Jwh-166 , CAS No.824961-41-3

CAS: 824961-41-3 Cat. No.: J1016561 Fórmula: C₂₅H₂₅NO₂ Peso molecular: 371.47 PubChem CID: 11372171

Storage

Room temperature

Specifications

Condiciones de almacenamiento de almacenamiento

Room temperature

Nombres e identificadores

• Sonrisas canónicas: CCCCCN1C=C(C2=CC=CC=C21)C(=O)C3=CC=CC4=C3C=CC(=C4)OC
• IUPAC Name: (6-methoxynaphthalen-1-yl)-(1-pentylindol-3-yl)methanone
• InChIKey: JCOOBICVPDFZNX-UHFFFAOYSA-N
• INCHI: 1S/C25H25NO2/c1-3-4-7-15-26-17-23(21-10-5-6-12-24(21)26)25(27)22-11-8-9-18-16-19(28-2)13-14-20(18)22/h5-6,8-14,16-17H,3-4,7,15H2,1-2H3
• Isómeros SMILES: CCCCCN1C=C(C2=CC=CC=C21)C(=O)C3=CC=CC4=C3C=CC(=C4)OC
• PubChem CID: 11372171
• Peso molecular: 371.47

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Clase: 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 Anisoles Alkyl aryl ethers 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 - Anisole - Phenol ether - Aryl ketone - Alkyl aryl ether - Substituted pyrrole - Benzenoid - Pyrrole - Heteroaromatic compound - Vinylogous amide - Ketone - Azacycle - Ether - Organooxygen compound - Organonitrogen compound - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Organic nitrogen compound - Aromatic heteropolycyclic compound
• Descripción: 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

Propiedades químicas y físicas

• Peso molecular: 371.500 g/mol
• XLogP3: 6.300
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 7
• Exact Mass: 371.189 Da
• Monoisotopic Mass: 371.189 Da
• Topological Polar Surface Area: 31.200 Ų
• Heavy Atom Count: 28
• Formal Charge: 0
• Complexity: 521.000
• 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

No vendor-verified protocols are provided for this item.

• Suggested starting points (research, general):
  • LC–MS calibration: Prepare serial dilutions (e.g., 1 mg/mL to 1 ng/mL) in MeOH or ACN; include internal standard if available. Assess linearity and matrix effects in spiked samples.
  • Receptor-binding assay: Prepare DMSO stocks (e.g., 10 mM), dilute into binding buffer to desired concentrations. Maintain constant DMSO across wells and include vehicle controls.
  • Functional assays (e.g., cAMP): Establish an 8–12 point concentration–response curve; preincubate per cell line protocol; limit final DMSO to assay tolerance.

These are general frameworks; optimize for your system and consult the primary literature. For compliance-sensitive applications, use certified reference standards where required.

Biological Roles

Biochemical context (literature-level, not item-specific claims):

• JWH-series ligands were developed to probe the endocannabinoid system. Many members exhibit high affinity for cannabinoid receptors CB1 and/or CB2; exact selectivity and potency for JWH‑166 should be verified from primary literature and not assumed.
• Mechanistic features:
  • Ligands often act as agonists at GPCRs (CB1/CB2), modulating adenylate cyclase, MAPK pathways, and ion channel activity via G-protein signaling in cellular systems.
  • Lipophilicity facilitates membrane partitioning and target engagement; nonspecific binding can occur—use appropriate controls.
• Experimental uses:
  • Radioligand displacement or fluorescence-based binding assays to derive Ki values.
  • Functional assays (e.g., cAMP inhibition, β‑arrestin recruitment) to assess efficacy and bias.
  • Structure–activity relationship (SAR) comparisons across JWH analog panels.
• Metabolic considerations (general): oxidative metabolism (e.g., by CYPs) and Phase II conjugation are common for this class; metabolite profiling may be relevant in analytical/toxicological research.

Note: No biomedical/therapeutic claims are made. This product is provided strictly for research use only.

Buffer Applications

Not typically applicable. JWH‑166 is a hydrophobic small-molecule ligand and does not serve as a buffer component. For biological assays, dissolve in an organic cosolvent (e.g., DMSO) and then dilute into the desired assay buffer (e.g., HEPES, PBS) while maintaining low final cosolvent percentages compatible with your system.

