Jwh-387 , CAS No.1366067-59-5

CAS: 1366067-59-5 Cat. No.: J980574 Formula: C₂₄H₂₂BrNO Peso molecolare: 420.34 PubChem CID: 71454233

Storage

Room temperature

Specifications

Condizioni di conservazione di stoccaggio

Room temperature

Nomi e identificatori

Sorrisi canonici

CCCCCN1C=C(C2=CC=CC=C21)C(=O)C3=CC=C(C4=CC=CC=C43)Br

IUPAC Name

(4-bromonaphthalen-1-yl)-(1-pentylindol-3-yl)methanone

InChIKey

GRWSWDKSCZKGSY-UHFFFAOYSA-N

INCHI

1S/C24H22BrNO/c1-2-3-8-15-26-16-21(19-11-6-7-12-23(19)26)24(27)20-13-14-22(25)18-10-5-4-9-17(18)20/h4-7,9-14,16H,2-3,8,15H2,1H3

Isomeri SMILES

CCCCCN1C=C(C2=CC=CC=C21)C(=O)C3=CC=C(C4=CC=CC=C43)Br

PubChem CID

71454233

Peso molecolare

420.34

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Classe Indoles and derivatives
      • Subclass Naphthoylindoles

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Classe: Indoles and derivatives
• Subclass: Naphthoylindoles
• Intermediate Tree Nodes: Not available
• Direct Parent: Naphthoylindoles
• Alternative Parents: Benzoylindoles Naphthalenecarboxylic acids and derivatives Indolecarboxylic acids and derivatives N-alkylindoles Indoles Aryl ketones Substituted pyrroles Aryl bromides Vinylogous amides Heteroaromatic compounds Azacyclic compounds Organonitrogen compounds Organobromides Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Naphthoylindole - Benzoylindole - 1-naphthalenecarboxylic acid or derivatives - Indolecarboxylic acid derivative - N-alkylindole - Naphthalene - Indole - Aryl ketone - Aryl bromide - Aryl halide - Benzenoid - Substituted pyrrole - Heteroaromatic compound - Vinylogous amide - Pyrrole - Ketone - Azacycle - Organobromide - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Organic nitrogen compound - Organohalogen compound - Aromatic heteropolycyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as naphthoylindoles. These are polycyclic compounds containing an indole moiety that is N-linked to the carboxamide group attached to naphthalene.
• 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

Proprietà chimiche e fisiche

• Peso molecolare: 420.300 g/mol
• XLogP3: 7.000
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 6
• Exact Mass: 419.088 Da
• Monoisotopic Mass: 419.088 Da
• Topological Polar Surface Area: 22.000 Ų
• Heavy Atom Count: 27
• Formal Charge: 0
• Complexity: 509.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• 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 applications and recommended protocols are not provided for this product.

General guidance for use as a small-molecule research ligand (not item-specific; verify in your system):

• Stock solution: Dissolve in anhydrous DMSO at an appropriate concentration (e.g., 10–50 mM). Vortex and, if needed, sonicate briefly.
• Working dilutions: Prepare fresh by serial dilution into assay buffer or culture medium, ensuring final DMSO ≤0.1–0.5% v/v. Include vehicle controls.
• Plate-based assays: Pre-wet tips and use low-bind plastics to reduce adsorption. Mix thoroughly after addition and equilibrate for the time appropriate to your readout (binding vs functional response).
• Stability checks: Inspect for precipitation or turbidity. Confirm concentration by UV or LC if quantitative accuracy is critical.
• Documentation: Record lot number, preparation date, solvent, and storage conditions to maintain data traceability.

Note:

• For any validated, product-specific protocols (e.g., WB/IHC/IF/FC are not applicable to small molecules), consult the CoA/Spec Sheet or contact technical support.

Biological Roles

Context (literature/general; no medical claims):

• JWH-series compounds are widely used as research ligands for the endocannabinoid system, which includes cannabinoid receptors CB1 (CNS-enriched) and CB2 (immune/peripheral tissues), endogenous ligands (anandamide, 2-AG), and associated metabolic enzymes (FAAH, MAGL).
• These ligands help delineate receptor binding sites, efficacy (full/partial agonism or antagonism), signaling bias (G protein vs β-arrestin pathways), desensitization, and receptor trafficking dynamics.
• Due to their high lipophilicity, such ligands partition into membranes and can exhibit slow on/off kinetics and apparent time-dependent potency; this is valuable for studying receptor residency and tolerance phenomena in vitro.

