Amfetaminil


Amfetaminil is a stimulant drug derived from amphetamine, which was developed in the 1970s and used for the treatment of obesity, ADHD, and narcolepsy. It has largely been withdrawn from clinical use following problems with abuse. The drug is a prodrug to amphetamine.

Chemistry

Stereochemistry

Amfetaminil is a molecule with two stereogenic centers. Thus, four different stereoisomers exist:
  • -2--2-phenylacetonitrile
  • -2--2-phenylacetonitrile
  • -2--2-phenylacetonitrile
  • -2--2-phenylacetonitrile

Synthesis

Schiff base formation between amphetamine and benzaldehyde gives benzalamphetamine . Nucleophilic attack of cyanide anion on the imine gives amfetaminil. Finally, reaction with nitrous acid gives. The rearrangement to a Sydnone then occurs to give . Feprosidnine is sans the phenyl group.