Hydroxychloroquine-dsulfate , CAS No.1854126-45-6

CAS: 1854126-45-6 Cat. No.: H1421165 Formula: C₁₈H₂₄D₄ClN₃O₅S Peso molecolare: 437.97

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Panoramica

Hydroxychloroquine-d 4 (sulfate) is the deuterium labeled Hydroxychloroquine sulfate. Hydroxychloroquine sulfate (HCQ sulfate) is a synthetic antimalarial agent which can also inhibit Toll-like receptor 7/9 (TLR7/9) signaling. Hydroxychloroquine sulfate is efficiently inhibits SARS-CoV-2 infection in vitro.

Specifications

Condizioni di conservazione di stoccaggio

Store at -20°C

Spedito in

Ice chest + Ice pads

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Nomi e identificatori

• Peso molecolare: 437.97

Application Protocols

No manufacturer protocols are provided for this item. General, non-clinical laboratory usage examples for small-molecule tool compounds like hydroxychloroquine “dsulfate” include:

• Stock preparation (general):
  • Prepare sterile aqueous or DMSO stock solutions; typical lab concentrations for screening range from 10 to 100 mM in DMSO or 10–50 mg/mL in water, subject to solubility. Filter sterilize (0.22 µm) if used in cell culture. Record exact concentration gravimetrically.
• Cell-based assays (general):
  • Titrate in a broad range (e.g., 0.1–50 µM) to map response; include vehicle controls. Monitor pH of media if adding aqueous stocks of the salt.
• Analytical calibration:
  • Prepare serial dilutions in 50:50 water–acetonitrile (0.1% formic acid) for LC–MS/MS. Store aliquots at –20 °C and avoid multiple freeze–thaw cycles.

These are illustrative, literature-style practices and are not item specifications. Optimize for your system and consult the SDS for safe handling.

Biological Roles

General research context (non-clinical):

• Hydroxychloroquine, as a 4-aminoquinoline, is widely used in cell and molecular biology as a lysosomotropic weak base. By accumulating in acidic organelles, it can elevate intralysosomal pH, perturb autophagosome–lysosome fusion, and modulate endosomal trafficking. These effects are leveraged to interrogate autophagy pathways, antigen processing, and endolysosomal signaling.
• The tertiary amine and aromatic quinoline features facilitate organelle accumulation through proton trapping (general mechanistic principle for cationic amphiphiles).
• In immunology research, hydroxychloroquine is employed to study TLR signaling modulation (e.g., TLR7/9 pathways) via endosomal pH effects and nucleic acid binding interactions (literature context). Use appropriate controls to distinguish pH-mediated from direct target interactions.
• In chemical biology workflows, the compound often serves as a benchmark when profiling new lysosome-targeting or autophagy-modulating chemotypes.

Important note: The above describes general biochemical roles observed for hydroxychloroquine-class compounds in laboratory systems. It does not imply or endorse any medical use. For quantitative potency, kinetics, or system-specific effects, consult primary literature and validate under your assay conditions. Salt form (“dsulfate”) may influence uptake and apparent potency due to differences in counterion and pH of stock solutions.

Buffer Applications

This item is not a buffering reagent. However, because hydroxychloroquine sulfate salts are typically water-soluble and basic, buffer considerations are relevant for preparing assay solutions (general guidance):

• Recommended diluents: Sterile water, PBS, or culture media, with attention to final pH and ionic strength.
• pH effects: As a weak base, the compound can slightly raise local pH upon dissolution in low-capacity media. Prepare concentrated stocks (e.g., in water or DMSO) and dilute into well-buffered solutions (HEPES, PBS) to maintain stable pH.
• Filtration: If sterile solutions are required, pass through 0.22 µm filters. Avoid adsorption losses by pre-wetting with buffer containing small amounts of carrier protein if consistent with your assay (verify for interference).
• Avoidance: Phosphate can form ion pairs with protonated amines; usually compatible, but monitor for precipitation at high concentrations or non-physiological pH.

No specific buffer recipes or buffering ranges apply to this compound itself. For exact solubility and stability in your chosen buffer, perform a small-scale compatibility test, as properties can vary with the precise sulfate stoichiometry of the “dsulfate” form.

Green Alternatives

When selecting solvents and processes for handling hydroxychloroquine sulfate salts, greener choices can reduce hazard and waste. The molecule itself is fixed; optimization focuses on media and operations.

