N-Phenylacetyl-L-prolylglycine ethyl ester

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N-Phenylacetyl-L-prolylglycine ethyl ester
Noopept.svg
Noopept.png
Clinical data
Trade namesNoopept
Other namesN-Phenylacetyl-l-prolylglycine ethyl ester; GVS-111
Legal status
Legal status
  • AU: S4 (Prescription only)
  • US: Unscheduled Not FDA approved
Identifiers
  • Ethyl 1-(phenylacetyl)-l-prolylglycinate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H22N2O4
Molar mass318.373 g·mol−1
3D model (JSmol)
  • c2ccccc2CC(=O)N1CCC[C@@H]1C(=O)NCC(=O)OCC
  • InChI=1S/C17H22N2O4/c1-2-23-16(21)12-18-17(22)14-9-6-10-19(14)15(20)11-13-7-4-3-5-8-13/h3-5,7-8,14H,2,6,9-12H2,1H3,(H,18,22)/t14-/m0/s1 ☒N
  • Key:PJNSMUBMSNAEEN-AWEZNQCLSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

-Phenylacetyl-l-prolylglycine ethyl ester is promoted as a nootropic and is a prodrug of cycloprolylglycine.[1] Other names include the brand name Noopept (Russian: Ноопепт), developmental code GVS-111; proposed INN omberacetam.[1][2][3]

Its synthesis was first reported in 1996.[1] It is orally available, and as of 2017 its metabolism and elimination half-life were not well understood, as cycloprolylglycine had not been measured in humans following administration.[1]

As of 2018 there have been many studies conducted in cells and in animal models, and there has been one clinical trial with 41 subjects comparing Noopept and piracetam in people with traumatic brain injury.[1]

Pharmacology[edit]

All theories regarding Noopept's mechanism of action are based on observations from animal studies. One oft-cited study (originally published in Russian) conducted on rats, suggests that Noopept works via the "antioxidant effect, the antiinflammatory action, and the ability to inhibit the neurotoxicity of excess calcium and glutamate, and to improve the blood rheology".[4] To date, no trial has been conducted on humans to confirm these theories.

Dosage[edit]

Noopept is frequently dosed at 10-30mg per day. However, there is no solid evidence indicating that any dose of Noopept is optimal. Few human trials have ever been carried out on Noopept, and as one meta-analysis notes, animal studies have used doses ranging from 0.1mg/kg bodyweight to 10mg/kg bodyweight.[5] Furthermore, no long-term studies have been done to evaluate the lasting effects of chronic use at any given dose; the longest human study lasted for 56 days.[6] There is, therefore, no dose of Noopept which may be called "safe".

Legal status[edit]

  • Russia: Noopept in Russia is a drug of medicine and is available without a prescription.[7]
  • United Kingdom: Omberacetam is illegal to produce, supply, or import under the Psychoactive Substance Act, which came into effect on May 26, 2016.[8]
  • United States: The Food and Drug Administration has issued import alerts for imports of omberacetam, considering it an analog of piracetam.[9] FDA considers such racetam-family substances Active Pharmaceutical Ingredients (APIs) that require new drug applications and adequate labelling before being imported.[10] Similarly, warnings have been issued for claims of medical and pharmacological effects of this officially non-drug substance.[11] Despite these FDA enforcement actions, omberacetam is sold in over-the-counter supplements in this US with some products formulated with dosages greater than pharmaceutical levels.[12]

See also[edit]

External links[edit]

References[edit]

  1. ^ a b c d e "Noopept Information". Examine.com. Retrieved 6 April 2017.
  2. ^ "Proposed INN List 117" (PDF). WHO Drug Information. 31 (2): 308. 2017.
  3. ^ "GVS 111". AdisInsight. Retrieved 12 May 2018.
  4. ^ Ostrovskaia RU, Gudasheva TA, Voronina TA, Seredenin SB (September 2002). "[The original novel nootropic and neuroprotective agent noopept]". Eksperimental'naia i Klinicheskaia Farmakologiia. 65 (5): 66–72. PMID 12596521.
  5. ^ Tardner, P (2020). "Finding the optimal dosage fornootropic agent Noopept: An analysis of available literature" (PDF). International Journal of Environmental Science and Technology.
  6. ^ Neznamov, G. G.; Teleshova, E. S. (2009). "Comparative studies of Noopept and piracetam in the treatment of patients with mild cognitive disorders in organic brain diseases of vascular and traumatic origin". Neuroscience and Behavioral Physiology. 39 (3): 311–321. doi:10.1007/s11055-009-9128-4. ISSN 0097-0549. PMID 19234797.
  7. ^ "Государственный реестр лекарственных средств".
  8. ^ "Psychoactive Substances Act 2016". Legislation.gov.uk.
  9. ^ Cohen, Pieter A.; Zakharevich, Igor; Gerona, Roy (1 March 2020). "Presence of Piracetam in Cognitive Enhancement Dietary Supplements". JAMA Internal Medicine. 180 (3): 458–459. doi:10.1001/jamainternmed.2019.5507. PMC 6902196. PMID 31764936.
  10. ^ "Import alert 66-66".
  11. ^ "FDA Warning letter: Peak Nootropics LLC aka Advanced Nootropics".
  12. ^ Cohen, Pieter A.; Avula, Bharathi; Wang, Yan Hong; Zakharevich, Igor; Khan, Ikhlas (23 September 2020). "Five unapproved drugs found in cognitive enhancement supplements". Neurology: Clinical Practice: 10.1212/CPJ.0000000000000960. doi:10.1212/CPJ.0000000000000960.