Niaprazine - 10mM in DMSO , CAS No.27367-90-4

CAS: 27367-90-4 Cat. No.: N656759 Fórmula: C₂₀H₂₅FN₄O Peso molecular: 356.4 Número EC: 248-431-5 PubChem CID: 71919

GRADE & PURITY 10mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Descripción general

Niaprazine is a histamine H1-receptor antagonist. Niaprazine has antihistamine and antiserotonin activities and can be used for sleep disorder research.

In Vitro

Niaprazine exhibits a low affinity for the vesicular monoamine transporter and for D2, α2, β, H1 and mAch receptors. Niaprazine, particularly the (+)stereoisomer, has a higher affinity for α1 (Ki = 77 nM) and 5-HT2 (Ki = 25 nM) binding sites, but is poorly recognized by 5-HT1A and 5-HT1B binding sites. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

Niaprazine (60 mg/kg; i.p.; once) treatment increases rat brain 5-hydroxyindole acetic acid (5-HIAA) concentrations 30 min after treatment, and reduced them at 3-8 hr after treatment. Niaprazine also produces a short-lasting depletion of rat brain noradrenaline (NA) and dopamine (DA). MCE has not independently confirmed the accuracy of these methods. They are for reference only. Animal Model: Male Sprague-Dawley rats (150-200 g)Dosage: 60 mg/kg Administration: Intraperitoneal injection; once Result: Increased rat brain 5-hydroxyindole acetic acid (5-HIAA) concentrations 30 min after treatment, and reduced them at 3-8 hr after treatment.

Specifications

Especificaciones y pureza

10mM in DMSO

Mecanismos bioquímicos y fisiológicos

Niaprazine is a histamine H1-receptor antagonist. Niaprazine has antihistamine and antiserotonin activities and can be used for sleep disorder research.

Condiciones de almacenamiento de almacenamiento

Store at -80°C

Enviado en

Dry ice packs + Cold packs

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Tipo de acción

ANTAGONIST

Nombres e identificadores

Isómeros SMILES

CC(CCN1CCN(CC1)C2=CC=C(C=C2)F)NC(=O)C3=CN=CC=C3

CAS alternativo

119328-74-4,27367-90-4,119306-37-5,34426-53-4 (tri-hydrochloride)

PubChem CID

71919

Términos de entrada MeSH

niaprazine;niaprazine trihydrochloride;Nopron

Peso molecular

356.4

Application Protocols

This catalog entry does not provide tested application protocols or recommended dilutions.

General protocols used for small-molecule tool compounds in receptor pharmacology (for reference only):

• Radioligand binding (membrane prep):
  • Prepare membranes expressing the receptor of interest; incubate with fixed radioligand concentration and serial dilutions of test compound (typically 0.1 nM–100 µM) in binding buffer (e.g., 50 mM Tris, pH 7.4, 4°C or RT).
  • Separate bound/free by filtration; quantify radioactivity; fit Ki using Cheng–Prusoff with experimentally determined KD.
• Functional assays (HTRF/cAMP/Ca2+ flux):
  • Plate cells stably expressing target GPCR; pre-incubate with compound dilutions; stimulate as appropriate; readout per kit protocol. Maintain DMSO ≤1% v/v.
• LC–MS stability assay:
  • Incubate compound in liver microsomes (0.5 mg/mL) with NADPH; sample over 0–60 min; quench with ACN containing internal standard; determine t1/2 and Clint.

Note: The above are general, literature-style workflows to contextualize use of small molecules like Niaprazine. They are not item-specific validated methods. Optimize conditions for your system and consult your institution’s SOPs.

Biological Roles

Context for research use only: The following describes literature-reported biochemical roles without implying therapeutic use.

