Thiopropamine

Thiopropamine

Thiopropamine
Systematic (IUPAC) name
1-(thiophen-2-yl)-2-aminopropane
Clinical data
Legal status
Identifiers
CAS Registry Number  YesY
PubChem CID:
ChemSpider  YesY
ChEMBL  YesY
Chemical data
Formula C7H11NS
Molecular mass 141.233 g/mol
 YesY   

Thiopropamine is a stimulant drug which is an analogue of amphetamine where the phenyl ring has been replaced by thiophene.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.[1][2]

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.[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

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