Phenylpiracetam

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Phenotropil
Phenylpiracetam.svg
Systematic (IUPAC) name
(R,S)-2-(2-oxo-4-phenylpyrrolidin-1-yl)acetamide
Clinical data
Trade namesPhenotropil; Carphedon
Pregnancy cat.
  • Unknown
Legal status
  • Legal
RoutesOral
Pharmacokinetic data
Bioavailability~100 %
MetabolismNone
Half-life3-5 hours
ExcretionUrine ~40% bile and perspiration ~60%
Identifiers
CAS number77472-70-9 YesY
ATC codeNone
PubChemCID 132441
ChemSpider116950 N
Chemical data
FormulaC12H14N2O2 
Mol. mass218.3 g/mol
Physical data
Boiling point486.4 °C (908 °F)
 N (what is this?)  (verify)
 
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Phenotropil
Phenylpiracetam.svg
Systematic (IUPAC) name
(R,S)-2-(2-oxo-4-phenylpyrrolidin-1-yl)acetamide
Clinical data
Trade namesPhenotropil; Carphedon
Pregnancy cat.
  • Unknown
Legal status
  • Legal
RoutesOral
Pharmacokinetic data
Bioavailability~100 %
MetabolismNone
Half-life3-5 hours
ExcretionUrine ~40% bile and perspiration ~60%
Identifiers
CAS number77472-70-9 YesY
ATC codeNone
PubChemCID 132441
ChemSpider116950 N
Chemical data
FormulaC12H14N2O2 
Mol. mass218.3 g/mol
Physical data
Boiling point486.4 °C (908 °F)
 N (what is this?)  (verify)

Phenylpiracetam (Phenotropil, Carphedon) is a phenylated analog of the nootropic drug piracetam which was developed in 1983 in Russia where it is available as a prescription drug. It has been used in humans as a CNS stimulant, a locomotor stimulant, a sports performance enhancer, and a nootropic (in which case, it can be up to 30-60 times more potent than piracetam). Research on animals has shown phenylpiracetam to have various actions such as anti-amnesic, antidepressant, anticonvulsant, antipsychotic, anxiolytic, and memory enhancement effects.[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]

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,[medical citation needed] phenylpiracetam is not scheduled by the DEA.[8]

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.

Physical data[edit]

Phenylpiracetam has a flash point of 247.9 °C and boiling point of 486.4 °C at 760 mmHg.[dubious ][9][unreliable source?]

See also[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. ^ 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. ^ List of Controlled Substances
  9. ^ CAS No.:77472-70-9