Phenylpiracetam

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Phenotropil
Phenylpiracetam.svg
Systematic (IUPAC) name
(R,S)-2-(2-oxo-4-phenylpyrrolidin-1-yl)acetamide
Clinical data
Trade names Phenotropil; Carphedon
Pregnancy cat. Unknown
Legal status Legal
Routes Oral
Pharmacokinetic data
Bioavailability ~100 %
Metabolism None
Half-life 3-5 hours
Excretion Urine ~40% bile and perspiration ~60%
Identifiers
CAS number 77472-70-9 YesY
ATC code None
PubChem CID 132441
ChemSpider 116950 N
Chemical data
Formula C12H14N2O2 
Mol. mass 218.3 g/mol
Physical data
Boiling point 486.4 °C (908 °F)
 N (what is this?)  (verify)

Phenylpiracetam (Phenotropil, Carphedon) is a phenylated analog[disambiguation needed] of the nootropic drug piracetam which was developed in 1983 in Russia where it is available as a prescription drug. It has been used as a CNS and locomotor stimulant with antipsychotic, antidepressant, anti-amnesic, anxiolytic, performance enhancing, and memory enhancing nootropic effects that can be up to 30-60 times more potent than piracetam.[1][2]

Pharmacology[edit]

A small number of low-scale 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.[3]

Phenylpiracetam reverses the depressant effects of the benzodiazepine diazepam, increases operant behavior, inhibits post-rotational nystagmus, prevents retrograde amnesia, and has anticonvulsant properties.[1][4][5]

Phenylpiracetam is typically prescribed as a general stimulant or to increase tolerance to extreme temperatures and stress.[6]

In Wistar rats with gravitational cerebral ischemia, Phenylpiracetam reduced the extent of neuralgic deficiency manifestations, retained the locomotor, research, and memory functions, increased the survival rate, and lead to the favoring of local cerebral flow restoration upon the occlusion of carotid arteries to a greater extent than did piracetam.[7]

In rats, it has been found to decrease the number of nACh and NMDA receptors and increase the density of D1, D2 and D3 receptors.[4]

When neuroleptic (antipsychotic) activity of phenotropil was studied in an experimental animal model, it showed marked neuroleptic activity in models of positive (apomorphine-induced verticalization test) and negative (5-HTP-induced hyperkinesis test) symptoms of psychoses as well as in the m-cholinergic pathway hyperactivation (arecoline-induced tremor test). The compound markedly antagonized haloperidol catalepsy. Used in a single dose or as a course treatment, phenotropil did not provoke nor intensify aggression. In contrast to typical and atypical antipsychotics, phenotropil had no sedative action and other adverse effects. It exhibited a positive effect on exploratory behavior and motor activity, had anxiolytic (anti-anxiety) and antidepressant action.[8]

Racemic phenylpiracetam and its enantiomers were tested for locomotor, antidepressant and memory-improving activity and influence on the central nervous system using general pharmacological tests in mice. In the open-field test, a significant increase in locomotor activity was observed after a single administration of R-phenylpiracetam at doses of 10 and 50 mg/kg and S-phenylpiracetam at a dose of 50 mg/kg. In the forced swim test, R-phenylpiracetam induced an antidepressant effect at doses of 100 and 50 mg/kg, and S-phenylpiracetam was active at a dose of 100 mg/kg. R-phenylpiracetam significantly enhanced memory function in a passive avoidance response test at a dose of 1 mg/kg; the S-enantiomer did not show any activity in this test. In conclusion, the antidepressant and increased locomotor activity relies on both R- and S-phenylpiracetam, but the memory-improving activity is only characteristic of R-phenylpiracetam.[2]

Availability[edit]

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 the name Phenotropil (but most drugstores sell it without prescriptions).

