F-Phenibut: Difference between revisions
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{{SubstanceBox/F-Phenibut}} | {{SubstanceBox/F-Phenibut}} | ||
'''F-Phenibut''' (also known as '''Fluorophenibut''', and ''' | '''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. | ||
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== | ||
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> | 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== | ||
[[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> | |||
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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*'''[[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::Temperature regulation loss]]''' | *'''[[Effect::Temperature regulation loss]]''' | ||
*'''[[Effect::Headaches]]''' - Moderate to high doses have been reported to | *'''[[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]]''' | ||
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|{{effects/cognitive| | |{{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 | *'''[[Effect::Compulsive redosing]]''' - This component is highly pronounced in comparison to [[phenibut]]. | ||
*'''[[Effect::Disinhibition]]''' | *'''[[Effect::Disinhibition]]''' | ||
*'''[[Effect:: | *'''[[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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{{#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: | |||
*[https://erowid.org/experiences/subs/exp_Smarts_Fluorophenibut.shtml Erowid Experience Vaults: Fluorophenibut] | |||
==Toxicity and harm potential== | ==Toxicity and harm potential== | ||
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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"> | [[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. | ||
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==Legal issues== | ==Legal issues== | ||
{{LegalStub}} | {{LegalStub}} | ||
*'''United Kingdom''' | |||
*'''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://en.wikipedia.org/wiki/4-Fluorophenibut 4-Fluorophenibut (Wikipedia)] | *[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: | [[Category:Gamma-Amino acid]] | ||
[[Category:Phenethylamine]] | |||
[[Category:Depressant]] | [[Category:Depressant]] | ||
[[Category:Anxiolytics]] | |||
[[Category:Nootropic]] | [[Category:Nootropic]] | ||
[[Category:Gabapentinoid]] | [[Category:Gabapentinoid]] | ||
[[Category:Research chemical]] | |||
{{#set:Featured=true}} | {{#set:Featured=true}} |