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{{SummarySheet}}
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| ''[[4F-EPH/Summary|Summary sheet: 4F-EPH]]''
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'''4F-EPH''' ('''4'-fluoro-ethylphenidate''') is an [[entactogenic]] [[psychoactive class::stimulant]], [[chemical class::substituted phenethylamine]], [[chemical class::piperidine]], and close analog of [[ethylphenidate]] and [[methylphenidate]] (ritalin).


4F-EPH has little to no history of human usage prior to its distribution online through [[research chemical]] vendors. It was initially developed as a replacement for [[ethylphenidate]] which became illegal in the United Kingdom due to a temporary blanket ban. Anecdotal reports suggest that 4F-EPH can be caustic to the nasal cavities, although not as much as [[EPH]].
'''4-Fluoroethylphenidate''' (commonly known as '''4F-EPH''') is a novel synthetic [[psychoactive class::stimulant]] of the [[chemical class::phenidate]] chemical class that produces long-lasting [[Euphoria|euphoric]] and [[stimulant|stimulating]] effects associated with potent [[monoamine]] [[reuptake inhibitor|reuptake inhibitors]] when [[Routes of administration|administered]]. It is a closely related structural analog of the commonly prescribed ADHD drug [[methylphenidate]] (known by the brand-names ''Ritalin'' and ''Concerta'') as well as a [[designer drug]] analog [[ethylphenidate]]. Based on its similarities to other memebers of this class, it is speculated to exert its activity as some form of double or triple [[monoamine]] [[reuptake inhibitor]].
 
Like other members of the [[substituted phenidate]] family, anecdotal reports suggest that 4F-EPH can be corrosive to the nasal cavities, albeit not to the degree of [[ethylphenidate]].
 
4F-EPH has little to no history of [[recreational drug use|recreational use]] and has yet to be documented being sold on the streets. It was initially developed as a replacement and successor for compounds like [[ethylphenidate]], which became illegal in the United Kingdom on April 2015, and later [[4F-MPH]]. In 2016, it became made available for sale on the online gray market as a [[research chemical]].
 
Due to its potent, long-lasting stimulant effect, likely habit-forming properties as well as unknown short and long-term toxicity profile, it is strongly recommended that one use proper [[harm reduction]] practices if choosing to use this substance.


==Chemistry==
==Chemistry==
{{chemistry}}
4F-EPH, or 4-fluoroethylphenidate, is a synthetic molecule of the [[phenidate]] and [[substituted phenethylamine]] classes. 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<sub>α</sub> which is incorporated into a [[piperidine]] ring ending at the terminal amine of the phenethylamine chain. It contains an ethyl acetate bound to R<sub>β</sub> of its structure and is fluorinated at R<sub>4</sub> of its phenyl ring.
4F-EPH is nearly identical in structure to 4F-MPH and therefore of methylphenidate (ritalin); the difference is that it has a fluorine atom bonded to the phenyl group at the 4 position. Amphetamine analogues containing fluorine, chlorine, bromine and methyl groups are typically stronger than those without.
 
4F-EPH is the 4-substituted flourine derivative of [[ethylphenidate]], and is structurally different to [[methylphenidate]] by elongation of the carbon chain and the addition of a fluorine group. ''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. 4F-EPH is a chiral compound, presumably produced as a racemic mixture.
 
