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4F-MPH: Difference between revisions
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'''4-Fluoromethylphenidate''' (commonly known as '''4F-MPH''') is a novel synthetic [[psychoactive class::stimulant]] of the [[chemical class::phenidate]] class that produces long-lasting [[Euphoria|euphoriant]], and [[stimulant|stimulating]] effects 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''). | '''4-Fluoromethylphenidate''' (commonly known as '''4F-MPH''') is a novel synthetic [[psychoactive class::stimulant]] of the [[chemical class::phenidate]] class that produces long-lasting [[Euphoria|euphoriant]], and [[stimulant|stimulating]] effects 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''). | ||
The two substances are believed to have very similar pharmacological mechanisms as [[monoamine]] [[reuptake inhibitors]] but have been reported to display distinctive [[subjective effects index|subjective effects]], with 4F-MPH being considered significantly more euphoric and recreational. Anecdotal reports suggest that it is considerably more potent with fewer uncomfortable side effects such as [[anxiety]], [[muscle spasms]] and [[compulsive redosing]].<ref>http://www.bluelight.org/vb/threads/770658-4-Fluoromethylphenidate-(4F-MPH)</ref> This perhaps owes to the fact that it has been shown to act as a higher efficiency [[dopamine]] reuptake inhibitor than the parent compound methylphenidate.<ref>Deutsch, H. M., Shi, Q., Gruszecka-Kowalik, E., | The two substances are believed to have very similar pharmacological mechanisms as [[monoamine]] [[reuptake inhibitors]] but have been reported to display distinctive [[subjective effects index|subjective effects]], with 4F-MPH being considered significantly more euphoric and recreational. Anecdotal reports suggest that it is considerably more potent with fewer uncomfortable side effects such as [[anxiety]], [[muscle spasms]] and [[compulsive redosing]].<ref>http://www.bluelight.org/vb/threads/770658-4-Fluoromethylphenidate-(4F-MPH)</ref> This perhaps owes to the fact that it has been shown to act as a higher efficiency [[dopamine]] reuptake inhibitor than the parent compound methylphenidate.<ref>{{cite journal | vauthors=((Deutsch, H. M.)), ((Shi, Q.)), ((Gruszecka-Kowalik, E.)), ((Schweri, M. M.)) | journal=Journal of Medicinal Chemistry | title=Synthesis and Pharmacology of Potential Cocaine Antagonists. 2. Structure−Activity Relationship Studies of Aromatic Ring-Substituted Methylphenidate Analogs | volume=39 | issue=6 | pages=1201–1209 | date=15 March 1996 | url=https://pubs.acs.org/doi/10.1021/jm950697c | issn=0022-2623 | doi=10.1021/jm950697c}}</ref><ref>{{cite journal | vauthors=((Schweri, M. M.)), ((Deutsch, H. M.)), ((Massey, A. T.)), ((Holtzman, S. G.)) | journal=The Journal of Pharmacology and Experimental Therapeutics | title=Biochemical and behavioral characterization of novel methylphenidate analogs | volume=301 | issue=2 | pages=527–535 | date= May 2002 | issn=0022-3565 | doi=10.1124/jpet.301.2.527}}</ref><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=1 March 2000 | url=https://pubs.acs.org/doi/10.1021/cr9700538 | issn=0009-2665 | doi=10.1021/cr9700538}}</ref> | ||
4F-MPH has an extremely short history of [[recreational drug use|recreational use]] | 4F-MPH has an extremely short history of [[recreational drug use|recreational use]]. It was initially developed as a replacement for [[ethylphenidate]] which became illegal in the United Kingdom on April 2015 following a temporary blanket ban. Shortly after, it became available for sale on the online gray market as a [[research chemical]] for global distribution. | ||
Due to its potent, long-lasting stimulant effect, likely habit-forming properties as well as unknown toxicity profile, it is strongly recommended that one use proper [[harm reduction]] practices if choosing to use this substance. | Due to its potent, long-lasting stimulant effect, likely habit-forming properties as well as unknown toxicity profile, it is strongly recommended that one use proper [[harm reduction]] practices if choosing to use this substance. | ||
==Chemistry== | ==Chemistry== | ||
4F-MPH is a synthetic molecule of the [[substituted phenethylamine]] and [[substituted phenidate]] classes, and a fluorinated analog of [[methylphenidate]]. 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 | 4F-MPH is a synthetic molecule of the [[substituted phenethylamine]] and [[substituted phenidate]] classes, and a fluorinated analog of [[methylphenidate]]. 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. Additionally, it contains a methyl acetate bound to R<sub>β</sub> or its structure. 4F-MPH is structurally identical to methylphenidate with the exception of a single fluorine atom bound to the four position on the phenethylamine core. | ||
