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{{SummarySheet}}
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| ''[[F-Phenibut/Summary|Summary sheet: F-Phenibut]]''
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'''F-Phenibut''' (also known as '''fluorophenibut''', '''fluorobut''', or '''fphenibut''') is a central nervous system [[psychoactive class::depressant]] and close analogue of its popular predecessor [[phenibut]]. F-Phenibut possesses an effect profile nearly identical to [[phenibut]] but with a several-fold increased potency in its active dose. This also includes a significantly quicker [[onset]] as well as a shorter [[duration|total duration]]. Very little is known about this substance, particularly [[Research chemicals#Toxicity and harm potential|its potential toxicity]] and addiction potential, but it has recently become available through online [[research chemical]] vendors.


In terms of its pharmacology, this compound can be classified as a [[GABApentinoid |gabapentinoid]], a class which contains other drugs such as  
'''F-Phenibut''' (also known as '''4-Fluorophenibut''', '''Fluorophenibut''', '''Fluorobut''', '''Baflofen''' and '''CGP-11130''') is a central nervous system [[psychoactive class::depressant]] and closely related structural analog of [[phenibut]]. F-Phenibut possesses an effect profile similar to [[phenibut]] but with a faster [[onset]], significantly increased potency, and shorter [[duration|total duration]].{{citation needed}} It has recently become available through online [[research chemical]] vendors, although little is known about this substance, particularly [[Research chemicals#Toxicity and harm potential|its potential toxicity]] and addiction potential.
[https://en.wikipedia.org/wiki/Baclofen baclofen], [[pregabalin]], [[gabapentin]], and [https://en.wikipedia.org/wiki/Gamma-Amino-beta-hydroxybutyric_acid GABOB].<ref name="one">Lapin, I. (2001). "Phenibut (beta-phenyl-GABA): A tranquilizer and nootropic drug" (pdf). CNS Drug Reviews | http://onlinelibrary.wiley.com/doi/10.1111/j.1527-3458.2001.tb00211.x/pdf</ref><ref>"Wyllie's Treatment of Epilepsy: Principles and Practice" | https://books.google.co.uk/books?id=j9t6Qg0kkuUC&pg=RA1-PA423&redir_esc=y#v=onepage&q&f=false</ref><ref>"Practical Management of Pain. Elsevier Health Sciences" | https://books.google.co.uk/books?id=kfcDAQAAQBAJ&pg=PA1006&redir_esc=y#v=onepage&q&f=false</ref> Fluorophenibut, like its parent compound, is a derivative of the naturally occurring inhibitory neurotransmitter γ-aminobutyric acid ([[GABA]]), but with an addition of a phenyl ring that allows it to cross the blood–brain barrier.<ref name="one">Lapin, I. (2001). "Phenibut (beta-phenyl-GABA): A tranquilizer and nootropic drug" (pdf). CNS Drug Reviews | http://onlinelibrary.wiley.com/doi/10.1111/j.1527-3458.2001.tb00211.x/pdf</ref>
 
The substance can be classified as a [[GABApentinoid |gabapentinoid]], a class which contains other substances such as [[gabapentin]], [[pregabalin]]<ref>{{cite book | vauthors=((Wyllie, E.)), ((Cascino, G. D.)), ((Gidal, B. E.)), ((Goodkin, H. P.)) | date=17 February 2012 | title=Wyllie’s Treatment of Epilepsy: Principles and Practice | publisher=Lippincott Williams & Wilkins | isbn=9781451153484}}</ref>, [[baclofen]], and [https://en.wikipedia.org/wiki/Gamma-Amino-beta-hydroxybutyric_acid GABOB].<ref name="one">{{cite journal | vauthors=((Lapin, I.)) | journal=CNS Drug Reviews | title=Phenibut (β-Phenyl-GABA): A Tranquilizer and Nootropic Drug | volume=7 | issue=4 | pages=471–481 | date=7 June 2006 | url=https://onlinelibrary.wiley.com/doi/10.1111/j.1527-3458.2001.tb00211.x | issn=1080563X | doi=10.1111/j.1527-3458.2001.tb00211.x}}</ref><ref>{{cite book | vauthors=((Benzon, H.)), ((Rathmell, J. P.)), ((Wu, C. L.)), ((Turk, D.)), ((Argoff, C. E.)), ((Hurley, R. W.)) | date=11 September 2013 | title=Practical Management of Pain E-Book | publisher=Elsevier Health Sciences | isbn=9780323170802}}</ref> It is a derivative of the naturally occurring inhibitory neurotransmitter γ-aminobutyric acid ([[GABA]]), with an addition of a phenyl ring that allows it to cross the blood–brain barrier.<ref name="one" />
 
