List of aminorex analogues

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This is a list of aminorex analogues. Aminorex itself is a stimulant drug with a 5-phenyl-2-amino-oxazoline structure. It was developed in the 1960s as an anorectic, [1] [2] [3] but withdrawn from sale after it was discovered that extended use produced pulmonary hypertension, often followed by heart failure, which resulted in a number of deaths. [4] A designer drug analogue 4-methylaminorex appeared on the illicit market in the late 1980s but did not attract significant popularity due to its steep dose-response curve and tendency to produce seizures. [5] [6] [7] [8] Pemoline , the 4-keto derivative of aminorex, had been discovered several years earlier, [9] and derivatives of this type appeared to be effective stimulants with comparatively low toxicity. [10] [11] Pemoline was sold for around 25 years as a therapy for ADHD and relief of fatigue, before being withdrawn from the market in 2005 because of rare but serious cases of liver failure. [12] [13] [14] [15] More recently in around 2014 another derivative 4,4'-dimethylaminorex started to be sold illicitly, but again swiftly lost popularity due to a spate of fatal overdose cases. [16] [17] [18] A number of related compounds are known, and new derivatives have continued to appear on the designer drug market. [19] [20] [21] [22] [23] [24]

Contents

List of substituted aminorex derivatives

StructureCommon nameChemical nameCAS number
Aminorex structure.svg Aminorex 5-phenyl-4,5-dihydro-1,3-oxazol-2-amine2207-50-3
Rexamino structure.png Rexamino4-phenyl-4,5-dihydro-1,3-oxazol-2-amine52883-35-9
4-fluoroaminorex structure.png 4'-Fluoroaminorex (4'-FAR)5-(4-fluorophenyl)-4,5-dihydro-1,3-oxazol-2-amine2967-77-3
Clominorex structure.svg Clominorex 5-(4-chlorophenyl)-4,5-dihydro-1,3-oxazol-2-amine3876-10-6
Fluminorex.svg Fluminorex 5-[4-(trifluoromethyl)phenyl]-4,5-dihydro-1,3-oxazol-2-amine720-76-3
MD-AR structure.png Methylenedioxyaminorex5-(3,4-methylenedioxyphenyl)-4,5-dihydro-1,3-oxazol-2-amine3865-98-3
2CB-AR structure.png 2C-B-aminorex (2C-B-AR)5-(2,5-dimethoxy-4-bromophenyl)-4,5-dihydro-1,3-oxazol-2-amine
NN-DMAR structure.png N,N-Dimethylaminorex (N,N-DMAR)N,N-dimethyl-5-phenyl-4,5-dihydro-1,3-oxazol-2-amine32968-41-5
Pemoline structure 2.svg Pemoline 2-amino-5-phenyl-1,3-oxazol-4(5H)-one2152-34-3
Thozalinone.svg Thozalinone 2-(dimethylamino)-5-phenyl-1,3-oxazol-4(5H)-one655-05-0
Fenozolone.svg Fenozolone 2-ethylamino-5-phenyl-1,3-oxazol-4-one15302-16-6
Cyclazodone structure.svg Cyclazodone 2-(cyclopropylamino)-5-phenyl-1,3-oxazol-4-one14461-91-7
N-methylcyclazodone structure.png N-Methylcyclazodone2-(cyclopropyl(methyl)amino)-5-phenyl-1,3-oxazol-4-one14461-92-8
Ephedroxane structure.png Ephedroxane [25] (4S,5R)-3,4-dimethyl-5-phenyl-1,3-oxazolidin-2-one16251-46-0
3-methylaminorex structure.png 3-Methylaminorex3-methyl-5-phenyl-2-oxazolidinimine75343-73-6
4-Methyl-Aminorex.svg 4-Methylaminorex (4-MAR)4-methyl-5-phenyl-4,5-dihydro-1,3-oxazol-2-amine3568-94-3
4EAR structure.png 4-Ethylaminorex (4-EAR)4-ethyl-5-phenyl-4,5-dihydro-1,3-oxazol-2-amine1364933-63-0
4-Isopropylaminorex structure.png 4-Isopropylaminorex4-isopropyl-5-phenyl-4,5-dihydro-1,3-oxazol-2-amine
4-Isobutylaminorex structure.png 4-Isobutylaminorex4-(2-methylpropyl)-5-phenyl-4,5-dihydro-1,3-oxazol-2-amine
4-Tertbutylaminorex structure.png 4-tert-butylaminorex4-(1,1-dimethylethyl)-5-phenyl-4,5-dihydro-1,3-oxazol-2-amine
4N-DMAR structure.png 4,N-Dimethylaminorex (4,N-DMAR)4,5-dihydro-N,4-dimethyl-5-phenyl-2-oxazolamine2207-49-0
34-DMAR structure.png 3,4-Dimethylaminorex (3,4-DMAR)3,4-dimethyl-5-phenyl-2-oxazolidinimine82485-31-2
4,4'-Dimethylaminorex.svg 4,4'-Dimethylaminorex (4,4'-DMAR)4-methyl-5-(4-methylphenyl)-4,5-dihydro-1,3-oxazol-2-amine1445569-01-6
2'-F-4MAR structure.png 2'-Fluoro-4-methylaminorex (2F-MAR)4-methyl-5-(2-fluorophenyl)-4,5-dihydro-1,3-oxazol-2-amine
3F-4MAR structure.png 3'-Fluoro-4-methylaminorex (3F-MAR)4-methyl-5-(3-fluorophenyl)-4,5-dihydro-1,3-oxazol-2-amine
4F-4MAR structure.png 4'-Fluoro-4-methylaminorex (4F-MAR)4-methyl-5-(4-fluorophenyl)-4,5-dihydro-1,3-oxazol-2-amine1364933-64-1
4C-MAR structure.png 4'-Chloro-4-methylaminorex (4C-MAR)4-methyl-5-(4-chlorophenyl)-4,5-dihydro-1,3-oxazol-2-amine
4'-Bromo-4-methylaminorex structure.png 4'-Bromo-4-methylaminorex (4B-MAR)4-methyl-5-(4-bromophenyl)-4,5-dihydro-1,3-oxazol-2-amine
4MEO-4MAR structure.png 4'-Methoxy-4-methylaminorex (4'-MeO-4-MAR)4-methyl-5-(4-methoxyphenyl)-4,5-dihydro-1,3-oxazol-2-amine1445570-65-9
345TM-4MAR structure.png 3',4',5'-Trimethoxy-4-methylaminorex (TM-4-MAR)4-methyl-5-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1,3-oxazol-2-amine1445571-92-5
MD4MAR structure.png 3',4'-Methylenedioxy-4-methylaminorex (MDMAR)4-methyl-5-(3,4-methylenedioyphenyl)-4,5-dihydro-1,3-oxazol-2-amine1445573-16-9

