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259869-55-1,MFCD27920876
Catalog No.:AA002R8A

259869-55-1 | 6H-Dibenzo[b,d]pyran, 3-(1,1-dimethylbutyl)-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-, (6aR,10aR)-

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1mg
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5mg
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$216.00   $151.00
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10mg
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  • Technical Information
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA002R8A
Chemical Name:
6H-Dibenzo[b,d]pyran, 3-(1,1-dimethylbutyl)-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-, (6aR,10aR)-
CAS Number:
259869-55-1
Molecular Formula:
C22H32O
Molecular Weight:
312.4889
MDL Number:
MFCD27920876
SMILES:
CCCC(c1ccc2c(c1)OC([C@H]1[C@H]2CC(=CC1)C)(C)C)(C)C
Properties
Computed Properties
 
Complexity:
459  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Heavy Atom Count:
23  
Hydrogen Bond Acceptor Count:
1  
Rotatable Bond Count:
3  
XLogP3:
6.4  

Literature

Title: Inhibition of interleukin-1β-induced endothelial tissue factor expression by the synthetic cannabinoid WIN 55,212-2.

Journal: Oncotarget 20160920

Title: CB2 receptor activation ameliorates the proinflammatory activity in acute lung injury induced by paraquat.

Journal: BioMed research international 20140101

Title: Therapeutic utility of cannabinoid receptor type 2 (CB(2)) selective agonists.

Journal: Journal of medicinal chemistry 20131114

Title: Cannabinoid agonists increase the interaction between β-Arrestin 2 and ERK1/2 and upregulate β-Arrestin 2 and 5-HT(2A) receptors.

Journal: Pharmacological research 20130201

Title: Cannabinoid-induced enhanced interaction and protein levels of serotonin 5-HT(2A) and dopamine D₂ receptors in rat prefrontal cortex.

Journal: Journal of psychopharmacology (Oxford, England) 20121001

Title: Design, synthesis, and pharmacological characterization of indol-3-ylacetamides, indol-3-yloxoacetamides, and indol-3-ylcarboxamides: potent and selective CB2 cannabinoid receptor inverse agonists.

Journal: Journal of medicinal chemistry 20120614

Title: Rational design, synthesis and anti-proliferative properties of new CB2 selective cannabinoid receptor ligands: an investigation of the 1,8-naphthyridin-2(1H)-one scaffold.

Journal: European journal of medicinal chemistry 20120601

Title: The activation of the cannabinoid receptor type 2 reduces neutrophilic protease-mediated vulnerability in atherosclerotic plaques.

Journal: European heart journal 20120401

Title: Activation of cannabinoid receptor 2 attenuates leukocyte-endothelial cell interactions and blood-brain barrier dysfunction under inflammatory conditions.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20120321

Title: Cannabinoid receptor-2 (CB2) agonist ameliorates colitis in IL-10(-/-) mice by attenuating the activation of T cells and promoting their apoptosis.

Journal: Toxicology and applied pharmacology 20120115

Title: Prolonged oral cannabinoid administration prevents neuroinflammation, lowers β-amyloid levels and improves cognitive performance in Tg APP 2576 mice.

Journal: Journal of neuroinflammation 20120101

Title: Discovery and optimization of 1-(4-(pyridin-2-yl)benzyl)imidazolidine-2,4-dione derivatives as a novel class of selective cannabinoid CB2 receptor agonists.

Journal: Journal of medicinal chemistry 20111027

Title: Antinociceptive effects induced through the stimulation of spinal cannabinoid type 2 receptors in chronically inflamed mice.

Journal: European journal of pharmacology 20111001

Title: Fluorinated cannabinoid CB2 receptor ligands: synthesis and in vitro binding characteristics of 2-oxoquinoline derivatives.

Journal: Bioorganic & medicinal chemistry 20110915

Title: Brain cannabinoid CB₂ receptors modulate cocaine's actions in mice.

Journal: Nature neuroscience 20110901

Title: Cannabinoid receptor agonists modulate oligodendrocyte differentiation by activating PI3K/Akt and the mammalian target of rapamycin (mTOR) pathways.

Journal: British journal of pharmacology 20110801

Title: The endocannabinoid system in rat gliosomes and its role in the modulation of glutamate release.

Journal: Cellular and molecular life sciences : CMLS 20110301

Title: Three-dimensional quantitative structure-selectivity relationships analysis guided rational design of a highly selective ligand for the cannabinoid receptor 2.

