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.
D000577:Amides / Q000138:chemical synthesis / Q000494:pharmacology; D000662:Amphetamines / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D000890:Anti-Infective Agents; D001522:Behavior, Animal / Q000187:drug effects; D066298:In Vitro Techniques; D051381:Rats; D013859:Thiocarbamates / Q000138:chemical synthesis / Q000494:pharmacology; D013890:Thiourea / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000494:pharmacology
D000577:Amides; D000662:Amphetamines; D000890:Anti-Infective Agents; D013859:Thiocarbamates; D013890:Thiourea