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Abandoned drugs
Binedaline
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    Binedaline

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    Binedaline
    Binedaline.png
    Clinical data
    Routes of
    administration    		 Oral
    ATC code
    • None
    Legal status
    Legal status
    • In general: unscheduled
    Identifiers
    • N,N,N-Trimethyl-N-(3-phenylindol-1-yl)ethane-1,2-diamine
    CAS Number
    PubChem CID
    ChemSpider
    UNII
    ChEMBL
    CompTox Dashboard (EPA)
    Chemical and physical data
    Formula C19H23N3
    Molar mass 293.414 g·mol−1
    3D model (JSmol)
    • c1cccc2c1c(cn2N(CCN(C)C)C)c3ccccc3
    • InChI=1S/C19H23N3/c1-20(2)13-14-21(3)22-15-18(16-9-5-4-6-10-16)17-11-7-8-12-19(17)22/h4-12,15H,13-14H2,1-3H3 checkY
    • Key:SXYFFMXPDDGOEK-UHFFFAOYSA-N checkY
     ☒NcheckY (what is this?)  (verify)

    Binedaline (also called binodaline or binedaline hydrochloride;) is a drug that was investigated as an antidepressant in the 1980s but was never marketed. It acts as a selective norepinephrine reuptake inhibitor (Ki = 25 nM), with relatively insignificant influence on the serotonin (Ki = 847 nM) and dopamine (Ki >= 2 μM) transporters. It has negligible affinity for the α-adrenergic, mACh, H1, or 5-HT2 receptors.

    Synthesis

    Thieme Synthesis: Patents:

    Grignard reaction of 2-aminobenzophenone [2835-77-0] (1) with methylmagnesium bromide and dehydration of the tertiary carbinol gives 2-(1-phenylvinyl)aniline [64097-92-3] (2). In an example of the Widman‐Stoermer Synthesis, treatment with nitrous acid followed by basification of the diazonium species with ammonia causes an intramolecular cyclization to afford 4-phenylcinnoline [21874-06-6] (3). Hydrogenation would give 4-Phenyl-1,4-dihydrocinnoline, CID:14175750 (4). The presence of acetic acid gives (5). The reaction with Methyl p-toluenesulfonate [80-48-8] leads to CID:20337750 (6). Acid hydrolysis gives N-methyl-3-phenylindol-1-amine [57647-15-1] (7). Sodamide is then used to abstract the amine proton; alkylation of then anionic species with 2-dimethylaminoethylchloride [107-99-3] (8) then concludes the synthesis of binedaline (9).

    See also

    Widman‐Stoermer Synthesis also used for the synthesis of Cintazone [2056-56-6].


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