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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.

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introduced as a prescription appetite suppresant in Germanymarker, Switzerlandmarker and Austriamarker in 1965, but was withdrawn in 1972 after it was found to cause pulmonary hypertension in approximately 0.2% of patients, and was linked to a number of deaths.

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). A similar synthesis has been also published.



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