Noopept - ≥98% , CAS No.157115-85-0

CAS: 157115-85-0 Cat. No.: N126590 Formula: C₁₇H₂₂N₂O₄ Molecular Weight: 318.37 EC Number: 839-170-3

GRADE & PURITY ≥98%

Synonyms

ethyl 1-(phenylacetyl)-L-prolylglycinate | 4QBJ98683M | D01808 | UNII-O6S620ML45 | SGS-111 | Ethyl N-[1-(Phenylacetyl)-L-prolyl]glycinate | AM84514 | ethyl 2-{[(2S)-1-(2-phenylacetyl)pyrrolidin-2-yl]formamido}acetate | N1120 | DVD-111 | N-(1-(Phenylacetyl

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Specifications

Synonyms

ethyl 1-(phenylacetyl)-L-prolylglycinate | 4QBJ98683M | D01808 | UNII-O6S620ML45 | SGS-111 | Ethyl N-[1-(Phenylacetyl)-L-prolyl]glycinate | AM84514 | ethyl 2-{[(2S)-1-(2-phenylacetyl)pyrrolidin-2-yl]formamido}acetate | N1120 | DVD-111 | N-(1-(Phenylacetyl

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

Description:IC50 Value: N/ANoopept (GVS-111) is a medication promoted and prescribed in Russia and neighbouring countries as a nootropic.in vitro: Nooglutil exhibits pharmacologically significant competition with a selective agonist of AMPA receptors ([G-

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

AGONIST

Note

Refer to SDS for more information. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

Pubchem Sid

488188513

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/488188513

Canonical Smiles

CCOC(=O)CNC(=O)C1CCCN1C(=O)CC2=CC=CC=C2

IUPAC Name

ethyl 2-[[(2S)-1-(2-phenylacetyl)pyrrolidine-2-carbonyl]amino]acetate

InChIKey

PJNSMUBMSNAEEN-AWEZNQCLSA-N

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

Isomeric SMILES

CCOC(=O)CNC(=O)[C@@H]1CCCN1C(=O)CC2=CC=CC=C2

RTECS

MC0814400

Molecular Weight

318.37

Reaxy-Rn

30236162

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=30236162&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Not available
• Direct Parent: Peptides
• Alternative Parents: Alpha amino acid esters N-acyl-alpha amino acids and derivatives Proline and derivatives Alpha amino acid amides Phenylacetamides Pyrrolidinecarboxamides N-acylpyrrolidines Tertiary carboxylic acid amides Secondary carboxylic acid amides Carboxylic acid esters Monocarboxylic acids and derivatives Azacyclic compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds Organonitrogen compounds Organopnictogen compounds
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Alpha peptide - Alpha-amino acid ester - Proline or derivatives - N-acyl-alpha amino acid or derivatives - Alpha-amino acid amide - Alpha-amino acid or derivatives - Phenylacetamide - N-acylpyrrolidine - Pyrrolidine carboxylic acid or derivatives - Pyrrolidine-2-carboxamide - Monocyclic benzene moiety - Benzenoid - Tertiary carboxylic acid amide - Pyrrolidine - Carboxamide group - Carboxylic acid ester - Secondary carboxylic acid amide - Azacycle - Monocarboxylic acid or derivatives - Organoheterocyclic compound - Organonitrogen compound - Hydrocarbon derivative - Organic oxygen compound - Organic nitrogen compound - Carbonyl group - Organic oxide - Organooxygen compound - Organopnictogen compound - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: solubility in DMSO:20 mg/mL, clear
• Sensitivity: Heat sensitive
• Specific Rotation[α]: -116° (C=0.4,CHCl3)
• Melt Point(°C): 96 °C
• Molecular Weight: 318.400 g/mol
• XLogP3: 1.500
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 318.158 Da
• Monoisotopic Mass: 318.158 Da
• Topological Polar Surface Area: 75.700 Ų
• Heavy Atom Count: 23
• Formal Charge: 0
• Complexity: 432.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

Item-specific, tested application data are not provided for this product.

