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| Product Name: | AMG 9810 | | Synonyms: | 3-[4-(TERT-BUTYL)PHENYL]-N-(2,3-DIHYDRO-1,4-BENZODIOXIN-6-YL)ACRYLAMIDE;AMG 9810;CS-2548;AMG 9810;AMG-9810;(2E)-N-(2,3-DIHYDRO-1,4-BENZODIOXIN-6-YL)-3-[4-(1,1-DIMETHYLETHYL)PHENYL]-2-PROPENAMIDE;3-(4-tert-Butyl-phenyl)-N-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-acrylamide;9810;(2E)-N-(2,3-Dihydro-1,4-benzodioxin-6-yl)-3-[4-(1,1-dimethylethyl)phenyl]-2-propanamide | | CAS: | 545395-94-6 | | MF: | C21H23NO3 | | MW: | 337.41 | | EINECS: | | | Product Categories: | Vanilloid/TRPV channel | | Mol File: | 545395-94-6.mol |  |
| | AMG 9810 Chemical Properties |
| Boiling point | 512.5±50.0 °C(Predicted) | | density | 1.175±0.06 g/cm3(Predicted) | | storage temp. | 2-8°C | | solubility | DMSO: >5mg/mL | | form | powder | | pka | 12.22±0.20(Predicted) | | color | white to beige | | InChI | 1S/C21H23NO3/c1-21(2,3)16-7-4-15(5-8-16)6-11-20(23)22-17-9-10-18-19(14-17)25-13-12-24-18/h4-11,14H,12-13H2,1-3H3,(H,22,23)/b11-6+ | | InChIKey | GZTFUVZVLYUPRG-IZZDOVSWSA-N | | SMILES | CC(C)(C)c1ccc(\C=C\C(=O)Nc2ccc3OCCOc3c2)cc1 |
| Hazard Codes | Xn | | Risk Statements | 22 | | WGK Germany | 3 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Oral
Aquatic Chronic 4 |
| | AMG 9810 Usage And Synthesis |
| In vivo | AMG9810 is effective at preventing capsaicin-induced eye wiping in a dose-dependent manner, and it reverses thermal and mechanical hyperalgesia in a model of inflammatory pain induced by intraplantar injection of complete Freund's adjuvant. At effective doses, AMG9810 does not show any significant effects on motor function. AMG9810 is the first cinnamide TRPV1 antagonist reported to block capsaicin-induced eye wiping behavior and reverse hyperalgesia in an animal model of inflammatory pain. AMG9810, promotes mouse skin tumor development. The topical application of AMG9810 results in a significant increase in the expression level of the epidermal growth factor receptor (EGFR) and its downstream Akt/mammalian target of rapamycin (mTOR)-signaling pathway. | | Description | AMG 9810 is a competitive antagonist of capsaicin activation of the vanilloid receptor 1 (TRPV1) (IC50s = 24.5 and 85.6 nM for human and rat, respectively). Additionally, it has been shown to compete with other modes of TRPV1 activation, including protons (IC50s = 92.7 and 294 nM for human and rat, respectively), heat (IC50s = 15.8 and 21 nM for human and rat, respectively), and the endogenous ligands: anandamide, N-arachidonyl dopamine (IC50s = 8.5 and 260 nM for human and rat, respectively), and oleoyldopamine. In a rat model of inflammatory pain induced by intraplantar injection of complete Freund’s adjuvant, 30-100 mg/kg AMG 9810 reverses thermal and mechanical hyperalgesia. | | Uses | AMG 9810 is a competitive antagonist of capsaicin activation of the vanilloid receptor 1 (TRPV1) (IC50s = 24.5 and 85.6 nM for human and rat, respectively). Additionally, it has been shown to compete with other modes of TRPV1 activation, including protons (IC50s = 92.7 and 294 nM for human and rat, respectively), heat (IC50s = 15.8 and 21 nM for human and rat, respectively), and the endogenous ligands: anandamide, N-arachidonyl dopamine (IC50s = 8.5 and 260 nM for human and rat, respectively), and oleoyldopamine. In a rat model of inflammatory pain induced by intraplantar injection of complete Freund’s adjuvant, 30-100 mg/kg AMG 9810 reverses thermal and mechanical hyperalgesia.[Cayman Chemical] | | Definition | ChEBI: 3-(4-tert-butylphenyl)-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-propenamide is a member of cinnamamides and a secondary carboxamide. | | Biological Activity | AMG 9810 is a potent and selective, competitive vanilloid TRPV1 receptor antagonist (IC 50 = 17 nM). Inhibits capsaicin-, proton-, heat- and endogenous ligand-induced activation of human and rat recombinant TRPV1 receptors. Displays antihyperalgesic properties in a rat model of inflammatory pain. | | Biochem/physiol Actions | AMG 9810is the cinnamide TRPV1 (vanilloid receptor 1) antagonist, that can prevent eye wiping behavior, stimulated by capsaicin and can inverse hyperalgesia in an animal model of inflammatory pain. It possesses antihyperalgesic properties. | | storage | +4°C (desiccate) | | references | [1]. gavva nr, tamir r, qu y, et al. amg 9810 [(e)-3-(4-t-butylphenyl)-n-(2, 3-dihydrobenzo[b][1,4] dioxin-6-yl)acrylamide], a novel vanilloid receptor 1 (trpv1) antagonist with antihyperalgesic properties. j pharmacol exp ther, 2005, 313(1):474-84. |
| | AMG 9810 Preparation Products And Raw materials |
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