Phenibut

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Structural formula
Structure of phenibut (β-phenyl-γ-aminobutyric acid)
1: 1 mixture of ( R ) -form (left) and ( S ) -form (right)
General
Surname Phenibut
other names
  • β-phenyl-γ-aminobutyric acid
  • ( RS ) -4-amino-3-phenylbutanoic acid ( IUPAC )
  • Fenibut
  • Phenybut
  • PhGABA
Molecular formula C 10 H 13 NO 2
External identifiers / databases
CAS number
EC number 214-079-6
ECHA InfoCard 100.012.800
PubChem 14113
ChemSpider 13491
DrugBank DB13455
Wikidata Q419559
Drug information
ATC code

N06 BX22

Drug class

Anxiolytic

Mechanism of action

GABA B agonist

properties
Molar mass
Physical state

firmly

Melting point

250–253  ° C (decomposition)

solubility
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315-319-335
P: ?
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Phenibut (also β-phenyl-γ-aminobutyric acid ) is a chemical compound from the group of phenylethylamines . As a derivative of the naturally occurring inhibitory neurotransmitter γ-aminobutyric acid ( GABA ), it is used as a dietary supplement. The extra phenyl ring allows the compound to cross the blood-brain barrier .

Phenibut was discovered in the former Soviet Union in the 1960s . Since then, it has been used there to treat post-traumatic stress disorders , anxiety and insomnia , among other things . The active ingredient is closely related to the muscle relaxant baclofen . Phenibut is legally marketed as a dietary supplement in the United States and some European countries .

The name Phenibut is the chemical name "β- Phenyl- l-γ-amino but derived tersäure".

history

Phenibut was first synthesized at the A. I. Heart Pedagogical Institute in Leningrad by Vsevolod Perekalin's team at the Institute of Experimental Medicine and then tested at the Academy of Medical Sciences of the USSR .

Clinical information

application areas

Phenibut is approved in Russia , Latvia and other Eastern European countries for the treatment of:

and is used preventively

Dosis, kind and Time of the Use

The dose varies between the different areas of application. For anxiety and agitation, the daily dose is between 750 mg and 1500 mg given three times a day. The duration of use is 2-3 weeks and can be extended to 4-6 weeks if necessary.

Side effects

Fatigue and nausea occur especially at the beginning of treatment or in the event of an overdose. Allergic reactions are rare. Phenibut has a hepatotoxic potential when used for a longer period or at a higher dose , so liver values may need to be checked .

Cases of tolerance development and dependence as well as withdrawal symptoms have been described in the literature, but no randomized controlled trial has been carried out in this area.

The cases documented so far showed withdrawal symptoms, which are also observed with benzodiazepines and can include insomnia , hallucinations and anxiety among other things .

pharmacology

Similar to the structurally related baclofen, phenibut acts as an agonist at the GABA B receptor . This distinguishes the active ingredient from the benzodiazepines , which act as allosteric ligands on the GABA A receptor. Phenibut may also bind to GABA A receptors in higher doses . Animal experiments provide evidence of an additional dopaminergic mechanism of action.

In animal studies, Phenibut has been found to improve interhemispheric transmission between the two halves of the brain; these effects confirm the positive effect of phenibut on the learning and memory processes and the status as a nootropic .

Animal experiments have also shown that phenibut citrate can reduce the harmful effects of alcohol by increasing oxidative phosphorylation .

Phenibut is a chiral molecule . There is thus an ( R ) - and an ( S ) - enantiomer . It is used pharmaceutically as a racemate . ( R ) -Phenibut is the pharmacologically active enantiomer, the eutomer . ( S ) -Phenibut is not active. The dissociation constants at the GABA B receptor for ( RS ) -phenibut, ( R ) -phenibut and baclofen are 177 ± 2, 92 ± 3 and 6 ± 1 μM, respectively. This means that baclofen has the highest affinity for the receptor and racemic phenibut the lowest.

After a single dose of 250 mg phenibut, a plasma half-life of 5.3 hours was determined. 65% of the dose was found unchanged in the urine.

