Quinidine methiodide - Moligand™, 10 mM in DMSO , CAS No.42982-87-6

CAS: 42982-87-6 Cat. No.: Q1497664 Formule: C₂₁H₂₇N₂O₂・I Poids moléculaire: 466.36 Numéro CE: 809-339-6 PubChem CID: 23620731

GRADE & PURITY Moligand™, 10 mM in DMSO

Storage

Argon charged,Desiccated,Store at -80°C

Shipped In

Dry ice packs + Cold packs

Vue d’ensemble

Quinidine methiodide is a metabolite of Quinidine. Quinidine is an antiarrhythmic agent.

Specifications

Spécifications et pureté

Moligand™, 10 mM in DMSO

Conditions de stockage de stockage

Argon charged,Desiccated,Store at -80°C

Expédié en

Dry ice packs + Cold packs

Ce produit nécessite l'expédition en chaîne froide. Les services terrestres et autres services économiques ne sont pas disponibles.

Grade

Moligand™

Noms et identifiants

Isomères SMILES

C[N@@+]12CC[C@@H](C[C@@H]1[C@H](C3=C4C=C(C=CC4=NC=C3)OC)O)[C@H](C2)C=C.[I-]

PubChem CID

23620731

Poids moléculaire

466.36

Application Protocols

No vendor-tested bioassay protocols, dilutions, or analytical methods are specified for this item.

General starting points (literature/general; adapt and validate):

• Stock preparation for screening:
  • Prepare 10–50 mM stocks in DMSO or water under dry, inert conditions. Filter (0.22 μm) aqueous solutions if sterility is required. Aliquot and store frozen to minimize freeze–thaw cycles.
• Chiral salt formation screen:
  • Combine equimolar Quinidine methiodide with carboxylic acid candidates in MeOH/EtOH; warm to dissolve, then cool slowly. Analyze solid/liquor by chiral HPLC. Iterate solvent systems (EtOH/acetone, ACN/EtOAc) to optimize selectivity.
• Anion exchange:
  • Dissolve Quinidine methiodide in MeOH; add 1.2–2.0 equiv of KPF6 or NaBF4; stir 1 h at rt; filter off KI. Concentrate and triturate product with Et2O to remove residual salts.
• Analytical confirmation:
  • Identity/purity by 1H/13C NMR, HRMS/ESI+ (observe quinidinium cation), and ion chromatography or AgNO3 test for residual iodide after metathesis.

These protocols are illustrative only. Optimize conditions to your substrate and scale, and consult your institution’s safety practices.

Biological Roles

Context for research use only (no clinical claims).

• Origin and scaffold:

  • Quinidine is a natural product alkaloid from Cinchona species; methiodide is its quaternized derivative with a permanent positive charge (literature/general).

• Physicochemical implications:

  • Quaternization markedly increases polarity and reduces passive membrane permeability relative to the tertiary amine parent. As a result, the methiodide often exhibits restricted transmembrane distribution (literature/general).

• Research uses in chemical biology (literature/general):

  • Tool compound for studying chiral recognition, ion-pairing interactions, and stereochemical effects on binding to polyanionic biomolecules (e.g., nucleic acids, acidic polysaccharides) in vitro.
  • May serve as a reference cation in assays probing the influence of cationic charge and chirality on transporters or ion-exchange media. Direct target-binding data are context-specific and not specified for this item.

• Enzymatic/metabolic considerations:

  • As a quaternary ammonium salt, metabolic N‑dealkylation is precluded at the quaternary center. The iodide counterion can be exchanged in biological buffers, potentially altering apparent activity; control anion composition in assays (literature/general).

Item-specific biological activity, targets, and potency values: Not specified for this item; refer to primary literature or generate in-house data under your assay conditions.

Buffer Applications

This compound is not a buffering agent and is not commonly used to prepare pH buffer systems.

