Sulfur-containing derivatives of amphetamine: thioureas, methanesulfonamides, and trifluoromethanesulfonamides.

Abstract

N-Methylthiourea, methanesulfonamide, and trifluoromethanesulfonamide derivatives of amphetamine, 4-nitroamphetamine, and 4-aminoamphetamine were synthesized. The N-methylthiourea derivative of amphetamine, as well as the triethylammonium salt of the dithiocarbamate, produced significant depressor effects in normotensive dogs. N,N'-Bis(methanesulfonyl)-1-methyl-2-(4-aminophenyl)ethylamine and N-trifluoromethanesulofonyl-1-methyl-2-phenylethylamine, but not N-methanesulfonyl-1-methyl-2-phenylethylamine and N-trifluoroacetyl-1-methyl-2-(4-trifluoromethanesulfonamido-phenyl))ethylamine, showed significant antiobesity effects in rats.