With respect to nomenclature, the methyl- in [[methylphenidate]] regards the side chain of one carbon atom, while phen- indicates the phenyl ring. Id- is contracted from a [[piperidine]] ring, and -ate indicates the acetate group containing the oxygen atoms. Like its parent molecule, 4F-MPH is a chiral compound, presumably produced as a racemic mixture. | With respect to nomenclature, the methyl- in [[methylphenidate]] regards the side chain of one carbon atom, while phen- indicates the phenyl ring. Id- is contracted from a [[piperidine]] ring, and -ate indicates the acetate group containing the oxygen atoms. Like its parent molecule, 4F-MPH is a chiral compound, presumably produced as a racemic mixture. | ||
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==Pharmacology== | ==Pharmacology== | ||
{{Stub}} | {{Stub}} | ||
4F-MPH is thought to act primarily as a [[dopamine and norepinephrine]] [[reuptake inhibitor]], meaning it effectively boosts the levels of dopamine and norepinephrine [[neurotransmitters]] in the brain by binding to and partially blocking the transporter proteins that normally clear these catecholamines from the synaptic cleft. This allows dopamine and norepinephrine to accumulate within the reward pathways in the brain, resulting in stimulating and euphoric effects. According to a | 4F-MPH is thought to act primarily as a [[dopamine]] and [[norepinephrine]] [[reuptake inhibitor]], meaning it effectively boosts the levels of dopamine and norepinephrine [[neurotransmitters]] in the brain by binding to and partially blocking the transporter proteins that normally clear these catecholamines from the synaptic cleft. This allows dopamine and norepinephrine to accumulate within the reward pathways in the brain, resulting in stimulating and euphoric effects. | ||
According to a pharmacological evaluation, the ''(±)-threo'' isomer of 4F-MPH is 2.15 times more effective at dopamine reuptake inhibition, and 2.7 times more at norepinephrine reuptake inhibition, than its parent compound methylphenidate. The ''(±)-erythro'' isomer, however, is 65 times less effective at dopamine reuptake inhibition and 45.6 times less effective at norepinephrine reuptake inhibition than methylphenidate. Neither racemate of 4F-MPH has a significant impact on serotonin reuptake.<ref>{{cite journal | vauthors=((McLaughlin, G.)), ((Morris, N.)), ((Kavanagh, P. V.)), ((Power, J. D.)), ((Dowling, G.)), ((Twamley, B.)), ((O’Brien, J.)), ((Hessman, G.)), ((Murphy, B.)), ((Walther, D.)), ((Partilla, J. S.)), ((Baumann, M. H.)), ((Brandt, S. D.)) | journal=Drug Testing and Analysis | title=Analytical characterization and pharmacological evaluation of the new psychoactive substance 4-fluoromethylphenidate (4F-MPH) and differentiation between the (±)- threo and (±)- erythro diastereomers: Analytical characterization and pharmacological evaluation of 4-fluoromethylphenidate | volume=9 | issue=3 | pages=347–357 | date= March 2017 | url=https://onlinelibrary.wiley.com/doi/10.1002/dta.2167 | issn=19427603 | doi=10.1002/dta.2167}}</ref> | |||
==Subjective effects== | ==Subjective effects== | ||
{{Preamble/SubjectiveEffects}} | {{Preamble/SubjectiveEffects}} | ||
{{effects/base | {{effects/base | ||
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|{{effects/physical| | |{{effects/physical| | ||
*'''[[Effect::Stimulation]]''' | *'''[[Effect::Stimulation]]''' - 4F-MPH is usually reported 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 [[methylphenidate]], [[modafinil]] and [[caffeine]]. At lower to moderate doses, it encourages general productivity but at higher dosages it can encourage physical activities such as dancing, socializing, running, or cleaning. The particular style of stimulation which 4F-MPH 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. This style of stimulation is extremely similar to [[methylphenidate]]. | ||
*'''[[Effect::Dehydration]]''' | *'''[[Effect::Dehydration]]''' | ||
*'''[[Effect::Appetite suppression]]''' | *'''[[Effect::Nausea]]''' - May occur at higher doses, although tends to fade after a short period. | ||
*'''[[Effect::Appetite suppression]]''' - This effect is reported to be less intense than [[amphetamine]] and [[methylphenidate]]. | |||
*'''[[Effect::Increased heart rate]]''' | *'''[[Effect::Increased heart rate]]''' | ||
