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PPPA (drug)
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    PPPA (drug)

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    PPPA
    3-phenoxy-3-phenylpropan-1-amine.svg
    Clinical data
    ATC code
    • None
    Identifiers
    • 3-Phenoxy-3-phenyl-1-propanamine
    CAS Number
    ChemSpider
    UNII
    Chemical and physical data
    Formula C15H17NO
    Molar mass 227.307 g·mol−1
    3D model (JSmol)
    • c1ccc(cc1)C(CCN)Oc2ccccc2
    • InChI=1S/C15H17NO/c16-12-11-15(13-7-3-1-4-8-13)17-14-9-5-2-6-10-14/h1-10,15H,11-12,16H2
    • Key:XYWLZHPZECQHMB-UHFFFAOYSA-N

    PPPA, or 3-phenoxy-3-phenylpropan-1-amine, is a drug which is described as an antidepressant. It was derived by Eli Lilly from the antihistamine diphenhydramine, a 2-diphenylmethoxyethanamine derivative with additional properties as a selective serotonin reuptake inhibitor (SSRI), and has been the basis for the subsequent discovery of a number of other antidepressant drugs.

    List of PPPA derivatives

    • Atomoxetine ((3R)-N-methyl-3-(2-methylphenoxy)-3-phenylpropan-1-amine) — NRI
    • Fluoxetine (N-methyl-3-(4-(trifluoromethyl)phenoxy)-3-phenylpropan-1-amine) — SSRI
    • N-Methyl-PPPA (N-methyl-3-phenoxy-3-phenylpropan-1-amine) — SNRI
    • Nisoxetine (N-methyl-3-(2-methoxyphenoxy)-3-phenylpropan-1-amine) — NRI
    • Norfluoxetine (3-(4-(trifluoromethyl)phenoxy)-3-phenylpropan-1-amine) — SSRI
    • Seproxetine ((S)-3-(4-(trifluoromethyl)phenoxy)-3-phenylpropan-1-amine) — SSRI

    Structurally related drugs include dapoxetine, duloxetine, edivoxetine, femoxetine, paroxetine, reboxetine, and viloxazine, all of which act, similarly, as monoamine reuptake inhibitors, and most of which are, again similarly, antidepressants.

    Zimelidine is an antidepressant and SSRI which was derived from the antihistamine pheniramine, which, similarly to its analogues brompheniramine and chlorpheniramine, possesses SNRI properties.Fluvoxamine, another antidepressant and SSRI, was developed from the antihistamine tripelennamine, which possesses SNDRI actions.

    See also

    Further reading

    • Wong DT, Bymaster FP, Engleman EA (1995). "Prozac (fluoxetine, Lilly 110140), the first selective serotonin uptake inhibitor and an antidepressant drug: twenty years since its first publication". Life Sci. 57 (5): 411–41. doi:10.1016/0024-3205(95)00209-o. PMID 7623609.

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