==Pharmacology==
==Pharmacology==
4F-EPH is believed to act as a higher efficiency [[dopamine]] [[reuptake inhibitor]] than the closely related [[methylphenidate]],<ref>Synthesis of methylphenidate analogues and their binding affinities at dopamine and serotonin transport sites (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/15026075</ref><ref>Quantitative structure-activity relationship studies of threo-methylphenidate analogs (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/20846865</ref><ref>Chemistry, design, and structure-activity relationship of cocaine antagonists (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/11749256</ref> meaning that it effectively boosts the levels of 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 to accumulate within the brain, resulting in stimulating and euphoric effects.
{{pharmacology}}
4F-EPH is believed to act as a higher efficiency [[dopamine]] [[reuptake inhibitor]] than the closely related [[methylphenidate]],<ref>{{cite journal | vauthors=((Davies, H. M. L.)), ((Hopper, D. W.)), ((Hansen, T.)), ((Liu, Q.)), ((Childers, S. R.)) | journal=Bioorganic & Medicinal Chemistry Letters | title=Synthesis of methylphenidate analogues and their binding affinities at dopamine and serotonin transport sites | volume=14 | issue=7 | pages=1799–1802 | date=5 April 2004 | issn=0960-894X | doi=10.1016/j.bmcl.2003.12.097}}</ref><ref>{{cite journal | vauthors=((Misra, M.)), ((Shi, Q.)), ((Ye, X.)), ((Gruszecka-Kowalik, E.)), ((Bu, W.)), ((Liu, Z.)), ((Schweri, M. M.)), ((Deutsch, H. M.)), ((Venanzi, C. A.)) | journal=Bioorganic & Medicinal Chemistry | title=Quantitative structure-activity relationship studies of threo-methylphenidate analogs | volume=18 | issue=20 | pages=7221–7238 | date=15 October 2010 | issn=1464-3391 | doi=10.1016/j.bmc.2010.08.034}}</ref><ref>{{cite journal | vauthors=((Singh, S.)) | journal=Chemical Reviews | title=Chemistry, design, and structure-activity relationship of cocaine antagonists | volume=100 | issue=3 | pages=925–1024 | date=8 March 2000 | issn=1520-6890 | doi=10.1021/cr9700538}}</ref> meaning that it effectively boosts the levels of dopamine [[neurotransmitters]] in the brain by binding to and partially blocking the transporter proteins that normally remove those [[monoamine]]s from the synaptic cleft. This allows dopamine to accumulate within the certain focalized regions of the brain, resulting in stimulating and euphoric effects.


