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1 : 1 mixture (racemate)
Systematic (IUPAC) name
(RS)-5-phenyl-4,5-dihydro-1,3-oxazol-2-amine
Identifiers
CAS number 2207-50-3
ATC code none
PubChem 16630
ChemSpider 15767
Chemical data
Formula C9H10N2O 
Mol. mass 162.19
SMILES eMolecules & PubChem
Therapeutic considerations
Pregnancy cat.  ?
Legal status Schedule III (CA) Schedule I (US)

Aminorex (Menocil, Apiquel, aminoxaphen, aminoxafen, McN-742) is an anorectic stimulant drug of the 2-amino-5-aryl oxazoline class. It is closely related to 4-methylaminorex. Aminorex has been shown to have locomotor stimulant effects, lying midway between dextroamphetamine and methamphetamine. It has been associated with pulmonary hypertension.[1]

Contents

History

It was discovered in 1961 by McNeil Laboratories (US patent 3115494), and was quickly found in 1962 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 It was introduced as a prescription appetite suppressant in Germany, Switzerland and Austria in 1965, but was withdrawn in 1972 after it was found to cause pulmonary hypertension in approximately 0.2% of patients, and was linked to a number of deaths.[2]

Synthesis

The synthesis was first reported in a structure-activity relationshipstudy 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. This racemic synthesis involved an addition/cyclization reaction of 2-amino-1-phenylethanol with cyanogen bromide (mechanism shown below).[3] A similar synthesis has been also published.[4]

Aminorex rxn mech.gif

See also

References

  1. ^ Gaine SP, Rubin LJ, Kmetzo JJ, Palevsky HI, Traill TA (November 2000). "Recreational use of aminorex and pulmonary hypertension". Chest 118 (5): 1496–7. PMID 11083709. http://www.chestjournal.org/cgi/pmidlookup?view=long&pmid=11083709. 
  2. ^ Fishman AP. (Jan 1991). "Aminorex to fen/phen - An epidemic foretold". Circulation (1): 156–161. ISSN 0009-7322. PMID 9884392. 
  3. ^ Poos GI, Carson JR, Rosenau JD, Roszowski AP, Kelley NM, McGowin J. (May 1963). "2-Amino-5-aryl-2-oxazolines. Potent New Anorectic Agents.". J. Med. Chem (3): 266–272. doi:10.1021/jm00339a011. PMID 14185981. 
  4. ^ Ueda S, Terauchi H, Yano A, Ido M, Matsumoto M, Kawasaki M. (Jan 2004). "4,5-Disubstituted-1,3-oxazolidin-2-imine derivatives: a new class of orally bioavailable nitric oxide synthase inhibitor.". Bioorg. Med. Chem. Lett. (2): 313–316. doi:doi:10.1016/j.bmcl.2003.11.010. PMID 14698148. 







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