Sequifenadine hydrochloride - ≥98% , CAS No.57734-70-0

CAS: 57734-70-0 Cat. No.: S1031513 Fórmula: C₂₂H₂₈ClNO Peso molecular: 357.93 Número EC: 681-157-8 PubChem CID: 50853316

GRADE & PURITY ≥98%

Storage

Room temperature

Specifications

Especificaciones y pureza

≥98%

Condiciones de almacenamiento de almacenamiento

Room temperature

Pureza

≥98%

Nombres e identificadores

• Sonrisas canónicas: CC1=CC=CC=C1C(C2CN3CCC2CC3)(C4=CC=CC=C4C)O.Cl
• IUPAC Name: 1-azabicyclo[2.2.2]octan-3-yl-bis(2-methylphenyl)methanol;hydrochloride
• InChIKey: WCYWFJOJKZCSAJ-UHFFFAOYSA-N
• INCHI: 1S/C22H27NO.ClH/c1-16-7-3-5-9-19(16)22(24,20-10-6-4-8-17(20)2)21-15-23-13-11-18(21)12-14-23;/h3-10,18,21,24H,11-15H2,1-2H3;1H
• Isómeros SMILES: CC1=CC=CC=C1C(C2CN3CCC2CC3)(C4=CC=CC=C4C)O.Cl
• PubChem CID: 50853316
• Peso molecular: 357.93

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Clase Benzene and substituted derivatives
      • Subclass Diphenylmethanes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Clase: Benzene and substituted derivatives
• Subclass: Diphenylmethanes
• Intermediate Tree Nodes: Not available
• Direct Parent: Diphenylmethanes
• Alternative Parents: Quinuclidines Toluenes Aralkylamines Piperidines Tertiary alcohols 1,3-aminoalcohols Trialkylamines Azacyclic compounds Organopnictogen compounds Organic zwitterions Organic chloride salts Hydrocarbon derivatives Aromatic alcohols
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Diphenylmethane - Quinuclidine - Aralkylamine - Toluene - Piperidine - 1,3-aminoalcohol - Tertiary alcohol - Tertiary amine - Tertiary aliphatic amine - Azacycle - Organoheterocyclic compound - Organic nitrogen compound - Aromatic alcohol - Organic zwitterion - Organic salt - Organic chloride salt - Hydrocarbon derivative - Organopnictogen compound - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Amine - Alcohol - Aromatic heteropolycyclic compound
• Descripción: This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
• 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: 357.900 g/mol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 357.186 Da
• Monoisotopic Mass: 357.186 Da
• Topological Polar Surface Area: 23.500 Ų
• Heavy Atom Count: 25
• Formal Charge: 0
• Complexity: 406.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 2

XLogP3

Application Protocols

No vendor-tested application protocols are provided for this SKU. General non-clinical research workflows include:

• Receptor-binding assay setup (general):

  • Prepare compound stocks at 10 mM in DMSO; perform 10‑point half-log dilutions.
  • Incubate with membrane prep expressing human H1 receptor and a radioligand tracer at ~Kd concentration; measure displacement to calculate Ki (Cheng–Prusoff correction).

• Cell-based functional antagonism (general):

  • Load cells (H1-expressing) with Ca2+ dye; preincubate with serial dilutions of compound; stimulate with histamine; read fluorescence changes to derive IC50.

• LC‑MS analytical method (general):

  • Column: C18, 2.1 × 50 mm, 1.7 µm; Mobile A: 0.1% formic acid in water; Mobile B: acetonitrile; Gradient 5–95% B in 5–7 min; ESI+ MRM/scan optimized per actual mass.

These are literature-style general methods and must be adapted and validated in your lab. No claims of performance are made for this specific lot.