See also

Related Research Articles

<span class="mw-page-title-main">Pemoline</span> Stimulant, used in the treatment of ADHD

Pemoline, sold under the brand name Cylert among others, is a stimulant medication which has been used in the treatment of attention-deficit hyperactivity disorder (ADHD) and narcolepsy. It has been discontinued in most countries due to rare but serious problems with liver toxicity. The medication was taken by mouth.

<span class="mw-page-title-main">4-Methylaminorex</span> Group of stereoisomers

4-Methylaminorex 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 stimulant.

<span class="mw-page-title-main">Aminorex</span> Chemical compound

Aminorex is a weight loss (anorectic) 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.

<span class="mw-page-title-main">Chlorphentermine</span> Weight loss medication

Chlorphentermine is a serotonergic appetite suppressant of the amphetamine family. Developed in 1962, it is the 4-chloro derivative of the better known appetite suppressant phentermine, which is still in current use.

<span class="mw-page-title-main">Thozalinone</span> Chemical compound

Thozalinone (USAN) is a psychostimulant that has been used as an antidepressant in Europe. It has also been trialed as an anorectic. Thozalinone is described as a "dopaminergic stimulant", and likely acts via inducing the release of dopamine and to a minimal extent norepinephrine; similar to analogue pemoline, it is reportedly devoid of abuse potential unlike other dopaminergic psychostimulants.

<span class="mw-page-title-main">Fluminorex</span> Chemical compound

Fluminorex 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.

<span class="mw-page-title-main">Clominorex</span> Chemical compound

Clominorex 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.

<span class="mw-page-title-main">Cyclazodone</span> Chemical compound

Cyclazodone 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 thozalinone. It displayed a favorable therapeutic index and margin of safety in comparison to pemoline and other N-lower-alkyl-substituted pemoline derivatives. The patents concluded that cyclazodone possessed properties efficacious in reducing fatigue and as a potential anorectic. Structural congeners of pemoline have been described as "excitants with unique properties distinguishing them from the sympathomimetic amines" whilst displaying less stimulatory activity and toxicity compared to amphetamine.

<span class="mw-page-title-main">Monoamine releasing agent</span> Class of compounds

A monoamine releasing agent (MRA), or simply monoamine releaser, is a drug that induces the release of a monoamine neurotransmitter from the presynaptic neuron into the synapse, leading to an increase in the extracellular concentrations of the neurotransmitter. Many drugs induce their effects in the body and/or brain via the release of monoamine neurotransmitters, e.g., trace amines, many substituted amphetamines, and related compounds.

