Ethylphenidate

Ethylphenidate
The skeletal formula of ethylphenidate
Chemical Nomenclature
Common names	Ethylphenidate
Systematic name	(RS)-ethyl 2-phenyl-2-piperidin-2-ylacetate <-- Class Membership -->
Class Membership
Psychoactive class	Stimulant
Chemical class	Amphetamine
Routes of Administration
Oral Dosage WARNING: Always start with lower doses due to differences between individual body weight, tolerance, metabolism, and personal sensitivity. See responsible use section. DISCLAIMER: PW's dosage information is a summary of data gathered from users and resources. It is NOT a recommendation and should be verified with other sources for accuracy. Threshold < 50 mg Light 50 mg Common 50 - 100 mg Strong 100 - 200 mg Heavy > 200 mg Duration Total 6 - 8 hours Onset < 1 hour Peak ~2 hours Offset ~4 hours Afterglow > 2 hours Insufflated Dosage WARNING: Always start with lower doses due to differences between individual body weight, tolerance, metabolism, and personal sensitivity. See responsible use section. DISCLAIMER: PW's dosage information is a summary of data gathered from users and resources. It is NOT a recommendation and should be verified with other sources for accuracy. Threshold < 10 mg Light 10 - 30 mg Common 30 - 50 mg Strong 50 - 100 mg Heavy > 100 mg Duration Total 4 - 6 hours Onset <10 minutes Peak ~2 hours Offset ~4 hours Afterglow > 2 hours

Summary sheet: Ethylphenidate

Ethylphenidate ((RS)-ethyl 2-phenyl-2-piperidin-2-ylacetate or EP) is an entactogenic stimulant, substituted phenethylamine, piperidine, and close analog of methylphenidate (ritalin). The two substances have very similar pharmacological mechanisms but distinctively different subjective effects as ethylphenidate can be considered as significantly more euphoric and recreational in its experience. It also displays stronger entactogenic properties than methylphenidate and other commonly prescribed amphetamines.

Ethylphenidate is most commonly distributed online through research chemical 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:

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

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.

Subjective effects

The effects listed below are based upon the subjective effects index and personal experiences of PsychonautWiki contributors. The listed effects will rarely (if ever) occur all at once, but heavier dosages will increase the chances and are more likely to induce a full range of effects.

Physical effects

The physical effects of ethylphenidate can be broken down into several components which progressively intensify proportional to dosage. These are described below and generally include:

• Stimulation - In terms of its effects on the physical energy levels of the user, ethylphenidate is usually considered to be energetic and stimulating in a fashion that is distinct but much weaker than that of amphetamine or methamphetamine and stronger than that of modafinil and caffeine. At lower to moderate doses, it encourages general productivity, but at higher dosages, it encourages physical activities such as dancing, socializing, running, or cleaning. The particular style of stimulation which ethylphenidate presents can be described as forced. This means that at higher dosages, it becomes difficult or impossible to keep still as jaw clenching, involuntarily bodily shakes and vibrations become present, resulting in extreme shaking of the entire body, unsteadiness of the hands, and a general lack of motor control.
• Dehydration
• Appetite suppression
• Vasoconstriction - Norepinephrine reuptake inhibition causes the sympathetic nervous system to constrict vessels and puts severe strain on the cardiovascular system with prolonged use.
• Increased heart rate

Cognitive effects

The cognitive effects of ethylphenidate can be broken down into several components which progressively intensify proportional to dosage. The general head space of ethylphenidate is described by many as one of extreme mental stimulation, increased focus, and powerful euphoria. It contains a large number of typical stimulant cognitive effects. Although negative side effects are usually mild at low to moderate dosages, they become increasingly likely to manifest themselves with higher amounts or extended usage. This particularly holds true during the offset of the experience.

The most prominent of these cognitive effects generally include:

• Thought acceleration
• Analysis enhancement
• Wakefulness
• Focus enhancement - This component is most effective at low to moderate dosages as anything higher will usually impair concentration.
• Empathy, love and sociability enhancement - These feelings of sociability, love and empathy are much stronger than that of methylphenidate. They are a little weaker and less sharp than those found on substances such as MDMA but still prove stronger and more consistent than many other stimulants of this class. This is capable of providing long-lasting therapeutic effects.
• Motivation enhancement
• Euphoria - The euphoric rush associated with ethylphenidate use, as result of dopamine reuptake inhibition, is very short-lived and compulsive, similarly to that of cocaine.
• Cognitive fatigue - This component can occur during the offset of this compound as a rebound effect which is usually equal in its intensity to the enhancements which occurred before it.

