This compound belongs to the class of organic compounds known as morpholines. These are organic compounds containing a morpholine moiety, which consists of a six-member aliphatic saturated ring with the formula C4H9NO, where the oxygen and nitrogen atoms lie at positions 1 and 4, respectively.
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.
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Application Protocols
No vendor-validated biological assay protocols are provided in the Product Data for this SKU. Below are general, literature-informed starting points for research use. Adjust to your system and consult primary sources.
Example: Generation of peroxynitrite-like activity in buffered solution
Prepare a fresh 1–10 mM linsidomine stock in minimal co-solvent (e.g., DMSO) or directly in buffer if soluble; filter-sterilize if needed.
Dilute into air-equilibrated phosphate buffer (50–100 mM, pH 7.4) to a final concentration of 50–500 µM for model protein nitration tests.
Include 0.1 mM EDTA to suppress metal-catalyzed side reactions.
Incubate substrate/protein for 15–60 min at 25 °C, protected from intense light.
Quench and analyze by LC–MS or immunoblotting for nitrated tyrosine as endpoint.
Example: NO-dominant condition
Degas buffer thoroughly (argon/nitrogen sparging) prior to adding linsidomine to reduce O2−/ONOO− pathways, then proceed with time-resolved NO detection (e.g., NO electrode) or Griess assay for nitrite accumulation.
Item-specific recommended dilutions, positive controls, or validated applications: Not specified for this item; refer to CoA/Spec Sheet.
Biological Roles
This section summarizes literature context for research use; no medical or therapeutic claims are made.
Functional role in research:
Model source of nitric oxide and peroxynitrite in vitro: linsidomine decomposes in aerated aqueous buffer to release NO and O2− that combine to ONOO−, a potent nitrating/oxidizing agent studied in redox biology.
Probing oxidative/nitrative modifications: used to induce tyrosine nitration, methionine oxidation, and DNA base modifications to evaluate protective mechanisms of antioxidants, enzymes, and small molecules.
Signaling mimicry: controlled NO flux can be used to interrogate NO-sensitive pathways (heme protein binding, S-nitrosation susceptibility) under non-physiological but informative conditions.
Experimental design notes:
Time dependence: biological responses correlate with the time profile of NO/ONOO− release; standardize incubation times and donor concentration.
Media composition: metal chelators, bicarbonate/CO2 (forming nitrosoperoxycarbonate), and thiols can significantly alter observed modifications.
Controls: include oxygen-depleted controls for NO-dominant chemistry and use alternative donors (e.g., DEA/NO, SNAP) to parse NO-specific from ONOO−-mediated effects.
Item-specific biological data (binding constants, cellular uptake, or target profiling) are not provided in the Product Data and should be obtained from primary literature for the conditions relevant to your system.
Buffer Applications
Linsidomine is not a buffer. However, its performance as a reactive species donor is highly buffer- and pH-dependent.
Practical guidance (literature/general):
Common buffers: phosphate (pH 7.0–7.4), HEPES (pH 7.2–7.6), or carbonate/bicarbonate (pH 8–10) depending on desired RNOS speciation. Bicarbonate can interact with peroxynitrite to form nitrosoperoxycarbonate, altering reactivity.
Ionic strength: maintain constant ionic strength to ensure reproducible kinetics and analytical readouts.
Metal chelation: include EDTA (e.g., 0.1–1 mM) if unintended metal-catalyzed side reactions are a concern.
Light/oxygen: protect from strong light when appropriate and control dissolved oxygen (air-equilibrated vs. deoxygenated) to bias NO vs. ONOO− formation.
Item-specific buffer compatibility or solubility limits are not provided; verify empirically under your assay conditions and consult the CoA/Spec Sheet if available.
Green Alternatives
As a specialized RNOS donor, linsidomine is selected for its mechanistic profile (simultaneous NO and O2− formation leading to ONOO−). When a different reactive nitrogen profile is sufficient, consider alternatives with greener attributes (stability, lower hazard, or simpler waste):
Alternative donors (literature comparison; selection depends on required species):
SNAP (S-nitroso-N-acetyl-DL-penicillamine): predominantly NO donor in aqueous buffer; slower, more controllable NO release; thiol-based chemistry may be preferable in some biological models.
DEA/NO (diethylamine NONOate): well-characterized first-order NO release with pH-dependent half-life; buffered aqueous systems with predictable kinetics.