• Pharmacology background (literature): Niaprazine is described in the open literature as an arylpiperazine-class ligand with activity at central nervous system receptors, frequently studied in the context of histaminergic and serotonergic receptor systems. Such scaffolds are used to probe receptor binding, functional antagonism/agonism, and signaling bias in vitro.
• Research applications:
  • Ligand–receptor interaction studies using radioligand binding assays, BRET/HTRF-based functional readouts, and electrophysiology or calcium flux to profile GPCR engagement.
  • Off-target screening across neurotransmitter receptor panels to assess selectivity, a common step in CNS-focused chemical biology.
• ADME-relevant properties (general for arylpiperazines): Basic nitrogens can drive pH-dependent ionization, influencing membrane permeability and distribution. Aromatic substituents modulate lipophilicity and plasma protein binding. These aspects are evaluated in microsomal stability, PAMPA/Caco-2, and plasma protein binding assays.
• Systems biology angle: Data from receptor profiling can be integrated into network models of neurotransmission to study how modulation of histamine/serotonin pathways influences downstream signaling cascades in cell systems.

Important: Actual potency, selectivity, and binding constants can vary with assay conditions and the exact form of the compound (free base vs. salt). Always consult primary literature and verify activity in your assay system before drawing conclusions.

Buffer Applications

This product is not a buffering reagent and does not constitute a classical buffer system. Accordingly, it is not typically used to set or maintain pH in biochemical experiments.

Practical guidance related to buffers when using this compound:

• Stock preparation: Dissolve in DMSO to make a concentrated stock; dilute into assay buffer immediately before use to minimize precipitation.
• Compatible assay buffers: Phosphate- or HEPES-based buffers (pH 6.8–7.6) are commonly used for receptor and enzyme assays. Include 0.1% BSA or 0.01–0.05% nonionic surfactant if nonspecific binding or precipitation is observed.
• pH considerations: For amine-containing ligands, slightly acidic buffers (e.g., pH 6.5–7.0 with 0.1% formic acid for LC–MS sample prep) can enhance solubility via protonation while remaining compatible with downstream analysis.

If you require an actual buffering agent, consider Good’s buffers (HEPES, MOPS) or phosphate systems selected for your assay’s pH and ionic strength requirements.

Green Alternatives

As a defined bioactive small molecule, Niaprazine does not have a direct “green alternative” because it is the target structure itself rather than a solvent or process reagent. However, greener practices can be applied to its handling and use in research workflows.

Greener practice suggestions (general):

• Solvent minimization: Use micro-scale DMSO stocks (high concentration) to reduce total solvent volume in screening campaigns.
• Greener analytics: Favor ACN–water over MeOH–water in HPLC when feasible, and optimize gradients to shorten run times and solvent use.
• Solid handling: Pre-weigh unit-dose aliquots in inert atmosphere to reduce repeat thawing and waste.
• Waste reduction: Consolidate DMSO and acetonitrile wastes; apply on-plate dilutions to minimize excess solution preparation.

Comparative considerations (for method development):

• DMSO vs. alternative dipolar aprotics (DMF/NMP): DMSO is generally preferred for both solvency and lower hazard classification relative to DMF/NMP. Use the minimum DMSO volume compatible with assay tolerance.
• Aqueous solubilization: Use volatile acids/bases (formic acid, ammonium bicarbonate) for LC–MS compatibility and easier waste processing vs. nonvolatile buffers.

Note: For synthetic production of arylpiperazines (outside the scope of this SKU’s intended use), greener choices can include ethanol or 2-MeTHF as solvents and catalytic rather than stoichiometric bases, but these are process-level choices not applicable to end-user handling of a finished compound.

Pharmaceutical Uses

No clinical or therapeutic claims are made. This product is supplied strictly for research use only.

Formulation and development context (research/manufacturing science, general):

• Reference standard: Niaprazine can serve as a reference compound in analytical method development (HPLC/LC–MS) for basic, moderately lipophilic small molecules. It assists with retention time windows, ionization behavior, and recovery studies.
• Preformulation studies: As an amine-containing scaffold (literature), it is suitable for salt screening (e.g., HCl, mesylate, maleate) to compare solubility and stability—strictly for research.
• Solid-state characterization: PXRD, DSC, and TGA can be employed to identify polymorphs/solvates where relevant. Moisture uptake studies (DVS) are recommended if hygroscopic behavior is suspected.
• Impurity profiling: Forced degradation (acid/base, oxidative, thermal, photolytic) guides stability-indicating method development; apply ICH Q1A principles as a research framework without implying clinical development.