Legal situation in German-speaking countries

This article or the following section is not adequately provided with supporting documents ( e.g. individual evidence ). Information without sufficient evidence could be removed soon. Please help Wikipedia by researching the information and including good evidence.

Phenibut is not covered by the BtMG or the AMG in Germany . There is constant controversy as to whether Phenibut is subject to the NPSG . The ligand R6 indicates a ban. This is an alkyl group, which is listed in section 1.2 b). As a counter-argument, reference is made to the carboxyl group that follows, which is not listed. The legal situation is still unclear. However , there are known cases where imported phenibut has been confiscated by customs .

Individual evidence

  1. ↑ J. Colonge, J.-M. Pouchol: Preparation De Pyrrolidones-2 et de Gamma-Aminoacides . In: Bulletin de la Societe Chimique de France . 1962, p. 598-603 .
  2. ↑ a b Patent DE2317180 : SS-Phenyl-Kleines Gamma-Aminobuttersaeurehydrochlorid and process for its production. Published October 17, 1974 , inventor: Perekalin Vsevolod Wasiljewits; Sopowa born Krutova Alexandra S; Lobacheva born Varlamowa Majj; Bung Gajlite Rasma Janow; Mikstajs Uldis Janowitsch. ‌
  3. ↑ Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of 4-amino-3-phenylbutyric acid in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 21, 2019, is reproduced from a self-classification by the distributor .
  4. ↑ a b c d Izyaslav Lapin: Phenibut (β-Phenyl-GABA): A Tranquilizer and Nootropic Drug . In: CNS Drug Reviews . tape 7 , no. 4 , December 2001, p. 471-481 , doi : 10.1111 / j.1527-3458.2001.tb00211.x , PMID 11830761 .
  5. ↑ GI Shulgina: On neurotransmitter mechanisms of reinforcement and internal inhibition . In: The Pavlovian Journal of Biological Science . tape 21 , no. 4 , December 1, 1986, pp. 129-140 , PMID 2431377 .
  6. ↑ a b Andriy V. Samokhvalov, C. Lindsay Paton Gay, Kam Balchand, Jürgen Rehm: dependence Phenibut . In: BMJ Case Reports . tape 2013 , February 7, 2013, p. bcr2012008381 , doi : 10.1136 / bcr-2012-008381 .
  7. ↑ a b c d Package insert Noofen 250 mg ( Memento from January 6, 2014 in the Internet Archive ) (PDF).
  8. ↑ Rhanda Marie M. Magsalin, Ahsan Khan Y.: Withdrawal symptoms after Internet purchase of Phenibut (β-phenyl-γ-aminobutyric acid HCl) . In: Journal of Clinical Psychopharmacology . tape 30 , no. 5 , October 2010, p. 648-649 , doi : 10.1097 / JCP.0b013e3181f057c8 , PMID 20841974 .
  9. ^ Entry by Phenibut on Gigas Nutrition accessed on September 17, 2019.
  10. ↑ Phenibut - the underdog among nootropics.Accessed September 17, 2019.
  11. ↑ Borodkina LE, Molodavkin GM, Tiurenkov IN .: Effect of phenibut on interhemispheric transmission in the rat brain . In: Eksp Klin Farmakol. 2009 Jan-Feb; 72 (1): 57-9. PMID 19334513 .
  12. ↑ VN Perfilova, OV Ostrovskii u. a .: Effect of Citrocard on functional activity of cardiomyocyte mitochondria during chronic alcohol intoxication. In: Bulletin of experimental biology and medicine. Volume 143, Number 3, March 2007, pp. 341-343, PMID 18225758 .
  13. ↑ Maija Dambrova, Liga Zvejniece, Edgars Liepinsh, Helena Cirule, Olga Zharkova, Grigory Veinberg, Ivars Kalvinsh: Comparative pharmacological activity of optical isomers of phenibut . In: European Journal of Pharmacology . tape 583 , no. 1 , March 31, 2008, p. 128-134 , doi : 10.1016 / j.ejphar.2008.01.015 , PMID 18275958 .
  14. ↑ Annex NpSG - individual standard. Retrieved June 20, 2020 .