==Chemistry==
==Chemistry==
F-phenibut is a derivative of GABA with a fluorine-substituted phenyl group in the β-position. It is a chiral molecule and thus has two potential configurations as (R)- and (S)-enantiomers.<ref>"Comparative pharmacological activity of optical isomers of phenibut." | https://www.ncbi.nlm.nih.gov/pubmed/18275958</ref> It has an almost identical chemical structure to baclofen (only replacing a chlorine with a fluorine atom in the para-position of the phenyl group).<ref>On neurotransmitter mechanisms of reinforcement and internal inhibition. | https://www.ncbi.nlm.nih.gov/pubmed/2431377</ref> Additionally, the widely prescribed gabapentinoid [[pregabalin]] also possesses a similar structure as phenibut, except that the phenyl group is instead replaced with an isobutyl group.
As with [[phenibut]], F-Phenibut is a derivative of [[GABA]], except with a fluorine-substituted phenyl group in the β-position of the molecule. It is a chiral molecule and thus has two potential configurations as (R)- and (S)-enantiomers.<ref>{{cite journal | vauthors=((Dambrova, M.)), ((Zvejniece, L.)), ((Liepinsh, E.)), ((Cirule, H.)), ((Zharkova, O.)), ((Veinberg, G.)), ((Kalvinsh, I.)) | journal=European Journal of Pharmacology | title=Comparative pharmacological activity of optical isomers of phenibut | volume=583 | issue=1 | pages=128–134 | date=31 March 2008 | issn=0014-2999 | doi=10.1016/j.ejphar.2008.01.015}}</ref> It has an almost identical chemical structure to baclofen (only replacing a chlorine with a fluorine atom in the para-position of the phenyl group).<ref>{{cite journal | vauthors=((Shulgina, G. I.)) | journal=The Pavlovian Journal of Biological Science | title=On neurotransmitter mechanisms of reinforcement and internal inhibition | volume=21 | issue=4 | pages=129–140 | date= December 1986 | issn=0093-2213 | doi=10.1007/BF02734511}}</ref> Additionally, the widely prescribed gabapentinoid [[pregabalin]] also possesses a similar structure as phenibut, except that the phenyl group is instead replaced with an isobutyl group in the S configuration. F-Phenibut is water soluble.


==Pharmacology==
==Pharmacology==
Due to the lack of research regarding the substance, all discussion regarding the pharmacology of it is purely speculation based upon its structural and subjective effect similarities to other [[depressants]] or [[gabapentinoid]] such as [[phenibut]], [[gabapentin]], and [[pregabalin]].
[[F-Phenibut/Summary|F-phenibut]] acts as a potent agonist of the GABA-B receptor and in this regard is more similar to [[baclofen]] than [[phenibut]].<ref>{{cite journal | vauthors=((Irie, T.)), ((Yamazaki, D.)), ((Kikura-Hanajiri, R.)) | journal=European Journal of Pharmacology | title=F-phenibut (β-(4-Fluorophenyl)-GABA), a potent GABAB receptor agonist, activates an outward-rectifying K+ current and suppresses the generation of action potentials in mouse cerebellar Purkinje cells | volume=884 | pages=173437 | date=5 October 2020 | url=https://www.sciencedirect.com/science/article/pii/S001429992030529X | issn=0014-2999 | doi=10.1016/j.ejphar.2020.173437}}</ref>


