Amfetaminil (also known as amphetaminil, ''N''-cyanobenzylamphetamine, and AN-1; brand name Aponeuron) is a

stimulant Stimulants (also known as central nervous system stimulants, or psychostimulants, or colloquially as uppers) are a class of drugs that increase alertness. They are used for various purposes, such as enhancing attention, motivation, cognition, ...

drug derived from

amphetamine Amphetamine (contracted from Alpha and beta carbon, alpha-methylphenethylamine, methylphenethylamine) is a central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, an ...

, which was developed in the 1970s and used for the treatment of

obesity Obesity is a medical condition, considered by multiple organizations to be a disease, in which excess Adipose tissue, body fat has accumulated to such an extent that it can potentially have negative effects on health. People are classifi ...

ADHD Attention deficit hyperactivity disorder (ADHD) is a neurodevelopmental disorder characterised by symptoms of inattention, hyperactivity, impulsivity, and emotional dysregulation that are excessive and pervasive, impairing in multiple ...

, and

narcolepsy Narcolepsy is a chronic neurological disorder that impairs the ability to regulate sleep–wake cycles, and specifically impacts REM (rapid eye movement) sleep. The symptoms of narcolepsy include excessive daytime sleepiness (EDS), sleep-r ...

. It has largely been withdrawn from clinical use following problems with

abuse Abuse is the act of improper usage or treatment of a person or thing, often to unfairly or improperly gain benefit. Abuse can come in many forms, such as: physical or verbal maltreatment, injury, assault, violation, rape, unjust practices, ...

. The drug is a

prodrug A prodrug is a pharmacologically inactive medication or compound that, after intake, is metabolized (i.e., converted within the body) into a pharmacologically active drug. Instead of administering a drug directly, a corresponding prodrug can be ...

Stereochemistry

Amfetaminil is a molecule with two stereogenic centers. Thus, four different stereoisomers exist: Amphetaminil Structural Formulae of four Stereoisomers

Amphetaminil Structural Formulae of four Stereoisomers

* (''R'')-2- ''R'')-1-Phenylpropan-2-ylamino2-phenylacetonitrile ( CAS number 478392-08-4) * (''S'')-2- ''S'')-1-Phenylpropan-2-ylamino2-phenylacetonitrile (CAS number 478392-12-0) * (''R'')-2- ''S'')-1-Phenylpropan-2-ylamino2-phenylacetonitrile (CAS number 478392-10-8) * (''S'')-2- ''R'')-1-Phenylpropan-2-ylamino2-phenylacetonitrile (CAS number 478392-14-2)

Synthesis

Schiff base formation between amphetamine (1) and benzaldehyde (2) gives benzalamphetamine 980-02-1(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 Sydnones are mesoionic heterocyclic chemical compounds possessing a C5-oxygenated 1,2,3-oxadiazole core, named after the city of Sydney, Australia. Like other mesoionic compounds they are dipolar, possessing both positive and negative charges wh ...

then occurs to giv
CID:88166659
(6). Feprosidnine is sans the phenyl group.

References

{{Phenethylamines Nitriles Norepinephrine-dopamine releasing agents Prodrugs Substituted amphetamines Wakefulness-promoting agents World Anti-Doping Agency prohibited substances