Ethylphenidate

Ethylphenidate (EPH) is a psychostimulant and a close analog of methylphenidate.

Ethylphenidate
Clinical data
Trade namesEPH
Routes of
administration
Insufflation, vaporized, intravenous, intramuscular, rectal, oral, sublingual
ATC code
  • none
Legal status
Legal status
Pharmacokinetic data
BioavailabilityVariable
Protein bindingUnknown
MetabolismHepatic transesterification of prodrugs methylphenidate and ethanol
ExcretionUrine, sweat
Identifiers
  • (RS)-Ethyl 2-phenyl-2-piperidin-2-ylacetate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC15H21NO2
Molar mass247.338 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 Y
  • Key:AIVSIRYZIBXTMM-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

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"), 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).

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.