4F-EPH: Difference between revisions

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'''4-Fluoroethylphenidate''' (commonly known as '''4F-EPH''') is a novel synthetic [[psychoactive class::stimulant]] of the [[chemical class::~~substituted phenethylamine~~]] ~~and [[~~chemical class~~::piperidine]] classes~~ 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]].

'''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]].

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==Chemistry==

4F-EPH, or 4-fluoroethylphenidate, 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 Rα which is incorporated into a piperidine ring ending at the terminal amine of the phenethylamine chain. It contains an ethyl acetate bound to R2 of its structure and is fluorinated at R4 of its phenyl ring.

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 Rα which is incorporated into a [[piperidine]] ring ending at the terminal amine of the phenethylamine chain. It contains an ethyl acetate bound to Rβ of its structure and is fluorinated at R4 of its phenyl ring.

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.

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==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 [[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.

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==

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*'''[[Effect::Wakefulness]]'''

}}

===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==

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*'''[[MDMA]]''' - The neurotoxic effects of MDMA may be increased when combined with other stimulants.

*'''[[Cocaine]]''' - This combination may increase strain on the heart.

==Legal status==

*'''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>The Misuse of Drugs Act 1971 (Amendment) Order 2017 ~~(Legislation.gov.uk)~~ | ~~http~~://www.legislation.gov.uk/uksi/2017/634/made</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==

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==References==

[[Category:Psychoactive substance]]

[[Category:Phenidate]]

[[Category:Research chemical]]

~~[[Category:Piperidine]]~~

[[Category:Stimulant]]

@@ Line 2: / Line 2: @@
 {{SubstanceBox/4F-EPH}}
-'''4-Fluoroethylphenidate''' (commonly known as '''4F-EPH''') is a novel synthetic [[psychoactive class::stimulant]] of the [[chemical class::substituted phenethylamine]] and [[chemical class::piperidine]] classes 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]].
+'''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]].
@@ Line 11: / Line 11: @@
 ==Chemistry==
-F-EPH, or 4-fluoroethylphenidate, 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<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>2</sub> of its structure and is fluorinated at R<sub>4</sub> of its phenyl ring.
+F-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.
 F-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.
@@ Line 17: / Line 17: @@
 ==Pharmacology==
 {{pharmacology}}
-F-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 [[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.
+F-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==
@@ Line 67: / Line 67: @@
 *'''[[Effect::Wakefulness]]'''
 }}
 }}
+===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==
@@ Line 85: / Line 87: @@
 {{DangerousInteractions/Stimulants|self=4F-EPH}}
 {{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 status==
 {{legalStub}}
-*'''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>The Misuse of Drugs Act 1971 (Amendment) Order 2017 (Legislation.gov.uk) | http://www.legislation.gov.uk/uksi/2017/634/made</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==
@@ Line 104: / Line 107: @@
 ==References==
-<references/>
+<references />
 [[Category:Psychoactive substance]]
+[[Category:Phenidate]]
 [[Category:Research chemical]]
-[[Category:Piperidine]]
 [[Category:Stimulant]]