Biological Roles

Literature/general context (not item-specific; no clinical claims):

• Sequifenadine is described in the literature as a histamine H1 receptor antagonist. H1 receptors are GPCRs mediating responses to histamine in peripheral and central tissues, coupling mainly via Gq/11 to mobilize intracellular Ca2+ and activate PLC signaling pathways.
• In pharmacological research, H1 antagonists are used as tool compounds to probe histamine-driven pathways, receptor binding kinetics, biased signaling, and downstream transcriptional responses.
• Biophysical/biochemical applications include radioligand displacement, fluorescence polarization, BRET-based receptor–β‑arrestin assays, and impedance-based functional readouts.
• ADME/PK characterization (general): amine-containing H1 antagonists often display high plasma protein binding, pH-dependent permeability, and substrate behavior toward certain CYPs or transporters; actual profiles are molecule-specific and must be measured for this compound and lot.

Note: For any biological testing, ensure the absence of interfering impurities and confirm the exact salt stoichiometry, as counterions can influence potency and assay variability.

Buffer Applications

This product is a small-molecule research compound and not a buffering reagent. It is not typically used to prepare buffer systems. For experimental work involving this compound:

• Prepare stock solutions in DMSO or aqueous acidic buffers (e.g., 10–50 mM; confirm solubility empirically) and dilute into the assay buffer of interest.
• Common assay buffers for GPCR pharmacology include HEPES (pH 7.2–7.4), PBS, or HBSS with appropriate cofactors. Select buffer composition to maintain compound solubility and receptor integrity.

Green Alternatives

Context: This item is an active small molecule rather than a solvent or reagent used in bulk. “Green alternatives” thus address handling and medium choices around its use (not substitution of the active itself).

Greener handling choices (general guidance):

• Prefer aqueous buffers and bio-based alcohols (ethanol) where compatible with solubility and assay integrity.
• Use DMSO judiciously (minimize stock concentration/volume; consider GBL or propylene carbonate only if analytically justified and safe for the system).
• For extractions during free-base/salt interconversion, choose ethyl acetate or MTBE instead of chlorinated solvents when feasible; verify recovery and purity.

Illustrative comparison (general):

• Acidic aqueous media (pH 2–5): often highest solubility; minimal VOCs; compatible with LC‑UV.
• Methanol vs ethanol: ethanol is generally preferred from a green-metrics perspective, though solubility may be slightly lower.
• DCM/CHCl3: avoid unless necessary; evaluate EtOAc/MEK/2‑MeTHF alternatives for workups.

Waste minimization:

• Prepare concentrated master stocks and aliquot to reduce repeated solvent use and freeze‑thaw cycles.
• Use microscale assays and mini-columns for purification to limit solvent volumes.

Pharmaceutical Uses

No therapeutic or clinical claims are made. Research/formulation context only:

• Hydrochloride salts of basic drugs are commonly used for formulation research, including salt screening, excipient compatibility, and stability-indicating studies (stress by heat, light, humidity, oxidative/peroxide challenge).
• Potential roles in preformulation research include:
  • Determining Hygroscopicity and deliquescence point for solid dosage feasibility (laboratory studies only).
  • Assessing solid-state forms (XRPD/DSC/TGA) for polymorph or solvate identification.
  • Building LC‑UV/LC‑MS methods for content uniformity and related substances.
• Pharmacopeial status: Not specified for this item; consult pharmacopeias and internal regulatory resources if compendial methods or monographs are required.

Physical Properties

Item-specific specifications (this SKU):

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point, boiling point, density, refractive index, pKa, logP/logD, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general expectations for hydrochloride salts of amine-containing antihistamines (not item-specific):

• Physical form: frequently crystalline solids (often white to off‑white) with defined melting ranges.
• Ionization: protonated amine(s) with pKa typically in the 8–10 range for tertiary amines, yielding good water solubility at neutral to mildly acidic pH. Exact pKa and solubility are structure-dependent.
• Solubility pattern: commonly highly soluble in water and polar protic solvents; variable solubility in alcohols; typically low solubility in nonpolar hydrocarbons. Confirm experimentally.

Practical notes:

• For analytical method development, determine actual aqueous solubility and pH‑solubility profile via small-scale tests (e.g., 1–10 mg in 1 mL water or buffer, followed by pH adjustment). Record true values on the batch CoA.

