Aminorex
Encyclopedia
Aminorex is an anorectic
stimulant
drug
of the 2-amino
-5-aryl
oxazoline
class developed by a team at McNeil in 1962. It is closely related to 4-methylaminorex. Aminorex has been shown to have locomotor stimulant effects, lying midway between dextroamphetamine
and methamphetamine
. Aminorex effects have been attributed to the release of catecholamines. The drug has been retired from the market after it was found to result in pulmonary hypertension
.
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in 1965, but was withdrawn in 1972 after it was found to cause pulmonary hypertension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.
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. 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.
Anorectic
An anorectic or anorexic , also known as anorexigenic or appetite suppressant, is a dietary supplement and/or drug which reduces appetite, food consumption, and as a result, causes weight loss to occur.-List of anorectics:Numerous pharmaceutical compounds are marketed as appetite suppressants.The...
stimulant
Stimulant
Stimulants are psychoactive drugs which induce temporary improvements in either mental or physical function or both. Examples of these kinds of effects may include enhanced alertness, wakefulness, and locomotion, among others...
drug
Drug
A drug, broadly speaking, is any substance that, when absorbed into the body of a living organism, alters normal bodily function. There is no single, precise definition, as there are different meanings in drug control law, government regulations, medicine, and colloquial usage.In pharmacology, a...
of the 2-amino
Amine
Amines are organic compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines,...
-5-aryl
Aryl
In the context of organic molecules, aryl refers to any functional group or substituent derived from an aromatic ring, be it phenyl, naphthyl, thienyl, indolyl, etc....
oxazoline
Oxazoline
Oxazoline is both the five-membered ring heterocyclic chemical compound with the formula C3H5NO and the class of compounds containing this ring.- See also :* Desoxazoline * Oxazole* Oxazolidine* Oxazolidinedione...
class developed by a team at McNeil in 1962. It is closely related to 4-methylaminorex. Aminorex has been shown to have locomotor stimulant effects, lying midway between dextroamphetamine
Dextroamphetamine
Dextroamphetamine is a psychostimulant drug which is known to produce increased wakefulness and focus as well as decreased fatigue and decreased appetite....
and methamphetamine
Methamphetamine
Methamphetamine is a psychostimulant of the phenethylamine and amphetamine class of psychoactive drugs...
. Aminorex effects have been attributed to the release of catecholamines. The drug has been retired from the market after it was found to result in pulmonary hypertension
Pulmonary hypertension
In medicine, pulmonary hypertension is an increase in blood pressure in the pulmonary artery, pulmonary vein, or pulmonary capillaries, together known as the lung vasculature, leading to shortness of breath, dizziness, fainting, and other symptoms, all of which are exacerbated by exertion...
.
History
It was discovered in 1962 by Edward John Hurlburt , and was quickly found in 1963 to have an anorecticAnorectic
An anorectic or anorexic , also known as anorexigenic or appetite suppressant, is a dietary supplement and/or drug which reduces appetite, food consumption, and as a result, causes weight loss to occur.-List of anorectics:Numerous pharmaceutical compounds are marketed as appetite suppressants.The...
effect in rats
RATS
RATS may refer to:* RATS , Regression Analysis of Time Series, a statistical package* Rough Auditing Tool for Security, a computer program...
. It was introduced as a prescription
Prescription drug
A prescription medication is a licensed medicine that is regulated by legislation to require a medical prescription before it can be obtained. The term is used to distinguish it from over-the-counter drugs which can be obtained without a prescription...
appetite suppressant in Germany
Germany
Germany , officially the Federal Republic of Germany , is a federal parliamentary republic in Europe. The country consists of 16 states while the capital and largest city is Berlin. Germany covers an area of 357,021 km2 and has a largely temperate seasonal climate...
, Switzerland
Switzerland
Switzerland name of one of the Swiss cantons. ; ; ; or ), in its full name the Swiss Confederation , is a federal republic consisting of 26 cantons, with Bern as the seat of the federal authorities. The country is situated in Western Europe,Or Central Europe depending on the definition....
and Austria
Austria
Austria , officially the Republic of Austria , is a landlocked country of roughly 8.4 million people in Central Europe. It is bordered by the Czech Republic and Germany to the north, Slovakia and Hungary to the east, Slovenia and Italy to the south, and Switzerland and Liechtenstein to the...
in 1965, but was withdrawn in 1972 after it was found to cause pulmonary hypertension
Pulmonary hypertension
In medicine, pulmonary hypertension is an increase in blood pressure in the pulmonary artery, pulmonary vein, or pulmonary capillaries, together known as the lung vasculature, leading to shortness of breath, dizziness, fainting, and other symptoms, all of which are exacerbated by exertion...
in approximately 0.2% of patients, and was linked to a number of deaths.
Synthesis
The synthesis was first reported in a structure-activity relationshipStructure-activity relationship
The structure–activity relationship is the relationship between the chemical or 3D structure of a molecule and its biological activity. The analysis of SAR enables the determination of the chemical groups responsible for evoking a target biological effect in the organism...
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. This racemic
Racemic
In chemistry, a racemic mixture, or racemate , is one that has equal amounts of left- and right-handed enantiomers of a chiral molecule. The first known racemic mixture was "racemic acid", which Louis Pasteur found to be a mixture of the two enantiomeric isomers of tartaric acid.- Nomenclature :A...
synthesis involved an addition/cyclization reaction of 2-amino-1-phenylethanol with cyanogen bromide
Cyanogen bromide
Cyanogen bromide is a pseudohalogen compound with the formula CNBr. It is a colorless solid that is widely used to modify biopolymers, fragment proteins and peptides, and synthesize other compounds.-Synthesis, basic properties, and structure:...
(mechanism shown below). A similar synthesis has been also published.
See also
- 4-Methylaminorex
- ClominorexClominorexClominorex is a centrally acting sympathomimetic which is related to other drugs such as aminorex and pemoline. It was developed as an appetite suppressant by McNeil Laboratories in the 1950s.-See also:* 4-Methylaminorex* Aminorex* Cyclazodone...
- CyclazodoneCyclazodoneCyclazodone is a centrally acting stimulant drug developed by American Cyanamid Company in the 1960s. The drug is related to other drugs such as pemoline and 4-methylaminorex. It is a banned stimulant under the World Anti-Doping Agency prohibited list....
- FenozoloneFenozoloneFenozolone was developed by Laboratoires Dausse in the 1960s and is a psychoactive drug and stimulant related to pemoline and 4-methylaminorex which acts as a norepinephrine-dopamine releasing agent .-See also:* 4-Methylaminorex...
- FluminorexFluminorexFluminorex is a centrally acting sympathomimetic which is related to other drugs such as aminorex and pemoline. It was developed as an appetite suppressant by McNeil Laboratories in the 1950s.-See also:* 4-Methylaminorex* Aminorex* Clominorex...
- PemolinePemolinePemoline was first synthesized in 1913 but it's activity was not discovered until the 1930s. Under the names it was used as a medication used to treat attention-deficit hyperactivity disorder and narcolepsy. Under the Convention on Psychotropic Substances, it is a Schedule IV drug...
- ThozalinoneThozalinoneThozalinone is a psychostimulant that has been used as an antidepressant in Europe. It has also been trialed as an anorectic. Thozalinone likely acts via inducing the release of norepinephrine and dopamine as with its analogues pemoline and aminorex.- References :...