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157115-85-0

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157115-85-0 Usage

Description

Noopept is the brand name for N-phenylacetyl-L-prolylglycine ethyl ester , a synthetic nootropic molecule. It has a similar effect to piracetam, in that it provides a mild cognitive boost after supplementation. It also provides a subtle psychostimulatory effect. Noopept is up to 1000-times more potent than the original racetam, Piracetam.

Chemical Properties

Noopept is a synthetic nootropic molecule grouped in the racetam class but structurally different from racetams.It is primarily water-soluble nootropic, but won't easily dissolve in water or juice. So it may help if you take it with a meal containing healthy fats.

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

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.

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.

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).

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 °CMolecular Mechanism Underlying the Action of Substituted Pro-Gly Dipeptide Noopept

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 6112) Jia et al. (2011), Neuroprotective and nootropic drug noopept rescues α-synuclein amyloid cytotoxicity; J. Mol. Biol., 414 6993) Ostrovskaya et al. (2008), Noopept stimulates the expression of NGF and BDNF in rat hippocampus; Bull. Exp. Biol. Med., 146 3344) Antipova et al. (2016), Dipeptide Piracetam Analogue Noopept Improves Viability of Hippocampal HT-22 Neurons in the Glutamate Toxicity Model; Bull. Exp. Biol. Med., 161 585) 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

Check Digit Verification of cas no

The CAS Registry Mumber 157115-85-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,5,7,1,1 and 5 respectively; the second part has 2 digits, 8 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 157115-85:
(8*1)+(7*5)+(6*7)+(5*1)+(4*1)+(3*5)+(2*8)+(1*5)=130
130 % 10 = 0
So 157115-85-0 is a valid CAS Registry Number.
InChI:InChI=1/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

157115-85-0 Well-known Company Product Price

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  • Sigma

  • (SML1144)  Noopept  ≥98% (HPLC)

  • 157115-85-0

  • SML1144-5MG

  • 609.57CNY

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  • Sigma

  • (SML1144)  Noopept  ≥98% (HPLC)

  • 157115-85-0

  • SML1144-25MG

  • 2,476.89CNY

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157115-85-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name (S)-Ethyl 2-(1-(2-phenylacetyl)pyrrolidine-2-carboxamido)acetate

1.2 Other means of identification

Product number -
Other names ethyl 2-[[(2S)-1-(2-phenylacetyl)pyrrolidine-2-carbonyl]amino]acetate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:157115-85-0 SDS

157115-85-0Synthetic route

glycine ethyl ester hydrochloride
623-33-6

glycine ethyl ester hydrochloride

C18H23NO4

C18H23NO4

N-phenylacetyl-L-prolylglycine ethyl ester
157115-85-0

N-phenylacetyl-L-prolylglycine ethyl ester

Conditions
ConditionsYield
With 4-methyl-morpholine In chloroform; N,N-dimethyl-formamide at -5 - 20℃; for 1.5h; Yield given;
(S)-1-(2-phenylacetyl)pyrrolidine-2-carboxylic acid
2752-38-7

(S)-1-(2-phenylacetyl)pyrrolidine-2-carboxylic acid

N-phenylacetyl-L-prolylglycine ethyl ester
157115-85-0

N-phenylacetyl-L-prolylglycine ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-methylmorpholine / CHCl3 / 0.03 h / -10 °C
2: N-methylmorpholine / CHCl3; dimethylformamide / 1.5 h / -5 - 20 °C
View Scheme
phenylacetyl chloride
103-80-0

phenylacetyl chloride

lead (II)-compound of ethanethiol

lead (II)-compound of ethanethiol

N-phenylacetyl-L-prolylglycine ethyl ester
157115-85-0

N-phenylacetyl-L-prolylglycine ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 86 percent / aq. NaOH / 0.25 h / 0 - 4 °C
2: N-methylmorpholine / CHCl3 / 0.03 h / -10 °C
3: N-methylmorpholine / CHCl3; dimethylformamide / 1.5 h / -5 - 20 °C
View Scheme
L-proline
147-85-3

