Reactions of amine drugs with sugars I Reaction of amphetamine with aldoses, glycosylamines, and bisulfite

Amphetamine bisulfite was reacted with D-glucose, D-mannose, N-phenylisopropyl-D-mannosylamine, and N-phenyl-D-mannosylamine. The effect of an aryl or alkyl amine as the amino substituent at C-1 of the aldose on the formation of amino sul-fonates was investigated. Alkyl substitution was found to yield bisulfite addition products, while aryl substitution yielded amino sulfonates. Mannose amphetamine sulfonate and glucose amphetamine sulfonate were synthesized.