Among other things, it is likely that this compound exerts its effects by binding to the α2δ-1 site of voltage-gated calcium channels in a manner which is similar to that of other gabapentinoids. By binding to this site, F-Phenibut may reduce the release of several excitatory [[neurotransmitter]]s, including [[glutamate]], [[substance P]], [[acetylcholine]], and [[norepinephrine]]. This, in turn, increases [[GABA]]ergic activity.{{citation needed}} As the GABA system is the most prevalent inhibitory receptor set within the brain{{citation needed}}, its modulation may be responsible for the relaxing, sedating, and calming effects of F-Phenibut on the central nervous system.
It is also possible that F-Phenibut binds to the α2δ-1 site of voltage-gated calcium channels in a manner similar to that of other [[gabapentinoids]]. By binding to this site, F-Phenibut may reduce the release of several excitatory [[neurotransmitter]]s, including [[glutamate]], [[substance P]], [[acetylcholine]], and [[norepinephrine]]. This, in turn, increases [[GABA]]ergic activity.{{citation needed}} As the GABA system is the most prevalent inhibitory receptor set within the brain{{citation needed}}, its modulation may be responsible for the relaxing, sedating, and calming effects of F-Phenibut on the central nervous system.


==Subjective effects==
==Subjective effects==
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In comparison to regular [[phenibut]], this compound has a significantly faster onset, a shorter duration, and slightly less stimulation. Early reports suggest that in comparison to other commonly used [[GABA]]genic depressants such as [[alcohol]] or [[benzodiazepines]], this compound produces less inebriation and more euphoria, giving it more recreational potential as well as a correspondingly higher risk of abuse.
In comparison to regular [[phenibut]], this compound has a significantly faster onset, a shorter duration, and slightly less stimulation. Early reports suggest that in comparison to other commonly used [[GABA]]genic depressants such as [[alcohol]] or [[benzodiazepines]], this compound produces less inebriation and more euphoria, giving it more recreational potential as well as a correspondingly higher risk of abuse.


===Physical effects===
{{effects/base
|{{effects/physical|
*'''[[Effect::Stimulation]]''' and '''[[Effect::Sedation]]''' - At lower doses, F-Phenibut has a mild physical and mental stimulation effect, encouraging movement, wakefulness, productivity and socialization. At higher doses, however, it becomes physically sedating, encouraging sleep and lethargy. Sleeping after dosing a small amount may result in a deep, restful sleep which can leave the user feeling refreshed and alert upon waking.
*'''[[Effect::Stimulation]]''' and '''[[Effect::Sedation]]''' - At lower doses, F-Phenibut has a mild physical and mental stimulation effect, encouraging movement, wakefulness, productivity and socialization. At higher doses, however, it becomes physically sedating, encouraging sleep and lethargy. Sleeping after dosing a small amount may result in a deep, restful sleep which can leave the user feeling refreshed and alert upon waking.
*'''[[Effect::Physical euphoria]]'''
*'''[[Effect::Physical euphoria]]'''
*'''[[Effect::Respiratory depression]]'''
*'''[[Effect::Respiratory depression]]'''
*'''[[Effect::Nausea]]''' - F-Phenibut can induce mild to extreme nausea depending greatly on dose and tolerance. It usually manifests roughly 5 hours after the initial dose and generally involves waves of nausea accompanied by excessive sweating and vomiting.
*'''[[Effect::Nausea]]''' - F-Phenibut can induce mild to extreme nausea depending greatly on dose and tolerance. It usually manifests roughly 90 minutes after the initial dose and generally involves waves of nausea accompanied by excessive sweating and vomiting.
*'''[[Effect::Motor control loss]]'''
*'''[[Effect::Motor control loss]]'''
*'''[[Effect::Stomach cramps]]'''
*'''[[Effect::Stomach cramps]]'''
*'''[[Effect::Dizziness]]'''
*'''[[Effect::Dizziness]]'''
*'''[[Effect::Increased perspiration]]'''
*'''[[Effect::Dehydration]]''' - Dehydration is typically reported to occur from regular multiday usage or excessive doses; however, it can also be present even in average doses of the substance (although perhaps to a lesser degree than phenibut).
*'''[[Effect::Dehydration]]''' - Dehydration is typically reported to occur from regular multiday usage or excessive doses; however, it can also be present even in average doses of the substance (although perhaps to a lesser degree than phenibut).
*'''[[Effect::Headaches]]''' - Moderate to high doses have been reported to be a induce a mild to strong headache, typically many hours after dosing or during the comedown period.
*'''[[Effect::Temperature regulation loss]]'''
*'''[[Effect::Headaches]]''' - Moderate to high doses have been reported to induce a mild to strong headache, typically many hours after dosing or during the comedown period.
*'''[[Effect::Muscle cramps]]''' - Muscle cramps and joint pain are sometimes accompanied at high doses.
*'''[[Effect::Muscle cramps]]''' - Muscle cramps and joint pain are sometimes accompanied at high doses.
*'''[[Effect::Frequent urination]]'''
*'''[[Effect::Frequent urination]]'''
*'''[[Effect::Appetite enhancement]]'''
*'''[[Effect::Appetite enhancement]]'''


