| Size | Price | Stock | Qty |
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| 50mg |
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| 100mg |
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| Other Sizes |
| Targets |
Beta-D-Glucopyranosyl nitromethane does not have a well-defined molecular target in biological systems. As a glycosylated nitromethane derivative, its mechanism of action is not clearly established. Some studies suggest that it may act as a substrate or inhibitor of glycosyltransferases, enzymes that transfer sugar moieties to acceptor molecules. The nitromethane group may also be involved in interactions with nitroreductases or other enzymes. The compound has been reported to exhibit a variety of biological activities, including anti-inflammatory, anti-tumor, and anti-viral properties, but specific targets have not been identified. The structural similarity to glucose suggests that it may interact with glucose transporters or glucose-metabolizing enzymes, but this has not been confirmed. It is primarily used as a research tool in glycobiology and carbohydrate chemistry.
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| ln Vitro |
In vitro, Beta-D-Glucopyranosyl nitromethane has been evaluated for its effects on cellular processes. In some reports, the compound has demonstrated anti-inflammatory activity by reducing the production of pro-inflammatory cytokines (e.g., TNF-alpha, IL-1beta, IL-6) in lipopolysaccharide (LPS)-stimulated macrophages. The anti-tumor activity has been observed in certain cancer cell lines, where the compound may inhibit cell proliferation and induce apoptosis. However, the reported potency is generally low, with IC50 values in the high micromolar to millimolar range. The compound may also be used as a substrate for studying enzyme kinetics of glycosyltransferases or glycosidases. In enzyme assays, the nitromethane group can act as a chromophore or a leaving group, allowing for continuous monitoring of enzyme activity. In cell-free systems, the compound is stable and can be used as a model compound for studying glycosidic bond hydrolysis. More detailed in vitro data are not widely available in the literature.
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| ln Vivo |
In vivo, Beta-D-Glucopyranosyl nitrosothis compound has been studied in animal models for its potential anti-inflammatory and anti-tumor effects, but the data are limited. In a mouse model of carrageenan-induced paw edema (inflammation), administration of the compound (dose not specified) was reported to reduce paw swelling, indicating anti-inflammatory activity. In xenograft models of certain cancers, it may inhibit tumor growth. However, these studies are not widely published or validated. The compound is not a standard therapeutic agent, and most of its in vivo effects are likely due to its glycosylated nature, which may improve solubility and cellular uptake. Beta-D-Glucopyranosyl nitromethane is not a drug candidate and is used primarily as a research reagent. Detailed in vivo protocols and efficacy data are not available in the public domain.
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| Enzyme Assay |
A typical non-cellular (cell-free) protocol for using Beta-D-Glucopyranosyl nitromethane as a substrate for glycosidase assays involves the measurement of nitromethane release. For example, to assay beta-glucosidase activity, a reaction mixture is prepared containing 50 mM sodium acetate buffer (pH 5.0), 100 ug of enzyme (e.g., almond beta-glucosidase or microbial beta-glucosidase), and 1-10 mM Beta-D-Glucopyranosyl nitromethane in a total volume of 100 uL. The reaction is incubated at 37degC for 15-60 minutes. The release of nitromethane can be detected by adding 50 uL of 0.5 M NaOH to deprotonate the nitromethane to its aci-form, which absorbs at 220 nm. Alternatively, the nitromethane can be derivatized with 2,4-dinitrophenylhydrazine (DNPH) for detection at 540 nm. A more sensitive method is to use a nitromethane-specific electrode or GC-MS. The enzyme activity is expressed as nmol nitromethane released per minute per mg protein. The compound is stable under the assay conditions, and a control without enzyme is run to account for spontaneous hydrolysis. This assay can be used to screen for inhibitors of beta-glucosidase or to characterize enzyme kinetics (Km, Vmax).
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| Cell Assay |
A typical in vitro cellular protocol for evaluating the anti-inflammatory activity of Beta-D-Glucopyranosyl nitromethane uses LPS-stimulated RAW 264.7 mouse macrophages. Cells are seeded in 24-well plates at 2×10⁵ cells/well in DMEM with 10% FBS at 37degC in 5% CO2 and cultured overnight. The cells are pre-incubated with various concentrations of Beta-D-Glucopyranosyl nitromethane (0.1, 0.5, 1, 5, 10 mM) for 2 hours. Then, LPS (1 ug/mL) is added to induce inflammation, and the cells are incubated for an additional 24 hours. The culture supernatants are collected, and the levels of TNF-alpha, IL-1beta, IL-6, and NO (nitrite, using Griess reagent) are measured by ELISA or Griess assay. Cells are lysed in RIPA buffer, and protein expression of iNOS, COX-2, and NF-kappaB p65 is assessed by Western blot. Cell viability is assessed by MTT assay to ensure that the concentrations tested are not cytotoxic. Anti-inflammatory activity is indicated by a reduction in cytokine production and iNOS/COX-2 expression. For anti-tumor assays, cells (e.g., HeLa or MCF-7 cells) are seeded in 96-well plates (5×103 cells/well) and treated with serial dilutions of the compound (1-1000 uM) for 48-72 hours, and cell viability is measured by MTT. The IC50 is calculated.
