Fluxametamide - 10mM in DMSO , CAS No.928783-29-3

CAS: 928783-29-3 Cat. No.: F654528 Fórmula: C₂₀H₁₆Cl₂F₃N₃O₃ Peso molecular: 474.26 Número CE: 813-746-4 PubChem CID: 135927338

GRAU & PUREZA 10mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Visão geral

Fluxametamide is an insecticide with wide spectrum, acts as an antagonist of GABA- and glutamate-gated chloride channels , with IC 50 of 1.95 nM and 225 nM for M. domestica GABACls and GluCls.

In Vitro

Fluxametamide is an antagonist of GABA- and glutamate-gated chloride channels, dose-dependently inhibits currents induced by GABA and glutamate in M. domestica GABACls and GluCls, with IC 50 values of 1.95 (1.18-3.21) nM and 225 (137-372) nM, respectively, and displays potent antagonistic activity against T. urticae GABACls with an IC 50 of 0.219 (0.127-0.381) nM. Fluxametamide inhibits GABA responses in the wild-type L. striatellus GABACls with IC 50 values of 1.40 (0.57-3.29) nM; in the A2′N mutant GABACls, the IC 50 value is 3.51 (2.17-5.69) nM. Moreover, Fluxametamide scarcely inhibits GABA (EC 50 )-induced currents in rat GABACls at 10 μM and with no inhibition on glycine (EC 50 )-induced current in human α1 GlyCls at tested concentrations. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

Fluxametamide shows significant insecticidal activity with an LD 50 (LD 95 ) value of 12.9 ± 4.9 ng/fly (38.7 ± 6.3 ng/fly) . MCE has not independently confirmed the accuracy of these methods. They are for reference only.

IC50& Target:IC50: 1.95 nM ( M. domestica GABACls), 225 nM ( M. domestica GluCls)

Especificações

Especificações e pureza

10mM in DMSO

Mecanismos bioquímicos e fisiológicos

Fluxametamide is an insecticide with wide spectrum, acts as an antagonist of GABA- and glutamate-gated chloride channels , with IC 50 of 1.95 nM and 225 nM for M. domestica GABACls and GluCls.

Condições de armazenamento de armazenamento

Store at -80°C

Enviado em

Dry ice packs + Cold packs

Este produto requer transporte de cadeia fria. Serviços terrestres e outros serviços econômicos não estão disponíveis.

Tipo de ação

ANTAGONIST

Nomes e identificadores

SMILES isoméricas

CC1=C(C=CC(=C1)C2=NOC(C2)(C3=CC(=CC(=C3)Cl)Cl)C(F)(F)F)C(=O)N/C=N\OC

PubChem CID

135927338

Peso molecular

474.26

Application Protocols

No manufacturer-validated protocols are provided for this item. The following general, non-validated procedures are offered as research starting points:

• Preparation of DMSO stock solution (general)

  1. Allow vial to equilibrate to room temperature in a desiccator (to prevent moisture condensation). Work quickly to limit warming.
  2. Add anhydrous DMSO to prepare a 10–50 mM stock, as solubility permits. Vortex and sonicate briefly if needed.
  3. If particulates persist, filter through a 0.22 µm PTFE syringe filter into an amber vial.
  4. Aliquot into low-bind microtubes; store at −80 °C (see Storage tab).

• Aqueous assay dilution (general)

  1. Pre-dilute the DMSO stock 10–100× with assay buffer containing 0.1–1% DMSO to reduce precipitation risk.
  2. Add pre-dilution to cells or receptor preparations to achieve the final test concentration while keeping DMSO within assay tolerance.
  3. Mix gently and incubate as per assay requirements; include vehicle controls at matched DMSO levels.

• LC–MS/MS calibration standard preparation (general)

  • Prepare a primary DMSO stock; serially dilute with acetonitrile:water (1:1) containing 0.1% formic acid. Use glass vials and internal standards. Verify stability in the autosampler (4–8 °C) and apply purity correction from the CoA.

