Ethylphenidate

Ethylphenidate
The skeletal formula of ethylphenidate
Chemical Nomenclature
Common names	Ethylphenidate
Systematic name	(RS)-ethyl 2-phenyl-2-piperidin-2-ylacetate
Class Membership
Psychoactive class	Stimulant
Chemical class	Phenethylamine / Piperidine
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 gathered from users and resources for educational purposes only. It is not a recommendation. This dosage and duration information has been sourced from TripSit Threshold < 10 mg Light 20 - 40 mg Common 40 - 100 mg Strong 100 - 150 mg Heavy 150 - 200 mg Duration Total 4 - 10 hours Onset 45 - 120 minutes Rectal 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 gathered from users and resources for educational purposes only. It is not a recommendation. This dosage and duration information has been sourced from TripSit Threshold < 5 mg Light 5 - 15 mg Common 15 - 30 mg Strong 30 - 50 mg Heavy 50 - 75 mg Duration Total 2 - 6 hours Onset 5 - 20 minutes

Summary sheet: Ethylphenidate

Ethylphenidate ((RS)-ethyl 2-phenyl-2-piperidin-2-ylacetate or EP) is a stimulant, 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

• 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
• Teeth grinding - This component can be considered to be less intense when compared with that of MDMA.

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:

• Focus enhancement - This component is most effective at low to moderate dosages as anything higher will usually impair concentration.
• 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.
• 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.
• Thought acceleration
• Analysis enhancement
• Wakefulness
• Motivation enhancement

After effects

The effects which occur during the offset of a stimulant experience generally feel negative and uncomfortable in comparison to the effects which occurred during its peak. This is often referred to as a "comedown" and occurs because of neurotransmitter depletion. Its effects commonly include:

• Cognitive fatigue
• Thought deceleration
• Anxiety
• Depression
• Wakefulness
• Irritability

Toxicity and harm potential

Main article: Research chemicals § 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 has very little history of human usage. Anecdotal evidence from people who have tried ethylphenidate within the community suggest that there do not seem to be any negative health effects attributed to simply trying this drug at low to moderate doses by itself and using it sparingly (but nothing can be completely guaranteed).

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.

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

It is strongly recommended that one use harm reduction practices when using this drug.

Tolerance and addiction potential

As with other stimulants, the chronic use of ethylphenidate can be considered moderately addictive with a high potential for abuse and is capable of causing psychological dependence among certain users. When addiction has developed, cravings and withdrawal effects may occur if a person suddenly stops their usage.

Tolerance to many of the effects of ethylphenidate develops with prolonged and repeated use. This results in users having to administer increasingly large doses to achieve the same effects. After that, it takes about 3 - 7 days for the tolerance to be reduced to half and 1 - 2 weeks to be back at baseline (in the absence of further consumption). ethylphenidate presents cross-tolerance with all dopaminergic stimulants, meaning that after the consumption of ethylphenidate all stimulants will have a reduced effect.

Psychosis

Main article: Stimulant psychosis

Abuse of compounds within the stimulant class at high dosages for prolonged periods of time can potentially result in a stimulant psychosis that may present with a variety of symptoms (e.g., paranoia, hallucinations, or delusions). A review on treatment for amphetamine, dextroamphetamine, and methamphetamine abuse-induced psychosis states that about 5–15% of users fail to recover completely. The same review asserts that, based upon at least one trial, antipsychotic medications effectively resolve the symptoms of acute amphetamine psychosis.

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 this compound induce powerful stimulation and their interaction may cause severe side effects. These can include thought loops, seizures, increased blood pressure, vasoconstriction, increased heart rate, and heart failure (in extreme cases).
• 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 respiratory depression. 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.
• 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 may increase strain on the heart.

Legal issues

Ethylphenidate is not controlled internationally and remains easily accessible 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.
• United Kingdom: This drug is illegal under the Psychoactive Substance Act, which came into effect on May 26th, 2016.

See also

• Responsible use
• Stimulant
• Methylphenidate
• Isopropylphenidate
• 4F-MPH

External links

• Ethylphenidate (Wikipedia)
• Ethylphenidate (TripSit)
• Ethylphenidate (Drugs-Forum)
• Ethylphenidate experiences (Erowid)