Amphetaminil

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Amphetaminil
Amphetaminil Structural Formulae.png
Systematic (IUPAC) name
2-phenyl-2-(1-phenylpropan-2-ylamino)acetonitrile
Clinical data
Legal status
Identifiers
CAS Number 17590-01-1 YesY
ATC code none
PubChem CID: 28615
ChemSpider 26613 YesY
KEGG D07446 YesY
ChEMBL CHEMBL2104064 N
Chemical data
Formula C17H18N2
Molecular mass 250.338
  • 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 YesY
  • Key:NFHVTCJKAHYEQN-UHFFFAOYSA-N YesY
 NYesY (what is this?)  (verify)

Amphetaminil (brand name Aponeuron; former developmental code name AN-1), also known as N-cyanobenzylamphetamine,[1] 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was developed in the 1970s and used for the treatment of obesity,[2] ADHD,[3][4] and narcolepsy.[5] It has largely been withdrawn from clinical use following problems with abuse.[6] The drug is a prodrug to amphetamine.[7][8]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

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)

References

  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  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. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.


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