Toxicity and harm potential

The toxicity and long-term health effects of recreational ethylphenidate use do not seem to have been studied in any scientific context and the exact toxic dosage is unknown. This is because ethylphenidate is a research chemical with very little history of human usage. Anecdotal evidence from people who have tried ethylphenidate suggests that there are no negative health effects attributed to simply trying the drug by itself at low to moderate doses or using it very sparingly (but nothing can be completely guaranteed). Independent research should always be done to ensure that a combination of two or more substances is safe before consumption.

It is worth noting that ethylphenidate crystals are particularly abrasive and somewhat caustic to mucous membranes. Careless use will deteriorate the chosen routes of administration so it is important to practice routine maintenance such as soaking the sinus cavity with water prior to and following insufflation.

Ethylphenidate is irritating to the sphincters at either end of the oesophagus causing laryngopharyngeal reflux which may damage the throat and pulmonary system and is not protected against the presence of gastric acid unlike the stomach and oesophagus.

It will also irritate lung tissue if inhaled, resulting in production of phlegm and an irritated cough.

Tolerance and addiction potential

In terms of its tolerance, ethylphenidate can be used multiple days in a row for extended periods of time, but acute tolerance does exist and builds up gradually over repeated extended use. This results in the user requiring an increase in dosage to achieve the same effects.

Ethylphenidate has potential for abuse on par with that of amphetamine or MDMA due to its lack of significant tolerance, euphoric effects and action upon dopamine transporters.

Dangerous interactions

Although many drugs are safe on their own, they can become dangerous and even life-threatening when combined with other substances. The list below contains some common potentially dangerous combinations, but may not include all of them. Certain combinations may be safe in low doses of each but still increase the potential risk of death. Independent research should always be done to ensure that a combination of two or more substances is safe before consumption.

• 25x-NBOMe - Both the NBOMe series and ethylphenidate induce powerful stimulation. Side effects such as thought loops, seizures, increased blood pressure, vasoconstriction, increased heart rate, and heart failure (in extreme cases) may occur.
• Alcohol - It is dangerous to combine alcohol, a depressant, with stimulants due to the risk of excessive intoxication. Stimulants decrease the sedative effect of alcohol which is the main factor most people consider when determining their level of intoxication. Once the stimulant wears off, the effects of alcohol will be significantly increased, leading to intensified disinhibition as well as other effects. If combined, one should strictly limit themselves to only drinking a certain amount of alcohol per hour.
• DXM - This combination may cause increased heart rate and panic attacks (in extreme cases).
• MXE - Increased heart rate and blood pressure may occur.
• Tramadol - This combination can increase the risk of seizures.
• MAOIs - This combination may increase the amount of neurotransmitters such as dopamine to dangerous or even fatal levels. Examples include syrian rue, banisteriopsis caapi, 2C-T-2, 2C-T-7, αMT, and some antidepressants.
• MDMA - The neurotoxic effects of MDMA may be increased when combined with other stimulants.
• Cocaine - This combination will increase strain on the heart.

Legal issues

Ethylphenidate is not controlled internationally and remains freely available through the use of online research chemical vendors. It is, however, illegal or at least potentially illegal within certain jurisdictions, each of which are listed below:

• USA: Ethylphenidate is not explicitly controlled in the US, but it could possibly be considered an analog of a Schedule II substance (methylphenidate) under the Federal Analog Act.
• Sweden: Ethylphenidate is illegal as of 15 December 2012.
• Jersey: Ethylphenidate is illegal under the Misuse of Drugs (Jersey) Law 1978.
• Australia: 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.
• Germany Ethylphenidate is illegal in Germany as of 05.07.2013.
• Austria: Ethylphenidate is illegal in Austria by the "Neue Psychoaktive Substanzen Gesetz" (new psychoactive substances act) since 1 January 2012.
• Denmark: Ethylphenidate is illegal in Denmark as of 1 February 2013.
• Great Britain: Ethylphenidate is illegal in Great Britain as of Friday 10th April 2015 (Temporary Blanket Ban)