Mepyramine maleateSelective H1 inverse agonist CAS# 59-33-6 |
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Quality Control & MSDS
3D structure
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| Cas No. | 59-33-6 | SDF | Download SDF |
| PubChem ID | 5284451 | Appearance | Powder |
| Formula | C21H27N3O5 | M.Wt | 401.46 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Synonyms | Pyrilamine maleate | ||
| Solubility | DMSO : ≥ 100 mg/mL (249.09 mM) *"≥" means soluble, but saturation unknown. | ||
| Chemical Name | (Z)-but-2-enedioic acid;N'-[(4-methoxyphenyl)methyl]-N,N-dimethyl-N'-pyridin-2-ylethane-1,2-diamine | ||
| SMILES | CN(C)CCN(CC1=CC=C(C=C1)OC)C2=CC=CC=N2.C(=CC(=O)O)C(=O)O | ||
| Standard InChIKey | JXYWFNAQESKDNC-BTJKTKAUSA-N | ||
| Standard InChI | InChI=1S/C17H23N3O.C4H4O4/c1-19(2)12-13-20(17-6-4-5-11-18-17)14-15-7-9-16(21-3)10-8-15;5-3(6)1-2-4(7)8/h4-11H,12-14H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;2-1- | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Selective inverse agonist for the H1 receptor. Inhibits histamine induced inositol phosphate (InsP) production (log EC50 = -7.94) and intracellular calcium mobilization. Sequesters Gq/11 protein, reducing its availability for other receptors associated with the same signaling pathway. |
Mepyramine maleate Dilution Calculator
Mepyramine maleate Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.4909 mL | 12.4545 mL | 24.9091 mL | 49.8182 mL | 62.2727 mL |
| 5 mM | 0.4982 mL | 2.4909 mL | 4.9818 mL | 9.9636 mL | 12.4545 mL |
| 10 mM | 0.2491 mL | 1.2455 mL | 2.4909 mL | 4.9818 mL | 6.2273 mL |
| 50 mM | 0.0498 mL | 0.2491 mL | 0.4982 mL | 0.9964 mL | 1.2455 mL |
| 100 mM | 0.0249 mL | 0.1245 mL | 0.2491 mL | 0.4982 mL | 0.6227 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Suppression by mepyramine maleate of the increased vascular permeability in passive cutaneous anaphylaxis in the chicken.[Pubmed:3188384]
Vet Res Commun. 1988;12(2-3):161-3.
Passive cutaneous anaphylaxis was produced in chickens pretreated with the antihistamine Mepyramine maleate. Quantitative estimation of the increased vascular permeability in the lesion revealed 79.5% suppression indicating its mediation largely by histamine. The findings suggest that the quantitative estimation of the increased vascular permeability, though time-consuming, is more precise than the visual assessment.
Efficacy of mepyramine maleate treatment in dogs with angioedema.[Pubmed:21033572]
Pol J Vet Sci. 2010;13(3):549-50.
Twenty-seven dogs with angioedema, were enrolled in this clinical study. The cases were randomly assigned to the treatment group (n=15) and untreated placebo control group (n=12). It was concluded that Mepyramine maleate has the potential to be helpful for dogs with angioedema.
[Comparative antiallergic and anti-inflammatory action of F1865, mepyramine maleate, desonide and disodium cromoglycate after cutaneous administration].[Pubmed:6425568]
J Pharmacol. 1984 Jan-Mar;15(1):37-51.
The actions of F 1865 (ethyl 4' methoxy 4 phenyl thiazolyl 2 oxamate), an inhibitor of the release of histamine from mast cell, desonide, a corticosteroid, Mepyramine maleate, an anti-H1 antihistaminic, and disodium cromoglycate were compared after cutaneous application in various experimental models of allergy and inflammation. F 1865 decreased IgE- and IgG-dependent passive cutaneous anaphylaxis in rats at doses having no effect on histamine- and serotonin-induced capillary permeability. Disodium cromoglycate showed the same activity spectrum, but its action was only found after intradermal application. The reduction of cutaneous anaphylaxis by desonide was found parallel to its inhibition of histamine effects, and to a lesser extent of serotonin effects. In the case of mepyramine, the antiallergic effect may be explained by its antihistaminic action. Desonide was highly active on cantharidin-induced non-immune inflammation and on non-immune and delayed hypersensitivity reactions induced by picryl chloride in mouse ear. Although far less active than the corticosteroid, F 1865, mepyramine and disodium cromoglycate did reduce the three types of reactions in mice. This evidenced a part played by histamine in such inflammations. Then it is likely that the inhibition of histamine release by F 1865 plays an important part in the effect of the compound observed in the various inflammations studied. However we cannot exclude actions against other mediators involved in these reactions.