Experimental uses (general):

• Receptor binding assays (radioligand displacement), second-messenger readouts (cAMP, Ca2+, ERK phosphorylation), and arrestin recruitment (BRET/HTRF).
• Benchmarking analytical methods in forensic toxicology.

Item-specific biological role:

• Not specified for this item; refer to primary literature for Jwh-387 (PubChem CID 71454233) and verify activity profiles before experimental use.

Cautions (general):

• Many synthetic cannabinoid ligands are potent at low nanomolar concentrations. Implement rigorous dilution accuracy and appropriate negative/positive controls. Confirm off-target effects by counter-screens (e.g., cytotoxicity, GPCR panels) when mechanistic fidelity is critical.

Buffer Applications

This product is not a buffering agent. However, for biological assays involving hydrophobic ligands, buffer handling can be critical.

General guidance (not item-specific):

• Stock preparation: Dissolve in anhydrous DMSO at 10–50 mM. For working solutions, dilute into assay buffer (e.g., HBSS, PBS, HEPES-buffered saline, or cell culture medium) with continuous mixing to a final DMSO content typically ≤0.1–0.5% v/v.
• Solubility aids: Add 0.1–1% fatty-acid–free BSA or 0.01–0.1% non-ionic surfactant (e.g., Pluronic F-127 or Tween-20) if precipitation occurs and if compatible with the assay.
• Adsorption mitigation: Use low-bind tubes and tips; pre-rinse plastics with dilute DMSO/buffer mix when working at low nanomolar concentrations.
• pH range: Follow the assay’s buffer system (PBS pH 7.2–7.4; HEPES pH 7.2–7.6 typical). The compound does not itself define a buffer range.

Item-specific buffer information:

• Not specified for this item; refer to CoA/Spec Sheet and validate compatibility in your specific assay matrix.

Green Alternatives

Green chemistry considerations for handling solutions of hydrophobic bioactive small molecules:

• While the compound itself is the research target and not replaceable by a “greener” analog for mechanistic studies, solvent and workflow choices can reduce environmental impact.

Greener solvent choices (general):

• Prefer ethanol or water–ethanol mixtures over chlorinated solvents when feasible for cleaning and preliminary dissolutions.
• Keep DMSO concentrations minimal in aqueous assays; although DMSO is relatively low hazard, reducing organic load is beneficial.
• Avoid dichloromethane/chloroform for routine processing; use ethyl acetate or isopropanol for extractions and glassware cleaning where compatible.

Operational improvements:

• Miniaturize assays (microscale plates) to reduce solvent and compound consumption.
• Use closed-vial preparation and aliquoting to limit evaporative losses and worker exposure.
• Implement solvent recycling for high-volume analytics (e.g., methanol/acetonitrile from LC systems) where institutional infrastructure exists.

Illustrative comparison (general; not item-specific):

• Chlorinated solvents: High environmental/health impact; avoid for routine work.
• Ethanol/IPA: Renewable routes available; better EHS profile; may have lower solvency for very hydrophobic compounds.
• Ethyl acetate: Biodegradable; good for cleaning; limited water miscibility may be a constraint.

Note: No item-specific “green” certified grade or alternative is provided in the Product Data.

Pharmaceutical Uses

This product is supplied strictly for research use only and is not intended for human or veterinary use, clinical diagnosis, or any form of therapeutic application.

Formulation/excipient role:

• None. As a bioactive small molecule research ligand, it is not used as a pharmaceutical excipient or processing aid.

Standards and compendia:

• No pharmacopeial monograph is indicated for this item. Any use as an analytical reference in regulated environments requires independent qualification according to your quality system.

Process development (general, non-clinical):

• If used to develop analytical methods (e.g., LC–MS/MS reference), ensure traceability of reference standards, assign expiry/retest dates, and maintain storage/handling controls to prevent degradation.

Regulatory caution:

• Some JWH-series compounds are controlled or scheduled in various jurisdictions. Ensure compliance with all applicable laws and institutional approvals before acquisition, possession, or use.

