| Size | Price | |
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| Other Sizes |
| Targets |
Xanthine oxidase; PIM-1 kinase; COX-2; PDE4B. N-Demethylricinine has been reported as a xanthine oxidase inhibitor. Derivatives based on its 2-pyridone core structure have been evaluated as competitive inhibitors of PIM-1 kinase, COX-2, and PDE4B. The compound’s core 2-pyridone moiety is recognized as a privileged pharmacophore in medicinal chemistry. Its mechanism of action involves inhibition of these enzymes, contributing to antitumor, anti-inflammatory, and antiproliferative activities.
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|---|---|
| ln Vitro |
N-Demethylricinine derivatives exhibit potent in vitro antitumor activity against a range of human cancer cell lines. The compound has been reported as a xanthine oxidase inhibitor. Structural analogs have been evaluated as inhibitors of PIM-1 kinase, COX-2, and PDE4B. Some synthesized derivatives have shown promising radiosensitizing properties, enhancing the efficacy of γ-radiation in cancer cell lines. The compound serves as a critical building block for synthesizing multi-targeted anticancer agents.
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| ln Vivo |
In vivo studies of N-demethylricinine are limited, as the compound is primarily used as a research tool and chemical intermediate. Ricinine and its derivatives are known to be metabolized in plants, with catabolism associated with the aging process. The compound’s derivatives have shown potential for in vivo evaluation in oncology research, particularly as radiosensitizers in combination with radiation therapy. Further in vivo studies are needed to characterize its pharmacokinetic and pharmacodynamic properties.
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| Enzyme Assay |
N-Demethylricinine is a xanthine oxidase inhibitor. Xanthine oxidase inhibition assays are performed using purified enzyme and xanthine substrate. The compound is incubated with the enzyme, and uric acid production is measured spectrophotometrically at 295 nm. The IC₅₀ value is calculated from the dose-response curve. For kinase inhibition studies, derivatives are tested against PIM-1 kinase using standard kinase activity assays with radiolabeled ATP or luminescent detection.
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| Cell Assay |
Cell-based assays for N-demethylricinine derivatives use various cancer cell lines to assess antitumor activity. Cells are cultured in appropriate medium and treated with derivatives at various concentrations. Cell viability is measured using MTT or SRB assays. Apoptosis is evaluated by flow cytometry using Annexin V/PI staining. Radiosensitizing properties are assessed by combining compound treatment with γ-radiation exposure. The compound’s xanthine oxidase inhibitory activity can be assessed in cell models of oxidative stress.
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| Animal Protocol |
In vivo studies of N-demethylricinine derivatives are conducted in mouse xenograft models of cancer. Derivatives are administered via intraperitoneal or intravenous injection, alone or in combination with radiation therapy. Tumor volume is measured over time to assess antitumor efficacy and radiosensitizing effects. Pharmacokinetic parameters are determined from blood samples collected at various time points. Tissue distribution and toxicity are assessed by histopathological examination.
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| ADME/Pharmacokinetics |
N-Demethylricinine has a molecular formula of C₇H₆N₂O₂ and a molecular weight of 150.13 g/mol. It appears as a white solid with a density of 1.27 g/cm³. The compound is soluble in DMSO (55 mg/mL, 366.35 mM). For in vivo formulation, it can be prepared in 10% DMSO + 40% PEG300 + 5% Tween 80 + 45% saline at 2 mg/mL. Storage: powder at -20°C for 3 years; in solvent at -80°C for 1 year.
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| Toxicity/Toxicokinetics |
Specific toxicity data for N-demethylricinine are limited. As a xanthine oxidase inhibitor, it may affect purine metabolism at high doses. Derivatives have shown antitumor activity, indicating biological activity at certain concentrations. The compound is intended for research use only and is not for human consumption. Standard laboratory safety practices should be followed when handling this compound.
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| References | |
| Additional Infomation |
According to reports, castor beans contain 4-methoxy-2-oxo-1,2-dihydropyridine-3-nitrile, and relevant data are available for reference.
N-Demethylricinine (4-Methoxy-2-oxo-1,2-dihydropyridine-3-carbonitrile) is a naturally occurring α-pyridone alkaloid and a ricinine derivative found in castor bean plants. It has been reported as a xanthine oxidase inhibitor and serves as a key precursor for developing anticancer molecules. Its 2-pyridone core is a privileged pharmacophore in medicinal chemistry, and derivatives have shown activity against PIM-1 kinase, COX-2, and PDE4B. Some derivatives have demonstrated radiosensitizing properties. The compound is for research use only. |
| Molecular Formula |
C7H6N2O2
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|---|---|
| Molecular Weight |
150.13
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| Exact Mass |
150.042
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| CAS # |
21642-98-8
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| PubChem CID |
2786702
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| Appearance |
Off-white to yellow solid
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
421.8±45.0 °C at 760 mmHg
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| Melting Point |
293ºC
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| Flash Point |
208.9±28.7 °C
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| Vapour Pressure |
0.0±1.0 mmHg at 25°C
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| Index of Refraction |
1.547
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| LogP |
-0.88
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
11
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| Complexity |
293
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| Defined Atom Stereocenter Count |
0
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| SMILES |
COC1=CC=NC(=C1C#N)O
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| InChi Key |
MWGIDWPSRDMIQN-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C7H6N2O2/c1-11-6-2-3-9-7(10)5(6)4-8/h2-3H,1H3,(H,9,10)
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| Chemical Name |
4-methoxy-2-oxo-1H-pyridine-3-carbonitrile
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| Synonyms |
N-Demethylricinine
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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) |
DMSO: 50 mg/mL (333.04 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (16.65 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (16.65 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.6609 mL | 33.3045 mL | 66.6089 mL | |
| 5 mM | 1.3322 mL | 6.6609 mL | 13.3218 mL | |
| 10 mM | 0.6661 mL | 3.3304 mL | 6.6609 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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