Practical guidance for use in buffered media (literature/general):

• Stock solutions: Prepare in water or DMSO, then dilute into your working buffer (e.g., phosphate, HEPES). Filter sterilize if required for biological assays.
• Ionic strength effects: The cationic nature can interact with polyanions; maintain consistent buffer composition (phosphate concentration, chloride content) to ensure assay reproducibility.
• Anion exchange: Iodide may exchange with buffer anions (Cl−, phosphate); document the final counterion environment if it may affect outcomes.

For details on suitable buffers and concentrations for your assay, follow established protocols for the biological system under study. No item-specific buffer recipes are provided.

Green Alternatives

Considerations for greener practice with Quinidine methiodide focus on solvent choices, counterion management, and process intensification rather than changing the core scaffold.

• Greener solvent substitutions (literature/general):

  • Prefer water or ethanol where solubility and performance allow; avoid halogenated solvents.
  • Where dipolar aprotics are necessary, limit DMF/DMSO volumes and employ high-recovery workups or switch to MeCN or 2‑MeTHF co-solvent if compatible.

• Counterion strategies:

  • Iodide has higher environmental impact than chloride in some contexts. If iodide is not mechanistically required, perform salt metathesis to less problematic anions (e.g., chloride, sulfate, organic carboxylates) and recover iodide for recycling when feasible (literature/general).

• Process improvements:

  • Use catalytic quantities in ion-pairing applications where possible; recover and reuse the chiral cation via anion exchange resins.
  • Employ aqueous ethanol crystallizations to reduce reliance on chlorinated solvents.

• Trade-offs:

  • Replacing I− with less nucleophilic anions (PF6−/BF4−) can improve lipophilicity but introduces persistent fluorinated species; weigh EHS profiles carefully.
  • Water-rich media are greener but may limit reaction scope or lead to hydrolysis of sensitive substrates.

• Example comparison (general):

  • Water/Ethanol vs DMF: greener, lower toxicity, easier waste handling, but may reduce substrate solubility; consider biphasic or micellar conditions to bridge the gap.

Pharmaceutical Uses

No excipient or pharmacopeial use is specified for this item. This product is supplied strictly for research use only.

General context (non-clinical, literature/general):

• Quaternary ammonium salts can sometimes function as ion-pairing agents in analytical method development, or as intermediates for generating alternative counterions with properties tailored for formulation research. However, Quinidine methiodide itself is not indicated here for formulation or manufacturing.
• The iodide counterion may be exchanged for others (e.g., chloride, sulfate, organic anions) to explore salt forms of the quinidinium cation in pre-formulation research. Any such work should remain within non-clinical, exploratory contexts.

Regulatory note:

• No USP/EP/JP monograph or pharmacopoeial status is provided. Do not use in humans or clinical applications.

For any formulation-related experiments, consult your institutional guidelines and ensure the intended use complies with research-only restrictions.

Physical Properties

Item-specific specifications such as melting point, water content, residual solvents, and UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

General/literature expectations for quinidinium methiodide salts (non-spec):

• State and appearance: Quaternary ammonium iodides are typically crystalline, hygroscopic solids; color can range from colorless to off-white (literature/general).
• Solubility: Expected to be freely soluble in water and polar organic solvents (MeOH, EtOH), and highly soluble in DMSO/DMF due to ionic character (literature/general). Solubility in nonpolar solvents is typically poor.
• Ionization: Permanently charged quaternary ammonium; no acid–base pKa relevant to the cation (literature/general).
• Partitioning: Very low logP for the salt; effective distribution often characterized by logD that reflects ionic character (literature/general).
• Hygroscopicity: Quaternary ammonium iodides can absorb moisture; handling under dry conditions is recommended (literature/general).
• Thermal behavior: Quaternary ammonium iodides often decompose before boiling; a sharp melting point may be observed for pure materials, but decomposition can occur upon heating (literature/general).

Note: Values above are provided as general guidance only. For this specific item’s physical constants (mp, solubility limits, refractive index, density, etc.), consult the Aladdin CoA/Spec Sheet supplied with the lot.

Quality and Grades

• Item-specific grade: Moligand™.

