Clomacran Explained

Iupac Name:3-(2-Chloro-9,10-dihydroacridin-9-yl)-N,N-dimethylpropan-1-amine
Tradename:Devryl, Olaxin,[1] Develar[2] [3]
Atc Prefix:N05A
Atc Suffix:X
Legal Br:C1
Legal Br Comment:[4]
Legal Uk:Withdrawn[5]
Cas Number:5310-55-4
Pubchem:21382
Chemspiderid:20095
Unii:5B1UZF65WW
Chebi:135273
Chembl:1615350
C:18
H:21
Cl:1
N:2
Smiles:CN(C)CCCC1C2=CC=CC=C2NC3=C1C=C(C=C3)Cl
Stdinchi: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
Stdinchikey:JFRLWWDJCFYFSU-UHFFFAOYSA-N
Density:1.120 g/cm3

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]

It was used to treat schizophrenia in the 1970s.[6] It was withdrawn from the market in the UK, due to liver toxicity, in 1982.[7] [8]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).

Notes and References

  1. Web site: Clomacran 5310-55-4 . 2023-08-25 . ChemicalBook . en.
  2. Book: Dictionary of Drugs . 1990 . Springer US . 978-1-4757-2087-7 . Elks J, Ganellin CR . Boston, MA . 297 . en . 10.1007/978-1-4757-2085-3 .
  3. News: 1986-11-05 . Substâncias e remédios sob controle . pt-br . Substances and drugs under control . 14 . . live . 2023-08-08 . https://web.archive.org/web/20230808230340/https://memoria.bn.br/pdf/030015/per030015_1986_00211.pdf . 2023-08-08.
  4. Web site: Anvisa . Brazilian Health Regulatory Agency . 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. live . https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 . 2023-08-03 . 2023-08-03 . . pt-BR . 2023-04-04.
  5. 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 . 10.56588/iabcd.v1i1.17 . 2583-3995 . free.
  6. Pecknold JC, Ban TA, Lehmann HE, Climan M . Clomacran in the treatment of schizophrenic patients: a comparison of two assessment methods . International Journal of Clinical Pharmacology and Biopharmacy . 11 . 4 . 299–303 . June 1975 . 1099021 .
  7. Web site: Clomacran . 2023-08-25 . PubChem . en . U.S. National Library of Medicine .
  8. Book: Mann's Pharmacovigilance . 2014 . Wiley . 978-0-470-67104-7 . Andrews EB, Moore N . 1st . en . 10.1002/9781118820186 .
  9. Zirkle Charles L, (1964 to Smith Kline French Lab).
  10. E Anderson & H Graboyes, (1973 to SmithKline Beecham Corp).
  11. Elvin L Anderson & Harold Graboyes, (1972 to Smith Kline and French Laboratories Ltd, GlaxoSmithKline LLC SmithKline Beecham Corp).
  12. Elvin L Anderson & Harold Graboyes, (1975 to SmithKline Beecham Corp).

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