Noopept
- Iupac Name：ethyl 2-[[(2S)-1-(2-phenylacetyl)pyrrolidine-2-carbonyl]amino]acetate
- CAS No.: 157115-85-0
- Molecular Weight：318.373
- Modify Date.: 2023-05-11 17:46
- Introduction: 1-(2-Phenylacetyl)-L-prolylglycine Ethyl Ester, is a synthetic dipeptide , having shown to have positive nootropic and cognitive effects in animals. The human studies have shown promising results, with potential application in the treatment of Alzheimer's disease. ethyl 2-[[(2S)-1-(2-phenylacetyl)pyrrolidine-2-carbonyl]amino]acetateSupplier
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1. Names and Identifiers
- 1.1 Name
- Noopept
- 1.2 Synonyms
(S)-ethyl 2-(1-(2-phenylacetyl)pyrrolidine-2-carboxaMido)acetate 1-(2-Phenylacetyl)-L-prolylglycine ethy ester Ethyl 1-(phenylacetyl)-L-prolylglycinate ethyl 2-[[(2S)-1-(2-phenylacetyl)pyrrolidine-2-carbonyl]amino]acetate Ethyl N-[1-(Phenylacetyl)-L-prolyl]glycinate Glycine, 1-(2-phenylacetyl)-L-prolyl-, ethyl ester Glycine, 1-(phenylacetyl)-L-prolyl-, ethyl ester Glycine, N-[1-(phenylacetyl)-L-prolyl]-, ethyl ester GVS 111 GVS-111 N-(1-(Phenylacetyl)-L-prolyl)glycine ethyl ester N-[1-(Phenylacetyl)-L-prolyl]glycine Ethyl Ester noopept powder Nootropic GVS-111 Nopept N-phenylacetyl-L-prolylglycine ethyl ester Omberacetam SGS 111
- 1.3 CAS No.
- 157115-85-0
- 1.4 CID
- 180496
- 1.5 EINECS(EC#)
- 1592732-453-0
- 1.6 Molecular Formula
- C17H22N2O4 (isomer)
- 1.7 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
- 1.8 InChkey
- PJNSMUBMSNAEEN-AWEZNQCLSA-N
- 1.9 Canonical Smiles
- CCOC(=O)CNC(=O)C1CCCN1C(=O)CC2=CC=CC=C2
- 1.10 Isomers Smiles
- CCOC(=O)CNC(=O)[C@@H]1CCCN1C(=O)CC2=CC=CC=C2
2. Properties
- 2.1 Density
- 1.202
- 2.1 Melting point
- 94.0 to 98.0 °C
- 2.1 Boiling point
- 547.3°Cat760mmHg
- 2.1 Refractive index
- 1.548
- 2.1 Flash Point
- 284.8°C
- 2.1 Precise Quality
- 318.15800
- 2.1 PSA
- 75.71000
- 2.1 logP
- 1.22820
- 2.1 Appearance
- white powder
- 2.2 Color/Form
- white to beige
- 2.3 pKa
- 13.41±0.20(Predicted)
- 2.4 StorageTemp
- -20°C
3. Use and Manufacturing
- 3.1 Usage
- 1-(2-Phenylacetyl)-L-prolylglycine Ethyl Ester, is a synthetic dipeptide , having shown to have positive nootropic and cognitive effects in animals. The human studies have shown promising results, with potential application in the treatment of Alzheimer's disease. ethyl 2-[[(2S)-1-(2-phenylacetyl)pyrrolidine-2-carbonyl]amino]acetateSupplier
4. Safety and Handling
- 4.1 RIDADR
- NONH for all modes of transport
- 4.1 RTECS
- MC0814400
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
no data available
2.2 GHS label elements, including precautionary statements
| Pictogram(s) | no data available |
| Signal word | no data available |
| Hazard statement(s) | no data available |
| Precautionary statement(s) | |
| Prevention | no data available |
| Response | no data available |
| Storage | no data available |
| Disposal | no data available |
2.3 Other hazards which do not result in classification
no data available
6. Synthesis Route
157115-85-0Total: 3 Synthesis Route
8. Other Information
- 8.0 体外研究
-
Nooglutil exhibits pharmacologically significant competition with a selective agonist of AMPA receptors ([G-3H]Ro 48-8587) for the receptor binding sites (with IC50 = 6.4 +/- 0.2 microM), while the competition of noopept for these receptor binding sites was lower by an order of magnitude (IC50 = 80 +/- 5.6 microM) [1]. GVS-111 significantly increased neuronal survival after H(2)O(2)-treatment displaying a dose-dependent neuroprotective activity from 10 nM to 100 microM, and an IC(50) value of 1.21+/-0.07 microM. GVS-111 inhibited the accumulation of intracellular free radicals and lipid peroxidation damage in neurons treated with H(2)O(2) or FeSO(4), suggesting an antioxidant mechanism of action [2].
- 8.1 体内研究
-
N-Phenylacetyl-L-prolylglycine ethyl ester (GVS-111) administered intravenously at a dose of 0.5 mg/kg/day, for the first time 1 h after ischaemic lesion and then for 9 post-operative days, with the last administration 15 min before testing, attenuated the deficit [3]. GVS-111 itself was not found in rat brain 1 h after 5 mg/kg i.p. administration up to limit of detection (LOD) under high performance liquid chromatography (HPLC) conditions [4]. The most pronounced antiinflammatory effect of dipeptide was observed on the model of adjuvant arthritis in rats, where the drug administered over 25 days in a daily dose of 0.5 mg/kg (i.m.) or 5 mg/kg (p.o.) significantly reduced the chronic immune inflammation (on the 12th day, by 94.0 and 74.1%, respectively) [5].