Mepyramine, a histamine H1 receptor inverse agonist, binds preferentially to a G protein-coupled form of the receptor and sequesters G protein.[Pubmed:15192105]
J Biol Chem. 2004 Aug 13;279(33):34431-9.
Accurate characterization of the molecular mechanisms of the action of ligands is an extremely important issue for their appropriate research, pharmacological, and therapeutic uses. In view of this fact, the aim of the present work was to investigate the mechanisms involved in the actions of mepyramine at the guinea pig H(1) receptor stably expressed in Chinese hamster ovary cells. We found that mepyramine is able to decrease the basal constitutive activity of the guinea pig H(1) receptor, to bind with high affinity to a G(q/11) protein-coupled form of the receptor and to promote a G protein-coupled inactive state of the H(1) receptor that interferes with the G(q/11)-mediated signaling of the endogenously expressed ATP receptor, as predicted by the Cubic Ternary Complex Model of receptor occupancy. The effect of mepyramine on ATP-induced signaling was specifically neutralized by Galpha(11) overexpression, indicating that mepyramine is able to reduce G protein availability for other non-related receptors associated with the same signaling pathway. Finally, we found a loss of mepyramine efficacy in decreasing basal levels of intracellular calcium at high Galpha(11) expression levels, which can be theoretically explained in terms of high H(1) receptor constitutive activity. The whole of the present work sheds new light on H(1) receptor pharmacology and the mechanisms H(1) receptor inverse agonists could use to exert their observed negative efficacy.
Does the [3H]mepyramine binding site represent the histamine H1 receptor? Re-examination of the histamine H1 receptor with quinine.[Pubmed:8114011]
J Pharmacol Exp Ther. 1994 Feb;268(2):959-64.
Mepyramine is a potent H1 receptor antagonist, and [3H]mepyramine generally is used to label histamine H1 receptors. However, we found that [3H]mepyramine labeled not only the H1 receptor but also a [3H]mepyramine binding protein (MBP) in the liver, which protein appears to be related to the subfamily of debrisoquine 4-hydroxylase (cytochrome P450IID) isozymes. The binding of [3H]mepyramine to the cloned H1 receptor was not affected by 1 microM quinine, an inhibitor of debrisoquine 4-hydroxylase. On the other hand, the binding to MBP in the liver membranes was completely inhibited by 1 microM quinine. These data indicate that the labeling by [3H]mepyramine of H1 receptors and MBP can be completely separated with 1 microM quinine. The majority of [3H] mepyramine binding sites in the cerebral cortex, thalamus and hypothalamus, hippocampus, heart, aorta, lung and spleen were H1 receptors. On the other hand, almost all [3H]mepyramine binding sites in the liver and kidney were MBP. Both H1 receptors and MBP were expressed in the stomach, ileum, cerebellum and adrenal gland. Kd values of [3H]mepyramine for membranes from the cerebellum and stomach in the presence of quinine, which tissues contain both H1 receptors and MBP, approached that value of the cloned H1 receptor. The improved [3H]mepyramine binding assay using quinine is a precise method to characterize H1 receptors by the separate determination of H1 receptors and MBP.
Distribution, properties, and functional characteristics of three classes of histamine receptor.[Pubmed:2164693]
Pharmacol Rev. 1990 Mar;42(1):45-83.
It is clear from the preceding overview of histamine receptor pharmacology that research into the pharmacology of histamine receptors is at an exciting stage of development. The rapid advance of molecular biology should soon see the structural identification and cloning of all three of the major vertebrate histamine receptors. Further work will continue toward enhancing our understanding of the control by histamine of intracellular signaling via H1- and H2-receptors, and the rapid explosion of work on the H3-receptor should begin to unravel the mechanisms underlying its actions, perhaps via effects on ionic channels. The potential role of histamine as an intracellular second messenger raises exciting possibilities, as does the search for a histamine receptor analogous to the ligand-gated ion channel in the invertebrate nervous system.
