This compound belongs to the class of organic compounds known as naphthalenes. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
External Descriptors
Not available
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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
373.400 g/mol
XLogP3
6.100
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
6
Exact Mass
373.165 Da
Monoisotopic Mass
373.165 Da
Topological Polar Surface Area
23.500 Ų
Heavy Atom Count
27
Formal Charge
0
Complexity
455.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
1
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
0
Covalently-Bonded Unit Count
1
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Recensioni
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Application Protocols
Item-specific, validated application protocols are not provided in the Product Data. General guidance for small-molecule library members and analytical standards is below (literature/general):
LC–MS reference standard preparation:
Prepare a 10–100 mM stock in anhydrous DMSO. For calibration curves, serially dilute into ACN:Water (50:50, 0.1% formic acid) to 1–1000 ng/mL. Store aliquots at −20 °C; avoid repeated freeze–thaw.
Use low-bind tubes and 0.2 µm PTFE filters to minimize adsorption and particulates.
Biochemical screening plate setup:
Dilute DMSO stocks into assay buffer (final DMSO ≤1% v/v). Verify solubility visually and by back-read UV/LC if precipitation is a risk.
Include DMSO-only wells and, if relevant, parent cinacalcet as a comparator for SAR.
Stability checks:
Assess bench-top stability (4–24 h at RT) and autosampler stability (4–24 h at 4–10 °C) by LC–MS. Track any reduction to the amine (−16 Da) over time.
These are non-binding recommendations; tailor to your instrumentation and assay requirements. For any validated, lot-specific protocols, refer to the CoA/Spec Sheet when available.
Biological Roles
Item is for research use only. No medical or clinical claims are made.
General/literature context:
Phase I metabolite analog: Tertiary amine N-oxides commonly appear as oxidative metabolites formed by flavin-containing monooxygenases (FMOs) or cytochrome P450-mediated pathways. Cinacalcet N-oxide represents the oxidized analog of the parent amine and can model biotransformation outcomes in vitro.
Physicochemical impact: N-oxide formation increases polarity and reduces basicity relative to the parent amine, which can affect passive permeability, plasma protein binding, and tissue distribution in biochemical assays (general principles).
Binding considerations: Protonation state shifts (reduced basicity at nitrogen, potential O-protonation under acidic conditions) may alter interaction patterns with biological macromolecules in target-agnostic binding studies.
Research utility:
Reference standard for LC–MS metabolite profiling to confirm oxidation products.
SAR probe to disentangle contributions of tertiary amine lone pair vs. hydrophobic/aromatic contacts in target engagement assays.
Cautionary notes:
N-oxides can undergo in situ reduction in some biological matrices (presence of reductases or reducing agents), potentially complicating interpretation; control experiments are recommended.
Verify solution stability in assay buffers (pH 6–8) and under light exposure; include time-course controls.
All statements above describe general biochemical behavior of tertiary amine N-oxides and do not specify performance or efficacy in any therapeutic context.
Buffer Applications
This compound is not a buffer reagent. It does not define a classical buffering system or pH range.
Practical handling in buffered systems (general):
Prepare concentrated stocks in DMSO or ethanol, then dilute into assay buffers (e.g., PBS, HEPES, Tris) keeping final organic content low (≤1% v/v) to maintain biological compatibility.
Check for precipitation upon dilution; if observed, increase the fraction of cosolvent slightly (e.g., 2–5% DMSO) or use surfactant-containing vehicles compatible with your assay.
Compatibility notes:
Avoid strongly reducing buffer components (e.g., excess dithionite, high DTT) that may reduce N-oxides.
Maintain neutral pH to minimize acid-catalyzed rearrangements; typical biochemical buffers pH 7.2–7.6 are suitable.
For actual buffering needs, select appropriate buffer systems (HEPES, MOPS, phosphate) based on desired pH and ionic strength.
Green Alternatives
Greener handling considerations typically apply to the choice of solvents and workup rather than substitution of the analyte itself.
Preferred solvents for solution prep and chromatography (general):
Aqueous-organic systems: Use water–acetonitrile or water–ethanol for analytical methods where feasible. ACN offers lower viscosity and is widely recyclable; ethanol is biorenewable but can broaden peaks for very polar analytes.
Avoid chlorinated solvents (DCM, DCE) for routine handling when nonchlorinated options (EtOAc, MeTHF) suffice.
Extraction | DCM | EtOAc or CPME | Slightly lower partitioning, but reduced toxicity.
Waste minimization:
Prepare concentrated master stocks to reduce solvent volume.
Use micro-scale assay formats and automated dilution to minimize disposable plastics.
Note: Any solvent changes must be validated for your specific analytical or assay context to ensure recovery, stability, and detection performance remain acceptable.