GSNO (S-nitrosoglutathione): endogenous-like NO donor; may be viewed as greener in biomimetic contexts; sensitive to light and metals.
Peroxynitrite stock solutions: direct ONOO− delivery avoids in situ generation but requires careful, cold preparation/handling and has higher immediate oxidizing hazard.
Trade-offs:
Linsidomine uniquely co-generates O2− in aerated media, enhancing ONOO− formation. Greener donors like SNAP/GSNO provide NO without superoxide, reducing nitrative stress but altering the chemistry modeled.
Waste minimization: donors with predictable half-lives (DEA/NO) may reduce overuse and residual hazardous species.
Recommendation: Match the donor to the minimal reactive species set necessary for your experiment, and choose aqueous buffers over organic media when possible to improve EHS profiles.
Pharmaceutical Uses
This product is supplied strictly for research use only. No clinical or therapeutic claims are made.
Linsidomine (SIN-1) and related sydnonimines have been investigated historically as NO donors; however, no pharmacopeial monograph or excipient role is indicated for this item in the Product Data.
As a laboratory reagent, it may be used to stress-test formulations or biomolecules against nitrative/oxidative conditions (e.g., forced degradation studies for structure–stability relationships), but such studies are non-clinical and exploratory.
Item-specific regulatory grade, residual solvent limits, and excipient status: Not specified for this item; refer to CoA/Spec Sheet.
Physical Properties
Item-specific physicochemical specifications (mp, bp, density, UV cutoff, residuals) are not provided in the Product Data for SKU L1073882. For authoritative numerical specifications, please refer to the product’s CoA/Spec Sheet.
Literature/general notes (for context; not item-specific specifications):
Physical state: typically obtained as a crystalline solid for research use; salts (e.g., hydrochloride) are commonly encountered in literature. Exact appearance for this item: Not specified for this item; refer to CoA/Spec Sheet.
Solubility: sydnonimine NO donors are generally soluble in polar media; many investigators prepare fresh aqueous or buffered stocks for immediate use. Exact solubility for this item: Not specified for this item; refer to CoA/Spec Sheet.
Stability considerations: susceptible to slow decomposition in solution with time, pH, and oxygen dependence (literature); dry, closed-storage conditions recommended. Item-specific stability data: Not specified for this item; refer to CoA/Spec Sheet.
pH behavior: NO/peroxynitrite formation from linsidomine exhibits pH dependence in literature studies; quantitative constants vary by medium and temperature. No item-specific pKa is provided.
Practical implications:
Prepare solutions freshly for kinetic or redox biology experiments.
Minimize extended exposure to elevated temperature, light, and air for working solutions where the exact redox speciation matters.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and guidance:
Research-use chemical quality typically emphasizes identity confirmation (NMR/IR/HRMS/HPLC), purity by chromatographic assay, and controlled residual solvents/metals. In the absence of stated numeric limits for this SKU, end-users should verify suitability for critical assays (e.g., kinetic NO release studies) via in-house QC (HPLC purity, water content, and functional activity where applicable).
UV absorbance background can matter in kinetic spectrophotometry of NO/peroxynitrite formation; for chromatographic monitoring, low-UV impurities are preferred. Item-specific UV cutoff and absorbance data: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/inhibitors: none are listed in the Product Data. If stabilizers are present in a supplied lot, they will appear on the CoA/Spec Sheet and may influence kinetic measurements.
Recommendation: For reproducible redox experiments, document lot numbers and perform small-scale method qualification (e.g., time-course of NO/peroxynitrite generation under your conditions) when transitioning between lots or suppliers.
Reaction and Applications
This compound is widely used as a research reagent to generate reactive nitrogen and oxygen species (RNOS) in situ.
Core application families (literature/general):
Nitric oxide (NO) donation under aqueous conditions; the decomposition pathway can produce NO and superoxide (O2−), which rapidly combine to form peroxynitrite (ONOO−) in aerated buffer.
Oxidative/nitrative chemistry models: protein tyrosine nitration assays, DNA/RNA/nucleotide oxidation/nitration studies, and small-molecule oxidative transformations under controlled RNOS fluxes.
Redox enzyme studies: probing heme and non-heme iron enzymes, S-nitrosation susceptibility, and antioxidant capacity assays.
