Thiopropamine

Stimulant drug From Wikipedia, the free encyclopedia

Thiopropamine, also known as 1-(2-thienyl)-2-aminopropane, is a stimulant drug of the arylalkylamine family. It is an analogue of amphetamine where the phenyl ring has been replaced by thiophene.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.[2][3]

Other namesThiophenylpropylamine; 1-Methyl-2-thiophen-2-yl-ethylamine; 2-(2-Aminopropyl)thiophene; 1-(2-Thienyl)-2-aminopropane
Legal status
  • CA: <Schedule I[1]
  • DE: Anlage I (Authorized scientific use only)
Quick facts Clinical data, Other names ...
Thiopropamine
Clinical data
Other namesThiophenylpropylamine; 1-Methyl-2-thiophen-2-yl-ethylamine; 2-(2-Aminopropyl)thiophene; 1-(2-Thienyl)-2-aminopropane
Legal status
Legal status
  • CA: <Schedule I[1]
  • 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
FormulaC7H11NS
Molar mass141.23 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)
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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.[4][5] 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.[6] Propan-2-amines are not metabolized by monoamine oxidases and most actually behave as competitive monoamine oxidase inhibitors.[7][8]

Chemistry

Derivatives

Derivatives of thiopropamine include the following:

See also

References

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