Ethylphenidate

ethylphenidate (also known as eph) is a novel stimulant substance of the piperidine class that produces traditional stimulant effects when administered.

it is a closely related analog of methylphenidate (brand names ritalin, concerta). the two substances have very similar pharmacological mechanisms but discernible differences in their subjective effects with ethylphenidate often considered to be recreational.

ethylphenidate is most commonly distributed as a research chemical by online vendors, due to its grey-area legal status in certain countries.

chemistry

ethylphenidate is a synthetic molecule of the substituted phenethylamine class. it contains a phenethylamine core featuring a phenyl ring bound to an amino -nh2 group through an ethyl chain. it is structurally similar to amphetamine, featuring a substitution at r_α which is incorporated into a piperdine ring ending at the terminal amine of the phenethylamine chain. additionally, it contains an ethyl acetate bound to r₂ or its structure. ethylphenidate is structurally differed to methylphenidate by elongation of the carbon chain. ethyl- regards the side chain of two carbon atoms, phen- indicates the phenyl ring, id- is contracted from a piperidine ring, and -ate indicates the acetate group containing the oxygens. ethylphenidate is a chiral compound, presumably produced as a racemic mixture.

pharmacology

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. this allows dopamine and norepinephrine to accumulate within the brain, resulting in stimulating and euphoric effects.

all available data on ethylphenidate’s pharmacokinetics are drawn from studies conducted on rodents. it has been found that ethylphenidate is more selective to the dopamine transporter (dat) than methylphenidate, having approximately the same efficacy as the parent compound, but with significantly less activity on the norepinephrine transporter (net). its dopaminergic pharmacodynamic profile is nearly identical to methylphenidate and is primarily responsible for its euphoric and reinforcing effects.

the following is ethylphenidate’s binding profile in the mouse, alongside methylphenidate’s. figures for both the racemic and the dextrorotary enantiomers are given:

ethylphenidate can be formed within the body (in the liver), when alcohol and methylphenidate are co-ingested. this is most common when large quantities of methylphenidate and alcohol are consumed at the same time, such as in non-medical use or overdose scenarios. a similar process is also known to occur when cocaine and alcohol are consumed together, forming cocaethylene. however, only a few percent of the consumed methylphenidate is converted to ethylphenidate, so a pharmacologically significant dose with measurable physiological effects would never be produced.