Reactions of amine drugs with sugars II Synthesis and in vivo evaluation of mannose amphetamine sulfonate and N-phenylisopropyl-d-mannamine

Mannose amphetamine sulfonate was synthesized from the reaction of amphetamine bisulfite with D-mannose. N-Phenylisopropyl-D-mannamine was synthesized by catalytic hydrogenation of N-phenylisopropyl-D-mannosylamine. The products were evaluated in vivo by the Williamson activity cage method. Mannose amphetamine sulfonate was found to have a significantly longer duration of activity and produced a higher level of mean activity, from 3.5hr. to 4.5hr. after administration, than dextroamphetamine sulfate. N-Phenylisopropyl-D-mannamine was found to be orally inactive at dosage levels of 10 and 50 mg./Kg. of body weight.