===Cognitive effects===
}}
 
|{{effects/cognitive|
*'''[[Effect::Empathy, love, and sociability enhancement]]''' - Unlike [[alcohol]] which merely increases sociability through [[disinhibition]], F-Phenibut presents entactogenic effects which, although much weaker than that of traditional [[entactogens]] such as [[MDMA]], are still prominent and well-defined even at moderate doses.
*'''[[Effect::Empathy, love, and sociability enhancement]]''' - Unlike [[alcohol]] which merely increases sociability through [[disinhibition]], F-Phenibut presents entactogenic effects which, although much weaker than that of traditional [[entactogens]] such as [[MDMA]], are still prominent and well-defined even at moderate doses.
*'''[[Effect::Compulsive redosing]]''' - This component is highly pronounced in comparison to [[phenibut]].
*'''[[Effect::Disinhibition]]'''
*'''[[Effect::Disinhibition]]'''
*'''[[Effect::Information processing suppression]]''' - High doses will usually induce a state of mild stupor and confusion.
*'''[[Effect::Analysis suppression]]''' - High doses will usually induce a state of mild stupor and confusion.
*'''[[Effect::Thought deceleration]]'''
*'''[[Effect::Thought deceleration]]'''
*'''[[Effect::Cognitive euphoria]]'''
*'''[[Effect::Cognitive euphoria]]'''
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*'''[[Effect::Anxiety suppression]]'''
*'''[[Effect::Anxiety suppression]]'''
*'''[[Effect::Depression]]''' - A low mood can be experienced as an after effect of high or frequent dosing.
*'''[[Effect::Depression]]''' - A low mood can be experienced as an after effect of high or frequent dosing.
*'''[[Effect::Amnesia]]''' - In comparison to many other GABAergics, this component is very weak except at very high doses
*'''[[Effect::Amnesia]]''' - In comparison to many other GABAergics, this component is very weak except at very high doses.
*'''[[Effect::Increased music appreciation]]'''
*'''[[Effect::Increased music appreciation]]'''
}}


}}
===Experience reports===
===Experience reports===
Anecdotal reports which describe the effects of this compound within our [[experience index]] include:
Anecdotal reports which describe the effects of this compound within our [[experience index]] include:
{{#ask: [[Category:F-Phenibut]][[Category:Experience]]|format=ul|Columns=1}}
{{#ask: [[Category:F-Phenibut]][[Category:Experience]]|format=ul|Columns=1}}
Additional experience reports can be found here:
Additional experience reports can be found here:
* [https://erowid.org/experiences/subs/exp_Smarts_Fluorophenibut.shtml Erowid Experience Vaults: Phenibut]
 