Phenylpiracetam has recently gained niche popularity from online nootropics suppliers in the US and other countries outside of Russia. Given its lack of abuse potential, Phenylpiracetam is not scheduled by the DEA, and is legal for personal use.[9]

Athlete Doping[edit]

Because it increases physical stamina and provides improved tolerance to cold weather,[6] it appears on the lists of banned substances issued by the World Anti-Doping Agency. This list is applicable in all Olympic sports.

Athletic disqualification[edit]

Russian biathlon Olympic silver medalist Olga Pyleva in the 2006 Winter Olympics was disqualified from attending further events following a positive drug test. She was subsequently banned from competition for two years.

In 2007, two young Russian riders returned a positive doping test result and received a two-year suspension by the International Cycling Union. The two riders, Anton Reshetnikov and Elena Kuchinskaya, used forbidden substances Carphedon and Furosemide.

In August 2008, Russian steeplechase runner Roman Usov was pulled out of the Beijing Olympics for what media reported was a possible positive test for phenylpiracetam.[10]

Physical Data[edit]

Phenylpiracetam has a flash point of 247.9 °C and boiling point of 486.4 °C at 760 mmHg.[11]

See also[edit]

External links[edit]

References[edit]

  1. ^ a b Malykh, A. G.; Sadaie, M. R. (2010). "Piracetam and Piracetam-Like Drugs". Drugs 70 (3): 287–312. doi:10.2165/11319230-000000000-00000. PMID 20166767.  edit
  2. ^ a b Zvejniece L, Svalbe B, Veinberg G, Grinberga S, Vorona M, Kalvinsh I, Dambrova M. (2011). "Investigation into stereoselective pharmacological activity of phenotropil.". Basic & Clinical Pharmacology & Toxicology, Nordic Pharmacological Society 109 (5): 407–12. doi:10.1111/j.1742-7843.2011.00742.x. PMID 21689376. 
  3. ^ Savchenko, A. I.; Zakharova, N. S.; Stepanov, I. N. (2005). "The phenotropil treatment of the consequences of brain organic lesions". Zhurnal nevrologii i psikhiatrii imeni S.S. Korsakova 105 (12): 22–26. PMID 16447562.  edit
  4. ^ a b Firstova, Yu. Yu.; Abaimov, D. A.; Kapitsa, I. G.; Voronina, T. A.; Kovalev, G. I. (2011). "The effects of scopolamine and the nootropic drug phenotropil on rat brain neurotransmitter receptors during testing of the conditioned passive avoidance task". Neurochemical Journal 28 (2): 130–141. doi:10.1134/S1819712411020048. 
  5. ^ Bobkov, I.; Morozov, I. S.; Glozman, O. M.; Nerobkova, L. N.; Zhmurenko, L. A. (1983). "Pharmacological characteristics of a new phenyl analog of piracetam--4-phenylpiracetam". Biulleten' eksperimental'noi biologii i meditsiny 95 (4): 50–53. PMID 6403074.  edit
  6. ^ a b Kim, S.; Park, J. H.; Myung, S. W.; Lho, D. S. (1999). "Determination of carphedon in human urine by solid-phase microextraction using capillary gas chromatography with nitrogen-phosphorus detection". The Analyst 124 (11): 1559–1562. doi:10.1039/a906027h. PMID 10746314. 
  7. ^ Tiurenkov IN; Bagmetov MN; Epishina VV. (2007). "Comparative evaluation of the neuroprotective activity of phenotropil and piracetam in laboratory animals with experimental cerebral ischemia". Eksp Klin Farmakol 70 (2): 24–29. PMID 17523446. 
  8. ^ Akhapkina VI, Akhapkin RV. (2013). "Identification and evaluation of the neuroleptic activity of phenotropil". Zh Nevrol Psikhiatr Im S S Korsakova 113 (7): 42–6. PMID 23994920. 
  9. ^ List of Controlled Substances
  10. ^ CNN, "Runners fail pre-Olympics doping tests", Retrieved on 2008-08-09.
  11. ^ CAS No.:77472-70-9