These are example workflows only; optimize for your specific system.

Biological Roles

This section provides general, literature-based context for isoxazoline insecticides; it is not item-specific dosing or efficacy guidance.

• Mechanistic class (literature)
  • Isoxazolines, including fluxametamide-class compounds, are reported to act as non-competitive modulators of insect ligand-gated chloride channels—principally GABA-gated chloride channels—and are categorized in IRAC Group 30 (GABA-gated chloride channel allosteric modulators). Some members of the class also affect glutamate-gated chloride channels.
• Biological rationale
  • Modulation of these channels disrupts inhibitory neurotransmission in target arthropods, leading to hyperexcitation. Selectivity is often derived from structural differences between insect and mammalian receptors; nevertheless, handle with caution and avoid exposure.
• Research utility
  • Serves as a chemical probe for studying insect neuroreceptor pharmacology, resistance mechanisms (e.g., channel subunit mutations), and structure–activity relationships (SAR) within the isoxazoline scaffold.
• Metabolism and fate (general research observations)
  • Lipophilic amide-containing compounds may undergo oxidative metabolism (e.g., N-dealkylation, aromatic hydroxylation) and amide hydrolysis in biological systems; actual pathways are species- and structure-dependent.

Important: The above is general literature information. This product is supplied strictly for research use only. No medical, veterinary, or field-use claims are made or implied.

Buffer Applications

Not typically applicable. Fluxametamide is a hydrophobic small-molecule research standard rather than a buffering reagent. For laboratory use, it may be dissolved in DMSO and subsequently diluted into assay buffers; ensure the final DMSO concentration is compatible with the biological system (commonly ≤0.1–1% v/v). If solubilization aids (e.g., surfactants) are used, validate their effects on assay readouts.

Green Alternatives

Context: Fluxametamide is a lipophilic isoxazoline insecticidal chemotype. "Green alternatives" here focus on greener solvents and practices for its laboratory handling and analysis rather than substituting the active itself.

• Solvent choices
  • Prefer acetone, ethanol, or ethyl acetate (where compatible) over chlorinated solvents for non-biological workflows. For chromatography, prioritize acetonitrile/methanol–water systems and minimize use of halogenated eluents.
• Process-intensity reduction
  • Miniaturize assays (microplate formats, microscale extraction) to reduce solvent consumption and waste.
  • Employ solid-phase extraction (SPE) with water-rich washes to limit organic solvent volumes in residue analysis.
• Energy and stability management
  • Consolidate sample preparation steps on ice/cold blocks; maintain frozen aliquots to limit rework due to degradation.
• Comparative considerations (informational)
  • DCM/chloroform vs EtOAc/Me-THF: Ethyl acetate or 2-methyltetrahydrofuran can often substitute for DCM in extractions and preparative steps, improving EHS profiles.
  • NMP/DMF vs Cyrene/propylene carbonate: For certain dissolutions, greener dipolar aprotic solvents may be viable if downstream assay compatibility is confirmed.
• Waste and environmental stewardship
  • Segregate halogenated from non-halogenated waste; evaluate adsorbent-based cleanup to extend mobile-phase lifetime.

Note: Substitution of the active compound itself is outside the scope of a research reference standard. Implement green chemistry via solvent and scale choices, and by adopting high-efficiency analytical methods.

Pharmaceutical Uses

Not applicable for this catalog item. Fluxametamide is provided for research use only and is not an excipient or pharmacopeial reagent. It is not intended for any therapeutic, diagnostic, or clinical application. Researchers may use it as a reference standard in analytical method development or as a probe compound in receptor pharmacology studies; any formulation experiments should be confined to in vitro/in vivo research under appropriate approvals and institutional biosafety oversight.

Physical Properties

Item-specific properties from Product Data:

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

Safety data and exact physicochemical specifications are not provided in the Product Data and should be confirmed on the current CoA/Spec Sheet and SDS.

