Amfetaminil

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Amfetaminil
Amphetaminil.svg
Amfetaminil.png
Clinical data
Trade names Aponeuron
Other namesAmphetaminil; AN-1; N-Cyanobenzylamphetamine; N-(α′-Cyanobenzyl)amphetamine
Routes of
administration 		Oral
Drug class Stimulant; Appetite suppressant; Norepinephrine–dopamine releasing agent
ATC code
  • none
Legal status
Legal status
Identifiers
  • 2-Phenyl-2-(1-phenylpropan-2-ylamino)acetonitrile
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.037.767 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C17H18N2
Molar mass 250.345 g·mol−1
3D model (JSmol)
  • N#CC(NC(C)Cc1ccccc1)c2ccccc2
  • 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 Yes check.svgY
  • Key:NFHVTCJKAHYEQN-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

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 [5] It has largely been withdrawn from clinical use following problems with abuse.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]

Contents

Chemistry

Stereochemistry

Amfetaminil is a molecule with two stereogenic centers. Thus, four different stereoisomers exist:

Amphetaminil Structural Formulae of four Stereoisomers.png

Synthesis

Synthesis: Amphetaminil synthesis.svg
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.

See also

References

  1. ↑ Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 13–. ISBN   978-94-011-4439-1.
  2. ↑ Harris LS (June 1986). "The stimulants and hallucinogens under consideration: a brief overview of their chemistry and pharmacology". Drug and Alcohol Dependence. 17 (2–3): 107–18. doi:10.1016/0376-8716(86)90002-5. PMID   2874966.
  3. ↑ Meyer-Probst B, Vehreschild T (August 1976). "[Influencing the lack of concentration in hyperkinetic school children with Aponeuron]". Psychiatrie, Neurologie, und Medizinische Psychologie (in German). 28 (8): 491–9. PMID   1005547.
  4. ↑ Paclt I, Florian J, Brunclíková J, Růzicková I (May 1996). "[Effect of Aponeuron in the treatment of children with hyperkinetic syndrome]". Ceska a Slovenska Psychiatrie (in Czech). 92 (Suppl 1): 41–57. PMID   8768943.
  5. ↑ Schlesser JL (1991). Drugs Available Abroad - A Guide to Therapeutic Drugs Approved Outside the US. Detroit: MEDEX Books.
  6. ↑ Winter E (September 1976). "[Drug abuse and dependence of the amphetamine type with special regard to Amphetaminil (Aponeuron(R))]". Psychiatrie, Neurologie, und Medizinische Psychologie (in German). 28 (9): 513–25. PMID   1005549.
  7. ↑ Dasgupta A (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.
  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. pp. 118–. ISBN   978-1-934863-59-6.
  9. ↑ Yashunskii VG, Gorkin VZ, Mashkovskii MD, Altshuler RA, Veryovkina IV, Kholodov LE (October 1971). "Synthesis and pharmacological effects of some alkyl-, aryl-, and aralkylsydnonimines". Journal of Medicinal Chemistry. 14 (10): 1013–5. doi:10.1021/jm00292a042. PMID   5165569.
  10. ↑ Klosa J (August 1975). "[The stability of amphetaminil. Syntheses with amphetaminil (author's transl)]". Arzneimittel-Forschung (in German). 25 (8): 1252–8. PMID   1242355.
  11. ↑ Klosa J (1975). "[On the crystallisation of amphetaminil base into its hydrochloride salt (author's transl)]". Arzneimittel-Forschung (in German). 25 (12): 1863–4. PMID   1243655.
  12. ↑ Beyer KH, Strassner W, Klinge D. "Amphetaminil [α-(1-benzylethylamino)-α-phenylacetonitrile]". Deutsche Apotheker Zeitung. 111 (19): 677–680.
  13. ↑ Kholodov LE (1967). "Sydnones and sydnonimines. XXXV. Salts and exocyclic derivatives of some sydnonimines". Zhurnal Organicheskoi Khimii. 3 (8): 1513–1518.
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