Journal: European journal of medicinal chemistry 20110201

Title: Cannabinoid receptor 2 and its agonists mediate hematopoiesis and hematopoietic stem and progenitor cell mobilization.

Journal: Blood 20110120

Title: Cannabinoid receptor 2 signaling does not modulate atherogenesis in mice.

Journal: PloS one 20110101

Title: Evaluation of cannabinoid receptor 2 and metabotropic glutamate receptor 1 functional responses using a cell impedance-based technology.

Journal: Journal of biomolecular screening 20101201

Title: 1-Bromo-3-(1',1'-dimethylalkyl)-1-deoxy-Δ(8)-tetrahydrocannabinols: New selective ligands for the cannabinoid CB(2) receptor.

Journal: Bioorganic & medicinal chemistry 20101115

Title: Beneficial paracrine effects of cannabinoid receptor 2 on liver injury and regeneration.

Journal: Hepatology (Baltimore, Md.) 20100901

Title: Emerging targets in osteoporosis disease modification.

Journal: Journal of medicinal chemistry 20100610

Title: Involvement of cannabinoid-1 and cannabinoid-2 receptors in septic ileus.

Journal: Neurogastroenterology and motility : the official journal of the European Gastrointestinal Motility Society 20100301

Title: Activation of the cannabinoid 2 receptor (CB2) protects against experimental colitis.

Journal: Inflammatory bowel diseases 20091101

Title: Synthetic cannabinoid receptor agonists inhibit tumor growth and metastasis of breast cancer.

Journal: Molecular cancer therapeutics 20091101

Title: Constitutive activity of cannabinoid-2 (CB2) receptors plays an essential role in the protean agonism of (+)AM1241 and L768242.

Journal: British journal of pharmacology 20090901

Title: Functional CB2 type cannabinoid receptors at CNS synapses.

Journal: Neuropharmacology 20090901

Title: Rational design, synthesis, and pharmacological properties of new 1,8-naphthyridin-2(1H)-on-3-carboxamide derivatives as highly selective cannabinoid-2 receptor agonists.

Journal: Journal of medicinal chemistry 20090625

Title: CB(2) cannabinoid receptor activation is cardioprotective in a mouse model of ischemia/reperfusion.

Journal: Journal of molecular and cellular cardiology 20090501

Title: CB1 cannabinoid receptor-dependent and -independent inhibition of depolarization-induced calcium influx in oligodendrocytes.

Journal: Glia 20090201

Title: Cannabinoid CB2 receptor potentiates obesity-associated inflammation, insulin resistance and hepatic steatosis.

Journal: PloS one 20090101

Title: The preventive effect of cannabinoids on reperfusion-induced ischemia of mouse kidney.

Journal: Experimental and toxicologic pathology : official journal of the Gesellschaft fur Toxikologische Pathologie 20080801

Title: Cannabinoid CB(1) receptor activation modulates spontaneous contractile activity in mouse ileal longitudinal muscle.

Journal: European journal of pharmacology 20080317

Title: Cannabinoids inhibit glioma cell invasion by down-regulating matrix metalloproteinase-2 expression.

Journal: Cancer research 20080315

Title: Regression of fibrosis after chronic stimulation of cannabinoid CB2 receptor in cirrhotic rats.

Journal: The Journal of pharmacology and experimental therapeutics 20080201

Title: Down-regulation of tissue inhibitor of metalloproteinases-1 in gliomas: a new marker of cannabinoid antitumoral activity?

Journal: Neuropharmacology 20080101

Title: Cannabinoid-mediated neuroprotection, not immunosuppression, may be more relevant to multiple sclerosis.

Journal: Journal of neuroimmunology 20080101

Title: Cannabinoid CB(2) receptor activation prevents bronchoconstriction and airway oedema in a model of gastro-oesophageal reflux.

Journal: European journal of pharmacology 20071114

Title: Influence of nicotinic receptor modulators on CB2 cannabinoid receptor agonist (JWH133)-induced antinociception in mice.

Journal: Behavioural pharmacology 20071101

Title: Pharmacomodulations around the 4-oxo-1,4-dihydroquinoline-3-carboxamides, a class of potent CB2-selective cannabinoid receptor ligands: consequences in receptor affinity and functionality.