Pharmaceutical Uses
No therapeutic or clinical use is claimed for this catalog item. It is supplied strictly for research and analytical applications.
Research/formulation roles (literature/general):
Reference standard in stability-indicating and impurity profiling methods for cinacalcet-related substances.
System suitability compound for LC–MS/UV methods targeting oxidized impurities or metabolites.
Forced-degradation studies: Inclusion of the N-oxide helps bracket oxidative pathways when validating methods per ICH Q2 principles (general analytical practice).
Pharmacopeial status:
No pharmacopeial monograph is cited here for cinacalcet N-oxide. If compendial references exist for related substances in specific monographs, consult the relevant pharmacopoeia. Item-specific status is not specified; refer to CoA/Spec Sheet.
Formulation context:
When used as a spike-in impurity or analytical control, dissolve in DMSO, ACN, or ethanol, then dilute with aqueous media compatible with your detection method. Verify solution stability and adsorption losses (especially at low ng/mL concentrations) using low-bind consumables.
All usage must remain within non-clinical, research, or method-development settings.
Physical Properties
Item-specific specifications have not been provided for this catalog entry. Where applicable, consult the CoA/Spec Sheet for lot-specific values. The following are literature/general expectations for tertiary amine N-oxides of cinacalcet-type scaffolds and should not be construed as product specifications.
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.
Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
General/literature tendencies for aryl-alkyl tertiary amine N-oxides:
Phase: Typically solid at ambient temperature; N-oxides often exhibit higher melting points than their parent tertiary amines due to increased polarity and potential for ionic resonance.
Solubility: Increased solubility in polar organic solvents (DMSO, methanol, ethanol, acetonitrile) compared to the parent amine; limited solubility in nonpolar solvents (hexanes, toluene). Aqueous solubility can be moderate to good depending on counterion and crystal form (if any); neutral N-oxides can still be water-miscible to a degree due to the polar N→O bond.
LogP/logD (literature expectation): Reduced logP relative to the parent cinacalcet due to N-oxide formation; exact value not specified here.
pKa behavior: Tertiary amine N-oxides are markedly less basic at nitrogen than tertiary amines; protonation occurs primarily at oxygen under strongly acidic conditions (literature generality).
Stability: Generally stable at room temperature; may be hygroscopic to mildly so and can undergo reduction back to the amine under strong reducing conditions or thermal stress.
Always verify handling and performance characteristics empirically for your assay context.
Quality and Grades
Item-specific quality details:
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on interpreting grades (general):
In the absence of an explicit analytical or HPLC grade designation, treat this as a research-grade reference compound from a small-molecule library. Typical acceptance criteria may include ID by NMR/HRMS and purity by HPLC ≥95% for screening purposes; verify on the CoA.
If labeled as HPLC-grade/reference standard in future documentation, expect tighter control of UV absorbance baselines and impurity profiles to support LC/UV or LC–MS quantitation.
Stabilizers/inhibitors: None are indicated in the Product Data. If a stabilizer is listed on the CoA, note any analytical interferences (e.g., additive UV bands or mass spectral ions) and remove by preparative chromatography if necessary.
What is specific to this item:
The listing is part of a “small molecules and compound library” category, suggesting suitability for method development, SAR, and in vitro screening. Lot-specific details (purity assay, residual solvents, water content, salt form, polymorph) are not specified here and should be taken from the CoA/Spec Sheet for your batch.
For regulated work (GLP/GMP), confirm whether additional documentation (CoA with traceability, impurity profiling) meets your internal quality system requirements.
Reaction and Applications
This compound is primarily valuable as a research reference material and oxidized analog of cinacalcet for analytical, SAR, and metabolism studies rather than as a bulk reagent. Relevant uses include:
Surrogate metabolite/standard: Tertiary amine N-oxides commonly arise as Phase I oxidative metabolites. The N-oxide can serve as a reference standard for LC–MS method development, retention-time locking, and MS/MS library building.
Stability-indicating methods: Inclusion of the N-oxide helps challenge-indicate oxidative degradation pathways when validating stability-indicating HPLC.
Medicinal chemistry/SAR:
Polarity tuning: Conversion to the N-oxide increases polarity and can elucidate the role of the dimethylamino moiety in binding vs. permeability in in vitro systems.
Reversibility: The N-oxide can be reduced back to the tertiary amine under mild conditions (e.g., PCl3, Zn/AcOH), enabling temporary polarity switching strategies.
Synthetic transformations (general):
While aryl amine N-oxides can serve as directing groups for C–H activation, the dimethyl tertiary amine N-oxide in this scaffold is more often used as a probe compound than as a synthetic handle.
