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Respiratory system drug stubs
Dacemazine
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    Dacemazine

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    Dacemazine
    Dacemazine.svg
    Clinical data
    ATC code
    • none
    Identifiers
    • 2-dimethylamino-1-phenothiazin-10-ylethanone
    CAS Number
    PubChem CID
    ChemSpider
    UNII
    ChEMBL
    CompTox Dashboard (EPA)
    Chemical and physical data
    Formula C16H16N2OS
    Molar mass 284.38 g·mol−1
    3D model (JSmol)
    • O=C(N1c3c(Sc2c1cccc2)cccc3)CN(C)C
    • InChI=1S/C16H16N2OS/c1-17(2)11-16(19)18-12-7-3-5-9-14(12)20-15-10-6-4-8-13(15)18/h3-10H,11H2,1-2H3 checkY
    • Key:HKUCYAHWPVLPFN-UHFFFAOYSA-N checkY
     ☒NcheckY (what is this?)  (verify)

    Dacemazine (INN, also known as Ahistan and Histantine) is a phenothiazine derivative which acts as a histamine antagonist at the H1 subtype. First described in 1951, it was never marketed as a drug on its own, although a combination of dacemazine and di-tert-butylnaphthalenesulfonate was sold as an antispasmodic and antitussive under the trade name Codopectyl. It was also assessed as a possible anticancer drug.

    Synthesis

    Synthesis: Patent (Ex 8):

    Amide formation between phenothiazine (1) and chloroacetyl chloride (2) gives 10-(Chloroacetyl)-phenothiazine [786-50-5] (3). The subsequent displacement of the remaining halogen with dimethylamine (4) completes the synthesis of dacemazine (5).



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