Amfetaminil

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Amphetaminil
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Amfetaminil
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
  • 2-Phenyl-2-(1-phenylpropan-2-ylamino)acetonitrile
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 checkY
  • Key:NFHVTCJKAHYEQN-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Amfetaminil (also known as amphetaminil, N-cyanobenzylamphetamine,

abuse.[6] The drug is a prodrug to amphetamine.[7][8]

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

Synthesis:[9][10][11][12][13]

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

  1. .
  2. .
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  4. .
  5. ^ Schlesser JL (1991). Drugs Available Abroad - A Guide to Therapeutic Drugs Approved Outside the US. Detroit: MEDEX Books.
  6. PMID 1005549
    .
  7. .
  8. .
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  10. .
  11. .
  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.