This article needs more reliable medical references for verification or relies too heavily on primary sources. Please review the contents of the article and add the appropriate references if you can. Unsourced or poorly sourced material may be challenged and removed. Find sources: "N-Phenylacetyl-L-prolylglycine ethyl ester" – news · newspapers · books · scholar · JSTOR (January 2021)

N-Phenylacetyl-L-prolylglycine ethyl ester

Clinical data
Trade names	Noopept
Other names	omberacetam; GVS-111; DVD-111; SGS-111; benzylcarbonyl-Pro-Gly-OEt
Legal status
Legal status	AU: S4 (Prescription only) 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.
Identifiers
IUPAC name Ethyl 1-(phenylacetyl)-l-prolylglycinate
CAS Number	157115-85-0 Y
PubChem CID	180496
ChemSpider	157065 N
UNII	4QBJ98683M
CompTox Dashboard (EPA)	DTXSID80166214
Chemical and physical data
Formula	C17H22N2O4
Molar mass	318.373 g·mol−1
3D model (JSmol)	Interactive image
SMILES c2ccccc2CC(=O)N1CCC[C@@H]1C(=O)NCC(=O)OCC
InChI 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
NY (what is this?)  (verify)

N-Phenylacetyl-l-prolylglycine ethyl ester is promoted as a nootropic and is a prodrug of cyclic glycine-proline.^[a][2] Other names include the brand name Noopept (Russian: Ноопепт), developmental code GVS-111, and proposed INN omberacetam.^[2][3][4]

Its synthesis was first reported in 1996.^[2] It is orally available. As of 2017, its metabolism and elimination half-life in humans were not well understood.^[2]

It has been evaluated for neuroprotective effects in treating brain injuries and stroke.^[5]

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".^[5] Studies in rats suggest, Noopept is a prodrug of the endogenous dipeptide cycloprolylglycine.^[6] Cycloprolylglycine is a modulator of AMPA receptors and exerts neuroprotective effects dependent upon AMPA- and TrkB-Receptor activation.^[7] In cell culture, cycloprolylglycine increases brain derived neurotrophic factor (BDNF).^[8]

Some studies suggest that the pharmacological properties of Noopept are derived from its action as an activator of Hypoxia-inducible factor (HIF-1).^[9][10]

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.^{[unreliable medical source?][11]} 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.^[12] There is, therefore, no dose of Noopept which may be called "safe".

• Hungary: As of 25 August 2020, Noopept is added to the controlled psychoactive substances list, prohibiting production, sale, import, storage and use.^[13]
• Russia: Noopept in Russia is a drug of medicine and is available without a prescription.^[14]
• 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.^[15] 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.^[16] FDA considers such racetam-family substances Active Pharmaceutical Ingredients (APIs) that require new drug applications and adequate labelling before being imported.^[17] Similarly, warnings have been issued for claims of medical and pharmacological effects.^[18] 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.^[19]

• Modafinil
• Nootropic
• Stimulant
• Traneurocin
• List of Russian drugs