Item-specific notes:

• Grade/purity, stabilizers, residual solvents, and formulation guidance are not specified for this item; consult the CoA/Spec Sheet for available analytical characterization.

Physical Properties

Item-specific properties:

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

Common physicochemical expectations for lipophilic cannabinoid-receptor ligands (literature/general, not item-specific):

• Physical state: Many JWH analogs are off-white solids or viscous oils with high lipophilicity.
• Solubility profile: Typically sparingly soluble in water; soluble in organic solvents such as DMSO, DMF, ethanol, methanol, acetone, and acetonitrile. For aqueous assays, stocks are often prepared in DMSO (e.g., 10–50 mM) and diluted into buffer containing carrier protein or surfactant to mitigate precipitation.
• Partitioning: High cLogP/logD expected due to multiple aromatic rings and limited HBD count (literature/general).
• Spectral properties: UV absorption commonly strong in the 200–300 nm region due to conjugated aromatics (literature/general). Specific ε/λmax values are compound-dependent and not provided here.
• Thermal behavior: Many analogs lack sharp melting points or show decomposition upon heating; exact MP/BP not provided for this item.

Not provided for this item (consult CoA/Spec Sheet):

• Melting/boiling point, density, refractive index, pKa, logP/logD, water solubility, UV cutoff, residual solvents, and elemental analysis.

Practical guidance (general):

• Assess solubility empirically at small scale. Filter 0.2 μm if preparing solutions for cell-based assays to remove particulates. Avoid prolonged exposure to strong light/oxidants that may degrade aromatic systems.

Quality and Grades

Item-specific grade/purity details:

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

How to interpret typical grades (general guidance):

• Research grade: Suitable for exploratory laboratory studies (e.g., in vitro receptor assays). May not include full trace contaminant profiling.
• Analytical/reference grade: Often accompanied by detailed analytical characterization (HPLC purity, NMR, MS) and is intended for use as a reference standard in method development or QC.
• Chromatography/HPLC grade (for solvents): Emphasizes low UV absorbance and minimal residue—less applicable here since this is a solid small-molecule reagent.

What to verify on receipt (best practices):

• Purity assay: Review HPLC/UPLC chromatograms, NMR spectra, and HRMS to confirm identity and purity. Check residual solvent levels if relevant to your application.
• Water/peroxide/metal specifications: Not specified for this item; refer to CoA/Spec Sheet. If your application is sensitive (e.g., bioassays), consider additional drying or re-purification.
• Stabilizers: Not specified for this item; refer to CoA/Spec Sheet. If no stabilizer is listed, protect from light/oxidants during storage and handling.

Lot-to-lot consistency:

• For quantitative biology/analytical applications, maintain a single lot for a complete study when feasible. Record exact lot number, storage history, and preparation notes to ensure reproducibility.

Reaction and Applications

Applicability to reactions:

• This product is a bioactive small molecule used as a research tool, not a general-purpose synthetic reagent. It is not typically employed as a catalyst, reagent, or solvent in preparative organic reactions.

Research applications (literature/general, no medical claims):

• Cannabinoid receptor pharmacology: “JWH-” ligands are widely used to probe CB1/CB2 receptor binding, signaling bias, and structure–activity relationships in vitro (radioligand displacement, GTPγS binding, β-arrestin recruitment, cAMP modulation) and in ex vivo receptor-competent tissues.
• Analytical reference: Employed as a reference standard for method development and validation (LC–MS/MS, GC–MS) in forensic/toxicological laboratories. Use requires appropriate certifications where regulated.
• Membrane partitioning studies: Useful in investigating ligand lipophilicity, membrane diffusion, and protein binding effects on apparent potency.

Practical tips (general):

• Prepare DMSO stocks, minimize freeze–thaw, and protect from light. Confirm concentration by UV or quantitative NMR where possible.
• Adsorptive loss can be significant at low nM–μM levels; use low-bind plastics/glass and include carrier proteins when compatible.
• Validate stability in the chosen assay medium over experimental timescales; re-prepare solutions if precipitation or degradation is observed.

Item-specific manufacturer applications:

• Not provided for this item; see catalog note: For research use only.

Reaction Conditions

This item is not generally used as a reagent or catalyst; therefore, standard synthetic “reaction conditions” are not applicable.

