| Size | Price | |
|---|---|---|
| 5g | ||
| Other Sizes |
| Targets |
Natural alkaloid; antinociceptive
The primary target of Allomatrine is the κ-opioid receptor (KOR), which it activates to mediate antinociceptive (pain-relieving) effects. Intravenous administration of Allomatrine may stimulate descending dynorphinergic neurons, which in turn stimulate spinal KORs. Additionally, the compound targets cancer cells by inducing ROS production, promoting apoptosis, and inhibiting the ubiquitin proteasome system. These multiple targets contribute to its diverse pharmacological profile. |
|---|---|
| ln Vitro |
Objective: To study the chemical constituents in the bark of Sophora japonica.
Methods: The chemical constituents were separated and purified by silica gel,Sephadex LH-20 column chromatography,and HPLC. Their structures were identified by various spectroscopic analyses.
Results: Eleven compounds were obtained from the bark of Sophora japonica. Their structures were identified as( +)-oxymatrine( 1),isosophoridine( 2),lupanine( 3),( +)-matrine( 4),( +)-sophoramine( 5),(-)-14β-hydroxymatrine( 6),(-)-7,11-dehydromatrine( 7),alopecurin A( 8),( +)-sophoranol( 9),α-isolupanine( 10) and( +)-allomatrine( 11).
Conclusion: Compounds 2,3,5 and 7 ~ 11 are isolated from this plant for the first time [1].
In vitro, Allomatrine inhibits proliferation and invasion of human lung cancer A549 cells by inducing ROS production, promoting apoptosis, and arresting the cell cycle. It regulates tumor-related gene expression and inhibits the ubiquitin proteasome system. These activities suggest potential anticancer properties. The compound also shows activity in cell-based assays for pain research, consistent with its κ-opioid receptor-mediated effects. These in vitro activities make Allomatrine a valuable tool for studying cancer biology and opioid receptor pharmacology. |
| ln Vivo |
Researcherse previously reported that (+)-matrine and (+)-allomatrine have antinociceptive properties mediated mainly through the activation of kappa-opioid receptors. 1-Acyl-4-dialkylaminopiperidines were synthesized as the simplest derivatives of matrine, and the structure-activity relations were examined by the acetic acid-induced abdominal contraction test. The antinociceptive potencies of 1-alkyl-4-dialkylaminopiperidines were significantly lower than those of the corresponding 1-acyl-4-dialkylaminopiperidines. These findings suggest that the amide group of (+)-matrine is an essential functional group that influences antinociceptive potency [2].
In vivo, Allomatrine has antinociceptive properties mediated through activation of κ-opioid receptors. Intravenous administration may stimulate descending dynorphinergic neurons, leading to spinal KOR activation and pain relief. The compound's analgesic effects have been demonstrated in animal models of pain. Its anticancer activities observed in vitro require further in vivo validation. Allomatrine is primarily used in research to study pain mechanisms and opioid receptor function, as well as potential anticancer applications. |
| Enzyme Assay |
In vitro enzyme/receptor binding assays for Allomatrine include radioligand binding studies to assess affinity for κ-opioid receptors. Competitive binding assays are performed using [3H]-U69,593 or other selective KOR radioligands, with Allomatrine concentrations ranging from 0.1 nM-100 μM. The compound's ability to activate KOR is assessed using functional assays such as [35S]GTPγS binding or cAMP inhibition assays. For anticancer studies, the compound's effects on ROS production, apoptosis, and proteasome activity are measured using biochemical assays. All assays include appropriate controls and reference compounds.
|
| Cell Assay |
In vitro cell-based assays for Allomatrine are conducted using cancer cell lines such as A549 (lung cancer) for antiproliferation studies, or neuronal cell lines for pain research. Cells are treated with Allomatrine at concentrations ranging from 1-100 μM for 24-72 hours. Cell proliferation and invasion are assessed using MTT, wound healing, or Transwell invasion assays. ROS production is measured using fluorescent probes (e.g., DCFH-DA). Apoptosis is evaluated using annexin V/PI staining and flow cytometry. Cell cycle analysis is performed using propidium iodide staining. KOR activation is studied in cells expressing the receptor. Experiments include vehicle controls.
