Thiopropamine

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Thiopropamine
Amthietamine structure.png
Systematic (IUPAC) name
1-(thiophen-2-yl)-2-aminopropane
Clinical data
Legal status
?
Identifiers
CAS number  YesY
ATC code ?
PubChem CID 6484133
ChemSpider 4984575 YesY
ChEMBL CHEMBL95500 YesY
Chemical data
Formula C7H11NS 
Mol. mass 141.233 g/mol
 YesY (what is this?)  (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Thiopropamine is a stimulant drug which is an analogue of amphetamine where the phenyl ring has been replaced by thiophene.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 dopamine releasing agent and norepinephrine 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[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. (1954). "3-Substituted Thiophenes. IX.1 3-Thienones and 5-(3-Thienyl)-hydantoins2". Journal of the American Chemical Society 77 (20): 5365–9. doi:10.1021/ja01646a054. 
  3. ^ Treiber, Alexander; Dansette, Patrick M.; El Amri, Hamid; Girault, Jean-Pierre; Ginderow, Daria; Mornon, Jean-Paul; Mansuy, Daniel (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): 1565–71. doi:10.1021/ja962466g. 
  4. ^ Dansette, P.M.; Thang, Do Cao; Mansuy, H. El Amri D.; Mansuy, D (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): 1624–30. 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 (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. (1976). "Inhibition of monoamine oxidase by amphetamine and related compounds". Biochemical Pharmacology 25 (18): 2073–7. doi:10.1016/0006-2952(76)90432-9. PMID 985546. 
  7. ^ Miller, Harold H.; Shore, Parkhurst A.; Clarke, David E. (1980). "In vivo monoamine oxidase inhibition by d-amphetamine". Biochemical Pharmacology 29 (10): 1347–54. doi:10.1016/0006-2952(80)90429-3. PMID 6901611.