Excipient status: Niaprazine is not an excipient and has no recognized pharmacopeial monograph as a formulation additive. Any handling in a pharmaceutical sciences lab should remain within nonclinical, non-GMP research contexts unless otherwise qualified.

Physical Properties

Item-specific physicochemical specifications are not listed on the product page for this SKU.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point (literature): Not available here; consult primary literature or PubChem for general reference values and note that salt form markedly affects MP.
• Boiling point (literature): Not typically applicable for solid, multi-functional bioactive scaffolds; decomposition may precede boiling under ambient pressure.
• Density/refractive index: Not specified for this item; refer to CoA/Spec Sheet.
• pKa/logP (literature, general for arylpiperazines): Basic piperazine nitrogens commonly show pKa values in the 5–10 range (conjugate acids), with overall logP often in the 1–4 range depending on substitution and salt form. These are class-wide, indicative values only.
• Solubility guidance (general):
  • Free bases of arylpiperazines are typically soluble in polar aprotic organic solvents (DMSO, DMF) and moderately in alcohols; water solubility varies with ionization state.
  • Salt forms (e.g., hydrochlorides) are often more water-soluble; verify form on your CoA.

Note: When planning analytical work (HPLC, LC–MS), begin with DMSO stock solutions (10–50 mM) and dilute into buffered aqueous media containing organic modifier (e.g., 30–60% acetonitrile or methanol) to mitigate precipitation. Always confirm with small-scale tests.

Quality and Grades

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

How to interpret quality for small-molecule research compounds (general guidance):

• Research grade: Typically optimized for discovery chemistry, screening, and in vitro assays. Purity is often ≥95% by HPLC/LC–MS, but confirm for your lot on the CoA (purity assay method, detection wavelength, and residual solvent profile).
• Identity confirmation: Look for supporting analytical data (1H NMR/13C NMR, LC–MS, and/or HRMS). For bioactive scaffolds, multiple orthogonal IDs are recommended prior to SAR work.
• Counter-ion and polymorph: If the compound is supplied as a salt, the counter-ion content (e.g., chloride %) and water of crystallization should be reported on the CoA; these can affect solubility and potency normalization.
• Stabilizers: Not specified for this item; refer to CoA/Spec Sheet. If present, stabilizers (e.g., antioxidants) should be accounted for during quantitation.

What is specific to this SKU:

• Storage and shipping stringency (−80°C; dry ice + cold packs) signal an emphasis on compound integrity for library/HTS use. Request the CoA associated with your lot to review exact purity, residual solvents, and any salt-form details before quantitative studies.

Reaction and Applications

This SKU is offered as a finished small-molecule research compound rather than as a general synthetic reagent. Accordingly, its most relevant applications lie in chemical biology and screening rather than as a stoichiometric reagent.

Research applications (literature/general for arylpiperazines):

• GPCR ligand studies: Arylpiperazines are a privileged scaffold for serotonergic, adrenergic, and histaminergic receptor research. Niaprazine is frequently cited in receptor-binding and functional assays as a reference or probe molecule (no clinical claims).
• CNS transporter/receptor panels: Used in SAR benchmarking, off-target profiling, and selectivity screening to contextualize new analogs.
• Analytical reference: Serves as a comparative standard in chromatographic method development (retention behavior of basic, moderately lipophilic compounds).

Practical tips:

• Prepare fresh DMSO stocks, protect from moisture and prolonged ambient exposure. For plate-based assays, pre-dilute to minimize precipitation upon addition to aqueous media.
• Use LC–MS to confirm integrity before and after assays; arylpiperazines can exhibit slow oxidative or hydrolytic changes under harsh conditions.

Not generally used in: organometallic catalysis, radical initiations, or as an acid/base catalyst. If you require a building block function (e.g., derivatization), consult the Synthetic Utility section for general late-stage modification guidance.

Reaction Conditions

Because Niaprazine is provided as a final small-molecule tool compound, there are no canonical “reaction conditions” for using it as a reagent. However, for researchers undertaking derivative synthesis or analytical handling, the following general, literature-based conditions may be relevant.

