabcd.v1i1.17.
- ↑ Pecknold, J. C.; Ban, T. A.; Lehmann, H. E.; Climan, M. (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. ISSN 0340-0026. PMID 1099021. https://pubmed.ncbi.nlm.nih.gov/1099021/.
- ↑ "Clomacran" (in en). PubChem. U.S. National Library of Medicine. https://pubchem.ncbi.nlm.nih.gov/compound/21382.
- ↑ (in en) Mann's Pharmacovigilance (1st ed.). Wiley. 2014. doi:10.1002/9781118820186. ISBN 978-0-470-67104-7.
- ↑ Zirkle Charles L, U.S. Patent 3,131,190 (1964 to Smith Kline French Lab).
- ↑ E Anderson & H Graboyes, U.S. Patent 3,781,358 (1973 to SmithKline Beecham Corp).
- ↑ 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).
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