Moligand™ designation (general meaning):

• Intended use: Library/screening-grade small molecules curated for discovery workflows, ligand screening, chemogenomic panels, and SAR exploration. Emphasis on structural authenticity and fitness for high-throughput assays.
• Typical quality controls (general): Identity confirmed by spectroscopic methods (e.g., NMR/MS), and purity suitable for screening. Exact purity %, residual solvent profile, and inorganic content are lot-specific.
• UV/LC suitability: While often compatible with LC/MS-based screening, “Moligand™” is not equivalent to HPLC grade solvent materials; absorbance cutoffs and LC baselines are not defined by this grade.

What is specific to this item:

• Storage stringency: Argon charged, desiccated, −80 °C storage suggests sensitivity to moisture/air and a desire to preserve long-term integrity for screening use.
• Shipping on dry ice + cold packs maintains low temperature and dryness throughout transit.

Not provided for this item; refer to CoA/Spec Sheet:

• Exact purity/assay (%), residual solvents, inorganic counterion verification, and water content.

Recommendations:

• Verify lot-specific CoA for purity and identity data prior to quantitative studies.
• If using in bioassays, consider preparing fresh stocks and verifying concentration by UV or qNMR where appropriate to ensure reproducibility.

Reaction and Applications

Use cases for Quinidine methiodide capitalize on its chiral quaternary ammonium cation and iodide counterion.

• Chiral ion-pairing and recognition (literature/general):

  • Formation of diastereomeric salts with chiral or prochiral acids for resolution studies or analytical chiral recognition.
  • Ion-pairing reagent in enantioselective transformations where a chiral cation modulates anionic transition states. Note: The methiodide is relatively hydrophilic; more lipophilic quaternized derivatives are commonly used for phase-transfer catalysis.

• Catalyst/ligand precursor (literature/general):

  • Starting point for further quaternization/anion exchange to produce tailored cinchonidinium catalysts used in asymmetric phase-transfer catalysis (e.g., enantioselective alkylations, Michael additions).

• Synthetic transformations involving iodide (literature/general):

  • Iodide acts as a nucleophile or halide source in Finkelstein-type exchanges and SN2 reactions; the bulky chiral cation can influence solubility and phase behavior.

• Practical tips:

  • Maintain dry conditions for reactions sensitive to water; choose MeOH/ACN/DMF for homogeneous phases.
  • For ion exchange (I− to PF6−/BF4−), dissolve in MeOH or ACN and add excess of the target anion’s salt (e.g., KPF6), then filter off precipitated KI.
  • For chiral salt formation, titrate equivalent acids under controlled stoichiometry and temperature; screen solvents to optimize crystallinity and diastereomeric enrichment.

Manufacturer applications: Not specified beyond “For research use only.” Expand usage according to your workflow’s synthetic or screening needs.

Reaction Conditions

General guidance for typical uses (literature/general; adapt to your system):

• Chiral salt formation/resolution:

  • Solvents: EtOH/MeOH, acetone, ACN, or mixed aqueous–alcohol systems.
  • Conditions: Equimolar amounts of Quinidine methiodide and the acidic substrate; gentle heating to dissolve, then slow cooling to crystallize. Seed to control polymorph. Temperatures: 0–25 °C for crystallization; dissolution up to 40–60 °C if needed.

• Anion metathesis (I− to PF6−/BF4−/OTf−):

  • Solvent: MeOH or ACN.
  • Reagents: KPF6, NaBF4, or AgOTf (precipitating KI/AgI drives equilibrium).
  • Conditions: 0–25 °C, 0.5–2 h, inert atmosphere to limit iodide oxidation.

• Ion-pair/phase-transfer-assisted reactions:

  • Media: Biphasic toluene or CH2Cl2 with aqueous base, or homogeneous polar organics (MeCN, toluene with phase-transfer additives).
  • Loadings: 1–20 mol% of chiral cation (when used catalytically). Temperature: 0–25 °C typical; adjust per substrate.
  • Notes: The methiodide’s hydrophilicity may reduce activity in nonpolar biphasic systems; consider more lipophilic derivatives or conduct in homogeneous polar media.

• Halide exchange (Finkelstein-type):

  • Solvent: Acetone/MeCN.
  • Conditions: Reflux or ambient, depending on substrate reactivity; iodide serves as nucleophile.

