Aminorex

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Aminorex
200px
Systematic (IUPAC) name
(RS)-5-phenyl-4,5-dihydro-1,3-oxazol-2-amine
Legal status
Legal status
Identifiers
CAS Number 2207-50-3
ATC code none
PubChem CID 16630
ChemSpider 15767
Chemical data
Formula C9H10N2O
Molar mass 162.19[[Script error: No such module "String".]]
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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]

History

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 It was introduced as a prescription appetite suppressant in Germany, Switzerland and Austria in 1965, but was withdrawn in 1972 after it was found to cause pulmonary hypertension in approximately 0.2% of patients, and was linked to a number of deaths.[2]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

File:Aminorex rxn mech.gif

See also

References

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ru:Аминорекс
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