Omberacetam

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Prodrug

title: "Omberacetam" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["nootropics", "racetams", "pyrrolidines", "ethyl-esters", "russian-drugs"] description: "Prodrug" topic_path: "geography/russia" source: "https://en.wikipedia.org/wiki/Omberacetam" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Prodrug ::

::data[format=table title="Infobox drug"]

FieldValue
Verifiedfieldschanged
Watchedfieldschanged
verifiedrevid424810394
IUPAC_nameEthyl 1-(phenylacetyl)--prolylglycinate
imageNoopept.svg
image_classskin-invert-image
width220
image2Noopept.png
image_class2bg-transparent
tradename
pregnancy_AU
pregnancy_US
legal_AUS4
legal_CA
legal_UK
legal_USUnapproved "New Drug" (as defined by 21 U.S. Code § 321(p)(1)). Use in dietary supplements, food, or medicine is unlawful; otherwise uncontrolled.
legal_status
CAS_number157115-85-0
CAS_number_Ref
UNII_Ref
UNII4QBJ98683M
PubChem180496
synonymsOmberacetam; GVS-111; DVD-111; SGS-111; Benzylcarbonyl-Pro-Gly-OEt; N-Phenylacetyl--prolylglycine ethyl ester
C
H22
N2
O4
SMILESc2ccccc2CC(=O)N1CCC[C@@H]1C(=O)NCC(=O)OCC
ChemSpiderID_Ref
ChemSpiderID157065
StdInChI_Ref
StdInChI1S/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
StdInChIKey_Ref
StdInChIKeyPJNSMUBMSNAEEN-AWEZNQCLSA-N
::

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 424810394 | IUPAC_name = Ethyl 1-(phenylacetyl)--prolylglycinate | image = Noopept.svg | image_class = skin-invert-image | width = 220 | image2 = Noopept.png | image_class2 = bg-transparent

| tradename = Noopept | pregnancy_AU = | pregnancy_US = | legal_AU = S4 | legal_CA = | legal_UK = | legal_US = Unapproved "New Drug" (as defined by 21 U.S. Code § 321(p)(1)). Use in dietary supplements, food, or medicine is unlawful; otherwise uncontrolled. | legal_US_comment = | legal_status = | CAS_number = 157115-85-0 | CAS_number_Ref = | UNII_Ref = | UNII = 4QBJ98683M | PubChem = 180496 | synonyms = Omberacetam; GVS-111; DVD-111; SGS-111; Benzylcarbonyl-Pro-Gly-OEt; N-Phenylacetyl--prolylglycine ethyl ester

| C = 17 | H = 22 | N = 2 | O = 4 | SMILES = c2ccccc2CC(=O)N1CCC[C@@H]1C(=O)NCC(=O)OCC | ChemSpiderID_Ref = | ChemSpiderID = 157065 | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = PJNSMUBMSNAEEN-AWEZNQCLSA-N

Omberacetam, also known as N-phenylacetyl--prolylglycine ethyl ester, is promoted as a nootropic and is a prodrug of cyclic glycine-proline. Other names include the brand name Noopept (), developmental code GVS-111.

Its synthesis was first reported in 1996. It is orally available. As of 2017, its metabolism and elimination half-life in humans were not well understood.

It has been evaluated for neuroprotective effects in treating brain injuries and stroke.

Pharmacology

One oft-cited study (originally published in Russian) conducted on rats, suggests that Noopept works via the "antioxidant effect, the anti-inflammatory action, and the ability to inhibit the neurotoxicity of excess calcium and glutamate, and to improve the blood rheology". Studies in rats suggest, Noopept is a prodrug of the endogenous dipeptide cycloprolylglycine. Cycloprolylglycine is a modulator of AMPA receptors and exerts neuroprotective effects dependent upon AMPA- and TrkB-Receptor activation. In cell culture, cycloprolylglycine increases brain derived neurotrophic factor (BDNF).

Some studies suggest that the pharmacological properties of Noopept are derived from its action as an activator of Hypoxia-inducible factor (HIF-1).

Dosage

Noopept is frequently dosed at 10–30 mg 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 0.1 mg/kg bodyweight to 10 mg/kg bodyweight. 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.

Legal status

  • Hungary: As of 25 August 2020, Noopept is added to the controlled psychoactive substances list, prohibiting production, sale, import, storage and use.
  • Russia: Noopept in Russia is a drug of medicine and is available without a prescription.
  • United Kingdom: Contrary to popular belief, omberacetam is not illegal to produce, supply, or import under the Psychoactive Substance Act in the UK, which came into effect on May 26, 2016 because it neither works as a CNS (central nervous system) depressant, nor as a CNS stimulant. However, sale and supply for human consumption are prohibited.
  • United States: The Food and Drug Administration has issued import alerts for imports of omberacetam, considering it an analog of piracetam. FDA considers such racetam-family substances Active Pharmaceutical Ingredients (APIs) that require new drug applications and adequate labelling before being imported. Similarly, warnings have been issued for claims of medical and pharmacological effects. Despite these FDA enforcement actions, omberacetam is sold in over-the-counter supplements in the US, with some products formulated with dosages greater than pharmaceutical levels.

Notes

References

References

  1. (2018-03-09). "INN Recommended List 79". WHO Drug Information.
  2. "Omberacetam". Springer Nature Switzerland AG.
  3. "Omberacetam". National Center for Advancing Translational Sciences (NCATS).
  4. "Noopept Information". [[Examine.com]].
  5. (2002). "[The original novel nootropic and neuroprotective agent noopept]". Eksperimental'naia i Klinicheskaia Farmakologiia.
  6. (1997). "The major metabolite of dipeptide piracetam analogue GVS-111 in rat brain and its similarity to endogenous neuropeptide cyclo-L-prolylglycine". European Journal of Drug Metabolism and Pharmacokinetics.
  7. (December 2022). "Neuroprotective Effect of the Neuropeptide Cycloprolylglycine Depends on AMPA- and TrkB-Receptor Activation". Doklady. Biochemistry and Biophysics.
  8. (July 2016). "Neuropeptide cycloprolylglycine increases the levels of brain-derived neurotrophic factor in neuronal cells". Doklady. Biochemistry and Biophysics.
  9. (September 2020). "Cognitive Enhancer Noopept Activates Transcription Factor HIF-1". Doklady. Biochemistry and Biophysics.
  10. (2016). "Molecular Mechanism Underlying the Action of Substituted Pro-Gly Dipeptide Noopept". Acta Naturae.
  11. (2020). "Finding the optimal dosage fornootropic agent Noopept: An analysis of available literature". International Journal of Environmental Science and Technology.
  12. (March 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.
  13. (25 August 2020). "Az új pszichoaktív anyaggá minősített anyagokról vagy vegyületcsoportokról szóló 55/2014. (XII. 30.) EMMI rendelet módosításáról". Magyarország Hivatalos Lapja.
  14. "Ноопепт". Государственный реестр лекарственных средств.
  15. "Psychoactive Substances Act 2016". Legislation.gov.uk.
  16. (March 2020). "Presence of Piracetam in Cognitive Enhancement Dietary Supplements". JAMA Internal Medicine.
  17. (7 September 2021). "Import alert 66-66". U.S. Food and Drug Administration.
  18. (5 February 2019). "Peak Nootropics LLC aka Advanced Nootropics". U.S. Food and Drug Administration.
  19. (June 2021). "Five Unapproved Drugs Found in Cognitive Enhancement Supplements". Neurology. Clinical Practice.

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nootropicsracetamspyrrolidinesethyl-estersrussian-drugs