Thiopropamine

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Thiopropamine
Legal status
Legal status
  • DE: Anlage I (Authorized scientific use only)
Identifiers
  • 1-(thiophen-2-yl)-2-aminopropane
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

phenyl ring has been replaced by thiophene.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.[1][2]

Pharmacology

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

Thiopropamine is likely to be

metabolized into active 4-hydroxymethiopropamine and thiophene S-oxides.[3][4] 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.[5] Propan-2-amines are not metabolized by monoamine oxidases and most actually behave as competitive monoamine oxidase inhibitors.[6][7]

References

  1. ^ Alles GA, Feigen GA (July 1941). "Comparative Physiological Actions of Phenyl-, Thienyl- and Furylisopropylamines". Journal of Pharmacology and Experimental Therapeutics. 72 (3): 265–75.
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