| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| Other Sizes |
| Targets |
bitter taste receptor (Tas2r); ggTas2r1[1]
Epiquinidine targets similar molecular targets as other cinchona alkaloids, including ion channels and receptors. As a stereoisomer of quinidine, it may exhibit different stereospecific interactions with biological targets. Quinidine is known to target sodium channels and potassium channels. Epiquinidine's stereochemistry may affect its binding affinity and pharmacological profile. Further research is needed to identify its specific molecular targets. |
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| ln Vitro |
Bitter taste is one of the basic taste modalities, warning against consuming potential poisons. Bitter compounds activate members of the bitter taste receptor (Tas2r) subfamily of G protein-coupled receptors (GPCRs). The number of functional Tas2rs is species-dependent. Chickens represent an intriguing minimalistic model, because they detect the bitter taste of structurally different molecules with merely three bitter taste receptor subtypes. We investigated the binding modes of several known agonists of a representative chicken bitter taste receptor, ggTas2r1. Because of low sequence similarity between ggTas2r1 and crystallized GPCRs (~10% identity, ~30% similarity at most), the combination of computational approaches with site-directed mutagenesis was used to characterize the agonist-bound conformation of ggTas2r1 binding site between TMs 3, 5, 6 and 7. We found that the ligand interactions with N93 in TM3 and/or N247 in TM5, combined with hydrophobic contacts, are typically involved in agonist recognition. Next, the ggTas2r1 structural model was successfully used to identify three quinine analogues (epiquinidine, ethylhydrocupreine, quinidine) as new ggTas2r1 agonists. The integrated approach validated here may be applicable to additional cases where the sequence identity of the GPCR of interest and the existing experimental structures is low[1].
In vitro studies of Epiquinidine have focused on its role as a chiral reagent and its stereochemical properties. The compound's interactions with biological targets may differ from quinidine due to its stereochemistry. As a cinchona alkaloid, it may exhibit similar activities to quinidine and quinine. These in vitro studies provide foundational data for understanding the compound's properties and its applications in stereochemical research. |
| ln Vivo |
In vivo studies of Epiquinidine are limited as the compound is primarily used as a research chemical and chiral reagent. Its stereoisomer, quinidine, is used clinically as an antiarrhythmic agent. Epiquinidine may exhibit different pharmacological effects due to its stereochemistry. However, comprehensive in vivo pharmacological studies specifically targeting Epiquinidine are not well documented. The compound is intended for research use only.
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| Enzyme Assay |
Site-directed mutagenesis[1]
In-vitro mutagenesis by PCR-mediated recombination44 was performed as detailed before19, 20, 45 using the cDNA of ggTas2r1 cloned in the vector pcDNA5/FRT available from previous experiments9 as template. Briefly, template cDNA was amplified in two separate reactions using CMV forward and the corresponding reverse mutagenesis primer and BGH reverse and the corresponding forward mutagenesis primer, respectively. Next, the two generated subfragments were fused in the following PCR reaction carried out in the presence of CMV forward and BGH reverse primers. The mutated ggTas2r1 coding region was ligated after EcoR I and NotI restriction with the vector pcDNA5/FRT, which has been modified to result in the in-frame addition of a 5′ sst3-tag and a 3′ hsv-tag9. For a list of oligonucleotides used for mutagenesis see Table 2. In vitro receptor binding assays for Epiquinidine typically involve testing its interactions with ion channels and receptors. Binding affinity is measured using radioligand binding assays or electrophysiological methods. The compound's stereochemistry may affect its binding affinity and selectivity. The compound's purity and identity are confirmed using analytical chemistry methods such as nuclear magnetic resonance spectroscopy, high-performance liquid chromatography, and mass spectrometry. |
| Cell Assay |
Calcium-mobilization assays[1]
The point-mutated expression constructs, the native ggTas2r1 construct, as well as empty expression vectors as controls were transiently transfected in HEK 293T cells stably expressing the chimeric Gα protein Gα16gust44, which were grown in 96-well plates exactly as described previously9. About 24 h after transfection, the cells were loaded with the calcium-sensitive dye Fluo4-AM in the presence of 2.5 mM probenecid, washed and placed in a fluorometric imaging plate reader). Different concentrations of the bitter compounds were automatically applied and changes in fluorescence were monitored. A second application of 100 nM SST-14 stimulating endogenous somatostatin receptors was included as vitality control. Dose-response relations were calculated with SigmaPlot as before. In vitro cell-based assays for Epiquinidine involve culturing cells to evaluate its effects on ion channel function. Cells expressing specific ion channels are treated with varying concentrations of the compound and channel activity is measured using patch-clamp electrophysiology or fluorescence-based assays. Cell viability is assessed using standard assays. All experiments are performed with appropriate controls to ensure statistical reliability. |
| Animal Protocol |
In vivo animal experiments for Epiquinidine would be conducted to evaluate its effects on cardiac function and other physiological parameters. Animals would be administered the compound and electrocardiographic parameters assessed. For toxicology studies, animals would be administered the compound and observed for signs of toxicity. Parameters assessed would include heart rate, ECG intervals, and tissue histopathology. Control groups receiving vehicle alone would be included for comparison.