Green Alternatives

Greenness considerations for JWH‑166 pertain to its handling and dissolution rather than substitution of the compound itself.

• Solvent choices (comparative, general):
  • Prefer ethanol or water/ethanol cosolvent systems over acetonitrile or DMF when compatible with the assay.
  • For LC–MS sample prep, methanol can substitute for acetonitrile in some methods to reduce supply-chain and toxicity concerns.

Greener solvent comparison (general guidance):

• DMSO: high solvency; relatively benign but viscous—use minimal volumes and recycle where possible.
• Ethanol: renewable feedstock, low toxicity; may impact bioassays at higher %.
• Methanol: effective, higher toxicity than ethanol; widely compatible with LC–MS.
• Acetonitrile: excellent for LC–MS but higher environmental footprint; consider MeOH if chromatographically acceptable.

Operational practices:

• Prepare concentrated master stocks to reduce solvent consumption.
• Use microscale assay formats (96/384-well) to limit chemical use and waste.
• Segregate halogenated from non-halogenated waste; implement solvent recovery where infrastructure allows.

Substitution of the active chemical itself is generally not applicable, as receptor pharmacology depends on the specific ligand structure.

Pharmaceutical Uses

This product is not offered with pharmacopeial status and is designated for research use only.

• Formulation/excipient role: Not applicable; JWH‑166 is an active research ligand rather than an excipient.
• Regulatory status: No USP/EP/JP monograph is indicated. Do not use in human or veterinary products.
• Preformulation (research context): If conducting in vitro formulation studies, typical vehicles include DMSO, PEG400, or lipid-based carriers for hydrophobic ligands; verify solubility, stability, and adsorption to plastics. These studies are solely for laboratory research.

Physical Properties

Item-specific physicochemical data are not provided in the current record. Do not treat literature values as specifications for this catalog item.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point: Not specified for this item; refer to CoA/Spec Sheet. (literature values for JWH-class compounds often lie in the 50–200 °C range depending on structure.)
• Boiling point: Not typically reported for these non-volatile solids; Not specified for this item; refer to CoA/Spec Sheet.
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index: Not applicable/typically not reported for solids; Not specified for this item; refer to CoA/Spec Sheet.
• Solubility (practical guidance; literature/general):
  • DMSO: many JWH analogs are readily soluble (prepare 10–50 mM stocks as needed); confirm empirically for JWH‑166.
  • Ethanol and methanol: moderate to good solubility common; sonication/warming may help.
  • Aqueous buffers: generally very low intrinsic solubility; use cosolvents (DMSO → dilute into buffer with vigorous mixing) or cyclodextrin vehicles for biological assays.
• LogP/logD, pKa: Not specified for this item; refer to CoA/Spec Sheet. (JWH analogs are typically lipophilic and neutral/weakly basic at physiological pH.)

Always confirm exact values for your lot from the CoA before setting specifications or method suitability criteria.

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet for assay method (e.g., HPLC/GC) and acceptance criteria.
• What grade means in practice:
  • For analytical/reference use, high chemical purity and well-characterized identity (NMR/HRMS) are critical. Low levels of structural isomers and residual solvents should be controlled and reported on the CoA.
  • For bioassay use, impurities with intrinsic activity at cannabinoid receptors can confound results; ensure impurity profiling is adequate for your application.
• Stabilizers: Not specified for this item; refer to CoA/Spec Sheet. Many JWH analogs do not require stabilizers if stored dry and protected from light; confirm for JWH‑166.
• Lot-specific documentation: Request CoA/SDS for your shipment to confirm identity (e.g., 1H NMR, LC–MS), purity, residual solvents, and water content if applicable.
• Chromatographic suitability: If using as an LC/MS reference, verify low UV baseline, absence of late-eluting non-volatile residues, and single dominant peak under your method. Adjust mobile phase pH/organic for adequate retention of hydrophobic analytes.

Reaction and Applications

This product is primarily intended as a reference/ligand material rather than as a synthetic reagent or solvent.