General research protocols (guidance only)

• Stock preparation: Dissolve in DMSO to 10–100 mM. Vortex/sonicate briefly. Filter through 0.22 µm PTFE for analytical work or sterile PES for cell assays.
• Working solutions: Dilute stock into buffer or media to desired concentration, maintaining final DMSO ≤0.1–0.5% v/v as assay permits. Prepare fresh just before use to limit hydrolysis.
• LC-MS sample prep: Quench biological samples with cold acetonitrile containing internal standard, centrifuge, and analyze supernatant by LC-MS/MS (ESI+, MRM). Include stability controls to assess ester hydrolysis during handling.
• Solid handling: Equilibrate container to ambient temperature before opening to prevent moisture condensation. Weigh rapidly in a low-humidity environment.

Controls and references

• Include vehicle controls and, where relevant, hydrolyzed-reference controls to benchmark stability and recovery.

Note: For validated, application-specific methods, consult the literature or develop in-house SOPs tailored to your instrumentation and assay design.

Biological Roles

General literature context (for research use only; no medical claims)

• Noopept is a dipeptidomimetic related to N-phenylacetyl-L-prolyl-glycine ethyl ester. It is studied as a chemical probe in neurochemistry, including investigations of peptide-like transport, metabolism of proline-containing peptidomimetics, and structure–activity relationships within small neutral dipeptide analogs.
• The compound is frequently examined for its interactions in neuronal models, including uptake/efflux characteristics and enzymatic stability, owing to its ester/amide functional groups that can undergo hydrolysis.

Biochemical properties (literature/general)

• Amphiphilic profile enables assessment of membrane permeability and protein binding in vitro.
• The aromatic chromophore supports straightforward analytical tracking (HPLC-UV, LC-MS/MS) in cell lysates and tissue homogenates for PK/ADME-style research in preclinical settings.
• Hydrolytic pathways (ester cleavage) and possible formation of related acids/alcohols are common foci for metabolic stability studies.

Practical research considerations

• When used as a probe in cell systems, control for vehicle effects (DMSO/ethanol) and confirm free concentration via binding or recovery assays.
• Time-course designs should account for potential hydrolysis in culture media; include quenched controls and internal standards for accurate quantitation.

Buffer Applications

Not typically applicable.

• Noopept is not a buffering agent and does not constitute a classical acid–base buffer system. For experiments involving this compound, select a buffer based on your biological or analytical method (e.g., PBS, HEPES, phosphate, acetate) and verify compatibility with Noopept’s solubility and stability. Co-solvents (DMSO/ethanol) may be required at low percentages to ensure complete dissolution.

Green Alternatives

Context

• Noopept is a target compound rather than a process solvent or auxiliary. “Greener alternatives” apply mainly to the choice of vehicles and analytical solvents when preparing or analyzing this compound.

Greener solvent choices (general guidance)

• Replace acetonitrile with ethanol/water or methanol/water gradients in HPLC when method performance permits.
• Prefer ethanol or isopropanol as co-solvents over DMF/DMAC when solubility allows.
• Use water-rich buffered systems for biological assays; minimize DMSO content while maintaining solubility and stability.

Comparison (general)

• DMSO: High solvency, excellent stability carrier; environmental burden is moderate; keep volumes small.
• Ethanol: Renewable, lower toxicity; may limit solubility.
• Isopropanol: Good compromise for reversed-phase methods; higher viscosity than acetonitrile.

Operational practices

• Prepare concentrated stock solutions to reduce overall solvent volumes.
• Employ microscale assays and 96/384-well formats to minimize waste.
• Utilize LC-MS methods that shorten run times and use aqueous-rich mobile phases to cut solvent consumption.

Note

• Selection of greener options must not compromise data quality or compound stability; verify recovery, adsorption, and hydrolysis profiles under revised conditions.

Pharmaceutical Uses

Not an excipient; research use only.

• This product is supplied strictly for research use. It is not formulated to pharmacopeial specifications and is not intended for human or veterinary use.
• In preclinical and formulation research contexts (literature/general), Noopept may serve as a model compound for permeability, stability, and dosage-form feasibility studies of small peptidomimetics. Potential vehicles include aqueous buffers with co-solvent (DMSO/ethanol), simple capsules for solid-state stability studies, or lipid-based systems; these are exploratory research applications only and must be validated case-by-case.
• No medical, therapeutic, or clinical claims are made or implied for this product.

