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Phenylpiracetam is a phenyl derivative of the synthetic drug piracetam and is a member of the racetam family.
It is structurally similar to piracetam, but contains an additional phyenyl group at the 4th position of the 2-oxopyrrolidine ring. [1]
Phenylpiracetam is marketed as Phenotropil and is reported to be fast absorbing and have high oral bioavailability. [2]
It is more potent than piracetam and is thought to be applicable in the treatment of a wider array of cognitive symptoms and indications. [2]
Phenylpiracetam has been observed to have strong anti-amnesic effects and has been shown to support memory consolidation, improve attention and facilitate learning. [3]
Phenylpiracetam was developed in Russia as a nootropic or cognitive enhancing compound. It was initially given to cosmonauts in the space program to help improve their work efficacy and abilities.
Product Name: Phenylpiracetam
Chemical Name: (R,S)-2-(2-oxo-4-phenylpyrrolidin-1-yl)acetamide
Formula: C12H14N2O2
Molecular Weight: 218.3 g/mol
CAS Number: 77472-70-9
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Phenylpiracetam Nootropic Research
Related Topics
Research into phenylpiracetam is in the early stages and the vast majority of scientific studies have taken place in Russia.
Consequently, phenylpiracetam has received comparatively little scholarly attention than older nootropics, such as piracetam.
However, there is sufficient evidence for phenylpiracetam to be listed as a banned substance by the World Anti-Doping Agency. [11]
The drug was introduced into clinical practice around the year 2000 and has been studied for its ability to treat disorders of the central nervous system (CNS) such as amnesia, stroke, memory loss, and other cognitive impairments. [2]
Phenylpiracetam Chemical Structure
Phenylpiracetam is a phenyl derivative of piracetam. The molecule contains a pyrrolidone ring with a chiral center at the ring’s fourth position.
Phenylpiracetam can be separated into two enantiomeric forms, known as R and S, on account of its chiral center.
While it could be separated into its enantiomeric forms, phenylpiracetam is used in its racemic form in a clinical setting. [1]
In one animal study (mouse) the R form of phenylpiracetam was found to be the most active enantiomer of the molecule compared to the S and racemic form. [1]
The authors hypothesized that the enantiomers of phenylpiracetam may have different affinities for the drug target site. [1]
Pharmacokinetics
The absorption time of phenylpiracetam in rodents was observed to be less than 1 hour with a half-life of 2.5-3 hours, based on a dose of 100mg/kg (intramuscular). [2, 4, 5]
The pharmacokinetic profile in humans remains unpublished. [2]
Phenylpiracetam Mechanisms of Action
As with piracetam and most of its derivatives, the particular modes of action of phenylpiracetam remain unknown. [2]
Most studies have focused on therapeutic effects and more research is needed to delineate the particular mechanism of action.
Experiments with lab animals indicate that the family known as racetams impact some of the brain’s main neurotransmitters, including cholinergic, GABAergic, dopaminergic and glutamatergic systems. [3]
Both piracetam and phenylpiracetam have been observed to increase dopamine and noradrenaline levels in the brain. [3]
Further, phenylpiracetam has been observed to increase the densities of glutamate (NMDA) receptors in the hippocampus, nicotinic receptors in the cortex and D3-dopamine receptors in the striatum. [3]
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Phenylpiracetam and Cognition
Phenylpiracetam (100mg/kg, intraperitoneally) was observed to eliminate the effect of scopolamine-induced amnesia in rats while decreasing the number of acetylecholine (nACh) and NMDA receptors in the brain. [3]
In the same experiment, phenylpiracetam was observed to increase the density of GABA-A (BDZ), dopamine D2 and D3 receptors, but was not observed to impact the binding characteristics of 5-HT2 receptors. [3]
In a study conducted at the Omsk State Medical Academy in Russia, researchers observed that phenotropil helped treat cognitive deficits and the resulting anxiety and depression.
The results were based on an open-label trial involving 99 adults between the age of 40 and 60 suffering from encephalopathy due to gliomas surgery, brain trauma, or acute lesions. [2, 6].