Practical tips:
Prepare DMSO stocks (e.g., 10–100 mM), store aliquots frozen to minimize freeze–thaw.
When assessing redox stability, avoid strong reducing agents and high-temperature chromatography that may induce partial deoxygenation.
For LC–MS, monitor characteristic [M+H]+ and [M+H–18]+ signals (loss of water is a common fragmentation for N-oxides; literature generality).
Reaction Conditions
The following conditions summarize literature/general practices for forming and interconverting tertiary amine N-oxides and are provided as guidance only. They are not specifications for this item.
Oxidation of tertiary amine to N-oxide (general):
m-CPBA (meta-chloroperoxybenzoic acid): 1.05–1.5 equiv in DCM or MeOH at 0–25 °C, 0.5–4 h. Quench with Na2SO3 and buffer; isolate N-oxide by extraction or chromatography. Often gives high conversions for dialkylarylamines.
Peracetic acid or H2O2/AcOH: 1.5–3 equiv at 0–25 °C; monitor to avoid overoxidation of sensitive aryl positions.
Urea–hydrogen peroxide (UHP) with TFAA or TFA: Mild, solvent such as MeCN; good for scale with minimal chlorinated waste.
Reduction of N-oxide back to tertiary amine (general):
PCl3 or POCl3 (0.5–1 equiv) in DCM or toluene at 0–25 °C, 0.5–2 h, followed by aqueous workup; typically efficient and chemoselective.
Zn/AcOH or Fe/AcOH: Mild, protic media; suitable when acid-sensitive groups are limited.
Mo(CO)6 in MeCN/H2O at reflux; neutral conditions compatible with many functionalities.
Workup and purification tips:
Maintain temperatures ≤25 °C during oxidation for complex aryl substrates to minimize byproducts.
Use polar eluents (EtOAc/MeOH mixtures) in chromatography; N-oxides strongly retain on silica—precondition with 1–2% triethylamine if tailing occurs.
Analytical monitoring:
LC–MS: Expect +16 Da shift vs. the parent amine; common fragmentation may include loss of 16 or 18 Da (literature generality).
Adapt these conditions to the cinacalcet scaffold only after small-scale trials and rigorous analytical verification.
Safety and Handling
Regulatory and GHS information (item-specific):
Signal Word: Not specified for this item; refer to SDS.
Hazard Statements (H-codes): Not specified for this item; refer to SDS.
GHS Classification/Pictograms: Not specified for this item; refer to SDS.
General laboratory precautions (for tertiary amine N-oxides; literature/general):
PPE: Lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Use in a fume hood to avoid inhalation of dust/aerosols.
Incompatibilities: Strong reducing agents (e.g., PCl3, SOCl2, TiCl3, Zn/acid) can reduce N-oxides to the parent amine; strong acids may lead to protonation at oxygen; strong bases generally compatible but may promote side reactions in sensitive substrates. Avoid contact with strong oxidizers that could attack aryl motifs.
Thermal/chemical stability: N-oxides are typically stable at ambient conditions; avoid prolonged heating above routine processing temperatures and avoid dehydrating reagents that may induce rearrangements in certain N-oxide classes (e.g., Polonovski-type conditions) though aliphatic dimethyl-amine N-oxides are comparatively robust under neutral conditions.
Spill/first aid (overview): For solids, avoid dusting; collect mechanically or dampen with compatible solvent (e.g., water/EtOH) and absorb. Skin/eye contact—flush with water for 15 minutes; remove contaminated clothing. Inhalation—move to fresh air. Ingestion—rinse mouth; seek medical advice. Always follow your institutional SOPs and consult the SDS.
Authoritative safety information resides in the product SDS; the above are general precautions for research use only.
Solvent Selection
Cinacalcet N-Oxide is an aryl–alkyl tertiary amine N-oxide and typically exhibits increased polarity versus the parent amine, guiding solvent choices for preparation and assays.
Poor to limited: Nonpolar hydrocarbons (hexanes, heptane) and weakly polar aromatics (toluene) without cosolvent.
Aqueous: Often improved relative to the parent amine but may still require a cosolvent; 0.1–1% DMSO or ethanol is commonly used in bioassays.
Polarity considerations:
The N→O group increases dipole moment and hydrogen-bond accepting capacity, lowering logP. This favors polar aprotic solvents for stock solutions and LC sample preparation.
When to choose which solvent:
Analytical stocks: DMSO (100 mM typical) for stability and compatibility with LC–MS; dilute into acetonitrile/water for injections.
Crystallization/purification: Alcohol/EtOAc mixtures or EtOAc/hexanes with polarity tuning; presence of N-oxide can give oiling-out—seed or use antisolvent crystallization.