Practical considerations:
Fresh preparation: make solutions immediately before experiments to ensure reproducible fluxes of NO/O2−; monitor time profiles if quantitation is required.
pH and oxygen: peroxynitrite yield depends strongly on pH and dissolved O2; standardize buffer composition and O2 content (air-equilibrated vs. deoxygenated) for inter-experiment comparability.
Scavengers and probes: pair with NO electrodes, Griess assay (NO2−), dihydrorhodamine 123 (ONOO− proxy), or tyrosine nitration readouts to validate reactive species.
Metal ions: transition metals can catalyze decomposition or radical pathways; add chelators (e.g., EDTA) if undesired catalysis is observed.
Extension to synthetic chemistry:
Use as a clean source of nitrating/nitrosating conditions in water-compatible systems where peroxynitrite intermediacy is desired to mimic biological oxidations.
Note: Item-specific activity data and kinetic constants are not provided; consult primary literature for mechanism and rate constants under your exact conditions.
Reaction Conditions
General guidance from literature for using linsidomine (SIN-1) as a source of reactive nitrogen/oxygen species; item-specific conditions are not provided in the Product Data.
Solvents/media:
Aqueous buffers (phosphate, HEPES, carbonate); temperature typically ambient (20–25 °C) for kinetic and biochemical assays.
Co-solvents: minimal DMSO or acetonitrile (≤1–5%) may be used to aid dissolution before dilution into buffer; verify no kinetic perturbation.
Concentrations and timing:
Working concentrations often range from low micromolar to low millimolar in assay media, with reaction times from minutes to hours depending on the endpoint (e.g., nitration extent). Optimize empirically.
Atmosphere:
Aerated (air-equilibrated) solutions favor concurrent production of NO and O2−, enhancing ONOO− formation; deoxygenated conditions bias toward NO-dominant chemistry.
Additives:
Metal chelators (e.g., EDTA 0.1–1 mM) to suppress metal-catalyzed side routes.
Scavengers or probes to map species contributions (e.g., uric acid as ONOO− scavenger; carboxy-PTIO as NO scavenger) for mechanistic clarity.
Analytics:
Monitor nitrite/nitrate (Griess), fluorescent probes (e.g., DHR123), UV–vis changes, or LC–MS of reaction products for quantitative assessment.
Note: Exact rate constants, half-lives, and activation parameters depend strongly on pH, ionic strength, temperature, and oxygen; consult the primary literature for your specific matrix.
Safety and Handling
Authoritative safety classification is not provided in the Product Data and may vary by supplier lot and salt form.
GHS information (item-specific):
Signal word: Not specified for this item; refer to SDS.
Hazard statements (H-phrases): Not specified for this item; refer to SDS.
GHS classification/pictograms: Not specified for this item; refer to SDS.
General laboratory safety guidance (literature/standard practice; not a substitute for the SDS):
Potential hazards: organic nitroso/mesoionic donors may be harmful if swallowed, inhaled, or in contact with skin; dust may be irritating. Some sydnonimines can decompose to release reactive nitrogen/oxygen species; avoid heating and contamination with strong acids/bases or oxidants/reductants unless intended.
PPE: wear lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). Handle powders in a fume hood to avoid dust inhalation.
Incompatibilities: strong oxidizers or reducers may induce undesirable decomposition; strong acids/bases can alter release kinetics of reactive species. Avoid contact with metals that catalyze redox decomposition.
First aid overview: in case of skin/eye contact, rinse with water for at least 15 minutes; remove contaminated clothing. If inhaled, move to fresh air. If ingested or upon any exposure with symptoms, seek medical attention. Always consult the SDS for detailed instructions.
Waste: collect solutions and contaminated materials as organic hazardous waste. Do not discharge to drain.
Always defer to the product-specific SDS and institutional EHS policies for definitive safety guidance.
Solvent Selection
Linsidomine is used primarily as a reactive nitrogen/oxygen species donor rather than as a solvent. Solvent choice is driven by the intended application (e.g., kinetic NO release in aqueous buffer) and by stability considerations.
Applicability: choose solvents that support intended redox chemistry while minimizing premature decomposition.
Typical choices (general literature guidance):
Aqueous buffers (phosphate, carbonate, or HEPES) for biological/kinetic assays; prepare fresh stocks and control pH stringently.
Polar aprotic co-solvents (e.g., acetonitrile, DMSO) in low percentages to aid dissolution before dilution into buffer; evaluate any effect on release kinetics.
Avoid:
Strongly acidic or basic media except when precisely controlling the release profile (literature shows pH dependence of NO and superoxide formation).