• Greener solvent choices for dissolution/processing (general):
  • Prefer water or aqueous buffers when feasible; they provide excellent solubility for amine sulfate salts and minimize VOCs.
  • Use ethanol over methanol where compatible with your assay, due to lower toxicity; both are bio-based options when sourced sustainably.
  • Prefer acetonitrile or ethanol/water over chlorinated solvents for analytical methods, balancing performance and EHS impact.
• Stock solutions and cleaning:
  • DMSO is effective for concentrated stocks; minimize use by preparing higher-concentration master stocks and aliquoting to reduce waste.
  • For equipment cleaning, hot water/ethanol rinses can replace halogenated solvents if residue profiles allow.

Comparison (general):

• Water/Buffer: Minimal environmental impact; excellent for salts; may require bioburden controls.
• Ethanol: Renewable routes available; flammable but less toxic than methanol.
• DMSO: Low volatility and good safety profile but persistent in wastewater; use sparingly.

Process tips:

• Employ microscale screening and DoE to reduce material usage.
• Consider ion-exchange workups rather than large-volume liquid–liquid extractions with chlorinated solvents when converting between salt and base forms.

Pharmaceutical Uses

No therapeutic or clinical claims are made for this product. For research use only.

Formulation-context information (general, non-clinical):

• Hydroxychloroquine salts are classic small-molecule actives; in a research and pre-formulation context, they are studied for solid-state form selection (salt stoichiometry, hydration state), polymorphism, and excipient compatibility.
• The sulfate counterion often enhances aqueous solubility and crystallinity relative to the free base, facilitating development of aqueous solutions for in vitro work.
• Relevant excipient interactions (general): Basic amines may interact with anionic polymers (e.g., HPMC phthalate), ion-exchange resins, and silica; assess adsorption and release in formulation screens.
• Analytical development: Salt identification and assay typically use HPLC with UV detection, LC–MS for identity/purity, and ion chromatography or ICP-OES (sulfur) to confirm sulfate content.

Pharmacopeial status, compendial monographs, and any excipient roles for this specific “dsulfate” form are not provided here and should be verified in appropriate references if pertinent to your work.

Physical Properties

Item-specific values for this catalog entry are not provided. Do not treat literature values as specifications. Always verify on the CoA/Spec Sheet for released lots.

• Appearance (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• Solubility (literature/general): Hydroxychloroquine sulfate salts are typically highly soluble in water and polar protic solvents; the free base is readily soluble in DMSO and alcohols and less so in nonpolar media. Exact solubility of the “dsulfate” form may differ and must be confirmed experimentally.
• pKa (literature/general for related 4-aminoquinoline tertiary amines): multi-basic with pKa values commonly in the ~8–10 range for the tertiary amine; the quinoline nitrogen is significantly less basic. Actual values depend on substitution and ionic form.
• LogP/LogD (literature/general): The protonated sulfate salt displays much lower apparent LogD at physiological pH than the neutral base; reported LogP for the free base of hydroxychloroquine is moderate (drug-like), while LogD is pH dependent.
• Melting point, boiling point, density, refractive index: Not specified for this item; refer to CoA/Spec Sheet.

Practical note (general): Salt stoichiometry (mono-, di-) can materially affect hygroscopicity, solubility, and thermal behavior; handle and characterize accordingly.

Quality and Grades

• Grade/purity (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• What the grade controls (general): For small-molecule research reagents, grade typically defines identity confirmation (NMR/HRMS/HPLC), purity threshold, residual solvents, and where relevant, salt stoichiometry and water content (Karl Fischer). For chromatographic or bioassay applications, low UV background and low inorganic content may also be specified.
• Salt form clarity: For amine sulfates, the exact stoichiometry (e.g., mono- vs “di”-sulfate), hydration level, and counterion identity are part of the quality definition because they influence assay potency (µmol per mg), solubility, and crystallinity. This must be stated on the CoA for precise molar calculations.
• Stabilizers: None specified for this item. If stabilizers or desiccants are included, they will be indicated on the CoA/Spec Sheet.
• Recommended verification on receipt:
  • Confirm identity by 1H/13C NMR in D2O or DMSO-d6 (salt form dependent) and HRMS (ESI+ typically shows the organic cation).
  • Check HPLC purity and assess counterion via ion chromatography or sulfate quantification if your application is molarity-critical.
  • Determine water content (KF) if hygroscopicity is a concern.

Refer to the lot-specific CoA for definitive quality attributes and acceptance criteria.

