Clomacran

Clomacran
Clinical data
Trade namesDevryl, Olaxin, Develar
ATC code
Legal status
Legal status
  • BR: Class C1 (Other controlled substances)
  • UK: Withdrawn
Identifiers
  • 3-(2-Chloro-9,10-dihydroacridin-9-yl)-N,N-dimethylpropan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H21ClN2
Molar mass300.83 g·mol−1
3D model (JSmol)
Density1.120 g/cm3 g/cm3
  • CN(C)CCCC1C2=CC=CC=C2NC3=C1C=C(C=C3)Cl
  • InChI=1S/C18H21ClN2/c1-21(2)11-5-7-14-15-6-3-4-8-17(15)20-18-10-9-13(19)12-16(14)18/h3-4,6,8-10,12,14,20H,5,7,11H2,1-2H3 checkY
  • Key:JFRLWWDJCFYFSU-UHFFFAOYSA-N checkY

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 It was withdrawn from the market in the UK, due to liver toxicity, in 1982.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). Dehydration by means of acid or simply heat gives the corresponding olefin (4). Catalytic reduction completes the synthesis of clomacran (5).

Synthesis of clomacran

See also

References

  1. 1 2 3 "Clomacran | 5310-55-4". ChemicalBook. Retrieved 2023-08-25.
  2. 1 2 Elks J, Ganellin CR, eds. (1990). Dictionary of Drugs. Boston, MA: Springer US. p. 297. doi:10.1007/978-1-4757-2085-3. ISBN 978-1-4757-2087-7.
  3. ↑ "Substâncias e remédios sob controle" [Substances and drugs under control] (PDF). Jornal do Brasil (in Brazilian Portuguese). 1986-11-05. p. 14. Archived (PDF) from the original on 2023-08-08. Retrieved 2023-08-08.
  4. ↑ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-03.
  5. 1 2 Dixit N, Patel C, Bhavsar M, Patel S, Rawal R, Solanki H (2022-05-02). "Quantitative Structure-activity Relationship (QSAR) study of Liver Toxic Drugs". International Association of Biologicals and Computational Digest. 1: 63–71. doi:10.56588/iabcd.v1i1.17. eISSN 2583-3995.
  6. ↑ 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. PMID 1099021.
  7. ↑ "Clomacran". PubChem. U.S. National Library of Medicine. Retrieved 2023-08-25.
  8. ↑ Andrews EB, Moore N, eds. (2014). Mann's Pharmacovigilance (1st ed.). Wiley. doi:10.1002/9781118820186. ISBN 978-0-470-67104-7.
  9. ↑ Zirkle Charles L, U.S. patent 3,131,190 (1964 to Smith Kline French Lab).
  10. ↑ E Anderson & H Graboyes, U.S. patent 3,781,358 (1973 to SmithKline Beecham Corp).
  11. ↑ Elvin L Anderson & Harold Graboyes, U.S. patent 3,692,834 (1972 to Smith Kline and French Laboratories Ltd, GlaxoSmithKline LLC SmithKline Beecham Corp).
  12. ↑ Elvin L Anderson & Harold Graboyes, U.S. patent 3,919,312 (1975 to SmithKline Beecham Corp).