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Aminorex
Aminorex, sold under the brand names Menocil and Apiquel among others, is a weight loss (anorectic) stimulant drug. It was withdrawn from the market after it was found to cause pulmonary hypertension (PPH). In the United States, aminorex is a Schedule I controlled substance.
Aminorex, in the 2-amino-5-aryloxazoline group, was developed by McNeil Laboratories in 1962. It is closely related to 4-methylaminorex (4-MAR). 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. It can be produced as a metabolite of the deworming medication levamisole, which is sometimes used as a cutting agent of illicitly produced cocaine.
Aminorex was formerly used as an appetite suppressant.
Aminorex is a serotonin–norepinephrine–dopamine releasing agent (SNDRA). Its EC50 values for induction of monoamine release are 26.4 nM for norepinephrine, 49.4 nM for dopamine, and 193 nM for serotonin. In addition to its monoamine-releasing activity, aminorex is a weak agonist of the serotonin 5-HT2 receptors, including of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors. Its EC50 values for activation of these receptors are 4,365 nM for 5-HT2A, 870 nM for 5-HT2B, and 525 nM for 5-HT2C.
Activation of serotonin 5-HT2B receptors by aminorex, either directly via agonism or indirectly via serotonin release, has been implicated in the development of pulmonary arterial hypertension and cardiac valvulopathy with the drug. However, its EC50 for serotonin 5-HT2B receptor activation is 33-fold higher than its EC50 value for induction of norepinephrine release and is almost 50-fold less potent than the serotonin 5-HT2B receptor agonism of dexnorfenfluramine. This seems to call into question the role of direct agonism of the serotonin 5-HT2B receptor in the toxicity of aminorex. Along similar lines, chlorphentermine, a related drug that has also been associated with such adverse effects, shows negligible direct serotonin 5-HT2B receptor agonistic activity. However, it is possible that metabolites of aminorex and chlorphentermine might be more potent in this action.
Aminorex does not appear to have been assessed at the trace amine-associated receptor 1 (TAAR1). However, several derivatives of aminorex, such as 4-methylaminorex (4-MAR) and 4,4'-dimethylaminorex (4,4'-DMAR), have been found to be inactive at the mouse and rat TAAR1. Many other monoamine releasing agents (MRAs), such as many amphetamines, are rodent and/or human TAAR1 agonists. Activation of the TAAR1 may auto-inhibit and thereby constrain the monoaminergic effects of these agents. Lack of TAAR1 agonism in the case of aminorex analogues might enhance their effects relative to MRAs possessing TAAR1 agonism.
Aminorex is a member of the 2-amino-5-phenyloxazoline group. It is structurally related to the substituted amphetamines like amphetamine and to the substituted phenylmorpholines like phenmetrazine.
A variety of derivatives and analogues of aminorex are known. These include 2'-fluoro-4-methylaminorex (2F-MAR), 2C-B-aminorex, 3',4'-methylenedioxy-4-methylaminorex (MDMAR), 4'-bromo-4-methylaminorex (4B-MAR), 4'-chloro-4-methylaminorex (4C-MAR), 4'-fluoro-4-methylaminorex (4F-MAR), 4-methylaminorex (4-MAR), 4,4'-dimethylaminorex (4,4'-DMAR), clominorex, cyclazodone, fenozolone, fluminorex, pemoline, and thozalinone, among others.
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Aminorex AI simulator
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Aminorex
Aminorex, sold under the brand names Menocil and Apiquel among others, is a weight loss (anorectic) stimulant drug. It was withdrawn from the market after it was found to cause pulmonary hypertension (PPH). In the United States, aminorex is a Schedule I controlled substance.
Aminorex, in the 2-amino-5-aryloxazoline group, was developed by McNeil Laboratories in 1962. It is closely related to 4-methylaminorex (4-MAR). 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. It can be produced as a metabolite of the deworming medication levamisole, which is sometimes used as a cutting agent of illicitly produced cocaine.
Aminorex was formerly used as an appetite suppressant.
Aminorex is a serotonin–norepinephrine–dopamine releasing agent (SNDRA). Its EC50 values for induction of monoamine release are 26.4 nM for norepinephrine, 49.4 nM for dopamine, and 193 nM for serotonin. In addition to its monoamine-releasing activity, aminorex is a weak agonist of the serotonin 5-HT2 receptors, including of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors. Its EC50 values for activation of these receptors are 4,365 nM for 5-HT2A, 870 nM for 5-HT2B, and 525 nM for 5-HT2C.
Activation of serotonin 5-HT2B receptors by aminorex, either directly via agonism or indirectly via serotonin release, has been implicated in the development of pulmonary arterial hypertension and cardiac valvulopathy with the drug. However, its EC50 for serotonin 5-HT2B receptor activation is 33-fold higher than its EC50 value for induction of norepinephrine release and is almost 50-fold less potent than the serotonin 5-HT2B receptor agonism of dexnorfenfluramine. This seems to call into question the role of direct agonism of the serotonin 5-HT2B receptor in the toxicity of aminorex. Along similar lines, chlorphentermine, a related drug that has also been associated with such adverse effects, shows negligible direct serotonin 5-HT2B receptor agonistic activity. However, it is possible that metabolites of aminorex and chlorphentermine might be more potent in this action.
Aminorex does not appear to have been assessed at the trace amine-associated receptor 1 (TAAR1). However, several derivatives of aminorex, such as 4-methylaminorex (4-MAR) and 4,4'-dimethylaminorex (4,4'-DMAR), have been found to be inactive at the mouse and rat TAAR1. Many other monoamine releasing agents (MRAs), such as many amphetamines, are rodent and/or human TAAR1 agonists. Activation of the TAAR1 may auto-inhibit and thereby constrain the monoaminergic effects of these agents. Lack of TAAR1 agonism in the case of aminorex analogues might enhance their effects relative to MRAs possessing TAAR1 agonism.
Aminorex is a member of the 2-amino-5-phenyloxazoline group. It is structurally related to the substituted amphetamines like amphetamine and to the substituted phenylmorpholines like phenmetrazine.
A variety of derivatives and analogues of aminorex are known. These include 2'-fluoro-4-methylaminorex (2F-MAR), 2C-B-aminorex, 3',4'-methylenedioxy-4-methylaminorex (MDMAR), 4'-bromo-4-methylaminorex (4B-MAR), 4'-chloro-4-methylaminorex (4C-MAR), 4'-fluoro-4-methylaminorex (4F-MAR), 4-methylaminorex (4-MAR), 4,4'-dimethylaminorex (4,4'-DMAR), clominorex, cyclazodone, fenozolone, fluminorex, pemoline, and thozalinone, among others.