Amfetaminil

Chemistry

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

References

1. (6 December 2012). "Concise Dictionary of Pharmacological Agents: Properties and Synonyms". Springer Science & Business Media.
2. (June 1986). "The stimulants and hallucinogens under consideration: a brief overview of their chemistry and pharmacology". Drug and Alcohol Dependence.
3. (August 1976). "[Influencing the lack of concentration in hyperkinetic school children with Aponeuron]". Psychiatrie, Neurologie, und Medizinische Psychologie.
4. (May 1996). "[Effect of Aponeuron in the treatment of children with hyperkinetic syndrome]". Ceska a Slovenska Psychiatrie.
5. (1991). "Drugs Available Abroad - A Guide to Therapeutic Drugs Approved Outside the US.". MEDEX Books.
6. (September 1976). "[Drug abuse and dependence of the amphetamine type with special regard to Amphetaminil (Aponeuron(R))]". Psychiatrie, Neurologie, und Medizinische Psychologie.
7. Dasgupta, Amitava. (2 July 2012). "Resolving Erroneous Reports in Toxicology and Therapeutic Drug Monitoring: A Comprehensive Guide". John Wiley & Sons.
8. 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.
9. (October 1971). "Synthesis and pharmacological effects of some alkyl-, aryl-, and aralkylsydnonimines". Journal of Medicinal Chemistry.
10. (August 1975). "[The stability of amphetaminil. Syntheses with amphetaminil (author's transl)]". Arzneimittel-Forschung.
11. (1975). "[On the crystallisation of amphetaminil base into its hydrochloride salt (author's transl)]". Arzneimittel-Forschung.
12. "Amphetaminil [α-(1-benzylethylamino)-α-phenylacetonitrile]". Deutsche Apotheker Zeitung.
13. (1967). "Sydnones and sydnonimines. XXXV. Salts and exocyclic derivatives of some sydnonimines.". Zhurnal Organicheskoi Khimii.