Aminorex (Menocil, Apiquel, aminoxaphen, aminoxafen, McN-742) is a weight loss (

anorectic An anorectic or anorexic is a drug which reduces appetite, resulting in lower food consumption, leading to weight loss. By contrast, an appetite stimulant is referred to as orexigenic. The term is (from the Greek ''ἀν-'' (an-) = "without" a ...

) stimulant drug. It was withdrawn from the market after it was found to cause pulmonary hypertension. 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

McNeil Laboratories McNeil Consumer Healthcare is an American medicals products company belonging to the Johnson & Johnson healthcare products group. It primarily sells fast-moving consumer goods such as over-the-counter drugs. History The company was founded on M ...

in 1962. It is closely related to

4-methylaminorex 4-Methylaminorex (4-MAR, 4-MAX) is a stimulant drug of the 2-amino-5-aryloxazoline class that was first synthesized in 1960 by McNeil Laboratories. It is also known by its street name "U4Euh" ("Euphoria"). It is banned in many countries as a s ...

. Aminorex has been shown to have locomotor stimulant effects, lying midway between

dextroamphetamine Dextroamphetamine is a central nervous system (CNS) stimulant and an amphetamine enantiomer that is prescribed for the treatment of attention deficit hyperactivity disorder (ADHD) and narcolepsy. It is also used as an athletic performance an ...

and methamphetamine. Aminorex effects have been attributed to the release of catecholamines. It can be produced as a metabolite of the worming medication

levamisole Levamisole, sold under the brand name Ergamisol among others, is a medication used to treat parasitic worm infections, specifically ascariasis and hookworm infections. It is taken by mouth. Side effects may include abdominal pain, vomiting, ...

, which is sometimes used as a cutting agent of illicitly produced

cocaine Cocaine (from , from , ultimately from Quechua: ''kúka'') is a central nervous system (CNS) stimulant mainly used recreationally for its euphoric effects. It is primarily obtained from the leaves of two Coca species native to South Ameri ...

History

It was discovered in 1962 by Edward John Hurlburt, and was quickly found in 1963 to have an

effect in rats. It was introduced as a prescription appetite suppressant in

Germany Germany,, officially the Federal Republic of Germany, is a country in Central Europe. It is the second most populous country in Europe after Russia, and the most populous member state of the European Union. Germany is situated betwe ...

, Switzerland and

Austria Austria, , bar, Östareich officially the Republic of Austria, is a country in the southern part of Central Europe, lying in the Eastern Alps. It is a federation of nine states, one of which is the capital, Vienna, the most populous ...

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 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 In chemistry, a racemic mixture, or racemate (), is one that has equal amounts of left- and right-handed enantiomers of a chiral molecule or salt. Racemic mixtures are rare in nature, but many compounds are produced industrially as racemates. ...

synthesis involves addition/cyclization reaction of 2-amino-1-phenylethanol with

cyanogen bromide Cyanogen bromide is the inorganic compound with the formula (CN)Br or BrCN. It is a colorless solid that is widely used to modify biopolymers, fragment proteins and peptides (cuts the C-terminus of methionine), and synthesize other compounds. ...

. A similar synthesis has been also published. In a search for a cheaper synthetic route, a German team developed an alternative routeDE Patent 2101424 2-amino-5-phenyl-2-oxazoline preparation which, by using chiral styrene oxide, allows an enantiopure product.

References

{{Monoamine releasing agents 5-HT2B agonists Anorectics Stimulants Serotonin receptor agonists Norepinephrine-dopamine releasing agents Withdrawn drugs Aminorexes

History

Synthesis

See also

References