Proxyfan oxalateHigh affinity H3 ligand CAS# 177708-09-7 |
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Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
Cas No. | 177708-09-7 | SDF | Download SDF |
PubChem ID | 71433557 | Appearance | Powder |
Formula | C17H20N2O5 | M.Wt | 332.4 |
Type of Compound | N/A | Storage | Desiccate at -20°C |
Solubility | Soluble to 100 mM in DMSO and to 100 mM in water | ||
Chemical Name | but-2-enedioic acid;5-(3-phenylmethoxypropyl)-1H-imidazole | ||
SMILES | C1=CC=C(C=C1)COCCCC2=CN=CN2.C(=CC(=O)O)C(=O)O | ||
Standard InChIKey | JQCZPVBHMZGGAV-UHFFFAOYSA-N | ||
Standard InChI | InChI=1S/C13H16N2O.C4H4O4/c1-2-5-12(6-3-1)10-16-8-4-7-13-9-14-11-15-13;5-3(6)1-2-4(7)8/h1-3,5-6,9,11H,4,7-8,10H2,(H,14,15);1-2H,(H,5,6)(H,7,8) | ||
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 | High affinity histamine H3 receptor ligand (pKi = 8.62) that acts as a protean agonist at recombinant and native receptors. In functional studies, activity ranges from full agonist to inverse agonist depending on system used. Displays partial agonist effects on cAMP inhibition and MAPK activity, neutral antagonist activity on histamine release and partial inverse agonism of [3H]-arachidonic acid release. |
Proxyfan oxalate Dilution Calculator
Proxyfan oxalate Molarity Calculator
1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
1 mM | 3.0084 mL | 15.0421 mL | 30.0842 mL | 60.1685 mL | 75.2106 mL |
5 mM | 0.6017 mL | 3.0084 mL | 6.0168 mL | 12.0337 mL | 15.0421 mL |
10 mM | 0.3008 mL | 1.5042 mL | 3.0084 mL | 6.0168 mL | 7.5211 mL |
50 mM | 0.0602 mL | 0.3008 mL | 0.6017 mL | 1.2034 mL | 1.5042 mL |
100 mM | 0.0301 mL | 0.1504 mL | 0.3008 mL | 0.6017 mL | 0.7521 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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The H3 receptor protean agonist proxyfan enhances the expression of fear memory in the rat.[Pubmed:15695163]
Neuropharmacology. 2005 Feb;48(2):246-51.
Consolidation of fear memory requires neural changes to occur in the basolateral amygdala (BLA), including modulation of histaminergic neurotransmission. We previously demonstrated that local blockade or activation of histamine H3 receptors in the BLA impaired or ameliorated, respectively, retention of fear memory. The histamine H3 receptor is a G-protein-coupled receptor (GPCR) displaying high constitutive activity that regulates histamine neurons in the brain. Proxyfan is a high-affinity histamine H3 receptor protean agonist exhibiting the full spectrum of pharmacological activities, from full agonist to full inverse agonist depending on the competition between constitutively active and quiescent H3 receptors in a given tissue or brain region. Therefore, protean agonists are powerful tools to investigate receptor conformation and may be useful in designing specific compounds selective for the various receptor conformations. In the present study we examined the effect of post-training, systemic or intra-BLA injections of proxyfan on contextual fear memory. Rats receiving intra-BLA, bilateral injections of 1.66 ng proxyfan immediately after fear conditioning showed stronger memory for the context-footshock association, as demonstrated by longer freezing assessed at retention performed 72 hr later compared to controls. Comparable results were obtained when doses as low as 0.04 mg/kg of proxyfan were injected systemically. Hence, our results suggest that proxyfan behaves as an H3 receptor agonist with a low level of constitutive activity of the H3 receptor in the rat BLA.
G protein-dependent pharmacology of histamine H3 receptor ligands: evidence for heterogeneous active state receptor conformations.[Pubmed:15821027]
J Pharmacol Exp Ther. 2005 Jul;314(1):271-81.
Previously reported pharmacological studies using the imidazole-containing histamine H3 receptor ligands GT-2331 (Cipralisant) and proxyfan resulted in a range of classifications (antagonist, agonist, and protean) for these compounds. We examined the role that the signaling system, with particular emphasis on the type of G protein, had on the pharmacology observed for H3 ligands. Ligands were assessed using assays measuring neurotransmitter release, cAMP, and guanosine 5'-O-(3-[35S]thio)triphosphate ([35S]GTPgammaS) binding. Whereas clobenpropit and ciproxifan were consistently antagonists, GT-2331, proxyfan, and imetit exhibited differential activity. Although GT-2331 and proxyfan exhibited little agonist activity in neurotransmitter release assays, both demonstrated full agonism relative to (R)-alpha-methylhistamine in cAMP assays. In [35S]GTPgammaS binding assays, GT-2331 and proxyfan demonstrated partial agonism. Imetit showed full agonism in most assays, but it was slightly less efficacious in a neurotransmitter release assay and in [35S]GTPgammaS binding at the human H3 receptor. To further examine these ligands, we coexpressed G alpha16 or chimeric G alpha q/i5 in human embryonic kidney cells expressing the human H3 receptor and assayed intracellular calcium and cAMP levels. GT-2331, proxyfan, and imetit demonstrated full agonism in all assays of cAMP activity. However, in cells expressing G alpha16, they exhibited minimal agonism in calcium mobilization assays, whereas imetit showed partial agonism. When G alpha q/i5 was used, the activity of both GT-2331 and proxyfan increased, whereas imetit became a full agonist. These results demonstrate that GT-2331 and proxyfan's differential pharmacology at the H3 receptor depends on the type of G protein used and provide indirect evidence for differential ligand-bound active states that mediate signaling by the H3 receptor.