Analytical handling (recommended practice):

• Stock solutions: 10–50 mM in anhydrous DMSO; store aliquots at −80°C to limit degradation and freeze–thaw.
• LC–MS: Mobile phases of water + 0.1% formic acid and acetonitrile or methanol; positive ESI typically provides strong response for basic amines.

Common transformations for arylpiperazines (general literature guidance):

• N-alkylation: Alkyl halides or sulfonates, mild base (e.g., K2CO3) in DMF/MeCN, 0–60°C, hours to overnight; monitor for over-alkylation.
• N-acylation/carbamoylation: Acid chlorides or activated carbonates, base (DIPEA/TEA) in DCM/THF, 0–25°C.
• Aryl substitution tuning: Electrophilic aromatic substitution or cross-coupling on suitably functionalized aryl precursors (Suzuki, Buchwald–Hartwig), Pd-catalyzed, 50–110°C depending on system.

Yields: Highly substrate-dependent; consult primary literature for the exact Niaprazine scaffold. These are general ranges and should not be taken as specifications for this item.

Always confirm the exact structure and functional groups for your lot before planning any transformation.

Safety and Handling

Hazard and GHS classification are not provided in the product data excerpt for this item. Treat as a research chemical of unknown acute toxicity and follow best laboratory safety practices at all times.

• GHS/Classification: Not specified for this item; refer to SDS.
• Signal word / H-statements / pictograms: Not specified for this item; refer to SDS.

General safety guidance (professional lab practice):

• Engineering controls: Work in a fume hood. Avoid inhalation of powders and aerosols; minimize dust generation.
• PPE: Lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). Consider double-gloving for extended handling.
• Hygiene: Avoid contact with skin, eyes, and clothing. Wash hands after handling. Do not eat or drink in lab areas.
• Incompatibilities (general for amine-containing organics): Strong oxidizers, acylating agents, and strong acids/bases that may lead to uncontrolled reactions or decomposition. Verify specific incompatibilities in SDS.
• First aid (overview; defer to SDS):
  • Inhalation: Move to fresh air; seek medical attention if symptoms occur.
  • Skin/eye contact: Rinse with copious water for 15 minutes; remove contaminated clothing; get medical attention as needed.
  • Ingestion: Rinse mouth; do not induce vomiting unless directed by medical personnel.
• Waste: Dispose via approved organic waste streams per institutional and regulatory requirements.

Transport and storage risks: Product is shipped cold (dry ice + cold packs) and stored at −80°C per item data; avoid repeated freeze–thaw and moisture ingress.

Solvent Selection

Niaprazine is a nitrogen-containing, amine-bearing small molecule (literature: arylpiperazine class). Ionization state and salt form dictate solubility and solvent choice.

• Stock solution strategy (general best practice):
  • Prepare concentrated stocks in DMSO (10–50 mM). DMSO offers broad solubility and is LC–MS compatible.
  • For aqueous assays, dilute DMSO stocks into buffer with 0.1–1% final DMSO to limit cosolvent effects; include surfactant (e.g., 0.01–0.05% Tween 80) if precipitation is observed.
• Alternative solvents: DMF and NMP have similar solvating power but may be less desirable in biological assays due to toxicity; use only if needed.
• Alcohols: Methanol and ethanol can dissolve many arylpiperazines at moderate concentrations; they are useful for UV/LC standards and short-term manipulations.
• Aqueous systems: Free bases show pH-dependent solubility. Mild acidification (e.g., 0.1% formic acid) can protonate amines and improve solubility for LC–MS sample prep.

Comparison (general):

• DMSO: highest solvating power; broadly compatible with HTS and LC–MS; may require dilution to ≤1% in bioassays.
• MeOH/EtOH: convenient, volatile; good for analytical standards; limited solubility for highly lipophilic analogs.
• ACN: weaker for bases relative to DMSO/DMF but excellent for HPLC blending with aqueous buffers.

Tip: Verify the salt form on your CoA. Hydrochloride salts are typically far more water-soluble than free bases; adjust solvent selection accordingly.

Storage and Reconstitution

Item-specific conditions from the product data:

• Storage temperature: Store at −80°C.
• Shipped in: Dry ice packs + cold packs.