For research applications (general, non-synthetic):

• Ligand testing in receptor assays often occurs at 0.1–10,000 nM concentrations depending on assay sensitivity and expected potency, with incubation times from minutes to hours. Optimize per assay type (radioligand displacement, cAMP, β-arrestin) and cell system.
• Vehicle controls: Match DMSO/ethanol percentage across wells (commonly ≤0.1–0.5% v/v) to exclude solvent effects.
• Temperature: Most cell-based assays at 20–37°C; binding assays may be run at 0–25°C to slow kinetics.

Stability considerations (general):

• Protect solutions from strong light and oxidants. Assess short-term stability in assay buffer; replace working solutions regularly if precipitation or loss of activity is detected.

Item-specific reaction/assay conditions:

• Not specified for this item; consult primary literature for Jwh-387 and validate conditions in pilot experiments before committing to large studies.

Safety and Handling

Authoritative safety information must come from the SDS for this specific lot.

Item-specific hazard data (as provided):

• Signal Word: Not specified for this item; refer to SDS.
• H-Statements: Not specified for this item; refer to SDS.
• GHS Classification/Pictograms: Not specified for this item; refer to SDS.

General laboratory precautions for lipophilic research ligands (literature/general):

• PPE: Wear lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Handle solids or powders in a fume hood to minimize inhalation/dermal exposure.
• Avoid ingestion, inhalation, and skin/eye contact. Wash hands thoroughly after handling. Decontaminate work surfaces after use.
• Incompatibilities: Avoid strong oxidizing agents, strong acids/bases, and reactive halogenating agents that may attack aromatic/indole-like systems.
• Engineering controls: Use containment (fume hood), avoid aerosolization and dust formation. For solution handling, cap tubes promptly to limit volatilization of organic solvents.
• First aid (overview; defer to SDS): Inhalation—move to fresh air, seek medical attention if symptoms persist. Skin—wash with soap and water, remove contaminated clothing. Eyes—rinse cautiously with water for several minutes, remove contact lenses if present. Ingestion—rinse mouth, do not induce vomiting, seek medical advice.
• Waste: Collect solid and solution waste in properly labeled containers as organic hazardous waste according to institutional and local regulations.

Special notes (general):

• Many synthetic cannabinoid ligands are biologically potent at low concentrations. Handle with heightened care to avoid accidental exposure. Use dedicated tools and secondary containment for weighing and solution prep.

Solvent Selection

Compound type and polarity (general for hydrophobic receptor ligands):

• Polarity: Strongly lipophilic/aromatic; practically insoluble in water but soluble in polar aprotic and some protic organic solvents.
• Recommended stock solvent (general): DMSO is preferred for biological assays due to compatibility with aqueous buffers on dilution; ethanol or methanol are alternatives for certain workflows.

Miscibility and handling (general):

• Prepare concentrated stocks (e.g., 10–50 mM in anhydrous DMSO), aliquot, and store sealed to minimize water uptake. Warm gently and vortex/sonicate to aid dissolution. For buffer dilution, add stock slowly with vigorous mixing; include 0.1–1% carrier (BSA) or 0.01–0.1% non-ionic surfactant to reduce precipitation and adsorption losses.

When to choose alternatives:

• Aqueous matrices: Use cosolvent systems (DMSO ≤0.1–0.5% v/v final) or cyclodextrin inclusion where compatible.
• LC/MS reference solutions: Methanol or acetonitrile can give cleaner baselines; include formic acid or ammonium acetate as needed for ionization, validating stability first.

Small comparison (general):

• DMSO: Excellent solvency; broadly assay-compatible at low %.
• Ethanol: Good solvency; more benign in some cell assays but may require higher %.
• Methanol: Strong solvency; watch toxicity in live-cell systems.
• Acetonitrile: Useful for analytics; limited biological compatibility.

Item-specific solvent data:

• Not specified for this item; refer to CoA/Spec Sheet for any solubility specifications or recommended solvents.

Storage and Reconstitution

Item-specific storage conditions:

• Storage Conditions: Room temperature (as provided). Maintain tightly closed in a dry, well-ventilated place, protected from light if feasible.
• Shipped In: Not specified for this item; refer to product label.