==Subjective effects==
==Subjective effects==
{{effectStub}}
{{effectStub}}
The effects listed below are based upon the [[subjective effects index]] and personal experiences of [[PsychonautWiki]] [[Special:TopUsers|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.
{{Preamble/SubjectiveEffects}}
===Physical effects===
{{effects/base
*'''[[Effect::Stimulation]]'''
|{{effects/physical|
*'''[[Effect::Dehydration]]'''
*'''[[Effect::Stimulation]]''' - 4F-EPH is considered to be mildly to moderately stimulating in a way that is quite unique for a dopaminergic stimulant and likely is the result of activity beyond dopamine and norepinephrine reuptake inhibition. Even in high doses it is much less stimulating and distinctively different than the closely related chemical [[4F-MPH]]. The style of stimulation can be described as smooth, with a slight to moderate energetic push similar to, but drastically weaker than [[methamphetamine]]. It is much subtler and less forced than that of [[4F-MPH]], [[methylphenidate]], and [[amphetamine]].
*'''[[Effect::Appetite suppression]]'''
*'''[[Effect::Dehydration]]''' - Relatively mild, provided one consumes an appropriate amount of water. Water should be sipped slowly at spaced intervals to prevent water intoxication.
*'''[[Effect::Increased heart rate]]'''
*'''[[Effect::Appetite suppression]]''' - This effect is mild.
*'''[[Effect::Teeth grinding]]''' - This component can be considered to be less intense when compared with that of [[MDMA]].
*'''[[Effect::Increased heart rate]]''' - 4F-EPH has a moderate effect on heart rate that is not concerning or uncomfortable at moderate doses.
*'''[[Effect::Increased blood pressure]]''' - A slight-moderate increase in blood pressure is seen with this compound, but only very excessive doses will usually raise it to problematic levels.
*'''[[Effect::Teeth grinding]]''' - This component can be considered to be less intense when compared with that of [[MDMA]]. It is very minimal at moderate doses and only excessive doses usually cause this effect. Even then it is rarely severe enough to reach an uncomfortable or damaging degree. Magnesium supplementation may reduce this.
*'''[[Effect::Pupil dilation]]''' - Pupil dilation is minimal at low-moderate doses, but can be pronounced during the offset of higher doses.
*'''[[Effect::Stamina enhancement]]''' - This component is much weaker than that of most other stimulants, such as [[methylphenidate]] and [[4F-MPH]].
*'''[[Effect::Vasoconstriction]]''' - This effect is much milder than that of most other dopaminergic stimulants at the peak, however it may rapidly become uncomfortable or even dangerous during the offset of very high doses or in individuals with circulatory problems. Blue or deep purple coloration or wrinkling of the skin of the extremities is a medical emergency if it isn't resolved quickly. Putting the hands and feet in a hot bath may help this effect, however fully submersing oneself in hot water is potentially dangerous.
*'''[[Effect::Nasal damage]]''' - 4F-EPH is notably less caustic than EPH ([[ethylphenidate]]), however it is still mildly to moderately caustic to the nasal cavities. It is recommended to perform a '''sterile''' saline nasal rinse 15 minutes after snorting this substance. Even with that precaution, intranasal use without significant breaks to allow the nasal cavities to repair themselves will likely still damage the nasal mucous membranes. It is unknown whether this results in permanent injury or simply acute damage.
*'''[[Effect::Increased libido]]''' - There is often a noticeable increase in libido at low-moderate doses, however this effect is much weaker than that experienced with [[4F-MPH]] and [[methamphetamine]]. The style of sexual stimulation induced is an increase in the emotional enjoyment and sensations of sexual activity, but with minimal effect on or even a reduction in the pleasure of orgasm. This effect is less distracting and can be ignored more easily than that induced by many other dopaminergic stimulants.
*'''[[Effect::Decreased libido]]''' - Decreased libido inconsistently occurs at any dose, but high doses increase the likelihood and may be related to unproven, but subjectively theorized serotonergic activity.
*'''[[Effect::Orgasm suppression]]''' - Orgasm suppression usually only occurs at high doses and can be described as difficulty reaching an orgasm despite increased or normal libido. This is present primarily in males.
*'''[[Effect::Temporary erectile dysfunction]]''' - This is a common occurrence at moderate-high doses. Note that it is extremely unsafe for the heart to try to counteract this by combining erectile dysfunction drugs with stimulants.
*'''[[Effect::Physical euphoria]]''' - A slight to moderate sense of pleasant well-being and physical comfort is often present at a low level throughout the peak and is strongest at moderate doses. This effect is similar to, but much weaker than that induced by [[methamphetamine]] and [[MDMA]]. It reduces or disappears when used in high doses or when repeatedly redosed.
*'''[[Effect::Spontaneous physical sensations]]''' - Highly euphoric, mild-distinct and all-encompassing sharp tingling sensations that fade rapidly into soft sensations before disappearing frequently occur during the initial "rush" of moderate-high doses. This is particularly powerful when vaporized or injected intravenously. It is comparable to that experienced during and shortly after orgasm, although a lot milder. This effect rarely if ever occurs when consumed orally, but may occur when administered via intranasal or sublingual routes, though it is usually to a lesser degree. The rush produced by 4F-EPH may last up to 15 minutes, however it most commonly lasts around 5 minutes. It diminishes in strength rapidly and eventually disappears when redosed repetitively.
*'''[[Effect::Perception of bodily lightness]]''' - A mild and pleasant feeling of lightness/floating as well as effortless movement in the entire body frequently occurs during the rush and often persists into the peak for some time. This may occur via any route. It is most common at moderate-high doses and tends to reduce or disappear at excessive doses.


