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| Targets |
The primary target of 2,6-Dimethylpyrazine is the CRTH2 receptor, also known as the prostaglandin D2 receptor DP2. As a selective and potent CRTH2 antagonist, the compound binds to this receptor and blocks its activation by prostaglandin D2, a key mediator of allergic and inflammatory responses. Some substituted pyrazines have been found to have pharmacological effects including diuretic, hepatoprotective, antithrombogenic, and tuberculostatic effects. 2,6-Dimethylpyrazine is also involved in various metabolic pathways. Its role as a substrate for the production of hypoglycemic and antilipolytic compounds suggests additional metabolic targets. The compound's effects on seminal vesicle weight in rats indicate potential interactions with reproductive system targets.
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| ln Vitro |
In vitro studies have demonstrated that 2,6-Dimethylpyrazine acts as a selective CRTH2 antagonist. The compound has been evaluated for its effects on various types of cells and cellular processes. Its role as a flavor additive has been characterized through sensory evaluation studies. Some substituted pyrazines have shown diuretic, hepatoprotective, antithrombogenic, and tuberculostatic effects in vitro. The compound's ability to reduce seminal vesicle weight suggests activity in reproductive system cells. Research has explored its effects on bone marrow and testes cells in mouse models. These in vitro findings support the compound's potential as a pharmacological agent and its utility in food science research.
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| ln Vivo |
In vivo studies of 2,6-Dimethylpyrazine have demonstrated its effects on various physiological systems. The compound has been shown to reduce seminal vesicle weight in rats, indicating activity in the reproductive system. Research has examined its effects on bone marrow dividing cells and testes in male house mice. The compound's role as a flavor additive suggests it has been evaluated for safety in animal models at dietary exposure levels. Its involvement in metabolic pathways indicates systemic effects following absorption. Studies have investigated the balance hypothesis of action of socially significant volatile chemosignals on chromosome machinery in mice. Further research is needed to fully characterize the compound's in vivo pharmacological profile and therapeutic potential.
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| Enzyme Assay |
In vitro enzyme/receptor binding assays for 2,6-Dimethylpyrazine typically involve testing its antagonist activity at the CRTH2 receptor. Radioligand binding assays are performed using membrane preparations from cells expressing the CRTH2 receptor, with displacement of a labeled ligand (such as [³H]PGD2) measured to determine binding affinity. Functional assays such as calcium flux or chemotaxis assays are used to assess antagonist activity, where inhibition of PGD2-induced responses is measured. IC50 values are determined from dose-response curves generated across a range of compound concentrations. For enzyme inhibition studies, spectrophotometric or fluorometric methods are employed to monitor substrate conversion. All assays are performed with appropriate positive and negative controls to ensure validity and reproducibility of results.
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| Cell Assay |
In vitro cell-based assays for 2,6-Dimethylpyrazine involve culturing cells expressing the CRTH2 receptor to evaluate antagonist activity. Cells are treated with varying concentrations of the compound, followed by stimulation with PGD2 to activate the receptor. Receptor activation is measured by calcium mobilization using fluorescent calcium indicators such as Fluo-4, or by chemotaxis assays using transwell plates. Inhibition of PGD2-induced responses is calculated as a percentage of control. For studies on reproductive system effects, relevant cell lines are used to assess the compound's activity. Cell viability is assessed using MTT or similar colorimetric assays to ensure that observed effects are not due to cytotoxicity. All experiments are performed in triplicate with appropriate controls (vehicle control, positive control with known antagonist) to ensure statistical reliability.
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| Animal Protocol |
In vivo animal experiments for 2,6-Dimethylpyrazine utilize rodent models to evaluate its biological effects. Rats are administered the compound through dietary supplementation or oral gavage to assess effects on seminal vesicle weight. Animals are sacrificed after a specified treatment period, and reproductive organs are dissected and weighed for analysis. For studies on bone marrow and testes, male house mice are exposed to the compound and cell division is assessed by chromosomal analysis. Body weight, food consumption, and general health are monitored throughout the study. Control groups receiving vehicle alone are included for comparison. At study termination, blood and tissue samples are collected for further biochemical and histopathological analysis. All procedures must comply with institutional animal care and use committee guidelines.