A dopamine releasing agent (DRA) is a type of drug which induces the release of dopamine in the body and/or brain. No selective and robust DRAs are currently known. On the other hand, many releasing agents of both dopamine and norepinephrine and of serotonin, norepinephrine, and dopamine are known. Serotonin–dopamine releasing agents (SDRAs), for instance 5-chloro-αMT, are much more rare and are not selective for dopamine release but have also been developed. Examples of major NDRAs include the psychostimulants amphetamine and methamphetamine, while an example of an SNDRA is the entactogen methylenedioxymethamphetamine (MDMA). These drugs are frequently used for recreational purposes and encountered as drugs of abuse. Selective DRAs, as well as NDRAs, have medical applications in the treatment of attention deficit hyperactivity disorder (ADHD).

<span class="mw-page-title-main">3-Fluoroamphetamine</span> Stimulant drug that acts as an amphetamine

3-Fluoroamphetamine is a stimulant drug from the amphetamine family which acts as a monoamine releaser with similar potency to methamphetamine but more selectivity for dopamine and norepinephrine release over serotonin. It is self-administered by mice to a similar extent to related drugs such as 4-fluoroamphetamine and 3-methylamphetamine.

<span class="mw-page-title-main">Substituted cathinone</span> Class of chemical compounds

Substituted cathinones, which include some stimulants and entactogens, are derivatives of cathinone. They feature a phenethylamine core with an alkyl group attached to the alpha carbon, and a ketone group attached to the beta carbon, along with additional substitutions. Cathinone occurs naturally in the plant khat whose leaves are chewed as a recreational drug.

<span class="mw-page-title-main">Substituted phenylmorpholine</span> Class of chemical compounds

Substituted phenylmorpholines, or substituted phenmetrazines alternatively, are chemical derivatives of phenylmorpholine or of the psychostimulant drug phenmetrazine. Most such compounds act as releasers of monoamine neurotransmitters, and have stimulant effects. Some also act as agonists at serotonin receptors, and compounds with an N-propyl substitution act as dopamine receptor agonists. A number of derivatives from this class have been investigated for medical applications, such as for use as anorectics or medications for the treatment of ADHD. Some compounds have also become subject to illicit use as designer drugs.

<span class="mw-page-title-main">2C-B-aminorex</span> Chemical compound

2C-B-aminorex (2C-B-AR) is a recreational designer drug with psychedelic effects. It is a substituted aminorex derivative which was first identified in Sweden in June 2019. Structurally, it is a hybrid of 4-bromo-2,5-dimethoxyphenethylamine (2C-B) and aminorex.

<span class="mw-page-title-main">4'-Fluoro-4-methylaminorex</span> Chemical compound

4'-Fluoro-4-methylaminorex is a recreational designer drug from the substituted aminorex family, with stimulant effects. It was first detected in Slovenia in 2018. It was made illegal in Italy in March 2020.

<span class="mw-page-title-main">MDMAR</span> Chemical compound

3',4'-Methylenedioxy-4-methylaminorex (MDMAR) is a recreational designer drug from the substituted aminorex family, with monoamine releasing effects.

<span class="mw-page-title-main">4C-MAR</span> Chemical compound

4'-Chloro-4-methylaminorex is a recreational designer drug from the substituted aminorex family, with stimulant effects. It has reportedly been sold since around 2021 and was first definitively identified in Austria in January 2022.

<span class="mw-page-title-main">2F-MAR</span> Chemical compound

2'-Fluoro-4-methylaminorex is a recreational designer drug from the substituted aminorex family, with stimulant effects, first reported in 2018.

<span class="mw-page-title-main">4B-MAR</span> Chemical compound

4'-Bromo-4-methylaminorex is a designer drug from the substituted aminorex family, first definitively identified in Austria in January 2022. Its pharmacological activity has not been reported, but it is believed to have stimulant effects.

<span class="mw-page-title-main">Substituted β-hydroxyamphetamine</span> Class of compounds based upon the β-hydroxyamphetamine structure

Substituted β-hydroxyamphetamines, also known as substituted phenylisopropanolamines, substituted phenylpropanolamines, substituted norephedrines, or substituted cathinols, are derivatives of β-hydroxyamphetamine with one or more chemical substituents. They are substituted phenethylamines, phenylethanolamines (β-hydroxyphenethylamines), and amphetamines (α-methylphenethylamines), and are closely related to but distinct from the substituted cathinones (β-ketoamphetamines). Examples of β-hydroxyamphetamines include the β-hydroxyamphetamine stereoisomers phenylpropanolamine and cathine and the stereospecific N-methylated β-hydroxyamphetamine derivatives ephedrine and pseudoephedrine, among many others.

References

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