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Antipsychotic
Pirenperone
Другие языки:

    Pirenperone

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    Not to be confused with Pipamperone.
    Pirenperone
    Pirenperone.svg
    Clinical data
    Other names R-47456; R-50656
    Identifiers
    • 3-[2-[4-(4-Fluorobenzoyl)piperidin-1-yl]ethyl]-2-methylpyrido[1,2-a]pyrimidin-4-one
    CAS Number
    PubChem CID
    ChemSpider
    UNII
    KEGG
    ChEBI
    ChEMBL
    CompTox Dashboard (EPA)
    ECHA InfoCard 100.071.081
    Chemical and physical data
    Formula C23H24FN3O2
    Molar mass 393.462 g·mol−1
    3D model (JSmol)
    • CC1=C(C(=O)N2C=CC=CC2=N1)CCN3CCC(CC3)C(=O)C4=CC=C(C=C4)F
    • InChI=1S/C23H24FN3O2/c1-16-20(23(29)27-12-3-2-4-21(27)25-16)11-15-26-13-9-18(10-14-26)22(28)17-5-7-19(24)8-6-17/h2-8,12,18H,9-11,13-15H2,1H3
    • Key:HXCNRYXBZNHDNE-UHFFFAOYSA-N

    Pirenperone (INN, USAN, BAN; developmental code names R-47456, R-50656) is a serotonin receptor antagonist described as an antipsychotic and tranquilizer which was never marketed. It is a relatively selective antagonist of the serotonin 5-HT2 receptors and has been used in scientific research to study the serotonin system. In the 1980s, the drug was found to block the effects of the lysergic acid diethylamide (LSD) in animals, and along with ketanserin, led to the elucidation of the 5-HT2A receptor as the biological mediator of the effects of serotonergic psychedelics.

    Synthesis

    The sidechain is formed from the cyclization of 2-aminopyridine with 2-Acetylbutyrolactone (2) in PPA gave 3-(2-hydroxyethyl)-2-methylpyrido[1,2-a]pyrimidin-4-one [41078-67-5] (3). Halogenation replaces the hydroxy with the chloride leaving group. Many syntheses do both steps in one-pot with phosphorus oxychloride.

    The 4-(4-Fluorobenzoyl)Piperidine [56346-57-7] has 12 known named uses.

    Patent (Ex XIX):

    The alkylation between 3-(2-chloroethyl)-2-methylpyrido[1,2-a]pyrimidin-4-one [41078-70-0] (1) and 4-(4-fluorobenzoyl)piperidine hydrochloride [25519-78-2] (2) afforded pirenperone (3).

    See also




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