*'''[[Effect::Abnormal heartbeat]]''' | *'''[[Effect::Abnormal heartbeat]]''' | ||
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*'''[[Effect::Teeth grinding]]''' - This component can be considered to be less intense when compared with that of [[MDMA]]. | *'''[[Effect::Teeth grinding]]''' - This component can be considered to be less intense when compared with that of [[MDMA]]. | ||
*'''[[Effect::Vasoconstriction]]''' | *'''[[Effect::Vasoconstriction]]''' | ||
*'''[[Effect::Increased libido]]''' | *'''[[Effect::Increased libido]]''' - Higher doses of 4F-MPH can increase sexual desire, although this enhancement is reported to be less intense and reliable than amphetamines and cocaine however stronger than normal methylphenidate. | ||
*'''[[Effect::Dizziness]]''' - May occur at higher doses, although tends to fade after a short period. | |||
*'''[[Effect::Spontaneous physical sensations]]''' | *'''[[Effect::Spontaneous physical sensations]]''' | ||
*'''[[Effect::Pupil dilation]]''' | |||
}} | }} | ||
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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::Anxiety]]''' | *'''[[Effect::Anxiety]]''' | ||
*'''[[Effect::Cognitive fatigue]]''' | *'''[[Effect::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. | ||
*'''[[Effect::Depression]]''' | *'''[[Effect::Depression]]''' | ||
*'''[[Effect::Irritability]]''' | *'''[[Effect::Irritability]]''' | ||
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Many users of this compound have reported positive, functional cognitive effects associated with the therapeutic aspect of traditional stimulants. This may owe to its similarities to [[methylphenidate]], in which these effects have been well-studied.{{citation needed}} | Many users of this compound have reported positive, functional cognitive effects associated with the therapeutic aspect of traditional stimulants. This may owe to its similarities to [[methylphenidate]], in which these effects have been well-studied.{{citation needed}} | ||
*'''[[Effect::Anxiety]]''' | *'''[[Effect::Anxiety]]''' - Anxiety with 4F-MPH is reported to be stronger and more common than that of other commonly used stimulants like [[amphetamine]] or [[cocaine]]. Similar to the closely related compound [[methylphenidate]]. | ||
*'''[[Effect::Analysis enhancement]]''' | *'''[[Effect::Analysis enhancement]]''' | ||
*'''[[Effect::Cognitive euphoria|Euphoria]]''' - The euphoric rush associated with 4F-MPH use (as result of [[dopamine]] [[reuptake inhibition]]) is very short-lived and compulsive, similar to that of [[cocaine]]. | *'''[[Effect::Cognitive euphoria|Euphoria]]''' - The euphoric rush associated with 4F-MPH use (as result of [[dopamine]] [[reuptake inhibition]]) is very short-lived and compulsive, similar to that of [[cocaine]].Although this rush is considered to be less reliably produced and intense than that of [[methamphetamine]]. | ||
*'''[[Effect:: | *'''[[Effect::Compulsive redosing]]''' - Compulsive redosing is reported but with less frequency than other common stimulants such as [[amphetamine]] or [[cocaine]], however at high or non-orally administered doses it is reported to be more common than the closely related compound [[methylphenidate]]. It is recommended to dose orally or set a limit to avoid using more than needed. | ||
*'''[[Effect::Ego inflation]]''' | *'''[[Effect::Ego inflation]]''' | ||
*'''[[Effect::Emotion suppression]]''' - This component has been reported as being more prominent than with other stimulants, and is in-line with the noted emotion-suppressing effects that have been observed with other stimulants, but particularly [[methylphenidate]] and related compounds. | *'''[[Effect::Emotion suppression]]''' - This component has been reported as being more prominent than with other stimulants, and is in-line with the noted emotion-suppressing effects that have been observed with other stimulants, but particularly [[methylphenidate]] and related compounds. | ||
*'''[[Effect::Focus enhancement]]''' - This component is most effective at low to moderate dosages as anything higher will usually impair concentration. | *'''[[Effect::Focus enhancement]]''' - This component is most effective at low to moderate dosages as anything higher will usually impair concentration. | ||
*'''[[Effect::Increased music appreciation]]''' | *'''[[Effect::Increased music appreciation]]''' | ||
*'''[[Effect::Time distortion]]''' - This can be described as the experience of time speeding up and passing much quicker than it usually would when sober. | |||
*'''[[Effect::Motivation enhancement]]''' | *'''[[Effect::Motivation enhancement]]''' | ||
