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Typical antipsychotic
Aceperone
Другие языки:

    Aceperone

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    Aceperone
    Aceperone.svg
    Clinical data
    Other names Acetabuton; R 3248
    ATC code
    • none
    Identifiers
    • N-({1-[4-(4-Fluorophenyl)-4-oxobutyl]-4-phenyl-4-piperidinyl}methyl)acetamide
    CAS Number
    PubChem CID
    ChemSpider
    UNII
    ChEMBL
    CompTox Dashboard (EPA)
    Chemical and physical data
    Formula C24H29FN2O2
    Molar mass 396.506 g·mol−1
    3D model (JSmol)
    Melting point 97 to 100 °C (207 to 212 °F)
    • Fc1ccc(cc1)C(=O)CCCN3CCC(c2ccccc2)(CC3)CNC(=O)C
    • InChI=1S/C24H29FN2O2/c1-19(28)26-18-24(21-6-3-2-4-7-21)13-16-27(17-14-24)15-5-8-23(29)20-9-11-22(25)12-10-20/h2-4,6-7,9-12H,5,8,13-18H2,1H3,(H,26,28)
    • Key:VDGZERMDPAAZEJ-UHFFFAOYSA-N

    Aceperone is a neuroleptic drug of the butyrophenone class. It is an α-noradrenergic blocking drug developed by Janssen Pharmaceutica in the 1960s.

    Aceperone has been used as a tool in the study of the biochemical basis of learning. Although aceperone does not block learning per se, it blocks access to an attentional mechanism by which animals ‘tune in’ to the relevant visual dimension when learning a visual discrimination task at doses below those that affect general behaviour.

    Synthesis

    Patent:

    The reduction of 1-Benzyl-4-cyano-4-phenylpiperidine [56243-25-5] (1) with lithium aluminium hydride gives 1-Benzyl-4-phenylpiperidine-4-methylamine [84176-77-2] (2). Acetylation of this primary amine would yield [7152-05-8] (3). The removal of the benzyl protecting group by catalytic hydrogenation gives N-[(4-phenyl-4-piperidinyl)methyl]acetamide [83763-23-9] (4). Alkylation with 4-Chloro-4'-Fluorobutyrophenone [3874-54-2] (5) affords aceperone (6).


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