Amfetaminil
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Amphetaminil
)Amphetamine-derived stimulant drug
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Amfetaminil (also known as amphetaminil, N-cyanobenzylamphetamine,
Stereochemistry
Amfetaminil is a molecule with two stereogenic centers. Thus, four different stereoisomers exist:
- (R)-2-[(R)-1-Phenylpropan-2-ylamino]-2-phenylacetonitrile (CAS number478392-08-4)
- (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.
References
- ISBN 978-94-011-4439-1.
- PMID 2874966.
- PMID 1005547.
- PMID 8768943.
- ^ Schlesser JL (1991). Drugs Available Abroad - A Guide to Therapeutic Drugs Approved Outside the US. Detroit: MEDEX Books.
- PMID 1005549.
- ISBN 978-1-118-34785-0.
- ISBN 978-1-934863-59-6.
- PMID 5165569.
- PMID 1242355.
- PMID 1243655.
- ^ Beyer KH, Strassner W, Klinge D. "Amphetaminil [α-(1-benzylethylamino)-α-phenylacetonitrile]". Deutsche Apotheker Zeitung. 111 (19): 677–680.
- ^ Kholodov LE (1967). "Sydnones and sydnonimines. XXXV. Salts and exocyclic derivatives of some sydnonimines". Zhurnal Organicheskoi Khimii. 3 (8): 1513–1518.
antagonists
receptor agonists
- Beloranib§
- Bimagrumab§
- Desiccated thyroid‡
- Metformin
- Metreleptin
- Naltrexone
- Setmelanotide
- Topiramate
- ZGN-1061
- Zonisamide
- Water
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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Amphetamines |
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Cathinones |
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Catecholamines (and close relatives) |
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