Thiopropamine is a stimulant drug which is an analogue of amphetamine where the phenyl ring has been replaced by thiophene.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.
^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.
^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.
^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. PMID1510686.
^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. PMID9076658.
^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. PMID6901611.