Thiopropamine

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Thiopropamine
Amthietamine structure.png
Thiopropamine.png
Legal status
Legal status
Identifiers
CAS Number 30433-93-3 YesY
PubChem (CID) 6484133
ChemSpider 4984575 YesY
UNII N60H4ZDD14
ChEMBL CHEMBL95500 YesY
Chemical and physical data
Formula C7H11NS
Molar mass 141.233 g/mol
3D model (Jmol) Interactive image
  (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Thiopropamine is a stimulant drug which is an analogue of amphetamine where the phenyl ring has been replaced by thiophene.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.[1][2]

Pharmacology[edit]

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[edit]

  1. ^ Alles, Gordon A.; Feigen, George A. (July 1941). "Comparative Physiological Actions of Phenyl-, Thienyl- and Furylisopropylamines". Journal of Pharmacology and Experimental Therapeutics. 72 (3): 265–75. 
  2. ^ Campaigne, E.; McCarthy, Walter C. (September 1954). "3-Substituted Thiophenes. VIII. 3-Thienylalkylamines". Journal of the American Chemical Society. 76 (17): 4466–4468. doi:10.1021/ja01646a054. 
  3. ^ Treiber, Alexander; Dansette, Patrick M.; El Amri, Hamid; Girault, Jean-Pierre; Ginderow, Daria; Mornon, Jean-Paul; Mansuy, Daniel (February 1997). "Chemical and Biological Oxidation of Thiophene:  Preparation and Complete Characterization of Thiophene S-Oxide Dimers and Evidence for Thiophene S-Oxide as an Intermediate in Thiophene Metabolism in Vivo and in Vitro". Journal of the American Chemical Society. 119 (7): 1565–1571. doi:10.1021/ja962466g. 
  4. ^ Dansette, P.M.; Thang, Do Cao; Mansuy, H. El Amri D.; Mansuy, D (August 1992). "Evidence for thiophene-s-oxide as a primary reactive metabolite of thiophene in vivo: Formation of a dihydrothiophene sulfoxide mercapturic acid". Biochemical and Biophysical Research Communications. 186 (3): 1624–1630. doi:10.1016/S0006-291X(05)81594-3. PMID 1510686. 
  5. ^ Yamada, H; Shiiyama, S; Soejima-Ohkuma, T; Honda, S; Kumagai, Y; Cho, AK; Oguri, K; Yoshimura, H (February 1997). "Deamination of amphetamines by cytochromes P450: Studies on substrate specificity and regioselectivity with microsomes and purified CYP2C subfamily isozymes". The Journal of Toxicological Sciences. 22 (1): 65–73. doi:10.2131/jts.22.65. PMID 9076658. 
  6. ^ Mantle, Timothy J.; Tipton, Keith F.; Garrett, Nigel J. (September 1976). "Inhibition of monoamine oxidase by amphetamine and related compounds". Biochemical Pharmacology. 25 (18): 2073–2077. doi:10.1016/0006-2952(76)90432-9. PMID 985546. 
  7. ^ Miller, Harold H.; Shore, Parkhurst A.; Clarke, David E. (May 1980). "In vivo monoamine oxidase inhibition by d-amphetamine". Biochemical Pharmacology. 29 (10): 1347–1354. doi:10.1016/0006-2952(80)90429-3. PMID 6901611.