Amfetaminil

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Amfetaminil
Amphetaminil Structural Formulae.png
Amfetaminil.png
Clinical data
ATC code
  • none
Legal status
Legal status
  • DE: Anlage II (Authorized trade only, not prescriptible)
Identifiers
CAS Number
PubChem CID
ChemSpider
KEGG
ChEMBL
ECHA InfoCard100.037.767 Edit this at Wikidata
Chemical and physical data
FormulaC17H18N2
Molar mass250.338 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was developed in the 1970s and used for the treatment of obesity,[2] ADHD,[3][4] and narcolepsy.[5] It has largely been withdrawn from clinical use following problems with abuse.[6] The drug is a prodrug to amphetamine.[7][8]

Stereochemistry[edit]

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

Amphetaminil Structural Formulae of four Stereoisomers.png

  • (R)-2-[(R)-1-Phenylpropan-2-ylamino]-2-phenylacetonitrile (CAS-Nr. 478392-08-4)
  • (S)-2-[(S)-1-Phenylpropan-2-ylamino]-2-phenylacetonitrile (CAS-Nr. 478392-12-0)
  • (R)-2-[(S)-1-Phenylpropan-2-ylamino]-2-phenylacetonitrile (CAS-Nr. 478392-10-4)
  • (S)-2-[(R)-1-Phenylpropan-2-ylamino]-2-phenylacetonitrile (CAS-Nr. 478392-14-2)

References[edit]

  1. ^ I.K. Morton; Judith M. Hall (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. The stimulants and hallucinogens under consideration: a brief overview of their chemistry and pharmacology. Drug and Alcohol Dependence 1986; 17:107.
  3. ^ Meyer-Probst B, Vehreschild T. Influencing the lack of concentration in hyperkinetic schoolchildren with Aponeuron. Psychiatrie, Neurologie und Medizinische Psychologie (Leipz) 1976; 28:491.
  4. ^ Paclt I, Florian J, Brunclikova J, Ruzickova I. Effect of Aponeuron in the treatment of children with hyperkinetic syndrome. (Czech). Ceska a Slovenska Psychiatrie. 1996 May;92 Suppl 1:41-57.
  5. ^ Schlesser JL. Drugs Available Abroad - A Guide to Therapeutic Drugs Approved Outside the US. MEDEX Books, Detroit, 1991.
  6. ^ Winter E. Drug abuse and dependence of the amphetamine type with special regard to Amphetaminil (Aponeuron(R)). (German). Psychiatrie, Neurologie und Medizinische Psychologie (Leipzig). 1976 Sep;28(9):513-25.
  7. ^ Amitava Dasgupta (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.