Ethylphenidate

Ethylphenidate
Clinical data
Routes of
administration		By mouth, insufflation, inhalation, sublingual, rectal, intramuscular, intravenous
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 checkY
  • Key:AIVSIRYZIBXTMM-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Ethylphenidate (EPH) is a central nervous system (CNS) stimulant and a close analog of methylphenidate.

Ethylphenidate acts as a norepinephrine–dopamine 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, being almost identical to methylphenidate in both structure and pharmacodynamics, likely also doesn't solely act as a "classical" reuptake inhibitor but primarily as an inverse agonist at the dopamine transporter (DAT), inducing dopamine transporter reversal and subsequent dopamine release from the axon terminal into the synaptic cleft in a manner similar to but distinct from amphetamines.[3]

  1. ^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  2. ^ "Substance Details Ethylphenidate". Retrieved 2024-01-22.
  3. ^ Heal DJ, Gosden J, Smith SL (December 2014). "Dopamine reuptake transporter (DAT) "inverse agonism"--a novel hypothesis to explain the enigmatic pharmacology of cocaine". Neuropharmacology. CNS Stimulants. 87: 19–40. doi:10.1016/j.neuropharm.2014.06.012. PMID 24953830.