Reaction media (if derivatized): Polar aprotics (MeCN, DCM, DCE) for mild transformations; avoid strongly reducing media which can revert the N-oxide.
Small comparison (general):
Versus the parent cinacalcet, the N-oxide shows better tolerance of aqueous-organic mixtures and reduced adsorption to plasticware, improving dose accuracy in screening plates.
Storage and Reconstitution
Item-specific storage and shipping:
Storage Conditions: Room temperature (per Product Data).
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
General storage guidance (literature/general):
Store in a tightly closed, light-protective container in a dry place. Consider desiccation to limit moisture uptake. Although room temperature storage is indicated, for long-term retention of analytical integrity, many labs keep aliquots at 2–8 °C or −20 °C—validate per your stability program.
Avoid proximity to reducing agents and strong acids. Segregate from oxidation-sensitive materials.
Reconstitution and working solutions:
Prepare concentrated stocks in anhydrous DMSO (e.g., 10–100 mM). Alternatively, use methanol or acetonitrile if compatible with downstream use.
Filter working solutions (0.2 µm PTFE) if particulate is suspected. For aqueous use, dilute into buffer maintaining low organic content; verify absence of precipitation.
Aliquot stocks to minimize freeze–thaw cycles. Typical practice: store small aliquots at −20 °C to maintain consistency across experiments.
Stability monitoring:
Periodically confirm identity/purity by HPLC/LC–MS (look for parent amine at −16 Da as a potential reduction product). Document solution stability under your specific conditions.
All directions support research use only. For authoritative handling and stability information, defer to the product’s SDS and CoA.
Structure and Identity
Cinacalcet N-Oxide is the tertiary amine N-oxide derivative of the small-molecule scaffold cinacalcet, supplied here as a research chemical standard.
Item-specific identifiers (from Product Data):
SKU: C993756
CAS: 1229224-94-5
PubChem CID: 78358349
InChIKey: 242828 (as provided; truncated/not a standard-length InChIKey)
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 (literature/general):
Functional group: Tertiary amine N→O (amine N-oxide), which introduces a formal N-oxide functionality, increasing polarity and hydrogen-bond accepting capacity relative to the parent tertiary amine.
Aromatic domains: Cinacalcet scaffolds contain a naphthyl ring and a 3-(trifluoromethyl)phenyl ring connected through an aliphatic tether to a dimethylamine; the N-oxide derives from oxidation of that tertiary amine.
Stereochemistry: The cinacalcet core contains a single stereogenic center in the benzylic region (parent drug is typically the (R)-enantiomer); the N-oxide formation does not create new stereocenters but may influence conformational preferences.
2D description (literature): Two aryl systems (naphthyl and m-CF3-phenyl) linked by a propyl chain terminating in a dimethylamino N-oxide [N(+)-O(–)] moiety.
Notes: Exact structural string identifiers (SMILES/InChI) and analytical confirmations for this catalog item are not specified here; consult the CoA/SDS for definitive identity data.
Synthetic Utility
While Cinacalcet N-Oxide is chiefly an analytical/SAR standard, tertiary amine N-oxides possess distinctive reactivity that can be leveraged in synthesis (literature/general):
Functional group behavior:
Polarity switch: N-oxide formation attenuates basicity at nitrogen and enhances hydrogen-bond acceptance at oxygen, enabling alternative chemoselectivity in acylation, alkylation (at oxygen under specific conditions), and supramolecular recognition.
Reductive deoxygenation: Conversion back to the tertiary amine using PCl3, POCl3, Zn/AcOH, or Mo(CO)6 provides a reversible protection/polarity-modulation strategy.
Named/related reactions (general):
Polonovski/Polonovski–Potier reactions: Under acylating conditions, amine N-oxides can undergo rearrangements to amides or generate iminium species; however, for a dimethyl tertiary amine embedded in a complex aryl–alkyl scaffold, such transformations require careful optimization to avoid overreaction of aromatic motifs.
Hofmann–Löffler–Freytag-type radical chemistry often engages ammonium species rather than neutral N-oxides; relevance here is limited.
Retrosynthetic value:
As a temporary oxidized handle, the N-oxide may modulate solubility and crystallinity to aid purification of cinacalcet analogs, then be reduced to the target amine.
Given the complexity of the cinacalcet scaffold (multiple aryl groups, CF3-phenyl, benzylic stereocenter), most laboratories will utilize the N-oxide primarily as a reference compound rather than a synthetic intermediate; any transformations should be validated on small scale with orthogonal analytics (LC–MS, NMR).
Target Specificity
Not applicable. This product is a small-molecule reference compound, not an antibody, enzyme, or affinity reagent. No target-binding specificity data are provided in the Product Data. For biological assay considerations, see the “Biological Roles” and “Application Protocols” sections.
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