Protic organic solvents that accelerate decomposition or introduce side reactions without benefit.
Comparison notes (general):
Versus SNAP/DEA/NO donors, linsidomine’s peroxynitrite generation in aerated solutions can be advantageous for oxidative chemistry models; however, it may exhibit more rapid, oxygen-dependent decomposition. This influences whether purely aqueous or mixed solvent systems are preferred.
Practical tips:
Prepare concentrated stock in minimal co-solvent, then immediately dilute into buffered media immediately before use.
Degas or aerate intentionally depending on whether NO-only or NO + O2− pathways are being modeled.
Storage and Reconstitution
Storage conditions (item-specific from Product Data): Room temperature.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
General guidance (literature/practice; confirm with CoA/SDS):
Keep container tightly closed in a dry place, protected from excessive heat and light. For long-term integrity of reactive donors, some users prefer cool, desiccated storage even if room temperature is acceptable for transport and short-term storage.
Reconstitution: prepare fresh solutions immediately before use in the intended buffer/medium. If a co-solvent is required for dissolution, minimize its final concentration and verify no impact on your assay.
Stability of solutions: solutions may decompose over time with pH- and oxygen-dependent kinetics. For quantitative assays, discard working solutions after the experiment and do not store for extended periods unless stability has been verified under your exact conditions.
Freeze–thaw: if aliquoting solutions, avoid repeated freeze–thaw cycles; however, due to solution instability, fresh preparation is generally preferred.
Always consult the product-specific CoA and SDS for definitive storage, handling, and stability information.
Structure and Identity
Linsidomine is a mesoionic sydnonimine derivative classically known in the literature as the NO/peroxynitrite donor “SIN-1.” It is widely used in redox and nitric oxide chemistry studies.
Item-specific registry data from Product Data:
CAS: 33876-97-0
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
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.
Literature structural identity (for reference; not item-specific):
Common name: Linsidomine (SIN-1)
Core motif: sydnonimine (mesoionic N-oxide/N-nitroso imine system) N-substituted with a morpholine ring (commonly referred to as 3‑morpholinosydnonimine in the literature).
2D description: a five-membered mesoionic ring bearing N–O/N=N-like delocalization (sydnonimine), attached through the exocyclic N to a six-membered morpholine (O-containing) heterocycle; overall planar mesoionic core with a saturated morpholine substituent.
Mesoionic sydnonimine ring capable of releasing NO-derived species.
Morpholine tertiary amine ether heterocycle.
No defined stereocenters; delocalized zwitterionic/mesoionic character in the sydnonimine core.
Synthetic Utility
Although primarily employed as a redox biology reagent, linsidomine has niche synthetic utility owing to its controlled release of reactive nitrogen/oxygen species.
Transformations (literature/general):
Nitration/nitrosation under mild, aqueous-compatible conditions via in situ generation of NO/ONOO−; useful for probing selective nitration of phenolic or activated aromatic substrates.
Oxidation of sulfur- and selenium-containing substrates (thioethers to sulfoxides/sulfones; selenides to selenoxides) in model systems.
Radical pathways: initiation of radical additions/oxidations mediated by peroxynitrite-like chemistry in biphasic or micellar media.
Strategic use:
Temporal control: donor concentration and buffer control allow time-resolved delivery of oxidants, complementing classical electrophilic nitration reagents (e.g., NO2BF4) with milder conditions.
Selectivity studies: valuable for mapping intrinsic substrate susceptibility to nitrative stress relevant to biomolecules.
Limitations:
Mixed-species environment (NO, NO2, O2−, ONOO−) complicates product distributions compared with single-oxidant reagents; analytical monitoring (HPLC/LC–MS) is recommended.
Metal-catalyzed side reactions can divert pathways; employ chelators when needed.
Item-specific performance metrics (yields, rates) are not provided; consult primary reports for substrates analogous to your system.
Target Specificity
Not applicable. This product is a small-molecule research reagent, not a biological affinity reagent. No antigen/epitope, species reactivity, clone, or isotype information applies.
For biochemical selectivity in redox systems: linsidomine does not bind a discrete biological target with high specificity; instead, it releases reactive species (NO, O2−, and derived oxidants) that react broadly with susceptible functional groups. Any “specificity” arises from experimental conditions (pH, oxygenation, presence of scavengers) rather than molecular recognition.
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