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Ethylphenidate EPH is a psychostimulant and a close analog of methylphenidate. Ethylphenidate acts as both a dopamine reuptake inhibitor and norepinephrine reuptake inhibitor , meaning it effectively boosts the levels of the norepinephrine and dopamine neurotransmitters in the brain, by binding to, and partially blocking the transporter proteins that normally remove those monoamines from the synaptic cleft. However, considering the close similarities between ethylphenidate and methylphenidate and the fact that methylphenidate, like cocaine , actually does not primarily act as a 'classical' reuptake inhibitor, but rather as an ' inverse agonist at the DAT ' also called a ' negative allosteric modulator at the DAT' , \\\\\\\\\\\\\\[1\\\\\\\\\\\\\\] it is at least very likely that ethylphenidate also primarily acts as an inverse DAT agonist instead of or at least only secondarily as a classical reuptake inhibitor which could be called a ' competitive antagonist at the DAT' using a similar terminology as 'negative allosteric modulator at the DAT', which per definition means that its mechanism is non-competitive. There have been anecdotal reports of a perforated septum resulting from even just a few uses of ethylphenidate by insufflation snorting. Some users also report the drug is extremely painful to insufflate. Ethylphenidate metabolizes into methylphenidate and ritalinic acid. Tiny amounts of ethylphenidate can be formed in vivo when alcohol also known formally as ethanol and methylphenidate are coingested, via hepatic transesterification. This carboxylesterase -dependent transesterification process is also known to occur when cocaine and alcohol are consumed together, forming cocaethylene. Ethylphenidate is more selective to the dopamine transporter DAT than methylphenidate, having approximately the same efficacy as the parent compound, \\\\\\\\\\\\\\[5\\\\\\\\\\\\\\] but has significantly less activity on the norepinephrine transporter NET. The eudysmic ratio for ethylphenidate is superior to that of methylphenidate. Figures for both the racemic and the dextrorotary enantiomers are given: \\\\\\\\\\\\\\[7\\\\\\\\\\\\\\]. From Wikipedia, the free encyclopedia. IUPAC name. Interactive image. These findings led us to conclude that the highly unusual stimulant profile of cocaine and related compounds, eg methylphenidate, is not mediated by monoamine reuptake inhibition alone. We describe the experimental findings which suggest cocaine serves as a negative allosteric modulator to alter the function of the dopamine reuptake transporter DAT and reverse its direction of transport. This results in a firing-dependent, retro-transport of dopamine into the synaptic cleft. Journal of Pharmaceutical and Biomedical Analysis. Drug Metabolism and Disposition. Journal of Clinical Psychopharmacology. Journal of Medicinal Chemistry. Journal of Pharmaceutical Sciences. Behavioural Pharmacology. Life Sciences. Retrieved Archived from the original on China Food and Drug Administration. Retrieved 1 October Adapromine Amantadine Bromantane Memantine Rimantadine. Oxiracetam Phenylpiracetam Phenylpiracetam hydrazide. ATC code : N06B. Monoamine reuptake inhibitors. Others: Antihistamines e. Others: A Amoxapine Antihistamines e. Amiodarone Amphetamines e. Hidden categories: CS1 maint: archived copy as title CS1 Chinese-language sources zh Articles without EBI source Chemical pages without DrugBank identifier Articles without KEGG source Drugboxes which contain changes to verified fields Drugboxes which contain changes to watched fields All articles with unsourced statements Articles with unsourced statements from June All articles with failed verification Articles with failed verification from May Articles with unsourced statements from January Namespaces Article Talk. Views Read Edit View history. Help Learn to edit Community portal Recent changes Upload file. Download as PDF Printable version. Wikimedia Commons. Hepatic transesterification of prodrugs methylphenidate and ethanol. Urine , sweat.

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Ethylphenidate EPH is a psychostimulant and a close analog of methylphenidate. Ethylphenidate acts as both a dopamine reuptake inhibitor and norepinephrine reuptake inhibitor , meaning it effectively boosts the levels of the norepinephrine and dopamine neurotransmitters in the brain, by binding to, and partially blocking the transporter proteins that normally remove those monoamines from the synaptic cleft. However, considering the close similarities between ethylphenidate and methylphenidate and the fact that methylphenidate, like cocaine , actually does not primarily act as a 'classical' reuptake inhibitor, but rather as an ' inverse agonist at the DAT ' also called a ' negative allosteric modulator at the DAT' , \\\\\\\\\\\\\\\\\[1\\\\\\\\\\\\\\\\\] it is at least very likely that ethylphenidate also primarily acts as an inverse DAT agonist instead of or at least only secondarily as a classical reuptake inhibitor which could be called a ' competitive antagonist at the DAT' using a similar terminology as 'negative allosteric modulator at the DAT', which per definition means that its mechanism is non-competitive. There have been anecdotal reports of a perforated septum resulting from even just a few uses of ethylphenidate by insufflation snorting. Some users also report the drug is extremely painful to insufflate. Ethylphenidate metabolizes into methylphenidate and ritalinic acid. Tiny amounts of ethylphenidate can be formed in vivo when alcohol also known formally as ethanol and methylphenidate are coingested, via hepatic transesterification. This carboxylesterase -dependent transesterification process is also known to occur when cocaine and alcohol are consumed together, forming cocaethylene. Ethylphenidate is more selective to the dopamine transporter DAT than methylphenidate, having approximately the same efficacy as the parent compound, \\\\\\\\\\\\\\\\\[5\\\\\\\\\\\\\\\\\] but has significantly less activity on the norepinephrine transporter NET. The eudysmic ratio for ethylphenidate is superior to that of methylphenidate. Figures for both the racemic and the dextrorotary enantiomers are given: \\\\\\\\\\\\\\\\\[7\\\\\\\\\\\\\\\\\]. From Wikipedia, the free encyclopedia. IUPAC name. Interactive image. These findings led us to conclude that the highly unusual stimulant profile of cocaine and related compounds, eg methylphenidate, is not mediated by monoamine reuptake inhibition alone. We describe the experimental findings which suggest cocaine serves as a negative allosteric modulator to alter the function of the dopamine reuptake transporter DAT and reverse its direction of transport. This results in a firing-dependent, retro-transport of dopamine into the synaptic cleft. Journal of Pharmaceutical and Biomedical Analysis. Drug Metabolism and Disposition. Journal of Clinical Psychopharmacology. Journal of Medicinal Chemistry. Journal of Pharmaceutical Sciences. Behavioural Pharmacology. Life Sciences. Retrieved Archived from the original on China Food and Drug Administration. Retrieved 1 October Adapromine Amantadine Bromantane Memantine Rimantadine. Oxiracetam Phenylpiracetam Phenylpiracetam hydrazide. ATC code : N06B. Monoamine reuptake inhibitors. Others: Antihistamines e. Others: A Amoxapine Antihistamines e. Amiodarone Amphetamines e. Hidden categories: CS1 maint: archived copy as title CS1 Chinese-language sources zh Articles without EBI source Chemical pages without DrugBank identifier Articles without KEGG source Drugboxes which contain changes to verified fields Drugboxes which contain changes to watched fields All articles with unsourced statements Articles with unsourced statements from June All articles with failed verification Articles with failed verification from May Articles with unsourced statements from January Namespaces Article Talk. Views Read Edit View history. Help Learn to edit Community portal Recent changes Upload file. Download as PDF Printable version. Wikimedia Commons. Hepatic transesterification of prodrugs methylphenidate and ethanol. Urine , sweat.

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