JWH 133

Cat. No. 1343

JWH 133 C22H32O [259869-55-1]

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Chemical Name: (6aR,10aR)-3-(1,1-Dimethylbutyl)-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran

Biological Activity

Potent CB2 selective agonist (Ki = 3.4 nM). Approx. 200-fold selective over CB1 receptors. Active in vivo, reducing spasticity in a murine model of multiple sclerosis. Activity also enhances the release of IL-10 by LPS/IFN-γ-stimulated macrophages and results in downregulation of the IL-12 subunit p40. Also available in water soluble emulsion (Cat. No. 1783).

Technical Data

M.Wt:
312.49
Formula:
C22H32O
Solubility:
Soluble to 100 mM in ethanol and to 50 mM in DMSO with gentle warming
Purity:
>98 %
Storage:
Store at +4°C
CAS No:
259869-55-1

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
All Tocris products are intended for laboratory research use only.

Certificate of Analysis / Product Datasheet / Safety Data Sheet

Certificate of Analysis / Product Datasheet
Select another batch:

Correa et al (2005) Activation of cannabinoid CB2 receptor negatively regulates IL-12p40 production in murine macrophages: role of IL-10 and ERK1/2 kinase signaling. Br.J.Pharmacol. 145 441. PMID: 15821753.

Baker et al (2000) Cannabinoids control spasticity and tremor in a multiple sclerosis model. Nature 404 84. PMID: 10716447.

Huffman et al (1999) 3-(1'-Dimethylbutyl)-1-deoxy-Δ8-THC and related compounds: synthesis of selective ligands for the CB2 receptor. Bioorg.Med.Chem. 7 2905. PMID: 10658595.

Pertwee (1999) Pharmacology of cannabinoid receptor ligands. Curr.Med.Chem. 6 635. PMID: 10469884.

If you know of a relevant reference for this product please let us know.

Citations are publications that use Tocris products. Selected citations for JWH 133 include:

Huang et al (2016) Cannabinoid receptor subtype 2 (CB2R) agonist, GW405833 reduces agonist-induced Ca2+ oscillations in mouse pancreatic acinar cells Scientific Reports 6 29757. PMID: 27432473.

Kruk-Slomka et al (2016) 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. Neural Plast 2016 9815092. PMID: 26839719.

Presley et al (2015) Preclinical evaluation of SMM-189, a cannabinoid receptor 2-specific inverse agonist. Eur Heart J 3 e00159. PMID: 26196013.

Rivera et al (2015) Pharmacological activation of CB2 receptors counteracts the deleterious effect of ethanol on cell proliferation in the main neurogenic zones of the adult rat brain. Front Cell Neurosci 9 379. PMID: 26483633.

Zhou et al (2015) Regional effects of endocannabinoid, BDNF and FGF receptor signalling on neuroblast motility and guidance along the rostral migratory stream. Pharmacol Res Perspect 64 32. PMID: 25481343.

Amenta et al (2014) Cannabinoid receptor type-2 stimulation, blockade, and deletion alters the vascular inflammatory responses to traumatic brain injury. J Neuroimmune Pharmacol 11 191. PMID: 25416141.

Carrillo-Salinas et al (2014) A cannabigerol derivative suppresses immune responses and protects mice from experimental autoimmune encephalomyelitis. PLoS One 9 e94733. PMID: 24727978.

Williams et al (2014) △(9)-Tetrahydrocannabinol treatment during human monocyte differentiation reduces macrophage susceptibility to HIV-1 infection. J Biol Chem 9 369. PMID: 24562630.

Fraga-Silva et al (2013) Treatment with CB2 agonist JWH-133 reduces histological features associated with erectile dysfunction in hypercholesterolemic mice. Clin Dev Immunol 2013 263846. PMID: 24302957.

Malenczyk et al (2013) CB1 cannabinoid receptors couple to focal adhesion kinase to control insulin release. J Biol Chem 288 32685. PMID: 24089517.

Marini et al (2013) Characterization of cannabinoid receptor ligands in tissues natively expressing cannabinoid CB2 receptors. Br J Pharmacol 169 887. PMID: 23711022.

García-Gutiérrez et al (2012) Chronic blockade of cannabinoid CB2 receptors induces anxiolytic-like actions associated with alterations in GABA(A) receptors. Br J Pharmacol 165 951. PMID: 21838753.

Molica et al (2012) Cannabinoid receptor CB2 protects against balloon-induced neointima formation. Am J Physiol Heart Circ Physiol 302 H1064. PMID: 22227125.

Montecucco et al (2012) The activation of the cannabinoid receptor type 2 reduces neutrophilic protease-mediated vulnerability in atherosclerotic plaques. FASEB J 33 846. PMID: 22112961.

Kimball et al (2010) Small intestinal cannabinoid receptor changes following a single colonic insult with oil of mustard in mice. Front Pharmacol 1 132. PMID: 21779244.

Trazzi et al (2010) CB1 cannabinoid receptors increase neuronal precursor proliferation through AKT/glycogen synthase kinase-3β/β-catenin signaling. Br J Pharmacol 285 10098. PMID: 20083607.

Defer et al (2009) The cannabinoid receptor type 2 promotes cardiac myocyte and fibroblast survival and protects against ischemia/reperfusion-induced cardiomyopathy. PLoS One 23 2120. PMID: 19246487.

Deveaux et al (2009) Cannabinoid CB2 receptor potentiates obesity-associated inflammation, insulin resistance and hepatic steatosis. J Neuroinflammation 4 e5844. PMID: 19513120.

Montecucco et al (2008) CB2 cannabinoid receptor agonist JWH-015 modulates human monocyte migration through defined intracellular signaling pathways. Am J Physiol Heart Circ Physiol 294 H1145. PMID: 18178718.

Rajesh et al (2008) CB2 cannabinoid receptor agonists attenuate TNF-alpha-induced human vascular smooth muscle cell proliferation and migration. Br J Pharmacol 153 347. PMID: 17994109.

Mukhopadhyay et al (2007) Pharmacological inhibition of CB1 cannabinoid receptor protects against doxorubicin-induced cardiotoxicity. J Am Coll Cardiol 50 528. PMID: 17678736.

Rajesh et al (2007) CB2-receptor stimulation attenuates TNF-alpha-induced human endothelial cell activation, transendothelial migration of monocytes, and monocyte-endothelial adhesion. Am J Physiol Heart Circ Physiol 293 H2210. PMID: 17660390.

Correa et al (2005) Activation of cannabinoid CB2 receptor negatively regulates IL-12p40 production in murine macrophages: role of IL-10 and ERK1/2 kinase signaling. Br J Pharmacol 145 441. PMID: 15821753.

Mathison et al (2004) Effects of cannabinoid receptor-2 activation on accelerated gastrointestinal transit in lipopolysaccharide-treated rats. Br J Pharmacol 142 1247. PMID: 15249429.

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Keywords: JWH 133, supplier, Potent, selective, CB2, agonists, cannabinoid, receptors, JWH133, cb2r, Tocris Bioscience, CB2 Receptor Agonist products

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