General/literature (class-level) properties for isoxazoline insecticides like fluxametamide (informational only):

• Physical state: typically crystalline solids with high purity for screening/reference use.
• Solubility: generally low aqueous solubility; soluble in polar aprotic organic solvents (DMSO, DMF, NMP) and moderately to well soluble in chlorinated solvents and acetone (literature, class trend). For biological testing, DMSO stock solutions are commonly prepared.
• Lipophilicity: often high (logP > 3, literature for the class), supporting membrane permeability but reducing water solubility.
• Stability: solid-state stability is generally good when protected from light and moisture; solutions in DMSO are typically stable for weeks at −20 to −80 °C (literature best practices). Light and elevated temperature may promote slow degradation.
• Melting/boiling points, density, refractive index, pKa, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet. Do not rely on class trends for quantitative use.

Note: Use literature information only as qualitative guidance; for quantitative specifications, consult the item-specific CoA/Spec Sheet.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

Guidance on research-use quality for small-molecule standards:

• Research-use only: Supplied for laboratory R&D, screening, and method development. Not for human or veterinary use, food, or household applications.
• Typical expectations (informational)
  • Reference/screening compounds are commonly offered at high chemical purity to support reproducible bioassays and analytical work. Exact assay/trace impurity limits, residual solvents, and water content are batch-dependent and must be verified on the CoA.
  • Chromatographic profiles (HPLC/UPLC), NMR, and MS data are frequently used to confirm identity and purity; please refer to the batch CoA for this item.
• Stabilizers/inhibitors
  • Not specified for this item; refer to CoA/Spec Sheet. When absent, users should minimize solution exposure to heat/light and avoid repeated freeze–thaw.
• Practical considerations
  • If using for quantitative bioassays or as a calibration reference, document purity-adjusted concentrations (correct for potency/purity) using the lot-specific CoA.
  • For LC–MS methods, confirm absence/presence of UV-active stabilizers or low-UV mobile-phase contaminants on the CoA before establishing analytical conditions.

Reaction and Applications

Scope: As supplied, fluxametamide is primarily used as a research reference compound and screening tool rather than as a stoichiometric reagent. Consequently, “reaction” use is limited; however, it has valuable applications in agrochemical mode-of-action studies and analytical method development.

Research applications (literature/class-level context for isoxazoline insecticides):

• Mode-of-action investigations
  • Probing ligand interactions at insect GABA-gated chloride channels (and, for some isoxazolines, glutamate-gated chloride channels) using electrophysiology (patch-clamp), radioligand displacement, and planar lipid bilayer assays.
• Resistance and cross-resistance studies
  • Benchmarking sensitivity profiles across insect strains/populations; positioning within IRAC MoA Group 30 (GABA-gated chloride channel allosteric modulators; literature, class-level).
• Analytical chemistry
  • Development/validation of LC–MS/MS methods for residue analysis and environmental fate studies (standard/sample prep, matrix effects, recovery optimization). Use purity-corrected standards and isotope-labeled internal standards where available.
• Formulation and delivery research
  • Solubility enhancement (co-solvents, cyclodextrins), microencapsulation, and stability-indicating assays to understand degradation pathways (hydrolysis/photolysis/oxidation) in model systems.

Practical tips

• Prepare well-characterized DMSO stocks; minimize freeze–thaw cycling.
• Verify adsorption losses; pre-condition vials/tips, or use low-bind plastics.
• Use light protection (amber glass/aluminum foil) and maintain cold chain during sample prep for stability.

Reaction Conditions

This product is not primarily a reagent; therefore, defined “reaction conditions” are not typically applicable. For research contexts where fluxametamide is studied (general guidance):

• Analytical method development
  • LC–MS/MS commonly employs reversed-phase C18 columns with water/acetonitrile (or methanol) mobile phases, 0.1% formic acid or ammonium formate as modifiers, and gradients ramping to high organic (≥80%) to elute lipophilic analytes. Source conditions and MRM transitions should be optimized empirically.
• Electrophysiology/pharmacology assays (general)
  • Stock solutions in DMSO; final assay DMSO ≤0.1–0.5% v/v where possible. Temperature near ambient (20–25 °C) unless protocol specifies otherwise. Equilibration times vary (minutes) depending on receptor expression system and membrane partitioning.
• Stability checks
  • Conduct short-term stability in the intended medium (light protection; chilled autosampler at 4–8 °C). Establish bench-top, autosampler, and freeze–thaw stability before routine use.