Individuals were administered 200 mg of phenotropil daily for one month. Using the Minimal State Examination (MMSE), individuals who received phenotropil exhibited improved cognition and a reduction in both anxiety and depression. [2]
A comparative study involving 180 patients with asthenia and chronic fatigue syndrome (CFS) was conducted by the National Research Center for Social and Forensic Psychiatry in Moscow, Russia.
In the active and placebo controlled trial, 68 individuals were administered phenylpiracetam, 65 piracetam and 47 placebo.
Based on ten-word memory tests and attention switching tests, 83% of asthenic patients and 87% of CFS patients responded well to phenylpiracetam treatment compared to 48% and 55% (respectively) to piracetam. [2, 7]
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Stroke Recovery
In a study involving 400 patients with ischemic stroke, 200 patients were administered 3 courses of phenylpiracetam at a dose of 400 mg/day and were found to have statistically improved neurologic function and quality of daily living activities. [8]
Epilepsy
In a study published in 1983, [9] researchers observed that phenylpiracetam exhibited anti-epileptic properties.
A summary of the trial noted that 300 mg/kg phenylpiracetam administered to rodents reduced the occurrence of drug-induced (metrazol) seizure by 50%. [2]
Safety and Side Effects
No specific information is available about the side effects of pramiracetam; however, it seems to be well tolerated by humans.
The majority of phenylpiracetam trials (durations ranging from 1 to 2 months) noted no adverse side effects. [2]
The only exception was a trial that examined the use of phenylpiracetam in the treatment of multiple sclerosis, [10] in which sleep disturbances were reported as adverse side effect. [2]
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- Zvejniece, Liga, et al. Investigation into stereoselective pharmacological activity of phenotropil. Basic Clin Pharmacol Toxicol. 2011 Nov;109(5):407-12.
- Malykh AG, Sadaie MR. Piracetam and piracetam-like drugs: from basic science to novel clinical applications to CNS disorders. Drugs. 2010 Feb 12;70(3):287-312.
- Firstova, Yu Yu, et al. The effects of scopolamine and the nootropic drug phenotropil on rat brain neurotransmitter receptors during testing of the conditioned passive avoidance task. Basic Clin Pharmacol Toxicol. 2011 Nov;109(5):407-12.
- Antonova, M. I., et al. Experimental Pharmacokinetics of Phenotropyl in Rats. Pharmaceutical Chemistry Journal. 2003;37(11): 571-572.
- Spektor, S.S. and A.S. Berlyand. Experimental pharmacokinetics of carphedon. Pharmaceutical Chemistry Journal. 1996 August;30(8): 489-490.
- Savchenko Alu, Zakharova NS, Stepanov IN. [The phenotropil treatment of the consequence of brain organic lesions.] [Article in Russian] Zh Nevrol Psikhiatr Im S S Korsakova. 2005;105(12):22-6.
- Akhapkina, V. I., A. I. Fedin, and A. S. Avedisova. Efficacy of Phenotropil for treatment of astenic and chronic fatigue syndromes. [Russian] Nervnye Bolezni. 2004;3: 28-32.
- Koval'chuk VV, et al Efficacy of phenotropil in the rehabilitation of stroke patients . Zh Nevrol Psikhiatr Im S S Korsakova. 2010;110(12 Pt 2):38-40.
- Bobkov IuG, Morozov IS, Glozman OM, Nerobkova LN, Zhmurenko LA.[Pharmacological characteristics of a new phenyl analog of piracetam--4-phenylpiracetam]. [Article in Russian]Biull Eksp Biol Med. 1983 Apr;95(4):50-3.
- Sazonov, D. V., O. V. Ryabukhina, and E. V. Bulatova. Use of phenotropil in complex treatment of multiple sclerosis. Nervnye Bolezni. 2006; 4: 18-21.
- World Anti-Doping Agency 2015 list of prohibited substances and methods. Section 6: Stimulants.
Article last updated on: July 24th, 2018 by Nootriment