===Cognitive effects===
}}
*'''[[Effect::Thought acceleration]]'''
 
*'''[[Effect::Analysis enhancement]]'''
|{{effects/cognitive|
*'''[[Effect::Wakefulness]]'''
*'''[[Effect::Thought acceleration]]''' - The thought acceleration induced by 4F-EPH is mild to moderate and is not usually strong enough to induce confusion. It tends towards semantic, emotional, social, and abstract thought patterns.
*'''[[Effect::Focus enhancement]]'''  
*'''[[Effect::Analysis enhancement]]''' - 4F-EPH has the capability of enhancing analytical ability, but only at low doses and very inconsistently. Moderate to high doses do not usually enhance logical analytical abilities and tend instead toward semantic and emotional thought patterns.
*'''[[Effect::Motivation enhancement]]'''
*'''[[Effect::Wakefulness]]''' - 4F-EPH is relatively weak in wakefulness-promoting abilities when compared to [[methylphenidate]], [[amphetamine]], and most other dopaminergic stimulants.
*'''[[Effect::Cognitive euphoria|Euphoria]]'''
*'''[[Effect::Focus enhancement]]''' - 4F-EPH does not have much potential for use a "functional" stimulant to complete mundane tasks, as the focus enhancement induced by 4F-EPH tends to be inconsistent and mild in strength. It is usually only at low doses that focus enhancement may occur. Moderate and high doses tend to decrease the ability to focus on mundane tasks due to the pleasant recreational effects of physical and empathetic euphoria and abstract thought patterns. 4F-EPH is, however, effective for creative and abstract tasks such as art and fiction writing.
*'''[[Effect::Motivation enhancement]]''' - This component is mild and usually present only at low doses. Moderate and high doses tend to instead strongly promote socialization and recreational activities such as gaming and watching movies.
*'''[[Effect::Cognitive euphoria|Euphoria]]''' - The cognitive euphoria of 4F-EPH is subtle, relaxing, and often very pleasant. It tends to promote feelings of physical and mental well-being, as well as creative thoughts. Very excessive doses may instead result in dysphoria.
*'''[[Effect::Increased music appreciation]]''' - 4F-EPH noticeably increases the enjoyment of music.
*'''[[Effect::Cognitive fatigue]]'''
*'''[[Effect::Cognitive fatigue]]'''
===After effects===
*'''[[Effect::Empathy, affection, and sociability enhancement]]''' - 4F-EPH may result in mild empathetic and affectionate feelings, particularly at lower doses. This substance commonly results in an intense drive to socialize with others that strengthens with increasing dosage.
 
}}
 
{{effects/aftereffects|
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:
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:
*'''[[Effect::Cognitive fatigue]]'''
*'''[[Effect::Thought deceleration]]'''
*'''[[Effect::Anxiety]]'''
*'''[[Effect::Anxiety]]'''
*'''[[Effect::Cognitive fatigue]]'''
*'''[[Effect::Depression]]'''
*'''[[Effect::Depression]]'''
*'''[[Effect::Irritability]]'''
*'''[[Effect::Motivation suppression]]'''
*'''[[Effect::Thought deceleration]]'''
*'''[[Effect::Wakefulness]]'''
*'''[[Effect::Wakefulness]]'''
*'''[[Effect::Irritability]]'''
}}
}}
===Experience reports===
Anecdotal reports which describe the effects of this compound within our [[experience index]] include:
{{#ask: [[Category:4F-EPH]][[Category:Experience]]|format=ul|Columns=1}}


==Toxicity and harm potential==
==Toxicity and harm potential==
{{Main|Research chemicals#Toxicity and harm potential}}
{{toxicity}}
{{Further|Research chemicals#Toxicity and harm potential}}
The toxicity and long-term health effects of recreational 4F-EPH use do not seem to have been studied in any scientific context and the exact toxic dosage is unknown. This is because 4F-EPH is a [[research chemical]] with very little history of human usage. Anecdotal evidence from people who have tried 4F-EPH suggests that there are no negative health effects attributed to simply trying the drug by itself at low to moderate doses and using it very sparingly (but nothing can be completely guaranteed).
The toxicity and long-term health effects of recreational 4F-EPH use do not seem to have been studied in any scientific context and the exact toxic dosage is unknown. This is because 4F-EPH is a [[research chemical]] with very little history of human usage. Anecdotal evidence from people who have tried 4F-EPH suggests that there are no negative health effects attributed to simply trying the drug by itself at low to moderate doses and using it very sparingly (but nothing can be completely guaranteed).


