Amfetaminil

Amfetaminil (also known as amphetaminil, N-cyanobenzylamphetamine, and AN-1; brand name Aponeuron) 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 It has largely been withdrawn from clinical use following problems with abuse.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.

Stereochemistry
Amfetaminil is a molecule with two stereogenic centers. Thus, four different stereoisomers exist:




 * (R)-2-[(R)-1-Phenylpropan-2-ylamino]-2-phenylacetonitrile (CAS number 478392-08-4)
 * (S)-2-[(S)-1-Phenylpropan-2-ylamino]-2-phenylacetonitrile (CAS number 478392-12-0)
 * (R)-2-[(S)-1-Phenylpropan-2-ylamino]-2-phenylacetonitrile (CAS number 478392-10-8)
 * (S)-2-[(R)-1-Phenylpropan-2-ylamino]-2-phenylacetonitrile (CAS number 478392-14-2)

Synthesis


Schiff base formation between amphetamine (1) and benzaldehyde (2) gives benzalamphetamine [2980-02-1] (3). Nucleophilic attack of cyanide anion on the imine (c.f. Strecker reaction) gives amfetaminil (4). Finally, reaction with nitrous acid gives (5). The rearrangement to a Sydnone then occurs to give CID:88166659 (6). Feprosidnine is sans the phenyl group.