L-proline

N-phenylacetyl-L-prolylglycine ethyl ester
157115-85-0

N-phenylacetyl-L-prolylglycine ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 86 percent / aq. NaOH / 0.25 h / 0 - 4 °C
2: N-methylmorpholine / CHCl3 / 0.03 h / -10 °C
3: N-methylmorpholine / CHCl3; dimethylformamide / 1.5 h / -5 - 20 °C
View Scheme
methylamine
74-89-5

methylamine

N-phenylacetyl-L-prolylglycine ethyl ester
157115-85-0

N-phenylacetyl-L-prolylglycine ethyl ester

N-phenylacetyl-L-prolylglycine methylamine

N-phenylacetyl-L-prolylglycine methylamine

Conditions
ConditionsYield
In methanol Ambient temperature;99%
N-phenylacetyl-L-prolylglycine ethyl ester
157115-85-0

N-phenylacetyl-L-prolylglycine ethyl ester

N-phenylacetyl-L-prolylglycine amide

N-phenylacetyl-L-prolylglycine amide

Conditions
ConditionsYield
With ammonia In methanol Ambient temperature;95%
N-phenylacetyl-L-prolylglycine ethyl ester
157115-85-0

N-phenylacetyl-L-prolylglycine ethyl ester

N-phenylacetyl-L-prolylglycine
157115-95-2

N-phenylacetyl-L-prolylglycine

Conditions
ConditionsYield
With sodium hydroxide for 3h;89.9%
N-phenylacetyl-L-prolylglycine ethyl ester
157115-85-0

N-phenylacetyl-L-prolylglycine ethyl ester

N-phenylacetyl-L-prolylglycine dimethylamide

N-phenylacetyl-L-prolylglycine dimethylamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 89.9 percent / 1 N aq. NaOH / 3 h
2: ethylmorpholine / dimethylformamide / 0.03 h / -10 °C
3: dimethylformamide / 0.5 h / -5 °C
View Scheme
N-phenylacetyl-L-prolylglycine ethyl ester
157115-85-0

N-phenylacetyl-L-prolylglycine ethyl ester

C20H26N2O6

C20H26N2O6

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 89.9 percent / 1 N aq. NaOH / 3 h
2: ethylmorpholine / dimethylformamide / 0.03 h / -10 °C
View Scheme

157115-85-0Downstream Products

157115-85-0Relevant articles and documents

Synthesis and antiamnesic activity of a series of N-acylprolyl-containing dipeptides

Gudasheva,Voronina,Ostrovskaya,Rozantsev,Vasilevich,Trofimov,Kravchenko,Skoldinov,Seredenin

, p. 151 - 157 (2007/10/03)

Eaters and amides of a series of N-acylprolyl-containing dipeptides were synthesized. It was established that these substances possess the ability to prevent memory decline evoked by maximal electroshock (MES) in a passive avoidance step-through paradigm. These N-acylprolyl-containing dipeptides were designed as analogues of pyroglutamyl-containing dipeptides, which we previously demonstrated to be highly active nootropics. Among the structure-activity relationships explored were the effect of N-acylsubstitution size, C-terminal substitution and the nature of the second amino acid. The optimal N-acyl moiety was the N-phenyl-acetyl group, while the optimal C-terminal substitution-esters were those derived from low alkyl alcohols. The optimal second amino acids were Asp, Glu or their fragments, Gly, β-Ala, GABA. Compound 1 (N-phenylacetylprolylglycine ethyl eater) was selected for further evalution in impaired cognitive functions. It was supposed that esters and unsubstituted amides of N-acylprolylglycines are prodrugs, which convert to the bioactive cyclo-(Pro-Gly) by virtue of enzymatic or chemical lability within the body.

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