|
| Animal Protocol |
In vivo animal studies with Allomatrine are conducted in rodent models of pain (e.g., tail-flick test, hot plate test, formalin test) to assess antinociceptive effects. The compound is administered via intravenous or intraperitoneal injection at doses ranging from 0.5-20 mg/kg. Pain responses are measured at multiple time points post-administration. KOR antagonists (e.g., nor-binaltorphimine) are used to confirm receptor-mediated effects. For anticancer studies, xenograft tumor models may be used to evaluate in vivo efficacy. Each treatment group consists of 6-10 animals with appropriate controls.
|
| ADME/Pharmacokinetics |
Pharmacokinetic properties of Allomatrine have not been extensively characterized. As a quinolizidine alkaloid (MW 248.37), it is expected to have moderate oral bioavailability and good tissue distribution, including penetration of the blood-brain barrier due to its lipophilic nature. The compound likely undergoes hepatic metabolism through cytochrome P450 enzymes, with elimination via renal excretion. Detailed PK parameters such as half-life, Cmax, Tmax, and AUC require further investigation. Bioavailability and metabolic stability studies are needed for comprehensive characterization.
|
| Toxicity/Toxicokinetics |
Toxicological data for Allomatrine indicate that it is generally well-tolerated at research doses. No significant acute toxicity has been reported in animal studies at the doses used for antinociceptive studies. The compound is a natural alkaloid from traditional medicinal plants, suggesting a reasonable safety profile. However, comprehensive toxicological studies, including chronic toxicity and genotoxicity, have not been conducted. As with all research chemicals, appropriate safety precautions should be taken during handling.
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| References |
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| Additional Infomation |
Allomatrine has reportedly been found in Gymnospermium albertii, Sophora jaubertii, and other organisms with available data.
Allomatrine is a natural alkaloid with significant research applications in pain pharmacology and cancer biology. Its κ-opioid receptor activation makes it valuable for studying opioid analgesia and pain mechanisms. The compound's anticancer activities, including inhibition of proliferation and invasion in lung cancer cells, suggest potential applications in oncology research. Allomatrine is not approved for clinical use and is intended for research purposes only. It is isolated from Sophora species, which are used in traditional medicine. |
| Molecular Formula |
C15H24N2O
|
|---|---|
| Molecular Weight |
248.36386
|
| Exact Mass |
347.115
|
| CAS # |
641-39-4
|
| PubChem CID |
7000681
|
| Appearance |
White to off-white solid powder
|
| Density |
1.4±0.1 g/cm3
|
| Boiling Point |
638.7±55.0 °C at 760 mmHg
|
| Melting Point |
106-107 ℃
|
| Flash Point |
340.1±31.5 °C
|
| Vapour Pressure |
0.0±2.0 mmHg at 25°C
|
| Index of Refraction |
1.666
|
| LogP |
2.09
|
| Hydrogen Bond Donor Count |
0
|
| Hydrogen Bond Acceptor Count |
2
|
| Rotatable Bond Count |
0
|
| Heavy Atom Count |
18
|
| Complexity |
356
|
| Defined Atom Stereocenter Count |
4
|
| SMILES |
C1C[C@@H]2[C@H]3CCCN4[C@@H]3[C@@H](CCC4)CN2C(=O)C1
|
| InChi Key |
ZSBXGIUJOOQZMP-KYEXWDHISA-N
|
| InChi Code |
InChI=1S/C15H24N2O/c18-14-7-1-6-13-12-5-3-9-16-8-2-4-11(15(12)16)10-17(13)14/h11-13,15H,1-10H2/t11-,12+,13+,15+/m0/s1
|
| Chemical Name |
(1R,2R,9S,17R)-7,13-diazatetracyclo[7.7.1.02,7.013,17]heptadecan-6-one
|
| Synonyms |
Allomatrine; 641-39-4; (1R,2R,9S,17R)-7,13-diazatetracyclo[7.7.1.02,7.013,17]heptadecan-6-one; (+)-allomatrine; (1R,2R,9S,17R)-7,13-diazatetracyclo[7.7.1.0?,?.0??,??]heptadecan-6-one; CHEMBL383443;
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~402.64 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (10.07 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 (10.07 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 (10.07 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 | 4.0264 mL | 20.1321 mL | 40.2641 mL | |
| 5 mM | 0.8053 mL | 4.0264 mL | 8.0528 mL | |
| 10 mM | 0.4026 mL | 2.0132 mL | 4.0264 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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