Journal: Journal of medicinal chemistry 20071101

Title: Anti-inflammatory property of the cannabinoid receptor-2-selective agonist JWH-133 in a rodent model of autoimmune uveoretinitis.

Journal: Journal of leukocyte biology 20070901

Title: Involvement of CB1 and CB2 receptors in the modulation of cholinergic neurotransmission in mouse gastric preparations.

Journal: Pharmacological research 20070901

Title: Mechanisms for the coupling of cannabinoid receptors to intracellular calcium mobilization in rat insulinoma beta-cells.

Journal: Experimental cell research 20070815

Title: Temporal variation in CB2R levels following T lymphocyte activation: evidence that cannabinoids modulate CXCL12-induced chemotaxis.

Journal: International immunopharmacology 20070301

Title: Design, synthesis, and biological evaluation of new 1,8-naphthyridin-4(1H)-on-3-carboxamide and quinolin-4(1H)-on-3-carboxamide derivatives as CB2 selective agonists.

Journal: Journal of medicinal chemistry 20061005

Title: Agonists of cannabinoid receptor 1 and 2 inhibit experimental colitis induced by oil of mustard and by dextran sulfate sodium.

Journal: American journal of physiology. Gastrointestinal and liver physiology 20060801

Title: Novel 4-oxo-1,4-dihydroquinoline-3-carboxamide derivatives as new CB2 cannabinoid receptors agonists: synthesis, pharmacological properties and molecular modeling.

Journal: Journal of medicinal chemistry 20060112

Title: The cannabinoid CB2 receptor selective agonist JWH133 reduces mast cell oedema in response to compound 48/80 in vivo but not the release of beta-hexosaminidase from skin slices in vitro.

Journal: Life sciences 20060102

Title: Activation of CB1 and CB2 receptors attenuates the induction and maintenance of inflammatory pain in the rat.

Journal: Pain 20051205

Title: Inhibitory effects of CB1 and CB2 receptor agonists on responses of DRG neurons and dorsal horn neurons in neuropathic rats.

Journal: The European journal of neuroscience 20050701

Title: Activation of cannabinoid CB2 receptor negatively regulates IL-12p40 production in murine macrophages: role of IL-10 and ERK1/2 kinase signaling.

Journal: British journal of pharmacology 20050601

Title: Prevention of Alzheimer's disease pathology by cannabinoids: neuroprotection mediated by blockade of microglial activation.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20050223

Title: Cannabinoid CB2 receptor activation inhibits mechanically evoked responses of wide dynamic range dorsal horn neurons in naïve rats and in rat models of inflammatory and neuropathic pain.

Journal: The European journal of neuroscience 20041101

Title: Cannabinoids inhibit the vascular endothelial growth factor pathway in gliomas.

Journal: Cancer research 20040815

Title: Anandamide is an endogenous inhibitor for the migration of tumor cells and T lymphocytes.

Journal: Cancer immunology, immunotherapy : CII 20040801

Title: Pharmacologic interaction between cannabinoid and either clonidine or neostigmine in the rat formalin test.

Journal: Anesthesiology 20030901

Title: Inhibition of guinea-pig and human sensory nerve activity and the cough reflex in guinea-pigs by cannabinoid (CB2) receptor activation.

Journal: British journal of pharmacology 20030901

Title: Topically administered CB(2)-receptor agonist, JWH-133, does not decrease intraocular pressure (IOP) in normotensive rabbits.

Journal: Life sciences 20030103

Title: Inhibition of skin tumor growth and angiogenesis in vivo by activation of cannabinoid receptors.

Journal: The Journal of clinical investigation 20030101

Title: Inhibition of glioma growth in vivo by selective activation of the CB(2) cannabinoid receptor.

Journal: Cancer research 20010801

Title: Cannabinoid receptor ligands: clinical and neuropharmacological considerations, relevant to future drug discovery and development.

Journal: Expert opinion on investigational drugs 20000701

Title: 3-(1',1'-Dimethylbutyl)-1-deoxy-delta8-THC and related compounds: synthesis of selective ligands for the CB2 receptor.

Journal: Bioorganic & medicinal chemistry 19991201

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Tags:259869-55-1 Molecular Formula|259869-55-1 MDL|259869-55-1 SMILES|259869-55-1 6H-Dibenzo[b,d]pyran, 3-(1,1-dimethylbutyl)-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-, (6aR,10aR)-