Catalog Number: 1343
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.

Water Soluble Emulsion also available.

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.
Additional Information
Other Product-Specific Information:
Background References
  1. Pharmacology of cannabinoid receptor ligands.
    Pertwee
    Curr.Med.Chem., 1999;6:635
  2. Cannabinoids control spasticity and tremor in a multiple sclerosis model.
    Baker et al.
    Nature, 2000;404:84
  3. Activation of cannabinoid CB2 receptor negatively regulates IL-12p40 production in murine macrophages: role of IL-10 and ERK1/2 kinase signaling.
    Correa et al.
    Br.J.Pharmacol., 2005;145:441
  4. 3-(1'-Dimethylbutyl)-1-deoxy-Δ8-THC and related compounds: synthesis of selective ligands for the CB2 receptor.
    Huffman et al.
    Bioorg.Med.Chem., 1999;7:2905
Citations:

The citations listed below are publications that use Tocris products. Selected citations for JWH 133 include:

24 Citations: Showing 1 - 10
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  1. Cannabinoid receptor subtype 2 (CB2R) agonist, GW405833 reduces agonist-induced Ca2+ oscillations in mouse pancreatic acinar cells
    Authors: Huang Et al.
    Scientific Reports 2016;6:29757
  2. 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.
    Authors: Kruk-Slomka Et al.
    Neural Plast 2016;2016:9815092
  3. Pharmacological activation of CB2 receptors counteracts the deleterious effect of ethanol on cell proliferation in the main neurogenic zones of the adult rat brain.
    Authors: Rivera Et al.
    Front Cell Neurosci 2015;9:379
  4. Regional effects of endocannabinoid, BDNF and FGF receptor signalling on neuroblast motility and guidance along the rostral migratory stream.
    Authors: Zhou Et al.
    Pharmacol Res Perspect 2015;64:32
  5. Preclinical evaluation of SMM-189, a cannabinoid receptor 2-specific inverse agonist.
    Authors: Presley Et al.
    Eur Heart J 2015;3:e00159
  6. A cannabigerol derivative suppresses immune responses and protects mice from experimental autoimmune encephalomyelitis.
    Authors: Carrillo-Salinas Et al.
    PLoS One 2014;9:e94733
  7. △(9)-Tetrahydrocannabinol treatment during human monocyte differentiation reduces macrophage susceptibility to HIV-1 infection.
    Authors: Williams Et al.
    J Biol Chem 2014;9:369
  8. Cannabinoid receptor type-2 stimulation, blockade, and deletion alters the vascular inflammatory responses to traumatic brain injury.
    Authors: Amenta Et al.
    J Neuroimmune Pharmacol 2014;11:191
  9. CB1 cannabinoid receptors couple to focal adhesion kinase to control insulin release.
    Authors: Malenczyk Et al.
    J Biol Chem 2013;288:32685
  10. Treatment with CB2 agonist JWH-133 reduces histological features associated with erectile dysfunction in hypercholesterolemic mice.
    Authors: Fraga-Silva Et al.
    Clin Dev Immunol 2013;2013:263846
  11. Characterization of cannabinoid receptor ligands in tissues natively expressing cannabinoid CB2 receptors.
    Authors: Marini Et al.
    Br J Pharmacol 2013;169:887
  12. The activation of the cannabinoid receptor type 2 reduces neutrophilic protease-mediated vulnerability in atherosclerotic plaques.
    Authors: Montecucco Et al.
    FASEB J 2012;33:846
  13. Cannabinoid receptor CB2 protects against balloon-induced neointima formation.
    Authors: Molica Et al.
    Am J Physiol Heart Circ Physiol 2012;302:H1064
  14. Chronic blockade of cannabinoid CB2 receptors induces anxiolytic-like actions associated with alterations in GABA(A) receptors.
    Authors: García-Gutiérrez Et al.
    Br J Pharmacol 2012;165:951
  15. CB1 cannabinoid receptors increase neuronal precursor proliferation through AKT/glycogen synthase kinase-3β/β-catenin signaling.
    Authors: Trazzi Et al.
    Br J Pharmacol 2010;285:10098
  16. Small intestinal cannabinoid receptor changes following a single colonic insult with oil of mustard in mice.
    Authors: Kimball Et al.
    Front Pharmacol 2010;1:132
  17. Cannabinoid CB2 receptor potentiates obesity-associated inflammation, insulin resistance and hepatic steatosis.
    Authors: Deveaux Et al.
    J Neuroinflammation 2009;4:e5844
  18. The cannabinoid receptor type 2 promotes cardiac myocyte and fibroblast survival and protects against ischemia/reperfusion-induced cardiomyopathy.
    Authors: Defer Et al.
    PLoS One 2009;23:2120
  19. CB2 cannabinoid receptor agonist JWH-015 modulates human monocyte migration through defined intracellular signaling pathways.
    Authors: Montecucco Et al.
    Am J Physiol Heart Circ Physiol 2008;294:H1145
  20. CB2 cannabinoid receptor agonists attenuate TNF-alpha-induced human vascular smooth muscle cell proliferation and migration.
    Authors: Rajesh Et al.
    Br J Pharmacol 2008;153:347
  21. Pharmacological inhibition of CB1 cannabinoid receptor protects against doxorubicin-induced cardiotoxicity.
    Authors: Mukhopadhyay Et al.
    J Am Coll Cardiol 2007;50:528
  22. CB2-receptor stimulation attenuates TNF-alpha-induced human endothelial cell activation, transendothelial migration of monocytes, and monocyte-endothelial adhesion.
    Authors: Rajesh Et al.
    Am J Physiol Heart Circ Physiol 2007;293:H2210
  23. Activation of cannabinoid CB2 receptor negatively regulates IL-12p40 production in murine macrophages: role of IL-10 and ERK1/2 kinase signaling.
    Authors: Correa Et al.
    Br J Pharmacol 2005;145:441
  24. Effects of cannabinoid receptor-2 activation on accelerated gastrointestinal transit in lipopolysaccharide-treated rats.
    Authors: Mathison Et al.
    Br J Pharmacol 2004;142:1247
Expand to show all 24 Citations
Average Rating: 5 (Based on 1 review)

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