General best practices (not item-specific):

• Protect from moisture and oxidants. Store in the original amber vial or otherwise shield from light to preserve stability of aromatic systems.
• Reconstitution: For assay use, prepare concentrated stock solutions in anhydrous DMSO (typical 10–50 mM). Filter (0.2 μm PTFE) if particulate is observed. Dispense single-use aliquots in inert, low-bind microvials to minimize freeze–thaw and adsorption losses.
• Short-term storage of solutions: DMSO stocks are commonly stable for weeks at 2–8°C and months at −20°C/−80°C when protected from moisture and light; confirm stability empirically for your application.
• Freeze–thaw: Avoid repeated freeze–thaw of solutions; use aliquots. Warm to room temperature before opening to prevent condensation ingress.

Item-specific parameters not provided (consult CoA/Spec Sheet):

• Exact shelf life/retest period, stabilizers (if any), and solution stability data.

Research use note:

• For research use only. Not for human or veterinary use.

Structure and Identity

Brief overview: This catalog entry refers to Jwh-387 (CAS 1366067-59-5), a small-molecule research chemical commonly discussed in the context of synthetic cannabinoid ligands.

• CAS: 1366067-59-5 (item-specific)
• InChIKey: 109926 (item-specific; as provided)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
• Synonyms: Not specified for this item; refer to CoA/Spec Sheet.

Structural features (literature/general, not item-specific):

• The “JWH-” series typically comprises indole- or indazole-based scaffolds bearing lipophilic aryl or heteroaryl acyl/amide/ketone substituents designed to engage the CB1/CB2 cannabinoid receptor binding pockets.
• Common motifs include a bicyclic indole/indazole core, a carbonyl linker (e.g., naphthoyl/benzoyl/other acyl), and a bulky hydrophobic aryl/alkyl tail to enhance membrane permeability and receptor affinity.

2D structural description (literature/general):

• Planar aromatic core (indole/indazole-like) connected through a carbonyl or equivalent linker to an extended hydrophobic substituent; overall highly aromatic and lipophilic, with few hydrogen-bond donors.

Important note:

• Exact constitutional and stereochemical details for Jwh-387 are not specified in this item’s data. For definitive identity (structure drawing, SMILES/InChI, elemental formula), consult the product’s Certificate of Analysis (CoA) or Specification Sheet and confirm against primary literature or databases (e.g., CAS Registry, PubChem CID 71454233).

Synthetic Utility

Not typically applicable. Jwh-387 is a finished bioactive small molecule used as a research ligand rather than as a building block or reagent in multistep synthesis.

General notes (literature/general):

• Indole/indazole-derived cannabinoid ligands are usually the targets of synthesis, not intermediates. They feature multiple aromatic rings and a polar linker (e.g., carbonyl), optimized for receptor binding.
• Functional group compatibility: These scaffolds, when present as substrates, are generally stable to mild bases, neutral conditions, and many transition-metal-catalyzed cross-couplings if appropriately protected; however, they can be sensitive to strong oxidants, electrophilic halogenation, or prolonged strong acid exposure affecting the heteroaromatic core.

If transformation is unavoidable (general cautions):

• Late-stage functionalization (e.g., N-alkylation on indole nitrogen) can alter receptor activity dramatically; any derivatization may invalidate biological comparisons.
• Purity-critical applications (receptor pharmacology) demand rigorous separation of positional isomers and residual catalysts. Validate identity by orthogonal methods (NMR, HRMS, HPLC/UPLC, possibly chiral analysis if stereocenters exist).

Item-specific synthetic roles:

• None provided; not positioned as a synthon or reagent in this catalog entry.

Target Specificity

Item-specific targeting details (antigen/epitope/clone/species) do not apply to small-molecule ligands and are not provided.

General context (literature/general):

• JWH-series compounds are frequently characterized as ligands of cannabinoid receptors CB1 and/or CB2; however, exact selectivity and efficacy profiles are compound-specific and must be verified experimentally.

For this product entry:

• Target specificity, Ki/EC50 values, receptor bias, and off-targets: Not specified for this item; refer to CoA/Spec Sheet and primary literature (e.g., PubChem CID 71454233) for any reported binding data. Perform internal confirmation under your assay conditions.