Chemistry:Amfetaminil
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Short description: Amphetamine-derived stimulant drug
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| Formula | C17H18N2 |
| Molar mass | 250.345 g·mol−1 |
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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was developed in the 1970s and used for the treatment of obesity,[2] ADHD,[3][4] and narcolepsy.[5] It has largely been withdrawn from clinical use following problems with abuse.[6] The drug is a prodrug to amphetamine.[7][8]
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
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
- ↑ Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. 6 December 2012. pp. 13–. ISBN 978-94-011-4439-1. https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA13.
- ↑ "The stimulants and hallucinogens under consideration: a brief overview of their chemistry and pharmacology". Drug and Alcohol Dependence 17 (2–3): 107–18. June 1986. doi:10.1016/0376-8716(86)90002-5. PMID 2874966.
- ↑ "[Influencing the lack of concentration in hyperkinetic school children with Aponeuron]" (in de). Psychiatrie, Neurologie, und Medizinische Psychologie 28 (8): 491–9. August 1976. PMID 1005547.
- ↑ "[Effect of Aponeuron in the treatment of children with hyperkinetic syndrome]" (in cs). Ceska a Slovenska Psychiatrie 92 (Suppl 1): 41–57. May 1996. PMID 8768943.
- ↑ Drugs Available Abroad - A Guide to Therapeutic Drugs Approved Outside the US.. Detroit: MEDEX Books. 1991.
- ↑ "[Drug abuse and dependence of the amphetamine type with special regard to Amphetaminil (Aponeuron(R))]" (in de). Psychiatrie, Neurologie, und Medizinische Psychologie 28 (9): 513–25. September 1976. PMID 1005549.
- ↑ Dasgupta, Amitava (2 July 2012). Resolving Erroneous Reports in Toxicology and Therapeutic Drug Monitoring: A Comprehensive Guide. John Wiley & Sons. pp. 96–. ISBN 978-1-118-34785-0. https://books.google.com/books?id=0mD9kKcUU8UC&pg=PT96.
- ↑ AHC Media, LLC (17 March 2014). Pediatric Trauma Care II: A clinical reference for physicians and nurses caring for the acutely injured child. AHC Media, LLC. pp. 118–. ISBN 978-1-934863-59-6. https://books.google.com/books?id=9fucAwAAQBAJ&pg=PA118.
- ↑ "Synthesis and pharmacological effects of some alkyl-, aryl-, and aralkylsydnonimines". Journal of Medicinal Chemistry 14 (10): 1013–5. October 1971. doi:10.1021/jm00292a042. PMID 5165569.
- ↑ "[The stability of amphetaminil. Syntheses with amphetaminil (author's transl)]" (in German). Arzneimittel-Forschung 25 (8): 1252–8. August 1975. PMID 1242355.
- ↑ "[On the crystallisation of amphetaminil base into its hydrochloride salt (author's transl)]" (in German). Arzneimittel-Forschung 25 (12): 1863–4. 1975. PMID 1243655.
- ↑ "Amphetaminil [α-(1-benzylethylamino)-α-phenylacetonitrile]". Deutsche Apotheker Zeitung 111 (19): 677–680.
- ↑ "Sydnones and sydnonimines. XXXV. Salts and exocyclic derivatives of some sydnonimines.". Zhurnal Organicheskoi Khimii 3 (8): 1513–1518. 1967.
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