Yields and enantioselectivities are substrate- and protocol-dependent; consult primary literature for specific transformations.

Safety and Handling

Item-specific hazard classification (GHS, pictograms, H‑statements) and appearance: Not specified for this item; refer to the SDS for authoritative information.

General laboratory safety guidance for quaternary ammonium iodide salts (non-binding):

• Hazards: May cause irritation to skin, eyes, and respiratory tract. Iodide salts can release iodine under strong oxidizing conditions. Dust may be harmful if inhaled (literature/general). No significant volatility.
• PPE: Use lab coat, safety goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Handle powders in a fume hood or ventilated enclosure to minimize dust exposure.
• Handling: Avoid moisture ingress; the product is stored desiccated. Minimize exposure to light/air to protect iodide from oxidation. Avoid contact with strong oxidizers and strong bases/acids that may promote decomposition.
• Storage (item-specific): Argon charged, desiccated, Store at −80 °C. Protect container integrity to maintain inert atmosphere.
• Shipping (item-specific): Shipped on dry ice packs + cold packs.
• First aid (overview; see SDS):
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin/Eyes: Rinse cautiously with water for several minutes; remove contact lenses if present; seek medical attention if irritation continues.
  • Ingestion: Rinse mouth; do not induce vomiting; obtain medical advice.

Always consult the product SDS for definitive hazard, toxicological, and first-aid information.

Solvent Selection

This product is a solid quaternary ammonium salt rather than a solvent. Solvent selection considerations below are for dissolving and using Quinidine methiodide in reactions or assays.

• Polarity and miscibility (literature/general):

  • Highly polar/ionic; favors water and polar organics.
  • Excellent solubility expected in H2O, MeOH, EtOH, and dipolar aprotics (DMSO, DMF). Poor in nonpolar solvents (hexanes, toluene) unless ion paired.

• Practical choices by application:

  • Screening/bioassay stocks: DMSO or water are typical. Filter-sterilize aqueous stocks if sterility is required for assay plates.
  • Organic synthesis: MeOH/EtOH, acetonitrile, or DMF facilitate salt metathesis, ion-pairing, or nucleophilic iodide participation. Water–organic biphasic systems may be used with phase-transfer strategies.
  • Crystallizations/resolutions: Mixed alcohol/ether systems or alcohol/acetone can tune ion pairing and crystallinity of diastereomeric salts (literature/general).

• When to choose alternatives:

  • If water sensitivity exists downstream, prefer anhydrous MeOH/ACN or DMSO over water.
  • For greener profiles, prioritize water or ethanol where solubility and process constraints allow.

• Notes:

  • Adjust counterion effects: Iodide can be exchanged (e.g., to PF6−, BF4−, OTf−) via metathesis using minimally soluble salts in MeOH/ACN if different solubility/lipophilicity is desired (literature/general).
  • Control pH/ionic strength in aqueous media to stabilize the salt and minimize iodide oxidation.

Storage and Reconstitution

• Item-specific storage

  • Store at −80 °C, under argon, in a desiccated environment.
  • Keep container tightly closed to preserve the inert atmosphere and exclude moisture/air.
  • Protect from light to minimize iodide oxidation.

• Shipping

  • Supplied on dry ice packs + cold packs to maintain low temperature and dryness during transit.

• Reconstitution and handling (general guidance):

  • Work quickly at ambient temperature to weigh out portions; allow vial to equilibrate to room temperature before opening to avoid condensation.
  • Prepare stock solutions in dry solvents (water, MeOH, EtOH, DMSO, or DMF as appropriate). For biological assays, sterile-filter aqueous stocks (0.22 μm) if required.
  • Aliquot stocks to single-use portions and store at −20 to −80 °C to avoid repeated freeze–thaw. Record solvent, concentration, and date.
  • If precipitation occurs upon dilution, gently warm and sonicate, or adjust solvent composition (increase polar fraction).

