Aminorex

Source: Wikipedia, the free encyclopedia.
Aminorex
Skeletal formula
Ball-and-stick model of aminorex
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
  • (RS)-5-Phenyl-4,5-dihydro-1,3-oxazol-2-amine
JSmol)
ChiralityRacemic mixture
  • NC1=NCC(C2=CC=CC=C2)O1
  • InChI=1S/C9H10N2O/c10-9-11-6-8(12-9)7-4-2-1-3-5-7/h1-5,8H,6H2,(H2,10,11) checkY
  • Key:SYAKTDIEAPMBAL-UHFFFAOYSA-N checkY
  (verify)

Aminorex (Menocil, Apiquel, aminoxaphen, aminoxafen, McN-742) is a weight loss (anorectic) stimulant drug. It was withdrawn from the market after it was found to cause pulmonary hypertension.[2] In the U.S., it is an illegal Schedule I drug, meaning it has high abuse potential, no accepted medical use, and a poor safety profile.

Aminorex, in the 2-amino-5-aryl oxazoline class, was developed by

cutting agent of illicitly produced cocaine.[5][6]

History

It was discovered in 1962 by Edward John Hurlburt,[7] and was quickly found in 1963 to have an anorectic effect in rats. It was introduced as a prescription appetite suppressant in Germany, Switzerland and Austria in 1965, but was withdrawn in 1972 after it was found to cause pulmonary hypertension in approximately 0.2% of patients, and was linked to a number of deaths.[4][8]

Synthesis

The synthesis was first reported in a

structure-activity relationship
study of 2-amino-5-aryl-2-oxazolines, where aminorex was found to be approximately 2.5 times more potent than D-amphetamine sulfate in inducing anorexia in rats, and was also reported to have CNS stimulant effects.

The

racemic synthesis involves addition/cyclization reaction of 2-amino-1-phenylethanol with cyanogen bromide.[9] A similar synthesis has been also published.[10] In a search for a cheaper synthetic route, a German team developed an alternative route[11]
which, by using chiral styrene oxide, allows an enantiopure product.

See also

References

  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. PMID 11083709. Archived from the original
    on 2013-01-12.
  3. ^ US 3161650, "2-Amino-5-Aryloxazoline Products" 
  4. ^
    PMID 9884392
    .
  5. PMID 19298880
    .
  6. PMID 21531521
    .
  7. ^ US 3115494, "2-amino-5, 6-dihydro-4ii-1, 3-oxazines and a process for their preparation" 
  8. PMID 12788841
    .
  9. PMID 14185981
    .
  10. PMID 14698148
    .
  11. ^ DE Patent 2101424 2-amino-5-phenyl-2-oxazoline preparation
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