Amphetaminil

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Amphetaminil
Amphetaminil Structural Formulae.png
Systematic (IUPAC) name
2-phenyl-2-(1-phenylpropanyl-2-amino)acetonitrile
Clinical data
Legal status
?
Identifiers
CAS number 17590-01-1
ATC code None
PubChem CID 28615
ChemSpider 26613 YesY
KEGG D07446 YesY
ChEMBL CHEMBL2104064
Chemical data
Formula C17H18N2 
Mol. mass 250.338
 YesY (what is this?)  (verify)

Amphetaminil (Aponeuron, AN-1) is a stimulant drug derived from amphetamine, which was developed in the 1970s and used for the treatment of obesity,[1] ADHD,[2][3] and narcolepsy.[4] It has largely been withdrawn from clinical use following problems with abuse.[5]

Stereochemistry[edit]

Amphetaminil 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)

Synthesis[edit]

It is synthesized by forming the Schiff's base of amphetamine with benzaldehyde, and then nucleophilic attack on the latter with cyanide anion.[6]

References[edit]

  1. ^ Harris LS. The stimulants and hallucinogens under consideration: a brief overview of their chemistry and pharmacology. Drug and Alcohol Dependence 1986; 17:107.
  2. ^ Meyer-Probst B, Vehreschild T. Influencing the lack of concentration in hyperkinetic schoolchildren with Aponeuron. Psychiatrie, Neurologie und Medizinische Psychologie (Leipz) 1976; 28:491.
  3. ^ 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.
  4. ^ Schlesser JL. Drugs Available Abroad - A Guide to Therapeutic Drugs Approved Outside the US. MEDEX Books, Detroit, 1991.
  5. ^ 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.
  6. ^ J. Klosa, DE 1112987  (1959); Chem. Abstr., 56: 3409d (1962).