Ethylphenidate

Ethylphenidate

Clinical data
Trade names	EPH
Routes of administration	Insufflation, vaporized, intravenous, intramuscular, rectal, oral, sublingual
ATC code	none
Legal status
Legal status	DE: Anlage II (Prohibited) UK: Class B Temporary Class Drug
Pharmacokinetic data
Bioavailability	Variable
Protein binding	Unknown
Metabolism	Hepatic transesterification of prodrugs methylphenidate and ethanol
Biological half-life	Less than 4hrs
Excretion	Urine
Identifiers
IUPAC name (RS)-ethyl 2-phenyl-2-piperidin-2-ylacetate
CAS Number	57413-43-1 Y
PubChem CID	3080846
ChemSpider	2338571 Y
UNII	984DG861KD
Chemical and physical data
Formula	C15H21NO2
Molar mass	247.33274 g/mol
3D model (Jmol)	Interactive image
SMILES CCOC(=O)C(C1CCCCN1)C2=CC=CC=C2
InChI 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?)

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

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.

There have been anecdotal reports of a perforated septum resulting from even just a few uses of ethylphenidate by insufflation (snorting). This is almost certainly due to ethylphenidate being caustic or containing caustic impurities, as users report that insufflation is extremely painful.

Ethylphenidate metabolizes into methylphenidate and ritalinic acid.

Tiny amounts of ethylphenidate can be formed in vivo 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. 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 (+)-enantiomer of methylphenidate. Additionally, only a few percent of the consumed methylphenidate is converted to ethylphenidate.

This carboxylesterase-dependent transesterification process is also known to occur when cocaine and alcohol are consumed together, forming cocaethylene.