Jwh-020 , CAS No.209414-09-5

CAS: 209414-09-5 Cat. No.: J978259 Formula: C₂₆H₂₇NO Molecular Weight: 369.500

Storage

Room temperature

Specifications

Storage

Room temperature

Names and Identifiers

Canonical Smiles

CCCCCCCN1C=C(C2=CC=CC=C21)C(=O)C3=CC=CC4=CC=CC=C43

IUPAC Name

(1-heptylindol-3-yl)-naphthalen-1-ylmethanone

InChIKey

IHKDUDCDUKFOKK-UHFFFAOYSA-N

INCHI

1S/C26H27NO/c1-2-3-4-5-10-18-27-19-24(22-15-8-9-17-25(22)27)26(28)23-16-11-13-20-12-6-7-14-21(20)23/h6-9,11-17,19H,2-5,10,18H2,1H3

Molecular Weight

369.500

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: 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 Vinylogous amides Heteroaromatic compounds Azacyclic compounds Organonitrogen compounds 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 - Substituted pyrrole - Benzenoid - Pyrrole - Heteroaromatic compound - Vinylogous amide - Ketone - Azacycle - Organooxygen compound - Organonitrogen compound - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Organic nitrogen compound - Aromatic heteropolycyclic compound
• Description: 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

Chemical and Physical Properties

• Molecular Weight: 369.500 g/mol
• XLogP3: 7.400
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 8
• Exact Mass: 369.209 Da
• Monoisotopic Mass: 369.209 Da
• Topological Polar Surface Area: 22.000 Ų
• Heavy Atom Count: 28
• Formal Charge: 0
• Complexity: 503.000
• 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

• No validated application protocols are provided for this item.

General starting points (research use only)

• Stock solution: Dissolve in anhydrous DMSO to 10 mM. Vortex and, if needed, sonicate briefly. Filter through a PTFE 0.2 µm syringe filter to remove particulates.
• Binding assay (membrane prep): Prepare assay buffer (e.g., 50 mM Tris-HCl, 2 mM MgCl2, 1 mM EDTA, 0.1% BSA, pH 7.4). Incubate membranes with tracer and serial dilutions (0.1 nM–10 µM) of test compound at 25–30 °C for 90 min. Terminate by rapid filtration; quantify bound tracer. Include non-specific binding controls.
• Cell-based signaling: Plate cells expressing CB receptors. Dose with serial dilutions (final DMSO ≤0.2% v/v). Measure cAMP or β-arrestin responses per kit instructions. Include vehicle and positive controls.
• Solution handling: Minimize light exposure; use glass vials. Pre-rinse plastic tips/tubes with working solution to mitigate adsorption.

These are literature-style templates, not item-specific validated methods. Optimize to your system and consult the SDS before handling.

Biological Roles

Item-specific

• No item-specific potency/affinity data are provided in the Product Data. Do not infer pharmacological parameters from this listing.

Literature/general (class-level; non-clinical)

• Class: Synthetic cannabinoid of the JWH naphthoylindole family. Members of this class often act as agonists at cannabinoid receptors CB1 and/or CB2, modulating Gi/o-coupled signaling pathways (e.g., inhibiting adenylyl cyclase, affecting MAPK signaling) in a tissue- and receptor-dependent manner.
• Experimental use: Employed as a tool compound to probe endocannabinoid system components, receptor selectivity, desensitization, and receptor–effector coupling in heterologous systems or native tissues.
• ADME considerations (in vitro context): Highly lipophilic; significant nonspecific binding to plasticware, proteins, and membranes can shift apparent potency. Serum proteins and lipid content influence free fraction.
• Off-targets: Aromatic, lipophilic ligands can exhibit ancillary interactions at unrelated targets at higher concentrations; appropriate counterscreens are recommended.

Important notes

• No medical or clinical claims are made. For research use only.
• Jurisdictional controls may apply to synthetic cannabinoids; ensure all uses are compliant with local regulations and institutional approvals.

Buffer Applications

Not typically applicable

• This product is a hydrophobic small-molecule ligand, not a buffering agent. It does not establish pH buffers.