• Applications (research use):
  • Analytical reference standard for method development and proficiency testing in forensic/toxicological workflows (e.g., LC–MS screening libraries). Ensure proper legal authorization where applicable.
  • Ligand in receptor-binding or signaling studies of the endocannabinoid system in biochemistry, membranes, or recombinant systems. Set up concentration–response experiments with rigorous controls.
• Not typically used as:
  • A catalyst, reagent, or solvent in organic synthesis.
• Practical notes:
  • Ensure precise massing (use an analytical balance, antistatic measures). Minimize exposure to ambient humidity and light.
  • Prepare stocks in dry, oxygen-free solvent if long-term stability is a concern; store as small aliquots at controlled temperature.
  • For bioassays, prefilter solutions (0.2 µm PTFE) to remove particulates before serial dilution.
• Method validation (analytical):
  • Establish linear dynamic range, carryover, and matrix effects. Monitor an internal standard where possible.
  • Evaluate stability in autosampler (e.g., 4–10 °C, 24–72 h) and during freeze–thaw cycles.

Reaction Conditions

Not typically applicable as this product is not used as a reagent. For laboratory handling and solution preparation, the following practical conditions may be helpful (general guidance):

• Stock solutions: 10–50 mM in anhydrous DMSO; vortex and sonicate if needed. Warm gently (≤40 °C) to aid dissolution; avoid prolonged heating.
• Working dilutions: Dilute stocks into assay buffer with vigorous mixing to achieve final organic solvent ≤0.1–0.5% v/v (confirm compatibility).
• Stability checks: Evaluate solution stability over intended assay timeframe (e.g., 24–48 h at 4–25 °C) and through 1–3 freeze–thaw cycles. Protect from light if chromophoric.
• Filtration: 0.2 µm PTFE syringe filters can reduce particulates prior to LC–MS or bioassay.

For any synthetic preparation of JWH‑166 in-house, consult peer-reviewed procedures for exact reagents, catalysts, and temperatures; do not extrapolate from unrelated JWH analogs without verification.

Safety and Handling

Safety details are limited in this listing. Always consult the SDS for authoritative information prior to use.

• GHS classification, pictograms, signal word, and H-statements: Not specified for this item; refer to SDS.
• General hazards (class-level, literature): Synthetic cannabinoid ligands may cause CNS and cardiovascular effects if accidentally ingested or inhaled; treat as toxic and handle with heightened caution.
• Engineering controls: Work in a certified fume hood when weighing or preparing solutions. Avoid aerosolization and dust generation.
• PPE: Safety glasses or splash goggles; lab coat; nitrile gloves (double-glove for extended handling). Consider respiratory protection if powders could become airborne and local ventilation is inadequate (per institutional policy/SDS).
• Hygiene: Prevent skin contact; do not eat/drink in lab; wash thoroughly after handling.
• Incompatibilities: Avoid strong oxidizing agents. Store away from acids/alkalis that may catalyze degradation.
• First aid (overview; defer to SDS):
  • Inhalation: Move to fresh air; seek medical attention.
  • Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing; obtain medical evaluation.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Spill response: Avoid raising dust. Cover with inert absorbent (e.g., vermiculite), collect mechanically, and dispose per regulations.
• Waste: Treat as hazardous organic waste under local regulations.
• Research use only: Not for human or veterinary use.

Solvent Selection

Because JWH‑166 is a lipophilic research ligand, solvent choice typically targets efficient dissolution for analytical or biological assays rather than use as a reaction solvent.

• Polarity/miscibility (general for JWH analogs):
  • Good solubility in high-boiling polar aprotic organics (DMSO, DMF) and moderate solubility in lower alcohols (EtOH, MeOH).
  • Very limited aqueous solubility; use cosolvents, surfactants, or inclusion complexes (e.g., HP‑β‑CD) for aqueous work.
• Practical recommendations:
  • Prepare concentrated DMSO stock solutions (e.g., 10–50 mM). Store aliquots to minimize freeze–thaw.
  • For in vitro assays, final DMSO content is typically ≤0.1–0.5% v/v to avoid solvent effects; confirm assay tolerance.
  • For LC–MS, dissolve in acetonitrile or methanol and dilute with water + 0.1% formic acid if needed for signal stability.
• Comparison (general):
  • DMSO: highest solvating power; biologically tolerated at low %.
  • Ethanol: acceptable for some cell-free assays; can affect membranes/cells.
  • Acetonitrile: preferred for LC–MS prep; less suitable for live-cell work.
• Avoid: neat aqueous buffers without a cosolvent; nonpolar alkanes unless required for specific extraction protocols.