Quality and Grades

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

Interpretation and guidance:

• In absence of an explicit grade (e.g., ≥98%, analytical standard, HPLC grade), rely on the batch-specific CoA for assay method, residual solvent levels, and impurity profile.
• For use as an analytical reference or in screening campaigns, confirm:
  • Assay methodology (e.g., qNMR, HPLC area% with calibration).
  • Counterion content and stoichiometry (e.g., monohydrochloride vs dihydrochloride), water content (Karl Fischer), and residual solvents.
  • Identity confirmation by orthogonal techniques (e.g., 1H/13C NMR, HRMS, ATR‑FTIR).
• Stabilizers: None are declared in the Product Data for this item. If your method is UV-based or mass-sensitive, assess background from potential stabilizers or counterions experimentally.

Documentation to request/retain:

• CoA (lot-specific), Spec Sheet, SDS, and if applicable, TDS or analytical method notes used to qualify the lot.

Reaction and Applications

Manufacturer Applications: Not specified in Product Data for this SKU.

Research and laboratory uses (general, non-clinical):

• Reference standard/control: Use as a positive control compound in receptor-binding or functional assays targeting histamine H1 receptor signaling pathways. Maintain rigorous documentation of concentration and counterion state.
• Analytical method development: Calibration and system suitability in LC‑UV or LC‑MS methods for related-compound analysis, salt screening, or stability-indicating methods; evaluate retention and ionization across pH.
• Form profiling: Salt screening, polymorph detection by DSC/XRPD, and hygroscopicity studies.
• Derivatization studies: If deprotonated to the free base, functionalization or prodrug exploration can be examined; however, sequifenadine is generally used as a target compound rather than a synthon.

Practical tips:

• Prepare DMSO or aqueous acidic stock solutions to ensure full dissolution; filter (0.22 µm) before bioassay use.
• Track pH upon dilution into buffers; precipitation can occur if the free base is generated.
• For LC‑MS, formic acid or ammonium formate (pH 3–4) often gives robust peak shape for cationic analytes.

Reaction Conditions

Not a general-purpose reagent; specific named reactions are not applicable. However, for handling and analytical preparation (general, not item-specific):

• Stock preparation: Dissolve at 10–50 mM in DMSO or water adjusted to pH 2–5 (e.g., 0.01–0.1 M HCl). Filter through 0.22 µm PTFE/nylon.
• Dilution into assay buffers: Add slowly with mixing to minimize local supersaturation; final DMSO commonly ≤0.1–1% v/v in cell-based assays.
• Free-base generation (if needed for partitioning): Adjust aqueous solution to pH >10 with NaOH, extract into EtOAc/MTBE; verify phase behavior and back‑extract as needed. Dry organic, evaporate gently (<40 °C) to avoid thermal degradation, then re-salt with HCl in Et2O/IPA.
• Stability checks: Conduct short-term solution stability at room temp and 4 °C over 24–72 h by LC‑UV/MS. Assess light sensitivity; store protected from light if degradation is detected.

All parameters should be experimentally verified for this compound and lot.

Safety and Handling

Product Data safety entries:

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

General laboratory safety guidance (not item-specific; consult SDS for authoritative details):

• Handle in a chemical fume hood to avoid inhalation of dust or aerosols. Avoid skin and eye contact; wear lab coat, nitrile gloves, and safety glasses.
• Avoid generating dust; use antistatic measures when weighing.
• Incompatibilities (general): strong oxidizers and strong bases/acids may affect salt form or cause degradation; segregate accordingly. Avoid moisture uptake if the material is hygroscopic (verify).
• 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 as needed. Always follow your institution’s SOPs.
• Disposal: Collect waste in properly labeled containers for organic solids; dispose per local regulations.

Note: No item-specific hazard classification is provided here—refer to the official SDS for this SKU before use.

Solvent Selection

Item-specific solubility is not provided. The following are general, literature-based considerations for small-molecule hydrochloride salts (not item-specific):

• Polarity class: Typically polar ionic; good affinity for water and polar protic solvents (MeOH, EtOH). Often soluble in DMSO for stock solutions.
• Miscibility profile (general):
  • Water: commonly high solubility at neutral to acidic pH; lower at high pH if the free base precipitates.
  • Alcohols: good solubility; methanol ≥ ethanol > isopropanol (trend varies by structure).
  • Aprotic polar: DMSO/DMF usually excellent for concentrated stocks.
  • Nonpolar (hexanes, toluene): typically poor.

