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Ethylphenidate

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Ethylphenidate
Clinical data
Routes of
administration		Insufflation, Vaporized, Intravenous, Intramuscular, Rectal, Oral, Sublingual
ATC code
  • none
Legal status
Legal status
  • Unscheduled (US)
Pharmacokinetic data
BioavailabilityVariable
Protein bindingUnknown
MetabolismHepatic transesterification of prodrugs methylphenidate and ethanol
Elimination half-lifeLess than 4hrs[note 1][citation needed]
ExcretionUrine
Identifiers
  • (RS)-ethyl 2-phenyl-2-piperidin-2-ylacetate
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC15H21NO2
Molar mass247.33274 g/mol g·mol−1
3D model (JSmol)
  • CCOC(=O)C(C1CCCCN1)C2=CC=CC=C2
  • InChI=1S/C15H21NO2/c1-2-18-15(17)14(12-8-4-3-5-9-12)13-10-6-7-11-16-13/h3-5,8-9,13-14,16H,2,6-7,10-11H2,1H3 checkY
  • Key:AIVSIRYZIBXTMM-UHFFFAOYSA-N checkY
  (verify)

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.

Ethylphenidate in its free base form is a highly caustic substance, and as a result, some anecdotal reports on internet forums such as Bluelight indicate that even just a few uses via the insufflation (snorted) route of administration can result in a perforated septum.[1][2][3]

Pharmacokinetics

Ethylphenidate is most commonly formed when ethanol and methylphenidate are coingested, via hepatic transesterification.[4] 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.[5] This carboxylesterase-dependent transesterification process is also known to occur when cocaine and alcohol are consumed together, forming cocaethylene.[6] However, the transesterfication process of methylphenidate to ethylphenidate, as tested in mice liver, was dominant in the inactive (-)enantiomer but showed a prolonged and increased maximal plasma concentration of the active(+)enanatiomer of methylphenidate[7]

Pharmacodynamics

All available data on ethylphenidate's pharmacokinetics are drawn from studies conducted on rodents. Ethylphenidate is more selective to the dopamine transporter (DAT) than methylphenidate, having approximately the same efficacy as the parent compound,[7] but has significantly less activity on the norepinephrine transporter (NET).[8] Its dopaminergic pharmacodynamic profile is nearly identical to methylphenidate, and is primarily responsible for its euphoric and reinforcing effects.[9]

The eudysmic ratio for ethylphenidate is superior to that of methylphenidate.[7]

The following is ethylphenidate's binding profile in the mouse, alongside methylphenidate's. Figures for both the racemic and the dextrorotary enantiomers are given:[8]

Compound Binding DAT Binding NET Uptake DA Uptake NE
d-methylphenidate 139 408 28 46
d-ethylphenidate 276 2479 24 247
dl-methylphenidate 105 1560 24 31
dl-ethylphenidate 382 4824 82 408

Legality

  • Ethylphenidate is not controlled internationally, see Convention on Psychotropic Substances
  • Ethylphenidate is not controlled in the Netherlands, as the Opium Law does not cover it, nor is there any law covering analogs of controlled drugs (methylphenidate is covered).
  • Ethylphenidate is not explicitly controlled in US but it could possibly be considered an analog of a Schedule II substance (methylphenidate) under the Federal Analog Act.
  • Ethylphenidate is illegal in Sweden as of 15 December 2012. [10]
  • Ethylphenidate is not controlled in the UK, as there is no generic legislation for ritalinic esters, nor is it explicitly named in the Misuse of Drugs Act
  • Australian state and federal legislation contains provisions that mean that analogues of controlled drugs are also covered by the legislation. Ethylphenidate would be an analogue of methylphenidate under this legislation.
  • Ethylphenidate is not controlled in Canada under the Controlled Drugs and Substances Act as the inclusion of methylphenidate in Schedule III only bans salts, not analogues (unlike drugs covered by Schedule I). [11]

Notes

  1. ^ Shorter lasting than methylphenidate according to subjective reports

References

  1. ^ http://www.bluelight.ru/vb/threads/611962-ethylphenidate-dosage/page2
  2. ^ http://www.drugs-forum.com/forum/showthread.php?t=156994
  3. ^ http://www.ukchemicalresearch.org/Thread-ethyl-ketamine?page=15
  4. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 10820132, please use {{cite journal}} with |pmid= 10820132 instead.
  5. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 10440465, please use {{cite journal}} with |pmid=10440465 instead.
  6. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 9423167, please use {{cite journal}} with |pmid=9423167 instead.
  7. ^ a b c Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 15828826, please use {{cite journal}} with |pmid=15828826 instead.
  8. ^ a b Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 17218796, please use {{cite journal}} with |pmid=17218796 instead.
  9. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 2020260, please use {{cite journal}} with |pmid=2020260 instead.
  10. ^ http://www.riksdagen.se/sv/Dokument-Lagar/Lagar/Svenskforfattningssamling/Forordning-19921554-om-kont_sfs-1992-1554/?bet=1992:1554
  11. ^ http://laws-lois.justice.gc.ca/eng/acts/C-38.8/page-26.html#h-30

See also

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