Reaction and Applications

This compound is primarily used as a bioactive small molecule standard and tool compound rather than as a synthetic reagent. Nevertheless, the underlying functional groups suggest certain chemistries (general guidance):

• Functional group profile (general):
  • Tertiary aliphatic amine (forms salts; can undergo quaternization or dealkylation under harsh conditions).
  • Phenoxy/anilino linkage to a 7-chloroquinoline core; aromatic C–Cl can participate in nucleophilic aromatic substitution (SNAr) under strong conditions, though substitution at C-4/C-7 is typically embedded in the scaffold and not routinely modified post-assembly.
  • Side-chain alcohol (can form esters or be oxidized; typically avoided to preserve biological activity).
• Applications in research (general, non-clinical):
  • Frequently used as a lysosomotropic base and autophagy flux modulator in cell biology; raises lysosomal pH and interferes with endo/lysosomal trafficking (mechanistic tool use; verify dose-response in your system).
  • Employed as an internal standard or reference in analytical method development (LC–MS/MS) for related 4-aminoquinoline analytes.
• Practical tips:
  • For organic transformations, the sulfate counterion may be exchanged for the free base to enhance solubility in nonpolar solvents.
  • Protect the side-chain hydroxyl if derivatization is required; tertiary amine protection/quaternization strategies can alter physicochemical properties substantially.

Note: No manufacturer applications were provided; adapt use to your validated laboratory protocols.

Reaction Conditions

No manufacturer-provided reaction conditions are associated with this product. As a complex bioactive scaffold, it is not routinely employed as a reagent. General notes for handling and minor derivatization (literature/general):

• Salt/base conversion: Dissolve the sulfate salt in water, basify carefully (e.g., NaHCO3 or Na2CO3, then NaOH as needed), and extract the free base into an organic solvent (EtOAc/CH2Cl2). Reconstitute the salt by treatment with sulfuric acid in alcohol/water and crystallize as needed.
• Acylation/sulfonylation of the anilino nitrogen: Carried out in polar aprotic solvents (DMF, DCM) with base (DIPEA/TEA) at 0–25 °C; monitor to avoid overacylation of the tertiary amine.
• Esterification of the side-chain alcohol: Standard DCC/DMAP or acid chloride methods in DCM/DMF at 0–25 °C; protect the tertiary amine if selectivity is required.
• Quaternization of the tertiary amine: Alkyl halides (e.g., MeI) in acetonitrile or acetone at ambient to reflux; generates permanently charged salts, often improving LC–MS response.

All conditions above are provided as general literature-style guidance, not specifications for this item. Validate on small scale and confirm identity/purity after any transformation.

Safety and Handling

Item-specific GHS information was not provided. Always consult the product’s SDS for authoritative safety data before use.

• GHS classification, signal word, H-statements, pictograms (item-specific): Not specified for this item; refer to SDS.
• Likely hazards (general for organic amine sulfate salts): May cause irritation to eyes/skin/respiratory tract. Avoid dust formation and inhalation of particulates. Handle powders in a fume hood or containment.
• Personal protective equipment (best practice):
  • Lab coat, suitable chemical-resistant gloves (e.g., nitrile), safety glasses or splash goggles.
  • Use respiratory protection if airborne dust cannot be controlled; follow institutional SOPs.
• Handling guidance:
  • Avoid contact with strong oxidizers. Though sulfate counterions are stable, the organic cation can be incompatible with strong bases/oxidants.
  • Use clean, dry tools; minimize exposure to ambient moisture if the salt is hygroscopic (verify on CoA/SDS).
• First-aid overview (general):
  • Skin/eye contact: Rinse with water for several minutes; remove contaminated clothing; seek medical attention if irritation persists.
  • Inhalation: Move to fresh air; obtain medical advice if symptoms occur.
  • Ingestion: Rinse mouth; seek medical advice. Do not induce vomiting unless directed by medical personnel.
• Spill/cleanup (general): Avoid dust; collect mechanically or with HEPA-filtered vacuum. Dispose according to local regulations.
• Storage incompatibilities: Separate from strong bases and oxidizing agents; avoid prolonged exposure to moisture and light unless stability data allow.

Solvent Selection

Because the product is provided as a sulfate salt of a basic, polar amine, solvent behavior will be driven by ionic character.

• Polarity/miscibility profile (literature/general):
  • Sulfate salts of tertiary amines are typically freely soluble in water and aqueous buffers (ionic character), and show high solubility in polar protic solvents (methanol, ethanol). Solubility in DMSO is usually excellent for both salt and base.
  • Solubility in aprotic, nonpolar solvents (DCM, toluene, ethers) is generally poor unless converted to the free base or used as an ion pair.
• Practical selection by use case:
  • Bioassays/cell studies: Prepare concentrated stocks in sterile water or DMSO; dilute into buffered media. Filter-sterilize if required. Confirm compatibility with your biological matrix.
  • Analytical (HPLC/LC–MS): Aqueous mobile phases with acetonitrile or methanol modifiers work well; adding a volatile acid (e.g., 0.1% formic acid) improves peak shape for basic analytes (general guidance).
  • Synthetic manipulation: If conversion to the free base is needed for organic-phase reactions or extractions, basify aqueous solutions and extract into an organic solvent; re-salt as needed after the transformation.
• Comparison (general):
  • Water: Best for ionic salts and biological work; may require pH control.
  • DMSO: Highest solubility and stable stocks at small volumes; mind final DMSO % in assays.
  • Alcohols: Good compromise for preparative handling; flammable and may affect downstream steps.

