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Clomacran

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Clomacran
Clinical data
Trade namesDevryl, Olaxin,[1]Develar[2][3]
ATC code
Legal status
Legal status
Identifiers
  • 3-(2-Chloro-9,10-dihydroacridin-9-yl)-N,N-dimethylpropan-1-amine
CAS Number
PubChemCID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC18H21ClN2
Molar mass300.83g·mol−1
3D model (JSmol)
Density1.120 g/cm3g/cm3[1]
  • 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,5,7,11H2,1-2H3checkY
  • Key:JFRLWWDJCFYFSU-UHFFFAOYSA-NcheckY

Clomacranis anantipsychotic drugof the dihydroacridineclass, developed in the 1970s[2]by the pharmaceutical companySmith, Kline & French(nowGlaxoSmithKline) 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It was used to treat schizophrenia in the 1970s.[6]It was withdrawn from the market in the UK, due to liver toxicity, in 1982.[4][7][8]

Synthesis

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Clomacran can be synthesized beginning with 2-chloroacridone (1) which is reacted with aGrignard reagentderived from 3-chloro-N,N-dimethylpropylamine (2) to afford the tertiary carbinol (3).[9][10][11][12]Dehydrationby means of acid or simply heat gives the corresponding olefin (4). Catalytic reduction completes the synthesis of clomacran (5).

Synthesis of clomacran

References

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  1. ^abc"Clomacran | 5310-55-4".ChemicalBook.Retrieved2023-08-25.
  2. ^abElks J, Ganellin CR, eds. (1990).Dictionary of Drugs.Boston, MA: Springer US. p. 297.doi:10.1007/978-1-4757-2085-3.ISBN978-1-4757-2087-7.
  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.Retrieved2023-08-08.
  4. ^abDixit 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.eISSN2583-3995.
  5. ^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).Archivedfrom the original on 2023-08-03.Retrieved2023-08-03.
  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.PMID1099021.
  7. ^"Clomacran".PubChem.U.S. National Library of Medicine.Retrieved2023-08-25.
  8. ^Andrews EB, Moore N, eds. (2014).Mann's Pharmacovigilance(1st ed.). Wiley.doi:10.1002/9781118820186.ISBN978-0-470-67104-7.
  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).
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