JWH 133 - CAS 259869-55-1
Category: Inhibitor
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Molecular Formula:
C22H32O
Molecular Weight:
312.49
COA:
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Targets:
Cannabinoid Receptor
Description:
JWH 133 is a synthetic cannabinoid and acts as a potent CB2 selective agonist with Ki value of 3.4 nM. It is used to synthesize CB2-selective cannabinoid receptor ligands. It is active in vivo and reduces spasticity in a murine model of multiple sclerosis.
Purity:
≥98% by HPLC
Synonyms:
JWH-133; JWH 133; JWH133. (6aR,10aR)-3-(1,1-Dimethylbutyl)-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran; 3-(1,1-dimethylbutyl)-6aR,7,10,10aR-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran
MSDS:
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InChIKey:
YSBFLLZNALVODA-RBUKOAKNSA-N
InChI:
InChI=1S/C22H32O/c1-7-12-21(3,4)16-9-10-17-18-13-15(2)8-11-19(18)22(5,6)23-20(17)14-16/h8-10,14,18-19H,7,11-13H2,1-6H3/t18-,19+/m0/s1
Canonical SMILES:
CCCC(C)(C)C1=CC2=C(C=C1)C3CC(=CCC3C(O2)(C)C)C
1.The Cannabinoid Receptor 2 Protects Against Alcoholic Liver Disease Via a Macrophage Autophagy-Dependent Pathway.
Denaës T;Lodder J;Chobert MN;Ruiz I;Pawlotsky JM;Lotersztajn S;Teixeira-Clerc F Sci Rep. 2016 Jun 27;6:28806. doi: 10.1038/srep28806.
Kupffer cells, the resident macrophages of the liver, play a major role in the pathogenesis of alcoholic liver disease. We have previously demonstrated that CB2 receptor protects against alcoholic liver disease by inhibiting alcohol-induced inflammation and steatosis via the regulation of Kupffer cell activation. Here, we explored the mechanism underlying these effects and hypothesized that the anti-inflammatory properties of CB2 receptor in Kupffer cells rely on activation of autophagy. For this purpose, mice invalidated for CB2 receptor (CB2(Mye-/-) mice) or for the autophagy gene ATG5 (ATG5(Mye-/-) mice) in the myeloid lineage, and their littermate wild-type mice were subjected to chronic-plus-binge ethanol feeding. CB2(Mye-/-) mice showed exacerbated alcohol-induced pro-inflammatory gene expression and steatosis. Studies in cultured macrophages demonstrated that CB2 receptor activation by JWH-133 stimulated autophagy via a heme oxygenase-1 dependent pathway. Moreover, JWH-133 reduced the induction of inflammatory genes by lipopolysaccharide in wild-type macrophages, but not in ATG5-deficient cells. The CB2 agonist also protected from alcohol-induced liver inflammation and steatosis in wild-type mice, but not in ATG5(Mye-/-) mice demonstrating that macrophage autophagy mediates the anti-inflammatory and anti-steatogenic effects of CB2 receptor.
2.The effect of cannabinoids on dinitrofluorobenzene-induced experimental asthma in mice.
Bozkurt TE;Kaya Y;Durlu-Kandilci NT;Onder S;Sahin-Erdemli I Respir Physiol Neurobiol. 2016 Sep;231:7-13. doi: 10.1016/j.resp.2016.05.012. Epub 2016 May 20.
Cannabinoids have anti-inflammatory effects and can produce bronchodilation in the airways. We have investigated the effects of cannabinoids on tracheal hyperreactivity and airway inflammation in dinitrofluorobenzene (DNFB)-induced experimental non-atopic asthma in mice. 5-hydroxytryptamine (5-HT)-induced contraction response was enhanced while carbachol- and electrical field stimulation-induced contractions, and isoprenaline-induced relaxation responses were remained unchanged in DNFB group. The increased 5-HT-induced contractions were inhibited by incubation with either atropine or tetrodotoxin. DNFB application resulted in increased macrophage number in the bronchoalveolar lavage fluid (BALF). In vivo ACEA (CB1 agonist) treatment prevented the increase in 5-HT contractions, while JWH133 (CB2 agonist) had no effect. However, neither ACEA nor JWH133 prevented the increase in macrophage number in BALF. In vitro ACEA incubation also inhibited the increase in 5-HT contraction in DNFB group. These results show that cannabinoid CB1 receptor agonist can prevent tracheal hyperreactivity to 5-HT in DNFB-induced non-atopic asthma in mice.
3.Correlations between the Memory-Related Behavior and the Level of Oxidative Stress Biomarkers in the Mice Brain, Provoked by an Acute Administration of CB Receptor Ligands.
Kruk-Slomka M;Boguszewska-Czubara A;Slomka T;Budzynska B;Biala G Neural Plast. 2016;2016:9815092. doi: 10.1155/2016/9815092. Epub 2015 Dec 29.
The endocannabinoid system, through cannabinoid (CB) receptors, is involved in memory-related responses, as well as in processes that may affect cognition, like oxidative stress processes. The purpose of the experiments was to investigate the impact of CB1 and CB2 receptor ligands on the long-term memory stages in male Swiss mice, using the passive avoidance (PA) test, as well as the influence of these compounds on the level of oxidative stress biomarkers in the mice brain. A single injection of a selective CB1 receptor antagonist, AM 251, improved long-term memory acquisition and consolidation in the PA test in mice, while a mixed CB1/CB2 receptor agonist WIN 55,212-2 impaired both stages of cognition. Additionally, JWH 133, a selective CB2 receptor agonist, and AM 630, a competitive CB2 receptor antagonist, significantly improved memory. Additionally, an acute administration of the highest used doses of JWH 133, WIN 55,212-2, and AM 630, but not AM 251, increased total antioxidant capacity (TAC) in the brain. In turn, the processes of lipids peroxidation, expressed as the concentration of malondialdehyde (MDA), were more advanced in case of AM 251. Thus, some changes in the PA performance may be connected with the level of oxidative stress in the brain.
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CAS 259869-55-1 JWH 133

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