No specific temperatures, catalysts, or yields are claimed for chemical reactions with this item. For any synthetic transformations or degradant studies, consult primary literature and conduct pilot experiments.

Safety and Handling

Item-specific hazard information (from Product Data):

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

General safety guidance (professional use; defer to SDS for authoritative details):

• Handling
  • Use in a certified chemical fume hood with appropriate local exhaust.
  • Wear suitable PPE: lab coat, nitrile gloves (change frequently), and splash goggles/face protection.
  • Avoid inhalation of dust/aerosols; minimize dermal exposure due to potential lipophilicity and bioactivity typical of insecticidal chemotypes.
• Storage and incompatibilities
  • Store at −80 °C as specified for this item. Keep container tightly sealed, desiccated, and protected from light.
  • Avoid strong oxidizers/reductants and strong acids/bases that may degrade amide/heterocycle motifs (general precaution).
• First-aid overview (consult SDS for specifics)
  • Skin/eye contact: Rinse with copious water for ≥15 minutes; remove contaminated clothing; seek medical evaluation.
  • Inhalation: Move to fresh air; monitor breathing; obtain medical attention.
  • Ingestion: Rinse mouth; do not induce vomiting unless directed by medical personnel; seek medical advice.
• Spill and waste
  • Avoid environmental release. Absorb small spills with inert material; collect for disposal as hazardous chemical waste according to institutional and local regulations.

Always consult the current SDS from Aladdin Scientific for definitive hazard classification and response measures.

Solvent Selection

Applicability: Fluxametamide is a nonpolar-to-moderately polar, lipophilic small molecule. Solvent choice drives successful stock preparation and assay compatibility.

• Stock preparation (common research practice)
  • DMSO is the preferred solvent for bioassay stocks due to excellent solvency and compatibility with aqueous assay media upon dilution (≤0.1–1% v/v DMSO final, assay-dependent).
  • Alternative solvents: DMF, NMP, acetone, acetonitrile; chlorinated solvents (e.g., dichloromethane) for synthetic/analytical workflows—not typically used directly in biological assays.
• Aqueous compatibility
  • Direct dissolution in water or buffers is typically poor for lipophilic isoxazolines. Use co-solvent approaches (DMSO or minimal Tween-80/Pluronic F-127 if assay-validated) and gradual dilution to prevent precipitation.
• Polarity and miscibility (general/class-level)
  • Likely high logP and low water solubility; anticipate the need for co-solvent systems.
• Practical tips
  • Prepare concentrated DMSO stocks (e.g., 10–50 mM as solubility permits), filter through 0.22 µm PTFE if particulate is present, and store aliquots at −80 °C.
  • Verify that plastics used (e.g., PP vs PS) are compatible; highly lipophilic compounds can adsorb to certain plastics. Use glass or low-binding plastics for accuracy.
• Comparison notes
  • Versus highly polar analytes, fluxametamide-like compounds demand higher organic content for HPLC (e.g., 70–95% acetonitrile or MeOH with water + 0.1% formic acid, method-dependent). Adjust gradients to avoid on-column precipitation.

Storage and Reconstitution

Item-specific conditions (from Product Data):

• Storage Conditions: Store at −80 °C.
• Shipped In: Dry ice packs + Cold packs.

