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CompTox Dashboard ( EPA) | |
ECHA InfoCard | 100.037.767 |
Chemical and physical data | |
Formula | C17H18N2 |
Molar mass | 250.345 g·mol−1 |
3D model ( JSmol) | |
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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 [5] It has largely been withdrawn from clinical use following problems with abuse.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 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 a Sydnone then occurs to give CID:88166659 (6). Feprosidnine is sans the phenyl group.
![]() | |
![]() | |
Clinical data | |
---|---|
ATC code |
|
Legal status | |
Legal status |
|
Identifiers | |
| |
CAS Number | |
PubChem CID | |
ChemSpider | |
UNII | |
KEGG | |
ChEMBL | |
CompTox Dashboard ( EPA) | |
ECHA InfoCard | 100.037.767 |
Chemical and physical data | |
Formula | C17H18N2 |
Molar mass | 250.345 g·mol−1 |
3D model ( JSmol) | |
| |
| |
![]() ![]() |
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 [5] It has largely been withdrawn from clinical use following problems with abuse.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 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 a Sydnone then occurs to give CID:88166659 (6). Feprosidnine is sans the phenyl group.