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| Trade names | Aponeuron |
| Other names | Amphetaminil; AN-1;N-Cyanobenzylamphetamine;N-(α′-Cyanobenzyl)amphetamine |
| Routes of administration | Oral |
| Drug class | Stimulant;Appetite suppressant;Norepinephrine–dopamine releasing agent |
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| ECHA InfoCard | 100.037.767 |
| Chemical and physical data | |
| Formula | C17H18N2 |
| Molar mass | 250.345 g·mol−1 |
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Amfetaminil (also known asamphetaminil,N-cyanobenzylamphetamine,[1] andAN-1; brand nameAponeuron) is astimulant drug derived fromamphetamine, which was developed in the 1970s and used for the treatment ofobesity,[2]ADHD,[3][4] andnarcolepsy.[5] It has largely been withdrawn from clinical use following problems withabuse.[6] The drug is aprodrug toamphetamine.[7][8]
Amfetaminil is a molecule with two stereogenic centers. Thus, four different stereoisomers exist:
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 aSydnone then occurs to giveCID:88166659 (6).Feprosidnine is sans the phenyl group.