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Norepinephrine–dopamine reuptake inhibitors
Diphenylprolinol
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    Diphenylprolinol

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    Diphenylprolinol
    Diphenylprolinol.svg
    Clinical data
    ATC code
    • none
    Legal status
    Legal status
    • DE: NpSG (Industrial and scientific use only)
    • UK: Class B
    Identifiers
    • diphenyl(pyrrolidin-2-yl)methanol
    CAS Number
    PubChem CID
    ChemSpider
    UNII
    CompTox Dashboard (EPA)
    ECHA InfoCard 100.118.791
    Chemical and physical data
    Formula C17H19NO
    Molar mass 253.345 g·mol−1
    3D model (JSmol)
    • OC(c1ccccc1)(c2ccccc2)C3NCCC3
    • InChI=1S/C17H19NO/c19-17(16-12-7-13-18-16,14-8-3-1-4-9-14)15-10-5-2-6-11-15/h1-6,8-11,16,18-19H,7,12-13H2 checkY
    • Key:OGCGXUGBDJGFFY-UHFFFAOYSA-N checkY
     ☒NcheckY (what is this?)  (verify)

    Diphenylprolinol (D2PM), or (R/S)-(±)-diphenyl-2-pyrrolidinyl-methanol, is a norepinephrine-dopamine reuptake inhibitor which is used as a designer drug.

    Pharmacology

    The dextrorotary (R)-(+)-enantiomer is the more pharmacologically active, although a variety of related derivatives have been studied.

    Side effects including chest pain (suggestive of possible cardiovascular toxicity) have been seen following recreational use of diphenylprolinol, although it was combined with glaucine in a party pill product, thus making it impossible to say for certain which drug was responsible.

    Other uses

    Diphenylprolinol can be used to prepare the chiral CBS catalyst, which is used for enantioselective organic synthesis.

    See also


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