Best practices for this item (general guidance):

• Upon receipt
  • Inspect the container for integrity and allow the shipment to equilibrate to room temperature in a desiccator before opening to prevent condensation.
• Long-term storage
  • Keep the solid (or supplied form) tightly sealed, under inert atmosphere if possible (dry nitrogen or argon), protected from light and moisture at −80 °C.
  • For working solutions, prepare single-use aliquots to avoid repeated freeze–thaw. Store solutions at −80 °C (preferred) or −20 °C for short-term use, in amber vials.
• Reconstitution
  • Use anhydrous DMSO for initial dissolution to prepare concentrated stocks (e.g., 10–50 mM, as solubility permits). Vortex/sonicate to aid dissolution. Avoid aqueous buffers for initial dissolution due to low water solubility typical of this chemotype.
• Stability considerations
  • Limit cumulative time at room temperature; keep on ice during handling. Protect from light.
  • Verify stability in intended matrices (buffers/serum/media) prior to long assay runs and establish acceptable storage intervals (bench-top, 4–8 °C autosampler, −20/−80 °C freezer) experimentally.

Research Use Note: For research use only.

Structure and Identity

Brief overview: Fluxametamide is a research-use small-molecule insecticidal chemotype (isoxazoline-class) commonly utilized as a reference standard and probe in agrochemical and neuropharmacological target studies.

• Item-specific identifiers (from Product Data)

  • SKU: F654528
  • Product Name: Fluxametamide
  • CAS: 928783-29-3
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • 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.

• Structural features (general/literature description)

  • Classified among isoxazoline insecticides; typical core contains an isoxazoline ring fused or linked to amide-bearing aromatic/heteroaromatic motifs.
  • Common functionality in this class includes: isoxazoline heterocycle, amide linkage(s), and halogenated/lipophilic substituents that enhance potency and metabolic stability (literature, class-level).

• 2D structure in words (literature/class-level)

  • A five-membered isoxazoline ring (N–O heterocycle) appended to an amide-containing aryl system; overall scaffold is rigid–lipophilic with polar amide functionality enabling limited H-bonding. Exact atom connectivity for this specific item is not provided here; consult the CoA/Spec Sheet/SDS for definitive structure strings.

Synthetic Utility

Primary role: Fluxametamide is supplied as a finished small molecule for research and analytical reference; it is not typically used as a building block. Nonetheless, it can support synthesis-focused investigations in the following ways (general guidance):

• Reference standard in synthetic campaigns
  • Benchmarking new isoxazoline analogs via comparative bioassays or analytical co-injection/retention-time matching.
• Degradation and metabolite mapping
  • Controlled hydrolysis/oxidation studies to generate and identify potential degradants or metabolites; informs stability-indicating methods and environmental fate assessments.
• Derivatization for analytics
  • Preparation of isotopically labeled analogs (e.g., 13C/2H) or reporter-tagged derivatives for quantitative LC–MS/MS or affinity assays (performed by specialized labs).
• Retrosynthetic insight (class-level)
  • Isoxazoline cores are often constructed via 1,3-dipolar cycloaddition (nitrile oxides to alkenes) or intramolecular cyclizations, followed by amide coupling to append aryl/heteroaryl units; such knowledge aids in designing close structural analogs for SAR.

Note: No item-specific reactivity data or functional-group transformations are provided for this product; consult primary literature for fluxametamide-specific synthetic routes.

Target Specificity

Item-specific target/antigen data are not applicable for this small molecule, and no such information is provided in the Product Data. For literature context only, isoxazoline insecticides are associated with modulation of insect GABA-gated chloride channels (IRAC Group 30). Do not construe this as an assay-validated target profile for the supplied lot; users should establish target engagement experimentally in their systems.

Perguntas frequentes

How should this product be stored?

Store at ?80 °C. Ultra-low temperature storage is required to maintain the specified shelf life.

How is this product shipped?

This product ships frozen with dry ice and cold packs. Unpack on arrival and transfer it to the storage condition stated above; handle dry ice with insulated gloves in a ventilated area.

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

The CAS Number is 928783-29-3, the molecular formula is C20H16Cl2F3N3O3, and the molecular weight is 474.26 g/mol.

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.