*[https://erowid.org/experiences/subs/exp_Smarts_Fluorophenibut.shtml Erowid Experience Vaults: Fluorophenibut]


==Toxicity and harm potential==
==Toxicity and harm potential==
{{Main|Research chemicals#Toxicity and harm potential}}
{{Further|Research chemicals#Toxicity and harm potential}}
F-Phenibut likely has a [[Toxicity::low toxicity]] relative to dose. However, it is [[Toxicity::potentially [[respiratory depression|lethal]] when mixed with [[depressants]] like [[alcohol]], [[benzodiazepines]] or [[opioids]]]].
F-Phenibut likely has a [[Toxicity::low toxicity]] relative to dose. However, it is [[Toxicity::potentially [[respiratory depression|lethal]] when mixed with [[depressants]] like [[alcohol]], [[benzodiazepines]] or [[opioids]]]].


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Tolerance will develop to the sedative-hypnotic effects [[Time to full tolerance::within a couple of days of continuous use]]. After cessation, the tolerance returns to baseline in [[Time to zero tolerance::7 - 14 days]]. Withdrawal symptoms or rebound symptoms may occur after ceasing usage abruptly following a few weeks or longer of steady dosing and may necessitate a [[tapering|gradual dose reduction]].
Tolerance will develop to the sedative-hypnotic effects [[Time to full tolerance::within a couple of days of continuous use]]. After cessation, the tolerance returns to baseline in [[Time to zero tolerance::7 - 14 days]]. Withdrawal symptoms or rebound symptoms may occur after ceasing usage abruptly following a few weeks or longer of steady dosing and may necessitate a [[tapering|gradual dose reduction]].


[[Withdrawal effects|Withdrawal symptoms]] likely include severe [[anxiety]], nervousness, hallucinations, tremors, agitation, [[dizziness]], tension, irritation, [[increased heart rate|rapid heartbeat]], [[physical fatigue|fatigue]], loss of appetite, [[nausea]], vomiting, [[psychosis]], and [[insomnia]] in a similar manner to phenibut.<ref name="three">David W. Group (25 February 2015). Encyclopedia of Mind Enhancing Foods, Drugs and Nutritional Substances, 2d ed. McFarland. pp. 186–. | https://books.google.co.uk/books?id=ZYqoBgAAQBAJ&pg=PA186&hl=en#v=onepage&q&f=false</ref>
[[Withdrawal effects|Withdrawal symptoms]] likely include severe [[anxiety]], nervousness, hallucinations, tremors, agitation, [[dizziness]], tension, irritation, [[increased heart rate|rapid heartbeat]], [[physical fatigue|fatigue]], loss of appetite, [[nausea]], vomiting, [[psychosis]], and [[insomnia]] in a similar manner to phenibut.<ref name="three">{{cite book | vauthors=((Group, D. W.)) | date=25 February 2015 | title=Encyclopedia of Mind Enhancing Foods, Drugs and Nutritional Substances, 2d ed. | publisher=McFarland | isbn=9780786441426}}</ref>


F-Phenibut presents cross-tolerance with [[Cross-tolerance::all [[GABA]]genic depressants]], meaning that after its consumption most depressants will have a reduced effect.
F-Phenibut presents cross-tolerance with [[Cross-tolerance::all [[GABA]]genic depressants]], meaning that after its consumption most depressants will have a reduced effect.