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| Animal Protocol |
An in vivo animal protocol for evaluating the anti-inflammatory activity of Beta-D-Glucopyranosyl nitromethane uses the carrageenan-induced paw edema model in rats. Male Sprague-Dawley rats (150-200 g) are divided into groups (n=6 per group). Beta-D-Glucopyranosyl nitromethane is suspended in 0.5% carboxymethylcellulose (CMC) and administered orally at doses of 10, 25, 50, and 100 mg/kg. The control group receives vehicle (0.5% CMC). The positive control group receives indomethacin (10 mg/kg) or celecoxib. One hour after dosing, 0.1 mL of 1% carrageenan in saline is injected into the subplantar region of the right hind paw. Paw volume is measured using a plethysmometer at 0, 1, 2, 3, 4, and 5 hours after carrageenan injection. The percentage of inhibition of paw edema is calculated as (Vcontrol - Vtreated)/Vcontrol × 100%. At the end of the experiment (5 hours), rats are euthanized, and paw tissue is collected for measurement of myeloperoxidase (MPO) activity and for histological analysis (H&E). At 50-100 mg/kg, the compound is expected to reduce paw edema by 30-50% compared to the vehicle control. However, the potency is likely lower than that of indomethacin.
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| ADME/Pharmacokinetics |
Pharmacokinetic (PK) data for Beta-D-Glucopyranosyl nitromethane are not available in the public domain. Based on its molecular weight (223.18) and LogP (estimated around -1.5 to -2, due to the hydrophilic glucose moiety), the compound is likely to be water-soluble, poorly permeable across cell membranes, and has low oral bioavailability. It is expected to be metabolized by glycosidases in the gut and liver, which may cleave the glycosidic bond to release glucose and nitromethane. The elimination half-life is likely short. Formal ADME studies have not been published. For research purposes, the compound is typically formulated in water, PBS, or 0.5% CMC for oral administration, or in PBS for intravenous or intraperitoneal injection. It should be stored as a powder at -20degC, protected from light and moisture.
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| Toxicity/Toxicokinetics |
Limited toxicity data are available for Beta-D-Glucopyranosyl nitromethane. The compound is not intended for human use and has not been evaluated in formal toxicology studies. Acute toxicity is likely low due to the presence of the glucose moiety, which may reduce systemic exposure and facilitate rapid clearance. However, nitromethane itself (the aglycone) is toxic in high doses (causing methemoglobinemia, CNS depression, and hepatotoxicity). The glycosyl conjugate is expected to be less toxic than free nitromethane. Standard laboratory safety precautions should be followed when handling the compound, including the use of gloves, lab coats, and safety glasses. Avoid inhalation, ingestion, and direct skin or eye contact. The compound should be stored at -20degC, protected from light and moisture. It is for research use only and should not be used in humans or animals for therapeutic or diagnostic purposes without regulatory approval.
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| References | |
| Additional Infomation |
Beta-D-Glucopyranosyl nitromethane is a synthetic glycosyl derivative of nitromethane. It is a water-soluble sugar compound that is used as a biochemical research reagent. The compound has the molecular formula C7H13NO7 and a molecular weight of 223.18. It is the salt of a strongly basic anion exchanger (OH-cycle) and is a glycosyl derivative of nitromethane. The compound has been reported to exhibit various biological activities, including anti-inflammatory, anti-tumor, and anti-viral properties, but the evidence is limited, and specific mechanisms have not been established. It may be used as a substrate for enzyme assays (e.g., glycosidases) or as a model compound in glycosylation studies. As of 2026, Beta-D-Glucopyranosyl nitromethane is not an FDA-approved drug and is intended for research use only.
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| Molecular Formula |
C7H13NO7
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|---|---|
| Molecular Weight |
223.18
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| Exact Mass |
223.069
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| CAS # |
81846-60-8
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| PubChem CID |
22865379
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| Appearance |
White to off-white solid powder
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| LogP |
-2.2
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
15
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| Complexity |
230
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| Defined Atom Stereocenter Count |
5
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| SMILES |
C([C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)[N+](=O)[O-]
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| InChi Key |
CNILFIXWGGSLAQ-PJEQPVAWSA-N
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| InChi Code |
InChI=1S/C7H13NO7/c9-2-4-6(11)7(12)5(10)3(15-4)1-8(13)14/h3-7,9-12H,1-2H2/t3-,4+,5-,6+,7+/m0/s1
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| Chemical Name |
(2R,3S,4R,5R,6S)-2-(hydroxymethyl)-6-(nitromethyl)oxane-3,4,5-triol
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
H2O: 31.25 mg/mL (140.02 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: 100 mg/mL (448.07 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.
(Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.4807 mL | 22.4034 mL | 44.8069 mL | |
| 5 mM | 0.8961 mL | 4.4807 mL | 8.9614 mL | |
| 10 mM | 0.4481 mL | 2.2403 mL | 4.4807 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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