Ethylphenidate (EP) is a potent psychostimulant that 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. It is most commonly formed when ethanol and methylphenidate are coingested, via hepatic transesterification.

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dbpedia-owl:Drug/atcPrefix
  • none
dbpedia-owl:Drug/casNumber
  • 57413-43-1
dbpedia-owl:Drug/iupacName
  • ethyl 2-phenyl-2-piperidin-2-ylacetate
dbpedia-owl:Drug/pubchem
  • 3080846
dbpedia-owl:atcPrefix
  • none
dbpedia-owl:casNumber
  • 57413-43-1
dbpedia-owl:iupacName
  • ethyl 2-phenyl-2-piperidin-2-ylacetate
dbpedia-owl:pubchem
  • 3080846
dbpedia-owl:thumbnail
dbpprop:abstract
  • Ethylphenidate (EP) is a potent psychostimulant that 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. It is most commonly formed when ethanol and methylphenidate are coingested, via hepatic transesterification. Ethylphenidate formation appears to be more common when large quantities of methylphenidate and alcohol are consumed at the same time, such as in non-medical use or overdose scenarios. 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, but has significantly less activity on the norepinephrine transporter (NET). It has nearly an identical dopaminergic pharmacodynamic profile as methylphenidate, possessing appreciable affinity for the inhibitory G protein-coupled dopamine subtype-2 receptors in the striatum and mesolimbic regions of the brain, including the nucleus accumbens, which is primarily responsible for its euphoric and reinforcing effects. Interestingly, the eudysmic ratio for ethylphenidate is superior to that seen for TMP. TEP is less stimulatory than TMP at 5mg/kg, although both compounds generalize at 10mg/kg. This is suggestive of a noradrenergic stimulatory effect present for TMP at lower doses.
dbpprop:atcPrefix
  • none
dbpprop:bioavailability
  • Variable
dbpprop:c
  • 15 (xsd:integer)
dbpprop:casNumber
  • 57413-43-1
dbpprop:eliminationHalfLife
  • Dependent on methylphenidate administration.
dbpprop:excretion
dbpprop:h
  • 21 (xsd:integer)
dbpprop:hasPhotoCollection
dbpprop:image
  • Ethylphenidate_3d_spin.gif
dbpprop:iupacName
  • ethyl 2-phenyl-2-piperidin-2-ylacetate
dbpprop:legalStatus
  • Presumably Controlled in the US
dbpprop:metabolism
  • Hepatic transesterification of prodrugs methylphenidate and ethanol
dbpprop:molecularWeight
  • 247.33274 g/mol
dbpprop:n
  • 1 (xsd:integer)
dbpprop:o
  • 2 (xsd:integer)
dbpprop:proteinBound
  • Unknown
dbpprop:pubchem
  • 3080846 (xsd:integer)
dbpprop:routesOfAdministration
  • N/A
dbpprop:smiles
  • CCOC(=O)C(C1CCCCN1)C2=CC=CC=C2
dbpprop:wikiPageUsesTemplate
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rdfs:comment
  • Ethylphenidate (EP) is a potent psychostimulant that 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. It is most commonly formed when ethanol and methylphenidate are coingested, via hepatic transesterification.
rdfs:label
  • Ethylphenidate
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