- 8.2 Description
- Noopept is the brand name for N-phenylacetyl-L-prolylglycine ethyl ester , a synthetic nootropic molecule.Noopept has a similar effect to piracetam, in that it provides a mild cognitive boost after supplementation. Noopept also provides a subtle psychostimulatory effect.
- 8.3 History
- Noopept (previously GVS-111) is a nootropic developed at the Zakusov Institute of Pharmacology (Russian Academy of Medical Sciences) by T. A. Gudasheva. It is one of several nootropics developed based on the structure of piracetam. Its advantage over piracetam is that it can be taken at a lower dose.
Noopept is a popular cognitive-enhancing supplement in the nootropic community. Proposed mechanism of actions based on preclinical studies include increasing acetylcholine signaling, increasing the expression of BDNF and NGF, protecting from glutamate toxicity, and increasing inhibitory neurotransmission in the brain.
www.alzdiscovery.org
- 8.4 Uses
- Noopept is a well-known nootropic that is often suggested as a first nootropic.Noopept is over 500 times more potentthan Piracetam.Like piracetam,it is capable of enhancing memory,learning,andfocus. Noopept is also a powerful antioxidant that prevents neurological disorders andhelps the brain grow.Because of this, it is thought to improve long-term memory. The human studies have shown promising results, with potential application in the treatment of Alzheimer's disease.
- 8.5 Biochem/physiol Actions
- Noopept is a nootropic and neuroprotective drug that normalizes the balance of the pro- and antioxidant systems. Noopept modulates a variety of physiological functions including cognition and anxiety. Noopept significantly weakens streptozotocin-Induced diabetes in rats.
- 8.6 Side effects
- Noopept is associated with some mild side effects based on limited clinical evidence. possible side effects of noopept included sleep disturbances (5/31 patients), irritability (3/31), and increased blood pressure (7/31) (Neznamov and Teleshova, 2009).
- 8.7 Preparation
- Noopept (ethyl ester of N-phenylacetyl-L-prolylglycine) was designed as a drug at State Zakusov Institute of Pharmacology. The synthesis of the drug is based on the original hypothesis of peptide design, according to which structures similar to known psychotropic agents are reproduced using appropriate amino acids. The non-peptide prototype of Noopept is the nootropic drug Piracetam.
1. Perform the carboxylation of N-phenylacetyl-L-proline and ethyl glycine in the presence of isobutyl chloroformate.
2. Add slowly isobutyl chloroformate (1.17 g, 8.6 mmol) to a solution of N-phenylacetyl-L-proline (2.0 g, 8.6 mmol) dissolved in a mixed solvent of THF and dichloromethane (1:1; THF/dichloromethane (v/v)).3.Stir the mixture for 4 h at 0 ～5 °C
Molecular Mechanism Underlying the Action of Substituted Pro-Gly Dipeptide Noopept
- 8.8 References
- 1) Ostrovskaya et al. (2007), The nootropic and neuroprotective proline-containing dipeptide noopept restores spatial memory and increases immunoreactivity to amyloid in an Alzheimer’s disease model; J. Psychopharmacol., 21 611
2) Jia et al. (2011), Neuroprotective and nootropic drug noopept rescues α-synuclein amyloid cytotoxicity; J. Mol. Biol., 414 699
3) Ostrovskaya et al. (2008), Noopept stimulates the expression of NGF and BDNF in rat hippocampus; Bull. Exp. Biol. Med., 146 334
4) Antipova et al. (2016), Dipeptide Piracetam Analogue Noopept Improves Viability of Hippocampal HT-22 Neurons in the Glutamate Toxicity Model; Bull. Exp. Biol. Med., 161 58
5) Ostrovskaya et al. (2014), Comparative activity of proline-containing dipeptide noopept and inhibitor of dipeptidyl peptidase-4 sitagliptin in a rat model of developing diabetes; Bull. Exp. Biol. Med., 156 342
9. Computational chemical data
- Molecular Weight: 318.373g/mol
- Molecular Formula: C17H22N2O4
- Compound Is Canonicalized: True
- XLogP3-AA: 1.5
- Exact Mass: 318.15795719
- Monoisotopic Mass: 318.15795719
- Complexity: 432
- Rotatable Bond Count: 7
- Hydrogen Bond Donor Count: 1
- Hydrogen Bond Acceptor Count: 4
- Topological Polar Surface Area: 75.7
- Heavy Atom Count: 23
- Defined Atom Stereocenter Count: 1
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADceB7OAAAAAAAAAAAAAAAAAAAAWAAAAAwAAAAAAAAAAABAAAAHgAQAAAADCjhmAYyCIPABACIAiHSGAACAAAgAAAIiIGIAIgKYDKAlTGXIAAglgCYiAcYiYCOAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
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Noopept
- Purity:99%Packing: 200kg/bag FOB
- Price: 450 USD/kg
- Time: 2023/05/31
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Noopept
- Purity:99%Packing: 200kg/bag FOB
- Price: 90 USD/g
- Time: 2023/05/31
Inquire
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