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Submit ReviewJWH 133
Description: Potent and selective CB2 agonist
Chemical Name: (6aR,10aR)-3-(1,1-Dimethylbutyl)-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran
Purity: ≥98% (HPLC)
Biological Activity for JWH 133
JWH 133 is a 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.
Technical Data for JWH 133
| M. Wt | 312.49 |
| Formula | C22H32O |
| Storage | Store at -20°C |
| Purity | ≥98% (HPLC) |
| CAS Number | 259869-55-1 |
| PubChem ID | 6918505 |
| InChI Key | YSBFLLZNALVODA-RBUKOAKNSA-N |
| Smiles | [H][C@]([C@]3([H])C(C)(C)O2)(CC(C)=CC3)C1=C2C=C(C(C)(C)CCC)C=C1 |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for JWH 133
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| ethanol | 31.25 | 100 | |
| DMSO | 6.25 | 20 |
Preparing Stock Solutions for JWH 133
The following data is based on the product molecular weight 312.49. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 3.2 mL | 16 mL | 32 mL |
| 5 mM | 0.64 mL | 3.2 mL | 6.4 mL |
| 10 mM | 0.32 mL | 1.6 mL | 3.2 mL |
| 50 mM | 0.06 mL | 0.32 mL | 0.64 mL |
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Product Datasheets for JWH 133
References for JWH 133
References are publications that support the biological activity of the product.
Baker et al (2000) Cannabinoids control spasticity and tremor in a multiple sclerosis model. Nature 404 84 PMID: 10716447
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
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 JWH 133, please let us know.
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Keywords: JWH 133, JWH 133 supplier, Potent, selective, CB2, agonists, cannabinoid, receptors, JWH133, cb2r, Receptors, 1343, Tocris Bioscience
37 Citations for JWH 133
Citations are publications that use Tocris products. Selected citations for JWH 133 include:
Hohmann et al (2019) On the influence of cannabinoids on cell morphology and motility of glioblastoma cells. PLoS One 14 e0212037 PMID: 30753211
Hytti (2017) CB2 receptor activation causes an ERK1/2-dependent inflammatory response in human RPE cells. Sci Rep 7 16169 PMID: 29170454
De Domenico (2017) Overactive type 2 cannabinoid receptor induces meiosis in fetal gonads and impairs ovarian reserve. Cell Death Dis 8 e3085 PMID: 28981118
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
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
Marini et al (2013) Characterization of cannabinoid receptor ligands in tissues natively expressing cannabinoid CB2 receptors. Br J Pharmacol 169 887 PMID: 23711022
Malenczyk et al (2013) CB1 cannabinoid receptors couple to focal adhesion kinase to control Ins release. J Biol Chem 288 32685 PMID: 24089517
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, Ins resistance and hepatic steatosis. J Neuroinflammation 4 e5844 PMID: 19513120
Sheng et al (2019) Antiallodynic Effects of Cannabinoid Receptor 2 (CB2R) Agonists on Retrovirus Infection-Induced Neuropathic Pain. Pain Res Manag 2019 1260353 PMID: 31354896
Fu (2017) Activation of cannabinoid receptor type 2 by JWH133 alleviates bleomycin-induced pulmonary fibrosis in mice. Oncotarget 8 103486 PMID: 29262578
Martínez-Martínez et al (2015) Cannabinoids receptor type 2, CB2, expression correlates with human colon cancer progression and predicts patient survival. Oncoscience 2 131 PMID: 25859556
Kazemi et al (2012) Effect of cannabinoid receptor activation on spreading depression. Iran J Basic Med Sci 15 926 PMID: 23493641
Navarrete et al (2012) Cannabinoid CB? receptor-mediated regulation of impulsive-like behaviour in DBA/2 mice. Br J Pharmacol 165 260 PMID: 21671903
Acevedo-Canabal et al (2019) Altered Swimming Behaviors in Zebrafish Larvae Lacking Cannabinoid Receptor 2. Cannabis Cannabinoid Res 4 88 PMID: 31236475
Khan et al (2018) Involvement of the CB2 cannabinoid receptor in cell growth inhibition and G0/G1 cell cycle arrest via the cannabinoid agonist WIN 55,212-2 in renal cell carcinoma. BMC Cancer 18 583 PMID: 29792186
Rossi et al (2013) The cannabinoid receptor type 2 as mediator of mesenchymal stromal cell immunosuppressive properties. PLoS One 8 e80022 PMID: 24312195
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
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
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
Presley et al (2015) Preclinical evaluation of SMM-189, a cannabinoid receptor 2-specific inverse agonist. Eur Heart J 3 e00159 PMID: 26196013
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
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
Balleza-Tapia et al (2018) TrpV1 receptor activation rescues neuronal function and network gamma oscillations from Aβ-induced impairment in mouse hippocampus in vitro. Elife 7 PMID: 30417826
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
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
Carrillo-Salinas et al (2014) A cannabigerol derivative suppresses immune responses and protects mice from experimental autoimmune encephalomyelitis. PLoS One 9 e94733 PMID: 24727978
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
Mukhopadhyay et al (2007) Pharmacological inhibition of CB1 cannabinoid receptor protects against doxorubicin-induced cardiotoxicity. J Am Coll Cardiol 50 528 PMID: 17678736
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
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
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
Underdown et al (2005) Anandamide reduces infarct size in rat isolated hearts subjected to ischaemia-reperfusion by a novel cannabinoid mechanism. Br J Pharmacol 146 809 PMID: 16158067
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Literature in this Area
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Cannabinoid Receptor Ligands Scientific Review
Written by Roger Pertwee, this review discusses compounds which affect the activity of the endocannabinoid system, focusing particularly on ligands that are most widely used as experimental tools and denotes compounds available from Tocris.