Heterocyclic analogs of amphetamine: Thioureas, dithiocarbamates, and negatively substituted amides

A series of heterocyclic analogs of amphetamine was synthesized. The heterocycles employed included the 2-furyl, 2-thienyl, 3-methyl-2-thienyl, 3-pyridyl, and 6-methyl-2-pyridyl rings. The aliphatic amine group was converted to the N-methylthiourea, dithiocarbamate, methanesulfonyl, trifluoromethanesulfonyl, and trifluoracetyl functions since similar conversions of the beta-phenethylamine structure had shown blood pressure-lowering effects and some loss of behavioral effects. p-Chlorophenyl and 1-naphthyl analogs were also converted to these derivatives. Behavioral and other biological effects, including antiarthritic, passive cutaneous anaphylactic, and antimicrobial, were observed. The 3-methyl-2-thienyl analog of amphetamine significantly increased papillary muscle contractile force without producing arhythmias.