It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this drug.
It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this drug.
===Tolerance and addiction potential===
===Tolerance and addiction potential===
As with other [[stimulant]]s, the chronic use of 4F-EPH can be considered [[Addiction potential::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.
As with other [[stimulant]]s, the chronic use of 4F-EPH can be considered [[Addiction potential::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.
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{{DangerousInteractions/Stimulants|self=4F-EPH}}
{{DangerousInteractions/Stimulants|self=4F-EPH}}
{{DangerousInteractions/MAOI|nt=dopamine}}
{{DangerousInteractions/MAOI|nt=dopamine}}
*'''[[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==
==Legal status==
{{legalStub}}
{{legalStub}}
*'''United Kingdom''' - This drug is illegal under the Psychoactive Substance Act, which came into effect on May 26th, 2016.<ref>Psychoactive Substances Act 2016 (Legislation.gov.uk) | http://www.legislation.gov.uk/ukpga/2016/2/contents/enacted</ref>
*'''Germany''': 4-Fluoroethylphenidate is controlled under the NpSG (''New Psychoactive Substances Act'')<ref>{{cite web|url=https://www.gesetze-im-internet.de/npsg/anlage.html|title=Anlage NpSG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 23, 2019|language=de}}</ref> as of November 26, 2016.<ref>{{cite web|url=https://www.bgbl.de/xaver/bgbl/start.xav?startbk=Bundesanzeiger_BGBl&jumpTo=bgbl116s2615.pdf#__bgbl__%2F%2F*%5B%40attr_id%3D%27bgbl116s2615.pdf%27%5D__1576017393518|title=Gesetz zur Bekämpfung der Verbreitung neuer psychoaktiver Stoffe|publisher=Bundesanzeiger Verlag|access-date=December 23, 2019|language=de}}</ref> Production and import with the aim to place it on the market, administration to another person and trading is punishable. Possession is illegal but not penalized.<ref>{{cite web|url=https://www.gesetze-im-internet.de/npsg/__4.html|title=§ 4 NpSG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 23, 2019|language=de}}</ref>
*'''Switzerland''': 4F-EPH is a controlled substance specifically named under Verzeichnis E.<ref>{{cite web|url=https://www.admin.ch/opc/de/classified-compilation/20101220/index.html|title=Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien|publisher=Bundeskanzlei [Federal Chancellery of Switzerland]|access-date=January 1, 2020|language=de}}</ref>
*'''Turkey:''' 4F-EPH is a classed as drug and is illegal to possess, produce, supply, or import.<ref>Cumhurbaşkanı Kararı CK Karar Sayısı : 1335 | https://resmigazete.gov.tr/eskiler/2019/07/20190720-19.pdf</ref>
*'''United Kingdom''': 4-Fluoroethylphenidate is a class B drug in the UK as of May 31st 2017, making it illegal to possess, produce or supply. <ref>{{Citation | title=The Misuse of Drugs Act 1971 (Amendment) Order 2017 | url=https://www.legislation.gov.uk/uksi/2017/634/made}}</ref>


==See also==
==See also==
*[[Responsible use]]
*[[Responsible use]]
*[[Methylphenidate]]
*[[Designer drug]]
*[[Stimulant]]
*[[Substituted phenidate]]
*[[Ethylphenidate]]
*[[Ethylphenidate]]
*[[Stimulant]]
*[[4F-MPH]]
 
==External links==
*[https://isomerdesign.com/PiHKAL/explore.php?id=634 4F-EPH (Isomer Design)]


==References==
==References==
<references/>
<references />
 
[[Category:Psychoactive substance]]
[[Category:Psychoactive substance]]
[[Category:Piperidine]]
[[Category:Phenidate]]
[[Category:Research chemical]]
[[Category:Stimulant]]
[[Category:Stimulant]]
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