Practical handling in buffers (general)

• For aqueous assay buffers (e.g., HEPES, Tris, PBS), introduce the compound from a concentrated DMSO or ethanol stock. Aim for final organic solvent content ≤0.1–0.5% v/v when compatible with the assay.
• To mitigate precipitation and adsorption: include 0.05–0.1% nonionic surfactant (e.g., Tween-80) or 0.1% fatty-acid–free BSA where biologically acceptable. Mix thoroughly and protect from light.

Green Alternatives

Context

• As a specialized bioactive ligand, this item does not have a direct “green substitute” for its biological activity. However, you can optimize greenness in how you formulate, handle, and dispose of it.

Greener practice recommendations (general)

• Solvent minimization: Prepare the most concentrated practical DMSO or ethanol stocks to reduce solvent volumes and waste.
• Solvent selection: Prefer ethanol over DMF/ACN for intermediate dilutions when biologically acceptable. Avoid chlorinated solvents for routine handling.
• Containers: Use amber glass vials to reduce photolysis, enabling longer shelf life and fewer discarded preparations.
• Workflows: Plan small-batch stocks sized to experiment to minimize expired material. Implement in-well dilution schemes to reduce intermediate solutions.
• Waste management: Segregate high-potency bioactive waste; employ adsorbent neutralization where appropriate and incineration per institutional policy.

Comparison (general)

• DMSO vs ethanol: Ethanol is generally greener and lower-toxicity, but DMSO offers higher solubility. Balance according to assay sensitivity to solvent.
• Aqueous co-solvents: PEG400 or cyclodextrins can enable aqueous delivery, reducing volatile organic solvent use; confirm they do not interfere with assay endpoints.

Pharmaceutical Uses

Not applicable to this catalog listing

• No excipient role, pharmacopeial status, or formulation use is specified for this item. This product is supplied strictly for research use only and is not for human or veterinary use.

General note (context only)

• Synthetic cannabinoids are studied in research settings to understand receptor pharmacology and structure–activity relationships. Any discussion of therapeutic applications is outside the scope of this product and is not implied.

Physical Properties

Item-specific (from Product Data)

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

Literature/General properties for naphthoylindole cannabinoids (reference only)

• Physical state: Usually crystalline solids with high lipophilicity and low aqueous solubility.
• Solubility (typical, literature): Poor in water; dissolves in organic solvents such as DMSO, DMF, ethanol, methanol, acetone, acetonitrile, dichloromethane, and toluene. Aqueous work typically requires co-solvent or surfactant.
• Partitioning: High LogP/logD expected (>4, literature, class-level), reflecting hydrophobic character and strong membrane partitioning.
• UV absorbance: Strong π–π* bands from 200–300 nm due to indole/naphthalene chromophores (literature, class-level). Exact UV cutoff or ε not specified for this item; refer to CoA/Spec Sheet.
• Melting/boiling points, density, refractive index, pKa: Not specified for this item; consult the primary literature or CoA/Spec Sheet for exact values.

Practical notes

• Prepare concentrated stocks in anhydrous DMSO or ethanol; dilute into buffered media last with vigorous mixing to avoid precipitation.
• Filter clarity can be limited by supersaturation; consider gentle heating (<40 °C) to assist dissolution, then cool before use. Always record and report the final DMSO content.

Quality & Grades

Item-specific (from Product Data)

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

Guidance on quality considerations (general)

• Identity confirmation: For small-molecule bioactives, identity is typically supported by NMR, MS, and HPLC/UPLC purity. Verify spectral data and chromatographic purity on the provided CoA.
• Purity context: For receptor pharmacology, minor impurities can confound potency/efficacy. Prefer ≥95% area-purity by HPLC UV at multiple wavelengths (literature best practice); exact specification is not provided for this item.
• Form: Free base vs. salt and polymorph can affect solubility and handling. The specific form for this item is not specified; consult the CoA.
• Stabilizers: None specified for this item. If stabilizers are present, they will appear on the label/CoA; stabilizers can influence analytical baselines and biological assays.
• Documentation: Use the lot-specific CoA/Spec Sheet as the governing document for assay acceptance criteria, residual solvents, and moisture content if applicable.

Reaction & Applications

Item-specific manufacturer applications

• Manufacturer Applications: Not specified for this item in the catalog entry.