• Stability notes

  • Hygroscopic materials can pick up water; ensure desiccant is active. Avoid prolonged exposure to air.
  • Iodide can oxidize to iodine under light/air/oxidants; maintain inert, dark storage. For lot-specific shelf-life and retest dates, refer to the CoA/Spec Sheet.

Research use only.

Structure and Identity

Quinidine methiodide is a quaternary ammonium salt derived from the cinchona alkaloid quinidine via N‑methylation with methyl iodide, yielding a permanently cationic quinidinium species paired with iodide.

• Item-specific identifiers

  • Product Name: Quinidine methiodide (SKU: Q1497664)
  • CAS: 42982-87-6
  • CID: 23620731
  • InChIKey: 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 description)

  • Core scaffold: Cinchona alkaloid framework containing a bicyclic quinuclidine fused to a quinoline ring via a chiral, oxygenated side chain.
  • Functional groups: Quaternary ammonium (permanent positive charge), secondary alcohol, vinyl functionality, quinoline heteroaromatic.
  • Stereochemistry: Multiple stereocenters inherited from quinidine (configurations as in quinidine; specific absolute configuration not restated here). The quaternization occurs at the bridgehead tertiary nitrogen, giving an N‑methyl quinidinium cation.
  • Counterion: Iodide (I−).

• Formula and mass (computed/literature, for the iodide salt)

  • Suggested molecular formula: C21H27IN2O2 (literature/computed from quaternization of quinidine)
  • Approximate molecular weight: ~466.36 g/mol (literature/computed)

• 2D structure in words

  • A quinoline ring (fused benzopyridine) connected through a chiral, oxygenated side chain to a rigid bicyclic quinuclidine bearing an N‑methyl substituent; the nitrogen bears a permanent positive charge balanced by iodide.

Synthetic Utility

Quinidine methiodide serves as a chiral, permanently cationic species valuable in asymmetric synthesis and ion-pair manipulations.

• Chiral counterion/auxiliary (literature/general):

  • Forms diastereomeric salts with carboxylates, phosphates, and sulfonates. These can be leveraged for chiral resolution, crystallographic determination of absolute configuration, and enantioenrichment by selective crystallization.

• Catalyst precursor (literature/general):

  • The quinidinium core is a platform for developing chiral phase-transfer catalysts. Although the methiodide is relatively hydrophilic, further N-alkylation (on oxygen or carbon substituents) and anion exchange can tailor lipophilicity and ion-pairing strength.

• Halide utility (literature/general):

  • The iodide counterion can participate in SN2/Finkelstein equilibria, or be swapped to PF6−/BF4−/OTf− via metathesis to modulate solubility and reactivity.

• Retrosynthetic value:

  • Enables chiral induction without covalent attachment, simplifying recovery: after reaction, the cation can be recovered by anion exchange or extraction into aqueous phases.

• Practical considerations:

  • Control water content to prevent diminished activity in PTC-like applications; ensure adequate agitation in biphasic systems.
  • Employ stoichiometric chiral salt formation under controlled temperatures to maximize diastereomeric differentiation; seed to improve reproducibility.

Item-specific catalytic performance data and enantioselectivities: Not specified for this item; consult literature or perform method scouting.

Target Specificity

Not applicable. This product is a small molecule reagent, not an antibody or biological targeting agent.

• Item-specific binding targets, receptor/channel specificity, or enzyme selectivity are not provided for this item. Any interaction data would be assay- and context-dependent and should be established empirically in your laboratory.

For mechanistic or binding studies, design controls to decouple effects of the cation (quinidinium core) from those of the counterion (iodide), and document buffer composition to ensure reproducibility.

Foire aux questions

What is Moligand??

Moligand? is one of Aladdin Scientific's premium product lines, formulated for high-purity applications across multiple workflows. Compared to standard grades in the same workflow, Moligand? products typically offer tighter specifications, more rigorous QC, and stronger lot-to-lot consistency.

How should this product be stored?

Store at ?80 °C, desiccated, under argon. It is supplied under an argon blanket; reseal under inert gas after each use.

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 42982-87-6, the molecular formula is C21H27N2O2?I, and the molecular weight is 466.36 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.