Always determine actual solubility for this specific “dsulfate” form experimentally.

Storage and Reconstitution

• Storage (item-specific): Store at -20°C. Protect from moisture and light. Follow any additional lot-specific instructions on the label/CoA.
• Shipping condition (item-specific): Shipped in ice chest with ice pads to maintain low temperature.
• Container handling: Allow the sealed container to equilibrate to room temperature before opening to minimize moisture condensation. Reseal promptly after use. If hygroscopic, store under inert atmosphere or with desiccant (verify on CoA/SDS).
• Reconstitution (general):
  • For biological assays, dissolve in sterile water or DMSO to prepare a concentrated stock. Gentle warming and vortexing may aid dissolution. Record exact mass and volume to compute molarity; for accuracy, use the lot-specific molecular weight from the CoA (important for salts where stoichiometry affects MW).
  • Filter sterilize through a 0.22 µm membrane when sterility is required.
• Aliquoting: Prepare single-use aliquots to avoid repeated freeze–thaw. Store aliquots at –20°C (aqueous) or –20°C to –80°C (DMSO) as appropriate; verify stability in your matrix.
• Stability: Item-specific shelf life and solution stability are not provided; refer to CoA/Spec Sheet. As a general practice, avoid prolonged exposure to elevated temperature, light, and high pH.

Research use only: Not for human or veterinary use.

Structure and Identity

• Item: Hydroxychloroquine-dsulfate (SKU: H1421165)
• CAS: 1854126-45-6
• 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.
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.

Structural overview (general chemistry knowledge):

• Hydroxychloroquine is a 4-aminoquinoline derivative bearing a 7-chloroquinoline core and a tertiary amino side chain that includes a hydroxyalkyl functionality. The sulfate or multi-sulfate (“dsulfate”) designation indicates protonated amine(s) paired with sulfate counterion(s). Exact stoichiometry for this specific item is not provided; consult the CoA for definitive salt form.
• Key functional groups (literature/general):
  • 7-chloro substituted quinoline ring (heteroaromatic system with a ring nitrogen and an annulated benzene ring)
  • Secondary anilino linkage at C-4 of the quinoline core
  • Tertiary aliphatic amine side chain (protonated in the sulfate salt)
  • Pendant hydroxy group on the side chain (confers increased polarity vs chloroquine)
• 2D description (general): A fused bicyclic quinoline ring bears a chloro substituent and an anilino link to a flexible carbon chain terminating in a tertiary amine; a hydroxy group is located on the side chain. The salt form is represented by sulfate counterions associated with the protonated amine center(s).

Synthetic Utility

This compound is a finished, complex heteroaromatic amine salt more commonly used as a tool compound than a building block. Still, understanding its reactivity aids in derivatization or analytical synthesis (general guidance):

• Quinoline core (heteroaromatic): Electron-deficient at specific positions; C–Cl at C-7 in related scaffolds can undergo SNAr with strong nucleophiles, though extensive changes typically abrogate canonical biological behavior.
• Anilino linkage at C-4: N–C(aryl) bond is robust; further N-functionalization (acylation, sulfonylation) can be done on the exocyclic aniline under controlled conditions.
• Tertiary aliphatic amine: Amenable to quaternization (e.g., methylation) to generate permanent cations for analytical standards; can be deprotected/modified with care. Salt/base toggling enables phase-transfer control in workups.
• Side-chain alcohol: Can be esterified or converted to carbamates/urethanes for prodrug-mimetic studies or analytical derivatives.

For synthetic route work, researchers typically start from 7-chloro-4-aminoquinoline intermediates and append the hydroxyalkylated side chain by nucleophilic substitution and reductive steps. Any modification should consider the impact on pKa, logD, and lysosomotropism if biological assays are intended.

Target Specificity

Not applicable. This product is a small-molecule compound, not an antibody or affinity reagent. No target antigen, clone, isotype, or species reactivity information applies. For biological studies, hydroxychloroquine-class compounds modulate endolysosomal biology broadly rather than acting as highly selective ligands; any putative targets should be validated within the context of your specific assay.