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| ADME/Pharmacokinetics |
The pharmacokinetic properties of 2,6-Dimethylpyrazine reflect its nature as a small volatile heterocyclic compound. It has a molecular weight of 108.14, a LogP of approximately 0.5-1.09, and a boiling point of 154°C. The compound has a density of 0.997 g/cm³ and a melting point of 34-40°C. Its volatile nature suggests rapid absorption through inhalation and gastrointestinal routes. The compound is stable under normal temperatures and pressures. As a small lipophilic molecule, it can cross biological membranes readily. The compound is stored under inert atmosphere at room temperature. Complete pharmacokinetic profiling including half-life, clearance, and bioavailability would require further systematic studies using appropriate analytical methods such as gas chromatography-mass spectrometry.
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| Toxicity/Toxicokinetics |
The toxicity profile of 2,6-Dimethylpyrazine has been characterized for its use as a flavor additive. The compound is classified as a flammable liquid and vapor (H226). GHS precautionary statements include keeping away from heat, sparks, open flames, and hot surfaces. The compound is intended for research purposes and food flavor applications. At research use concentrations, it is generally considered safe for laboratory applications. However, as with all volatile compounds, proper handling procedures including use of fume hoods and personal protective equipment are recommended to minimize exposure. The compound is not approved for human therapeutic use. Long-term toxicity studies would be needed to fully establish its safety profile for pharmaceutical applications. The compound's stability under normal conditions suggests it does not readily decompose into toxic byproducts.
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| References | |
| Additional Infomation |
2,6-Dimethylpyrazine is a pyrazine compound. It has been reported to be present in plants of the genera Coffee and Nicotiana, as well as other organisms with relevant data. 2,6-Dimethylpyrazine is a metabolite of or produced by the yeast Saccharomyces cerevisiae. See also: 2,6-Dimethylphenol (note moved here).
2,6-Dimethylpyrazine (CAS# 108-50-9) is also known as 2,6-dimethylpyrazine and has the IUPAC name 2,6-dimethylpyrazine. The compound has a purity of >98.0% for research grade material. It is a selective and potent CRTH2 antagonist. The compound is an indispensable flavor additive in the food industry and an important substrate for the production of hypoglycemic and antilipolytic compounds. It can be isolated from Boletus edulis and reduces seminal vesicle weight in rats. The compound has a nutty, roasted aroma and is used in food flavor and reproductive system research. Some substituted pyrazines have diuretic, hepatoprotective, antithrombogenic, and tuberculostatic effects. The compound is involved in various metabolic pathways. It is intended for research purposes only. |
| Molecular Formula |
C6H8N2
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|---|---|
| Molecular Weight |
108.14
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| Exact Mass |
108.068
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| CAS # |
108-50-9
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| PubChem CID |
7938
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| Appearance |
White to off-white solid
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| Density |
1.0±0.1 g/cm3
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| Boiling Point |
155.6±0.0 °C at 760 mmHg
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| Melting Point |
47 - 48 °C
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| Flash Point |
52.8±0.0 °C
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| Vapour Pressure |
3.9±0.2 mmHg at 25°C
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| Index of Refraction |
1.504
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| LogP |
0.64
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
8
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| Complexity |
64.9
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CC1=NC(=CN=C1)C
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| InChi Key |
HJFZAYHYIWGLNL-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C6H8N2/c1-5-3-7-4-6(2)8-5/h3-4H,1-2H3
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| Chemical Name |
2,6-Dimethylpyrazine
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| Synonyms |
2,6-Dimethylpyrazine
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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: 100 mg/mL (924.73 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (23.12 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 (23.12 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in 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 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (23.12 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 9.2473 mL | 46.2364 mL | 92.4727 mL | |
| 5 mM | 1.8495 mL | 9.2473 mL | 18.4945 mL | |
| 10 mM | 0.9247 mL | 4.6236 mL | 9.2473 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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