Ethylphenidate

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Ethylphenidate
Systematic (IUPAC) name
ethyl 2-phenyl-2-piperidin-2-ylacetate
Identifiers
CAS number 57413-43-1
ATC code  ?
PubChem 3080846
Chemical data
Formula C15H21NO2 
Mol. mass 247.33274 g/mol
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

?
Legal status
Routes N/A

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.

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]


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[edit] 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.
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