Storage and Reconstitution

• Storage (from Product Data): Room temperature. Protect from moisture and direct light. If long-term storage is anticipated, consider desiccation and an inert atmosphere to minimize degradation.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Reconstitution:
  • Recommended solvents: DMSO (primary), ethanol or methanol (secondary), selected based on assay compatibility.
  • Procedure: Allow vial to equilibrate to room temperature in a desiccator before opening. Accurately weigh the required amount, dissolve in a minimal volume of anhydrous solvent with vortexing/brief sonication. Prepare single-use aliquots to avoid repeated freeze–thaw.
• Solution storage (general guidance):
  • DMSO stocks: Store aliquots at −20 °C or 2–8 °C, protected from light; verify stability before critical use.
  • Aqueous working solutions: Prepare fresh; many hydrophobic ligands show limited stability and adsorb to plastics—use low-binding tubes.
• Shelf life: Not specified for this item; refer to CoA/Spec Sheet.
• Research Use Only: As stated by the manufacturer, for research use only.

Structure and Identity

Brief overview: JWH-166 is cataloged as a synthetic research chemical in the JWH cannabinoid ligand family. Item-specific structural identifiers are largely not provided in the current product record.

• CAS: 824961-41-3 (from Product Data)
• PubChem CID: 11372171 (from Product Data)
• InChIKey: 156790 (from Product Data)
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.

Structural features (general, literature-level for JWH-class ligands):

• Typical of JWH-series ligands are indole or related heteroaromatic cores acylated/alkylated by arylcarbonyl or related lipophilic moieties that confer affinity for cannabinoid receptors (CB1/CB2). The exact substitution pattern for JWH‑166 should be confirmed from primary literature or the CoA.
• 2D depiction (descriptive, literature-level): Most JWH analogs present a planar heteroaromatic ring (e.g., indole) conjugated to an aryl carbonyl-bearing lipophilic fragment, producing an amphipathic pharmacophore (heteroatom donor/acceptor plus hydrophobic surface). Confirm the precise scaffold for JWH‑166 via the supplied CoA/SDS or peer-reviewed references.

Identity confirmation guidance (general):

• Verify against authoritative identifiers (CAS, CID) and orthogonal analytical data (1H/13C NMR, HRMS, IR). Retention time matching to a certified reference standard is recommended for analytical use.

Synthetic Utility

Not a general-purpose synthetic reagent. JWH‑166 is typically a target or standard rather than a building block.

• Retrosynthetic note (general, JWH-class): Many JWH analogs arise from acylation or alkylation of heteroaromatic cores (e.g., indoles) followed by introduction of lipophilic aryl or cycloalkyl motifs. If your work involves analog synthesis, consult primary literature for the specific route to JWH‑166 (choice of acyl chloride/anhydride, coupling conditions, and purification strategy).
• Purification considerations (general): Flash chromatography on silica with gradient hexanes/EtOAc or hexanes/MTBE is common; for highly lipophilic analogs, consider reverse-phase preparative HPLC.
• Analytical control: NMR (including 2D experiments to confirm regiochemistry), HRMS, and HPLC purity profiling are essential. Check for positional isomers and residual starting heterocycles.

Target Specificity

Target and selectivity information specific to JWH‑166 is not provided in this product record.

• Target(s): Not specified for this item; refer to CoA/Spec Sheet and primary literature.
• Selectivity/profile: Not specified for this item; refer to CoA/Spec Sheet and primary literature.

Note: Although many JWH compounds interact with cannabinoid receptors, do not assume CB1/CB2 potency or selectivity for JWH‑166 without verified data.