Phenylpiracetam

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Phenylpiracetam
Clinical data
Trade namesPhenotropil; Carphedon
Pregnancy
category
  • Unknown
Routes of
administration		Oral (tablets)
ATC code
  • None
Legal status
Legal status
  • AU: S4 (Prescription only)
  • US: Unapproved "New Drug" (as defined by 21 U.S. Code § 321(p)(1)). Use in dietary supplements, food, or medicine is unlawful; otherwise uncontrolled.
  • RU: Rx-only
Pharmacokinetic data
Bioavailability~100%
MetabolismNone
Onset of action20-40 minutes
Elimination half-life3–5 hours
ExcretionUrine (~40%), bile and perspiration (~60%)
Identifiers
  • (R,S)-2-(2-oxo-4-phenylpyrrolidin-1-yl)acetamide
JSmol)
ChiralityRacemic mixture
Boiling point486.4 °C (907.5 °F)
  • C1=CC=CC=C1C2CN(C(C2)=O)CC(=O)N
  • InChI=1S/C12H14N2O2/c13-11(15)8-14-7-10(6-12(14)16)9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H2,13,15) ☒N
  • Key:LYONXVJRBWWGQO-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Phenylpiracetam (

psychopharmacologist Valentina Ivanovna Akhapkina (Валентина Ивановна Ахапкина).[2][unreliable source?] In Russia it is now available as a prescription drug. Research on animals has indicated that phenylpiracetam may have anti-amnesic, antidepressant, anticonvulsant, anxiolytic, and memory enhancement effects.[3][4]

Human research

Phenylpiracetam is typically prescribed as a general stimulant or to increase tolerance to extreme temperatures and stress.[5]

A few small clinical studies have shown possible links between prescription of phenylpiracetam and improvement in a number of encephalopathic conditions, including lesions of cerebral blood pathways, traumatic brain injury and certain types of glioma.[6]

Phenylpiracetam has been researched for the treatment of Parkinson's disease.[7]

Clinical trials were conducted at the Serbsky State Scientific Center for Social and Forensic Psychiatry. The

Russian Center of Vegetative Pathology are reported to have confirmed the effectiveness of Phenylpiracetam(Phenytropil) describing the following effects: improvement of regional blood flow in ischemic regions of the brain, reduction of depressive and anxiety disorders, increase the resistance of brain tissue to hypoxia and toxic effects, improving concentration and mental activity, a psychoactivating(sic) effect, increase in the threshold of pain sensitivity, improvement in the quality of sleep, and an anticonvulsant action, though with the side effect of an anorexic effect in extended use.[2][unreliable source?
]

Animal Model Research

Phenylpiracetam has been shown to reverse the depressant effects of the benzodiazepine diazepam, increases operant behavior, inhibits post-rotational nystagmus, prevents retrograde amnesia, and has anticonvulsant properties in animal models.[3][8][9]

In

carotid arteries to a greater extent than did piracetam.[10]

Operant behavior

In tests against a

d-amphetamine
, and phenylpiracetam. Rats administered 100 mg/kg phenylpiracetam performed, on average, 375% more work than rats given placebo, and consumed little non-preferred rat chow. In comparison, rats administered 1mg/kg d-amphetamine or 10 mg/kg methylphenidate performed, on average, 150% and 170% more work respectively, and consumed half as much non-preferred rat chow.

Present data show that (R)-phenylpiracetam increases motivation, i.e., the work load, which animals are willing to perform to obtain more rewarding food. At the same time consumption of freely available normal food does not increase. Generally this indicates that (R)-phenylpiracetam increase motivation [...] The effect of (R)-phenylpiracetam is much stronger than that of methylphenidate and amphetamine.[11]

Pharmacology

Phenylpiracetam binds to

α4β2
nicotinic acetylcholine receptors in the mouse brain cortex with IC50 = 5.86 μM.[8]

Experiments performed on

sleep disorders showed an increase in extracellular dopamine levels after administration. The patent asserts discovery of phenylpiracetam's action as a dopamine reuptake inhibitor[11]
as its basis.

The peculiarity of this invention compared to former treatment approaches for treating sleep disorders is the so far unknown therapeutic efficacy of (R)-phenylpiracetam, which is presumably based at least in part on the newly identified activity of (R)-phenylpiracetam as the dopamine re-uptake inhibitor

Both enantiomers of phenylpiracetam have been described in peer-reviewed research as

noradrenaline reuptake inhibitor (thus, an NDRI) with 11-fold lower affinity to NET than to DAT, while the S enantiomer has no such effect.[13]

History

Pilot-cosmonaut Aleksandr Serebrov described being issued and using Phenylpiracetam, as well as it being included in the Soyuz spacecraft's standard emergency medical kit, during his 197-days working in space aboard the Mir space station. He reported "the drug acts as the equalizer of the whole organism, "tidying it up", completely excluding impulsiveness and irritability inevitable in the stressful conditions of space flight."[2]

Availability

Phenotropil
Phenotropil 100 mg from Russia

While not prescribed as a pharmaceutical in the West, in Russia it is available as a prescription medicine under names Phenotropil, Actitropil, Nanotropil.

Phenylpiracetam is not scheduled by the U.S. Drug Enforcement Administration.[14]

Athlete doping

Phenylpiracetam has been shown to possess a stimulant action in animal models and thus appears on the list of stimulants banned for in-competition use by the World Anti-Doping Agency. This list is applicable in all Olympic sports.[15][11]

See also

References

  1. ^ "WHO Drug Information, Vol. 24, No. 1, 2010" (PDF). p. 56. Archived from the original (PDF) on May 21, 2014. Retrieved 31 December 2015.
  2. ^ a b c "Фенотропил: закономерное лидерство" [Phenotropil: natural leadership]. Medi.ru (in Russian). Archived from the original on August 6, 2017. Retrieved July 24, 2023.
  3. ^
    S2CID 12176745
    .
  4. PMID 21689376
    .
  5. PMID 10746314
    .
  6. PMID 16447562
    .
  7. ^ WO application 2014005721, Russ H, Dekundy A, Danysz W, "Use of (r)-phenylpiracetam for the treatment of parkinson's disease", published 2014-01-09, assigned to Merz Pharma GmbH & Co. KGaA 
  8. ^
    S2CID 5845024
    .
  9. PMID 6403074
    .
  10. PMID 17523446
    .
  11. ^ a b c EP application 20140000021, "Use of (r)-phenylpiracetam for the treatment of sleep disorders", published 2015-07-08, assigned to Merz Pharma GmbH and Co KGaA 
  12. S2CID 215731963
    .
  13. ^
    S2CID 13658335
    .
  14. ^ "List of Controlled Substances" (PDF). Division Control Division. Drug Enforcement Administration, U.S. Department of Justice. 20 July 2021. Archived from the original (PDF) on 17 April 2016. Retrieved 16 September 2013.
  15. ^ "Prohibited List" (PDF). World Anti-Doping Agency (WADA). January 2017. p. 6.
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