Ethylphenidate

Ethylphenidate is a stimulant drug. It is formed inside the body when alcohol is consumed alongside the ADHD medication methylphenidate, by transesterification in the liver.^[1] Ethylphenidate formation appears to be more common when large quantities of methylphenidate and alcohol are consumed at the same time, such as in abuse or overdose scenarios.^[2] This process is also known to occur when cocaine and alcohol are consumed together, forming cocaethylene.

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Ethylphenidate is a more selective dopamine reuptake inhibitor than methylphenidate, having around the same potency as a dopamine reuptake inhibitor compared to the parent compound,^[3] but significantly less activity as a noradrenaline reuptake inhibitor.^[4]

References

1. ^ Markowitz JS, DeVane CL, Boulton DW, Nahas Z, Risch SC, Diamond F, Patrick KS. Ethylphenidate formation in human subjects after the administration of a single dose of methylphenidate and ethanol. Drug Metabolism and Disposition. 2000 Jun;28(6):620-4.
2. ^ Markowitz JS, Logan BK, Diamond F, Patrick KS. Detection of the novel metabolite ethylphenidate after methylphenidate overdose with alcohol coingestion. Journal of Clinical Psychopharmacology. 1999 Aug;19(4):362-6.
3. ^ Patrick KS, Williard RL, VanWert AL, Dowd JJ, Oatis JE Jr, Middaugh LD. Synthesis and pharmacology of ethylphenidate enantiomers: the human transesterification metabolite of methylphenidate and ethanol. Journal of Medicinal Chemistry. 2005 Apr 21;48(8):2876-81.
4. ^ Williard RL, Middaugh LD, Zhu HJ, Patrick KS. Methylphenidate and its ethanol transesterification metabolite ethylphenidate: brain disposition, monoamine transporters and motor activity. Behavioural Pharmacology. 2007 Feb;18(1):39-51.