Physical Properties

Item-specific specifications

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general reference values (not product specifications)

• Aggregate state: Typically an off-white to white crystalline solid (literature).
• Melting behavior: Often reported to melt/decompose in the ~95–105 °C range (literature; varies by polymorph and purity).
• Solubility profile: Readily soluble in DMSO and DMF; soluble to moderately soluble in ethanol and methanol; low to moderate aqueous solubility that can be improved with pH adjustment or co-solvents (literature).
• Partitioning: Amphiphilic peptidomimetic; logP/logD values reported near neutrality are modest, reflecting both aromatic and peptide-like moieties (literature, qualitative).
• pKa: No strongly ionizable groups in the neutral range beyond the amide/secondary amine; overall neutral to weakly basic behavior; practical ionization is limited (literature, qualitative).
• UV: Aromatic ring confers UV absorbance ~200–230 nm and ~250–280 nm regions (literature), enabling HPLC-UV quantitation.

Notes for users

• If quantitative solubility, density, refractive index, or exact thermal transitions are required for your lot, consult the Certificate of Analysis (CoA) for definitive values.
• Avoid overheating during characterization; thermal analysis may show overlapping melt/decomposition due to ester/amide functionalities.

Quality & Grades

Item-specific

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

How to interpret common grades (general guidance)

• Research grade: Suitable for most discovery and method-development workflows (e.g., in vitro assays, reference standards), typically supported by NMR/LC-MS/HPLC CoA metrics.
• HPLC grade/Reference standard grade (if applicable): Emphasis on chemical purity and low UV-absorbing impurities; often accompanied by chromatographic purity and residual solvent/metals data.
• Stabilizers: None listed for this item. If stabilizers or form-specific excipients are present, they will appear on the CoA/Spec Sheet.

Quality control recommendations (general)

• Identity: Confirm by 1H/13C NMR and LC-MS; aromatic and peptidomimetic resonances provide diagnostic patterns.
• Purity: HPLC-UV at multiple wavelengths (e.g., 210/254 nm) is recommended due to the aromatic chromophore; consider ELSD/charged aerosol if non-UV impurities are a concern.
• Residual solvents/water: Karl Fischer for water; HS-GC for residual solvents when your application is moisture/solvent-sensitive.
• Solid form: If polymorphism matters to your application, assess by DSC/XRPD.

Note: When a specific numeric purity or impurity limit is required for method validation or regulated work, rely on the lot-specific CoA.

Reaction & Applications

Applicability overview

• As supplied, Noopept is most often used as a research analyte/ligand in biochemical, neurochemistry, and transport studies rather than as a general-purpose synthetic reagent.

Analytical and assay applications (general/literature)

• Quantitation: Amenable to LC-UV or LC-MS/MS due to aromatic chromophore and moderate ionization efficiency in positive ESI. Typical reverse-phase methods: C18 column, water/acetonitrile with 0.1% formic acid, gradient elution.
• Stability studies: Examine hydrolysis (ester cleavage) under acidic/basic conditions; track formation of corresponding acids/alcohols by LC-MS.
• Permeability/transport: Used in in vitro PAMPA or Caco-2 models to study peptidomimetic transport (literature context; not a product performance claim).

Chemical reactivity notes (general)

• The ethyl ester can undergo hydrolysis (acidic, basic, or enzymatic). The amide linkage is comparatively stable but can be engaged in peptide-coupling or exchange under forcing conditions.
• Aromatic ring supports standard electrophilic substitutions only in precursor syntheses; in the final molecule it serves primarily as a hydrophobic/π-system handle.

Practical tips

• For solution studies, prepare concentrated DMSO stocks and dilute into assay media immediately before use.
• Minimize exposure to strong base/acid during handling to limit ester hydrolysis; keep solutions cool and use fresh aliquots.