===Dangerous interactions===
===Dangerous interactions===
Although many substances 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. [https://www.google.com/ Independent research] should always be done to ensure that a combination of two or more substances is safe before consumption.
{{DangerousInteractions/Intro}}
*'''[[Depressants]]''' (''[[1,4-Butanediol]], [[2-methyl-2-butanol]], [[alcohol]], [[barbiturates]], [[GHB]]/[[GBL]], [[methaqualone]], [[opioids]]'') - This combination can result in dangerous or even fatal levels of [[respiratory depression]]. These substances potentiate the [[muscle relaxation]], [[sedation]] and [[amnesia]] caused by one another and can lead to unexpected loss of consciousness at high doses. There is also an increased risk of vomiting during unconsciousness and death from the resulting suffocation. If this occurs, users should attempt to fall asleep in the [[recovery position]] or have a friend move them into it.
{{DangerousInteractions/Depressants}}
*'''[[Dissociatives]]''' - This combination can result in an increased risk of vomiting during unconsciousness and death from the resulting suffocation. If this occurs, users should attempt to fall asleep in the [[recovery position]] or have a friend move them into it.
*'''[[Stimulants]]''' - It is dangerous to combine F-Phenibut with [[stimulant]]s due to the risk of excessive intoxication. Stimulants decrease the [[sedation|sedative]] effect of F-Phenibut, which is the main factor most people consider when determining their level of intoxication. Once the stimulant wears off, the effects of F-Phenibut will be significantly increased, leading to intensified [[disinhibition]] as well as [[F-Phenibut#Subjective effects|other effects]]. If combined, one should strictly limit themselves to only using a certain amount of F-Phenibut per hour. This combination can also potentially result in severe dehydration if hydration is not monitored.


==Legal issues==
==Legal issues==
{{LegalStub}}
{{LegalStub}}
*'''United Kingdom''' - It may be illegal to produce, supply, or import this substance under the Psychoactive Substance Act 2016, which blanketly applies the aforementioned restrictions on all "psychoactive substances" with exemptions for alcohol, nicotine and "medicinal products."<ref>Psychoactive Substances Act 2016 (Legislation.gov.uk) | http://www.legislation.gov.uk/ukpga/2016/2/contents/enacted</ref>
 
*'''Germany:''' F-Phenibut is not a controlled substance under the BtMG.<ref>{{Citation | title=Anlage I BtMG - Einzelnorm | url=http://www.gesetze-im-internet.de/btmg_1981/anlage_i.html}}</ref> It is legal, as long as it is not sold for human consumption, according to §2 AMG.<ref>{{Citation | title=§ 2 AMG - Einzelnorm | url=https://www.gesetze-im-internet.de/amg_1976/__2.html}}</ref>
*'''Switzerland''': F-Phenibut is not controlled under Buchstabe A, B, C and D. It could be considered legal.<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>
*'''United Kingdom:''' It may be illegal to produce, supply, or import this substance under the Psychoactive Substance Act 2016, which blanketly applies the aforementioned restrictions on all "psychoactive substances" with exemptions for alcohol, nicotine and "medicinal products."<ref>{{Citation | title=Psychoactive Substances Act 2016 | url=https://www.legislation.gov.uk/ukpga/2016/2/contents/enacted}}</ref>


==See also==
==See also==
*[[Responsible use]]
*[[Responsible use]]
*[[Research chemical]]
*[[Research chemical]]
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==External links==
==External links==
*[https://erowid.org/experiences/subs/exp_Smarts_Fluorophenibut.shtml F-Phenibut (Erowid Experiences)]
 
*[https://en.wikipedia.org/wiki/4-Fluorophenibut 4-Fluorophenibut (Wikipedia)]
*[https://isomerdesign.com/PiHKAL/explore.php?id=628 F-Phenibut (Isomer Design)]


==References==
==References==
<references/>
<references />
 
[[Category:Psychoactive substance]]
[[Category:Psychoactive substance]]
[[Category:Gamma-Amino acid]]
[[Category:Phenethylamine]]
[[Category:Depressant]]
[[Category:Depressant]]
[[Category:Anxiolytics]]
[[Category:Nootropic]]
[[Category:Gabapentinoid]]
[[Category:Research chemical]]
{{#set:Featured=true}}
{{#set:Featured=true}}
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