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Antidepressant
Cericlamine
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    Cericlamine

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    Cericlamine
    Cericlamine.svg
    Clinical data
    Routes of
    administration    		 Oral
    ATC code
    • None
    Pharmacokinetic data
    Elimination half-life 8 hours
    Identifiers
    • 3-(3,4-Dichlorophenyl)-2-(dimethylamino)-2-methylpropan-1-ol
    CAS Number
    PubChem CID
    ChemSpider
    UNII
    Chemical and physical data
    Formula C12H17Cl2NO
    Molar mass 262.17 g·mol−1
    3D model (JSmol)
    • CC(CC1=CC(=C(C=C1)Cl)Cl)(CO)N(C)C
    • InChI=1S/C12H17Cl2NO/c1-12(8-16,15(2)3)7-9-4-5-10(13)11(14)6-9/h4-6,16H,7-8H2,1-3H3
    • Key:FWYRGHMKHZXXQX-UHFFFAOYSA-N

    Cericlamine (INN; developmental code JO-1017) is a potent and moderately selective serotonin reuptake inhibitor (SSRI) of the amphetamine family (specifically, a derivative of phentermine, and closely related to chlorphentermine, a highly selective serotonin releasing agent) that was investigated as an antidepressant for the treatment of depression, anxiety disorders, and anorexia nervosa by Jouveinal but did not complete development and was never marketed. It reached phase III clinical trials in 1996 before development was discontinued in 1999.

    Synthesis

    Revised patent: Orig patent: Asymmetric:

    Arylation of methacrylic acid with a diazonium salt of 3,4-dichloroaniline (or 3,4-dichloro-benzenediazonium salt), is carried out according to the Meerwein reaction catalysed by a metallic halide. For the next step, the halide is displaced by dimethylamine, then esterification is performed, followed by reduction with a metal hydride.

    See also


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