Reaction Conditions

This product is primarily used as an analyte or research probe. For groups pursuing chemical manipulations, the following are general, literature-style conditions for functional groups present in Noopept (not product specifications):

• Ester hydrolysis (to carboxylic acid):
  • Basic: Aqueous NaOH or K2CO3 in MeOH/H2O (0–25 °C), minutes to hours; monitor by LC-MS. Neutralize and isolate under mild conditions to avoid amide cleavage.
  • Acidic: Dilute HCl or H2SO4 in MeOH/H2O (reflux or ambient with longer times). Risk of amide hydrolysis at elevated temperatures.
• Transesterification:
  • Alcohol solvent with catalytic acid (e.g., p-TsOH) or base (e.g., NaOMe) at 0–25 °C to reflux, depending on target ester.
• Analytical LC conditions (for quantitation):
  • Column: C18, 2.1–4.6 mm ID; Mobile phase: water (0.1% formic acid)/acetonitrile or methanol; Gradient: 5–95% organic over 5–15 min; Detection: 210–230 and 254–280 nm; MS: ESI+. Retention/time must be optimized per instrument.

Expected observations

• Clean conversion in ester reactions if temperature and pH are controlled; amide bond remains intact under mild conditions.

Always validate on small scale and consult peer-reviewed procedures when adapting these conditions.

Safety & Handling

Authoritative safety information must be obtained from the product SDS.

Item-specific (from Product Data)

• GHS classification, Signal Word, Hazard (H) statements, Pictograms: Not specified for this item; refer to SDS.
• Storage: Store at −20 °C.
• Shipping: Shipped in ice chest with ice pads.

General laboratory guidance (not product specifications; follow your institutional EHS rules)

• Likely hazard profile: Low-volatility organic solid; handle as a potentially harmful substance. Avoid inhalation of dust, ingestion, and skin/eye contact.
• PPE: Laboratory coat, safety goggles, and suitable chemical-resistant gloves (e.g., nitrile). Handle powders in a fume hood or with local exhaust ventilation.
• Incompatibilities: Strong oxidizing agents; strong acids/bases may cause hydrolysis of the ester/amide. Avoid prolonged exposure to moisture and heat.
• First aid overview: In case of skin/eye contact, rinse with water for at least 15 minutes and seek medical attention as needed. If inhaled, move to fresh air. If ingested, rinse mouth; do not induce vomiting; seek medical advice. Always consult SDS for definitive instructions.
• Spill/cleanup: Avoid dust generation. Collect with inert absorbent or damp disposable towels; dispose according to local regulations.
• Stability considerations: Protect from light, moisture, and elevated temperature to minimize hydrolysis/oxidation. Use desiccation and inert-atmosphere storage for long-term stability when practical.

Solvent Selection

Compound type and polarity (general)

• Noopept is an amphiphilic peptidomimetic featuring an aromatic ring and amide/ester groups. It is typically more soluble in polar aprotic solvents than in pure water.

Practical solvent choices (literature/general)

• Stock solutions: DMSO (common up to 10–100 mM), DMF (similar), ethanol (lower maxima), or mixed aqueous buffers with co-solvent (e.g., 10–30% v/v DMSO or ethanol).
• Aqueous media: Solubility can be improved by gentle warming (≤40 °C), sonication, or pH adjustment (slightly basic conditions increase solubility but may promote slow ester hydrolysis). Use promptly after dissolution.
• Compatibility: For biological assays, keep final DMSO ≤0.1–0.5% v/v when possible; verify assay tolerance.

Comparison (general guidance)

• DMSO vs ethanol: DMSO generally affords higher solubility and stability; ethanol may be preferable for cell-sensitive systems.
• PBS vs plain water: Buffers stabilize pH but salts may influence solubility; adding 0.1–0.5% surfactant (e.g., polysorbate) can help in specialized formulations.

Notes

• Filter sterilization (0.22 µm) is recommended for cell-based work; assess adsorption losses by container material (glass preferred over some plastics for aromatic compounds).

Storage & Reconstitution

Item-specific (from Product Data)

• Storage conditions: Store at −20 °C.
• Shipping: Shipped in ice chest with ice pads.
• Research use: For research use only.