Likely research uses (general, non-clinical)

• Reference ligand in cannabinoid receptor research: Commonly used in vitro for receptor binding, signaling (e.g., cAMP inhibition, β-arrestin recruitment), and structure–activity relationship (SAR) comparisons within the JWH naphthoylindole series.
• Analytical standard: Qualitative/quantitative calibration for forensic or toxicological analytical method development (e.g., LC–MS/MS panels). Use in accordance with local regulations.

Not typically used as a synthetic reagent

• This compound is a bioactive small molecule rather than a building block or catalyst; it is not generally employed as a coupling partner or reagent in organic synthesis. See Synthetic Utility for limited methodological context.

Practical tips (general)

• Prepare fresh DMSO stocks; minimize freeze–thaw. Pre-adsorption to plastics can reduce effective concentration—pre-rinse plastics with solvent or use silanized glassware.
• For binding assays, include 0.1% BSA to reduce nonspecific binding; validate free fraction via equilibrium dialysis or microsomal binding as needed.
• Light sensitivity: Aromatic indoles can undergo photodegradation; protect solutions from light.

Reaction Conditions

Not directly applicable

• This product is not intended as a reagent for chemical transformations; specific reaction conditions are therefore not applicable.

Assay conditions (general, for biological experiments)

• Stock preparation: 1–10 mM in anhydrous DMSO (or ethanol). Store aliquots at ≤–20 °C protected from light; thaw immediately before use.
• In vitro binding: Typical buffers include Tris or HEPES with 2–5 mM MgCl2, 0.1% BSA; temperature 25–37 °C; incubation 60–120 min depending on radioligand/non-radioactive tracer system. Optimize based on receptor expression and membrane prep.
• Cellular assays: Final DMSO 0.1–0.5% v/v; exposure times from minutes (acute signaling) to hours (gene expression). Include solvent controls and concentration–response curves spanning at least 8 half-log steps.

All parameters above are general literature guidance for hydrophobic GPCR ligands and are not item-specific specifications.

Safety & Handling

Item-specific (from Product Data)

• GHS Classification: Not specified for this item; refer to SDS.
• Signal Word: Not specified for this item; refer to SDS.
• Hazard (H-) Statements: Not specified for this item; refer to SDS.
• Pictograms: Not specified for this item; refer to SDS.
• Storage Conditions: Room temperature (per product data). Protect from light and moisture for best stability (general good practice).

General safety guidance (literature/class-based; defer to SDS for authoritative details)

• Potential hazards: Synthetic cannabinoids may exhibit acute biological activity. Avoid inhalation, ingestion, or skin contact. Handle as a toxic research chemical in a chemical fume hood.
• PPE: Lab coat, nitrile gloves (double-gloving recommended for weighed solids), splash goggles. Use dedicated tools for microgram–milligram handling to prevent cross-contamination.
• Engineering controls: Use containment when weighing (draft enclosure or balance hood). Avoid generating dust/aerosols.
• Incompatibilities: Strong oxidizers may degrade indole-containing compounds; avoid prolonged exposure to light and air.
• First aid (overview): If inhaled—move to fresh air; if on skin—wash with soap and water; if in eyes—rinse cautiously with water for several minutes; if ingested—rinse mouth, seek medical attention. Provide SDS to responders.
• Waste: Collect as halogen-free organic waste unless otherwise directed. Decontaminate tools and surfaces with suitable organic solvent followed by detergent wash.
• Regulatory note: Synthetic cannabinoids can be subject to jurisdiction-specific controls. Ensure all ordering/handling complies with local regulations.

Solvent Selection

Item-specific

• No item-specific solvent specifications are provided; refer to CoA/Spec Sheet.