*'''[[Effect::Memory enhancement]]''' | *'''[[Effect::Memory enhancement]]''' | ||
*'''[[Effect::Suggestibility suppression]]''' | |||
*'''[[Effect::Thought acceleration]]''' | *'''[[Effect::Thought acceleration]]''' | ||
*'''[[Effect::Thought organization]]''' - This component has been reported as being more prominent than with other stimulants, which has led some users to adopt it for productive or functional purposes rather than hedonic ones. | *'''[[Effect::Thought organization]]''' - This component has been reported as being more prominent than with other stimulants, which has led some users to adopt it for productive or functional purposes rather than hedonic ones. | ||
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===Experience reports=== | ===Experience reports=== | ||
There are currently no anecdotal reports which describe the effects of this compound within our [[experience index]]. Additional experience reports can be found here: | There are currently no anecdotal reports which describe the effects of this compound within our [[experience index]]. Additional experience reports can be found here: | ||
* [https://www.erowid.org/experiences/subs/exp_4Fluoromethylphenidate.shtml Erowid Experience Vaults: 4-Fluoromethylphenidate] | |||
*[https://www.erowid.org/experiences/subs/exp_4Fluoromethylphenidate.shtml Erowid Experience Vaults: 4-Fluoromethylphenidate] | |||
==Toxicity and harm potential== | ==Toxicity and harm potential== | ||
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===Tolerance and addiction potential=== | ===Tolerance and addiction potential=== | ||
In terms of its tolerance, 4F-MPH 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. | In terms of its tolerance, 4F-MPH 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. Tolerance is reported to build quicker than [[methylphenidate]]. | ||
4F-MPH 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. | 4F-MPH 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. | ||
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{{DangerousInteractions/Intro}} | {{DangerousInteractions/Intro}} | ||
{{DangerousInteractions/Stimulants|self=4F-MPH}} | {{DangerousInteractions/Stimulants|self=4F-MPH}} | ||
{{DangerousInteractions/MAOI|nt=dopamine}} | {{DangerousInteractions/MAOI|nt=dopamine}} | ||
== | ==Legal status== | ||
{{legalStub}} | {{legalStub}} | ||
*'''Germany''': 4-Fluoromethylphenidate | |||
*'''United Kingdom''': 4-Fluoromethylphenidate is a class B drug in the UK as of 31st May 2017 and is illegal to possess, produce or supply. <ref>The Misuse of Drugs Act 1971 (Amendment) Order 2017 | *'''Germany''': 4-Fluoromethylphenidate was 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>, but has been accidentally legalized in September 2022. It is considered to be legal again. | ||
*'''United States''': 4-Fluromethylphenidate is a Schedule I controlled substance in the state of Alabama.<ref> | *'''Italy''': 4F-MPH is a schedule I substance and is illegal to possess, produce, sell and buy. | ||
*'''Switzerland''': 4F-MPH 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-MPH is a classed as drug and is illegal to possess, produce, supply, or import.<ref>Cumhurbaşkanı Kararı Karar Sayısı : 1335 | https://resmigazete.gov.tr/eskiler/2019/07/20190720-19.pdf</ref> | |||
*'''United Kingdom''': 4-Fluoromethylphenidate is a class B drug in the UK as of 31st May 2017 and is 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> | |||
*'''United States''': 4-Fluromethylphenidate is a Schedule I controlled substance in the state of Alabama.<ref>{{Citation | title=Alabama SB333, 2014, Regular Session | url=https://legiscan.com/AL/text/SB333/id/988417}}</ref> | |||
==See also== | ==See also== | ||
*[[Responsible use]] | *[[Responsible use]] | ||
*[[Designer drug]] | *[[Designer drug]] | ||
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==External links== | ==External links== | ||
*[https://en.wikipedia.org/wiki/4-Fluoromethylphenidate 4F-MPH (Wikipedia)] | *[https://en.wikipedia.org/wiki/4-Fluoromethylphenidate 4F-MPH (Wikipedia)] | ||
*[https://isomerdesign.com/PiHKAL/explore.php?id=630 4F-MPH (Isomer Design)] | *[https://isomerdesign.com/PiHKAL/explore.php?id=630 4F-MPH (Isomer Design)] | ||
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==References== | ==References== | ||
<references /> | <references /> | ||
[[Category:Psychoactive substance]] | [[Category:Psychoactive substance]] | ||
[[Category:Phenidate]] | |||
[[Category:Research chemical]] | [[Category:Research chemical]] | ||
[[Category:Stimulant]] | [[Category:Stimulant]] | ||