General best practices (not product specifications)

• Solid storage: Keep tightly sealed in the original container, protected from light and moisture; use a desiccant. Allow vial to warm to room temperature before opening to avoid condensation.
• Reconstitution: Prepare concentrated stock solutions in dry DMSO (preferred), DMF, or ethanol. For aqueous applications, dilute the organic stock into buffer immediately before use. Gentle warming (≤40 °C) and brief sonication can aid dissolution.
• Aliquoting: Divide stock into single-use aliquots (e.g., 10–100 µL) and store at −20 °C or below. Avoid repeated freeze–thaw cycles.
• Stability: Working solutions in aqueous media may undergo slow ester hydrolysis, especially at elevated temperature or extreme pH; prepare fresh and use promptly. Monitor by LC if critical.
• Disposal: Dispose of unused material and solutions according to institutional and local regulations for organic laboratory chemicals.

If stricter stability or impurity limits are required for your workflow, consult the lot-specific CoA for retest intervals and analytical verification.

Structure & Identity

Brief description: Noopept is a small-molecule peptidomimetic (phenylacetyl–L-prolyl–glycine ethyl ester), commonly used as a research probe in neurochemistry and peptide transport studies.

Item-specific (from Product Data)

• SKU: N126590
• Product Name: Noopept
• CAS: 157115-85-0
• PubChem CID: 180496
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.

Literature identity (general reference, not a product specification)

• Preferred IUPAC name (literature): Ethyl (2S)-2-[(phenylacetyl)amino]prolinate
• Synonym: N-phenylacetyl-L-prolylglycine ethyl ester; GVS-111
• Molecular formula (literature): C17H22N2O4
• Molecular weight (literature): ~318.37 g/mol

Structural features (general)

• Functional groups: aromatic phenyl ring; amide (phenylacetamide); secondary amide within a dipeptidomimetic backbone; ethyl ester of glycine carboxylate; secondary amine embedded in a proline ring.
• Ring systems: proline pyrrolidine ring; phenyl ring.
• Stereochemistry: L-configuration at the proline-derived stereocenter [(S)- at the α-carbon].
• 2D description: A phenylacetyl carbonyl linked to an amide nitrogen that is bound to the proline nitrogen; the proline α-carbon bears an ethyl esterified glycine carboxyl; overall a compact, moderately polar, amphiphilic peptidomimetic.

Synthetic Utility

General synthetic perspective (not a primary building block offering)

• Noopept contains both an amide and an ethyl ester within a proline-based scaffold, rendering it a useful model substrate for studying chemoselective transformations in peptidomimetic systems.

Functional group reactivity (literature/general)

• Ester: Susceptible to hydrolysis (acidic, basic, or enzymatic) to the corresponding carboxylic acid; amenable to transesterification under standard conditions (e.g., alcohol, acid/base catalysis) with consideration of amide stability.
• Amide: Relatively inert; can be engaged under peptide-coupling or activating conditions (e.g., carbodiimides, uronium reagents) if derivatization is desired on precursors.
• Aromatic ring: Primarily a hydrophobic handle; electrophilic substitutions are relevant to precursors rather than the final molecule.

Utility in methods development

• Serves as a benchmark for LC method optimization (UV response, retention in RP systems) and hydrolysis kinetics modeling of peptidomimetic esters.
• Useful for assessing protecting-group strategies and selective hydrolysis in complex peptide-like molecules.

Note

• If you intend to derivatize or use Noopept as a substrate, validate chemoselectivity to prevent unwanted backbone cleavage or racemization at the proline stereocenter.

Target Specificity

Not applicable to this product type.

• Noopept is a small-molecule research chemical, not an antibody or affinity reagent. No antigen/epitope, clone, isotype, or species-reactivity data are applicable.

Frequently Asked Questions

What is the purity of this product?

This product is supplied at ≥98% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at ?20 °C. Freezer storage is required to maintain the specified shelf life.

How is this product shipped?

This product ships in an insulated container with ice pads. Unpack on arrival and transfer it to the storage condition stated above.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 157115-85-0, the molecular formula is C17H22N2O4, and the molecular weight is 318.37 g/mol. InChIKey PJNSMUBMSNAEEN-AWEZNQCLSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.