Literature/general guidance for hydrophobic, aromatic ligands (naphthoylindoles)

• Primary stock solvents: Anhydrous DMSO (most common), ethanol, or DMF. Typical stock concentrations: 1–10 mM (up to 50 mM if solubility permits). Filter if necessary.
• Aqueous use: Dilute stocks into buffered saline or culture media with vigorous mixing. Maintain final DMSO ≤0.1–0.5% v/v for cell assays (check cell-line tolerance). Consider 0.5–1% w/v fatty-acid–free BSA or 0.05–0.1% Tween-80 to reduce precipitation/adsorption if biologically compatible.
• Polarity/miscibility profile (class-level): Immiscible with water; miscible with polar aprotics and many organics (acetone, acetonitrile, DCM, toluene). High hydrophobicity promotes adsorption to plastics—prefer glass vials and glass syringes for preparation and storage.
• When to choose alternatives: If DMSO is incompatible with your readout, ethanol or PEG400:water co-solvent systems may be used. For in vitro binding assays, Tris or HEPES buffers with 0.1% BSA and ≤0.1% DMSO are common.

Quick comparison (general)

• DMSO: Highest solvating power; may affect some assays.
• Ethanol: Volatile; easier removal; lower solvating power than DMSO.
• DMF: Strong solvent but less desirable biologically; consider only for stock prep with immediate dilution.

Storage & Reconstitution

Item-specific (from Product Data)

• Storage Conditions: Room temperature.
• Shipped In: Not specified for this item.

General best practices (supplemental guidance)

• Solid material: Store tightly capped in an amber glass vial under dry, inert atmosphere if possible. Protect from light. Although room temperature is indicated, many users keep long-term reference standards at 2–8 °C or –20 °C to maximize stability; follow your QA guidance.
• Solution stability: Prepare small aliquots of DMSO or ethanol stock (e.g., 10 mM). Store aliquots at –20 °C protected from light. Avoid repeated freeze–thaw; discard aliquots showing precipitation, discoloration, or abnormal LC–MS/HPLC profiles.
• Reconstitution: Bring vial to room temperature before opening to prevent moisture condensation. Add calculated volume of anhydrous solvent, vortex until fully dissolved. Record final concentration and solvent.
• Documentation: Retain lot-specific CoA and any stability statements as the controlling specifications for storage and use.

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

Structure & Identity

Item-specific (from Product Data)

• SKU: J978259
• Product Name: Jwh-020
• CAS: 209414-09-5
• InChIKey: 141008 (as provided; format appears non-standard)
• 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.

Literature/General identification (for reference only; not item-specific specs)

• Common classification: Synthetic cannabinoid; naphthoylindole class (JWH series)
• PubChem CID: 10406802 (literature)
• Structural features (class-level): Indole core N-alkylated at N1, acylated at C3 with a naphthoyl group; overall highly lipophilic aromatic framework.
• 2D structure (verbal, class-level): An indole ring system bearing an N-alkyl substituent; the 3-position of the indole is linked via a carbonyl (–C(=O)–) to a naphthyl ring. The arrangement yields a planar, conjugated aryl–carbonyl–heteroaryl motif common to JWH naphthoylindoles.

Notes

• Exact stereochemistry is typically not applicable (achiral). If a specific isomer or salt form applies, it is not specified for this item; refer to CoA/Spec Sheet.

Synthetic Utility

Scope

• This compound is a finalized small-molecule ligand and is not commonly used as a reagent, catalyst, or building block in routine synthesis.

Context (general)

• Naphthoylindole scaffolds are typically accessed via acylation of indole-3-carboxylates or via Friedel–Crafts-type acylations at the indole 3-position followed by N-alkylation. While informative for preparing analogs, such transformations are upstream of this item’s intended research use as a reference ligand/standard.

Applications in synthesis (limited)

• Analytical reference: Serves as an external standard for validating synthetic routes to related analogs (HPLC/LC–MS method development, retention time matching, MS fragmentation comparison).
• SAR libraries: Used as a benchmark comparator when evaluating new analog syntheses in medicinal chemistry campaigns targeting CB receptors.

If you require a precursor or functionalized intermediate for analog synthesis, please consult our building-block categories; this product is not positioned as a synthetic intermediate.

Target Specificity

Item-specific

• No target specificity, affinity, or selectivity data are provided for this item. Refer to the primary literature and the lot-specific CoA if available.

General note

• Compounds in the JWH naphthoylindole class frequently engage CB1 and/or CB2 receptors; however, do not assume quantitative selectivity or potency for this specific item based on class membership. Always determine activity empirically in your assay system.