Reconstitution (general guidance for small-molecule tool compounds):

• Use anhydrous solvent (preferably DMSO) to prepare concentrated stock solutions (e.g., 10–50 mM).
• Aliquot immediately into single-use vials or tubes to avoid repeated freeze–thaw. Target aliquot volumes that match a single experiment.
• Protect from moisture and light during handling; purge headspace with inert gas if long-term storage of the solid is anticipated.

Handling tips:

• Thaw aliquots on ice or at room temperature just before use; mix thoroughly to ensure homogeneity. Avoid prolonged exposure at room temperature.
• For aqueous working solutions, dilute DMSO stocks directly into pre-chilled buffer while vortexing to minimize precipitation; use promptly.

Stability notes:

• Without item-specific stability data, assume limited bench stability. Maintain cold chain and minimize exposure to air/water.
• Record preparation date, concentration, solvent, and lot/aliquot IDs for traceability.

For any lot-specific guidance (hygroscopicity, exact solubility, salt form), consult the Certificate of Analysis (CoA) or Specification Sheet accompanying your shipment.

Structure and Identity

Brief overview: Niaprazine is a well-known small-molecule research chemical that appears in many receptor pharmacology studies. For this specific catalog item, structural identifiers are not provided on the product page.

• CAS: 27367-90-4 (literature identifier)
• PubChem CID: 71919 (literature identifier)
• 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.
• Synonyms (literature): Reported in the literature as a member of the phenylpiperazine/arylpiperazine chemical class.

Structural features (literature/general):

• Core motif: Often described as an aryl-substituted piperazine scaffold in the open literature, a privileged motif in GPCR ligand chemistry.
• Functional groups typical for this class: secondary/tertiary amines (basic), aryl rings that enable π–π and cation–π interactions in receptors.
• 2D description (generic, literature-based): a six-membered aromatic (aryl) ring linked to a saturated piperazine ring (diazacyclohexane), sometimes bearing additional substituents that tune basicity and lipophilicity.

Important note: The exact isomerism, substitution pattern, and salt/form for SKU N656759 are not disclosed in the product data presented here. Always verify definitive identifiers and structure against the Certificate of Analysis (CoA) or product Specification Sheet supplied with your lot.

Synthetic Utility

As supplied, Niaprazine is a finished small molecule rather than a synthetic building block. Nonetheless, researchers may pursue analog generation or tagging for SAR and mechanistic studies.

General strategies for derivatives (literature/common for arylpiperazines):

• N-functionalization: Alkylation or acylation of piperazine nitrogens alters basicity and receptor affinity; useful for SAR or prodrug-like modifications.
• Aryl substitutions: Electron-donating/withdrawing groups on the aryl ring modulate binding and physicochemical properties (logP, pKa).
• Isotopic labeling: 2H/13C/15N labels facilitate metabolic tracing and quantitative LC–MS; radiolabels (3H/14C) are used in receptor binding assays within licensed facilities.
• Conjugation handles: Installation of linkers (e.g., PEGylated chains, alkynes/azides) enables pull-down probes or imaging conjugates for target engagement studies.

Caveats:

• The exact substitution pattern and salt/form of this SKU are not specified here; tailor any derivatization plan to the confirmed structure from the CoA and primary literature.
• Protecting-group strategy may be required to achieve regioselective modification on a piperazine core.

Bottom line: Treat this compound as a benchmark scaffold for SAR exploration and tool development rather than as a commodity reagent in multi-step synthesis.

Target Specificity

Item-specific target-binding data are not provided on the product page for this SKU.

• Tested targets and potencies: Not specified for this item; refer to CoA/Spec Sheet and primary literature.

Literature/general context:

• Niaprazine is often discussed as an arylpiperazine ligand in receptor pharmacology, with activity reported at histaminergic and serotonergic systems in vitro. Exact Ki/IC50 values vary by study, species, assay format, and compound form (free base vs. salt). Avoid extrapolating between assay systems without cross-validation.

Recommendations for users:

• Validate target engagement in your in-house assay using appropriate positive and negative controls.
• Normalize concentrations to free base equivalents if working with a salt form, and report lot-specific purity.
• Consider comprehensive selectivity panels (e.g., radioligand binding across GPCRs) to map off-target profiles relevant to your project.