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| ADME/Pharmacokinetics |
The pharmacokinetic properties of Epiquinidine reflect its nature as a cinchona alkaloid. It has a molecular weight of 324.42 and the molecular formula C20H24N2O2. As a lipophilic alkaloid, it would be absorbed through the gastrointestinal tract and distributed throughout the body. The compound is expected to be metabolized through standard xenobiotic pathways in the liver. Complete pharmacokinetic profiling would require further systematic studies.
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| Toxicity/Toxicokinetics |
The toxicity profile of Epiquinidine has been evaluated in the context of its use as a research chemical. As a cinchona alkaloid, it may have effects similar to quinidine and quinine, which can cause cardiac arrhythmias and other adverse effects at high doses. Proper handling procedures including use of personal protective equipment are recommended when working with the compound. The compound is not approved for human therapeutic use and is intended for research purposes only.
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| References | |
| Additional Infomation |
Quinine is an alkaloid extracted from the bark of the cinchona tree. It is used as an antimalarial drug and is the active ingredient in cinchona extracts, which have been used to treat malaria since before 1633. Quinine is also a mild antipyretic and analgesic, and has been used to treat the common cold. It was widely used as a bittering agent and flavoring agent, and is still used to treat babesiosis. Quinine is also effective against certain muscle disorders, particularly nocturnal leg cramps and congenital myotonia, because it has a direct effect on muscle cell membranes and sodium channels. The mechanism of its antimalarial action is not fully understood.
See also: Quinidine (note moved to); Quinine sulfate (note moved to). Epiquinidine (CAS# 572-59-8) is a cinchona alkaloid and the pseudo-enantiomer of quinidine. It has the molecular formula C20H24N2O2 and a molecular weight of 324.42. The compound is a stereoisomer of quinidine, differing in the configuration at the C9 position. It is used as a chiral reagent and in research applications for studying stereochemistry and alkaloid pharmacology. |
| Molecular Formula |
C20H24N2O2
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|---|---|
| Molecular Weight |
324.42
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| Exact Mass |
324.184
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| CAS # |
572-59-8
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| PubChem CID |
94175
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| Appearance |
White to off-white Solid-Liquid Mixture
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| Density |
1.218g/cm3
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| Boiling Point |
495.88ºC at 760 mmHg
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| Melting Point |
111-113°
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| Flash Point |
253.699ºC
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| Index of Refraction |
1.638
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| LogP |
3.111
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
24
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| Complexity |
457
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| Defined Atom Stereocenter Count |
4
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| SMILES |
COc1ccc2nccc(C(O)C3CC4CCN3CC4C=C)c2c1 |TLB:20:19:16.15:13.12,10:12:19.18:16.15|
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| InChi Key |
LOUPRKONTZGTKE-AFHBHXEDSA-N
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| InChi Code |
InChI=1S/C20H24N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3/t13-,14-,19+,20+/m0/s1
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| Chemical Name |
(R)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
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| Synonyms |
Epiquinidine; 572-59-8; (9R)-6'-Methoxycinchonan-9-ol; 9-epi-Quinidine; GNF-Pf-180; RN974X9U97; (R)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol; .beta.-Quinine;
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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 (308.24 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.71 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 (7.71 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 (7.71 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 | 3.0824 mL | 15.4121 mL | 30.8242 mL | |
| 5 mM | 0.6165 mL | 3.0824 mL | 6.1648 mL | |
| 10 mM | 0.3082 mL | 1.5412 mL | 3.0824 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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