Selection tips:

• Bioassays/HTS: prefer aqueous buffers or DMSO stocks (e.g., 10–50 mM) diluted into assay media; pre-check precipitation upon dilution.
• Purification/recovery: if converting to free base, adjust pH > pKa to partition into organic phase (EtOAc/MTBE/CH2Cl2), then re-salt as needed.
• NMR: D2O for salt form; CD3OD or DMSO‑d6 as general alternatives.

Always verify with a small-scale solubility test and document true values for your lot.

Storage and Reconstitution

• Storage conditions (Product Data): Room temperature. Store tightly closed in the original container. Protect from excessive humidity. If hygroscopic behavior is observed, consider desiccant storage.
• Shipped in: Not specified for this item; refer to accompanying documents.

Reconstitution and handling (general guidance; verify experimentally):

• Prepare concentrated stocks in DMSO (e.g., 10–50 mM) or in water with slight acidification (e.g., 0.01–0.1 M HCl) to ensure complete dissolution.
• Filter sterilize solutions for biological assays (0.22 µm). Aliquot into single-use vials to avoid repeated freeze‑thaw.
• Aqueous stock stability should be assessed at intended storage conditions (e.g., 4 °C for 1–7 days); for longer-term, store frozen (−20 to −80 °C) if compatible with your application. Document any precipitation upon thawing.

Research use only: As noted in Product Data, this material is For research use only. Consult the CoA and SDS for lot-specific details (assay, water content, residual solvents, and safety).

Structure and Identity

• Item name: Sequifenadine hydrochloride (SKU: S1031513)
• CAS: 57734-70-0 (Product Data)
• PubChem CID: 50853316 (Product Data)
• InChIKey: 395120 (Product Data; note this string is provided as-is in the listing)
• 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 overview (general/literature context):

• Sequifenadine is known in the literature as a small-molecule histamine H1 receptor antagonist. The hydrochloride indicates a protonated amine salt form, typically conferring increased aqueous solubility relative to the free base (general property of hydrochloride salts; not item-specific).
• Typical features for H1 antagonists include one or more tertiary amine or cationic centers and aryl/heteroaryl lipophilic fragments; exact placement and substitution must be verified from a definitive structure record (consult CoA/SDS or structural databases for this exact SKU).

2D structure description (general guidance):

• Expect an organic cation (protonated amine) paired with Cl−. The cation often contains an arylated aliphatic scaffold. Without the SMILES/InChI, the precise ring systems and stereochemistry cannot be asserted for this catalog item.

Synthetic Utility

This compound is typically a target molecule or reference standard rather than a general synthon. Nonetheless, general considerations apply (not item-specific):

• If converted to the free base, functional group interconversions on aryl or aliphatic positions (e.g., halogenations, oxidations, N‑alkylations) may be explored for SAR or impurity profiling.
• The hydrochloride salt form is valuable for:
  • Generating impurity markers by controlled degradation (acid/base stress, oxidative stress) to qualify stability-indicating methods.
  • Establishing counterion exchange protocols (ion-exchange resins or acid/base workups) for salt screening.
• In analytical synthesis contexts, sequifenadine-related structures can serve as scaffolds for preparing isotopically labeled standards (e.g., 2H, 13C) to support LC‑MS quantitation.

Note: Without the explicit structure on this SKU page, plan synthetic work only after confirming the exact structural constitution and stereochemistry from an authenticated source (CoA/SDS or primary literature).

Target Specificity

No item-specific biological target validation is provided in the Product Data for this SKU. Literature generally categorizes sequifenadine as a histamine H1 receptor antagonist, but definitive potency, selectivity profile across histamine receptor subtypes (H1–H4), and off-target interactions must be determined experimentally for your lot and assay system.

For internal method files, consider documenting:

• Binding affinity (Ki) in radioligand displacement vs a canonical H1 tracer (literature method),
• Functional antagonism (IC50) in calcium mobilization or impedance assays,
• Off-target panel screening (e.g., GPCR/CNS panels) to define selectivity.

Note: These are general recommendations; no tested targets or potencies are claimed for this catalog item.