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Norepinephrine–dopamine reuptake inhibitors
Thiopropamine
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    Thiopropamine

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    Thiopropamine
    Thiopropamine.svg
    Thiopropamine.png
    Legal status
    Legal status
    • DE: Anlage I (Authorized scientific use only)
    Identifiers
    • 1-(thiophen-2-yl)-2-aminopropane
    CAS Number
    PubChem CID
    ChemSpider
    UNII
    ChEMBL
    CompTox Dashboard (EPA)
    Chemical and physical data
    Formula C7H11NS
    Molar mass 141.23 g·mol−1
    3D model (JSmol)
    • CC(N)Cc1sccc1
    • InChI=1S/C7H11NS/c1-6(8)5-7-3-2-4-9-7/h2-4,6H,5,8H2,1H3 checkY
    • Key:NYVQQTOGYLBBDQ-UHFFFAOYSA-N checkY
      (verify)

    Thiopropamine is a stimulant drug which is an analogue of amphetamine where the phenyl ring has been replaced by thiophene. It has similar stimulant effects to amphetamine but with around one third the potency. The N-methyl and thiophen-3-yl analogues are also known and are somewhat more potent, though still generally weaker than the corresponding amphetamines.

    Pharmacology

    Like amphetamine and most of its analogues, thiopropamine most likely is a norepinephrine–dopamine reuptake inhibitor and/or releasing agent.

    Thiopropamine is likely to be metabolized into active 4-hydroxymethiopropamine and thiophene S-oxides. These are further deaminated by CYP2C in liver transforming them into inactive 1-(Thiophen-2-yl)-2-propan-2-one which is a phenylacetone derivative. Propan-2-amines are not metabolized by monoamine oxidases and most actually behave as competitive monoamine oxidase inhibitors.


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