Phenylpiracetam

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Phenotropil
Systematic (IUPAC) name
(RS)-2-(2-oxo-4-phenylpyrrolidin-1-yl)acetamide
Clinical data
Pregnancy cat.Unknown
Legal statusLegal
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
Systematic (IUPAC) name
(RS)-2-(2-oxo-4-phenylpyrrolidin-1-yl)acetamide
Clinical data
Pregnancy cat.Unknown
Legal statusLegal
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 derivative of the nootropic drug piracetam. It is used as a stimulant nootropic drug that can be up to 30-60 times more potent than piracetam.[1] It was developed in Russia in 1983, and 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.[2]

Pharmacology[edit]

Phenylpiracetam reverses the depressant effects of the benzodiazapine diazepam, increases operant behavior, inhibits post-rotational nystagmus, prevents retrograde amnesia and has anticonvulsant properties.[1][3][4]

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

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.[3]

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.

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.[6]

Doping[edit]

Because it increases physical stamina and provide improved tolerance to cold weather, 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 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.[7]

Physical Data[edit]

Phenylpiracetam has a flash point of 247.9°C and boiling point of 486.4°C at 760 mmHg.[8]

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. ^ 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
  3. ^ 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. 
  4. ^ 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
  5. ^ 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. PMID 10746314. 
  6. ^ List of Controlled Substances
  7. ^ CNN, "Runners fail pre-Olympics doping tests", Retrieved on 2008-08-09.
  8. ^ CAS No.:77472-70-9