Amfetaminil

Amfetaminil (also known as amphetaminil, N-cyanobenzylamphetamine,^[1] 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developed in the 1970s and used for the treatment of obesity,^[2] ADHD,^[3][4] and narcolepsy.^[5] It has largely been withdrawn from clinical use following problems with abuse.^[6] The drug is a prodrug to amphetamine.^[7][8]

Amfetaminil

Clinical data
ATC code	none
Legal status
Legal status	DE: Anlage II (Authorized trade only, not prescriptible) US: Schedule IV
Identifiers
IUPAC name 2-Phenyl-2-(1-phenylpropan-2-ylamino)acetonitrile
CAS Number	17590-01-1 Y
PubChem CID	28615
ChemSpider	26613 Y
UNII	0XU0V77JVE
KEGG	D07446 Y
ChEMBL	ChEMBL2104064 N
CompTox Dashboard (EPA)	DTXSID80864783
ECHA InfoCard	100.037.767
Chemical and physical data
Formula	C17H18N2
Molar mass	250.345 g·mol−1
3D model (JSmol)	Interactive image
SMILES N#CC(NC(C)Cc1ccccc1)c2ccccc2
InChI InChI=1S/C17H18N2/c1-14(12-15-8-4-2-5-9-15)19-17(13-18)16-10-6-3-7-11-16/h2-11,14,17,19H,12H2,1H3 Y Key:NFHVTCJKAHYEQN-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

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

Synthesis:^{[9][10][11][12][13]}

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.