2-Arachidonylglycerol
Chemical Name: (5Z,8Z,11Z,14Z)-5,8,11,14-Eicosatetraenoic acid, 2-hydroxy-1-(hydroxymethyl)ethyl ester
Biological Activity
2-Arachidonylglycerol is a endogenous cannabinoid ligand that acts as a potent agonist at GPR55 (EC50 values are 3, 519 and 618 nM at GPR55, CB1 and CB2 respectively; Ki values are 472 and 1400 nM at CB1 and CB2 respectively). Found in the brain at concentrations 1000-fold higher than that of anandamide. Effects are enhanced by combined administration with 2-palmitoylglycerol (Cat. No. 2206) in vivo. Also antagonizes bacterial quorum sensing receptor QseC. Protects mice from enteric infection by Enterobacteriaceae pathogens.Technical Data
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.
Background References
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The endocannabinoid/endovanilloid N-arachidonoyl dopamine (NADA) and synthetic cannabinoid WIN55,212-2 abate the inflammatory activation of human endothelial cells.
Wilhelmsen K, Khakpour S, Tran A, Sheehan K, Schumacher M, Xu F, Hellman J
J Biol Chem, 2014;289(19):13079-100. -
The orphan receptor GPR55 is a novel cannabinoid receptor.
Ryberg et al.
Br.J.Pharmacol., 2007;152:1092 -
Identification of an endogenous 2-monoglyceride, present in canine gut, that binds to cannabinoid receptors.
Mechoulam et al.
Biochem.Pharmacol., 1995;50:83 -
Evidence that the cannabinoid CB1 receptor is a 2-arachidonoylglycerol receptor.
Sugiura et al.
J.Biol.Chem., 1999;274:2794 -
Endocannabinoids inhibit the induction of virulence in enteric pathogens.
Ellermann et al.
Cell, 2020; -
Evidence that 2-arachidonoylglycerol but not N-palmitoylethanolamine or anandamide is the physiological ligand for the cannabinoid CB2 receptor.
Sugiura et al.
J.Biol.Chem., 2000;275:605
Product Datasheets
Citations for 2-Arachidonylglycerol
The citations listed below are publications that use Tocris products. Selected citations for 2-Arachidonylglycerol include:
22 Citations: Showing 1 - 10
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Endocannabinoids inhibit the induction of virulence in enteric pathogens.
Authors: Ellermann Et al.
Cell 2020;
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Endocannabinoid Signaling Mediates Local Dendritic Coordination between Excitatory and Inhibitory Synapses.
Authors: Hu Et al.
Cell Rep 2019;27:666
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Nongenomic Glucocorticoid Suppression of a Postsynaptic Potassium Current via Emergent Autocrine Endocannabinoid Signaling in Hypothalamic Neuroendocrine Cells following Chronic Dehydration.
Authors: Wu and Tasker
Eneuro 2017;4
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Retromer stops beta-arrestin 1 mediated signaling from internalized cannabinoid 2 receptors.
Authors: Nogueras-Ortiz
Mol Biol Cell 2017;28(24):3554
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The anti-inflammatory mediator palmitoylethanolamide enhances the levels of 2-arachidonoyl-glycerol and potentiates its actions at TRPV1 cation channels.
Authors: Petrosino Et al.
Br J Pharmacol 2016;173:1154
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Increasing levels of the endocannabinoid 2-AG is neuroprotective in the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine mouse model of Parkinson's disease.
Authors: Mounsey Et al.
Pharmacol Res 2015;273:36
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Ligand-specific endocytic dwell times control functional selectivity of the cannabinoid receptor 1.
Authors: Flores-Otero Et al.
Nat Commun 2014;5:4589
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Diacylglycerol lipase regulates lifespan and oxidative stress response by inversely modulating TOR signaling in Drosophila and C. elegans.
Authors: Lin Et al.
Aging Cell 2014;13:755
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Differential modulation of nociceptive versus non-nociceptive synapses by endocannabinoids.
Authors: Higgins Et al.
Mol Pain 2013;9:26
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The inhibition of 2-arachidonoyl-glycerol (2-AG) biosynthesis, rather than enhancing striatal damage, protects striatal neurons from malonate-induced death: a potential role of cyclooxygenase-2-dependent metabolism of 2-AG.
Authors: Valdeolivas Et al.
Br J Pharmacol 2013;4:e862
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Activation of cannabinoid receptor type 1 (Cb1r) disrupts hepatic Ins receptor signaling via cyclic AMP-response element-binding protein H (Crebh)-mediated induction of Lipin1 gene.
Authors: Chanda Et al.
J Cell Biol 2012;287:38041
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Increasing 2-arachidonoyl glycerol signaling in the periphery attenuates mechanical hyperalgesia in a model of bone cancer pain.
Authors: Khasabova Et al.
J Biol Chem 2011;64:60
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Peripheral antinociceptive effects of inhibitors of monoacylglycerol lipase in a rat model of inflammatory pain.
Authors: Guindon Et al.
Br J Pharmacol 2011;163:1464
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Endocannabinoid-dependent LTD in a nociceptive synapse requires activation of a presynaptic TRPV-like receptor.
Authors: Yuan and Burrell
J Neurophysiol 2010;104:2766
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Cannabinoid regulation of nitric oxide synthase I (nNOS) in neuronal cells.
Authors: Carney Et al.
J Neuroimmune Pharmacol 2009;4:338
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Pretreatment with electroacupuncture induces rapid tolerance to focal cerebral ischemia through regulation of endocannabinoid system.
Authors: Wang Et al.
Stroke 2009;40:2157
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Molecular reconstruction of mGluR5a-mediated endocannabinoid signaling cascade in single rat sympathetic neurons.
Authors: Won Et al.
J Neurosci 2009;29:13603
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Endothelium-dependent metabolism by endocannabinoid hydrolases and cyclooxygenases limits vasorelaxation to anandamide and 2-arachidonoylglycerol.
Authors: Ho and Randall
Exp Neurol 2007;150:641
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Modulation of P-glycoprotein activity by cannabinoid molecules in HK-2 renal cells.
Authors: Nieri Et al.
Br J Pharmacol 2006;148:682
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Biophysical properties of voltage-gated Na+ channels in frog parathyroid cells and their modulation by cannabinoids.
Authors: Okada Et al.
J Exp Biol 2005;208:4747
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Disruption of endocannabinoid release and striatal long-term depression by postsynaptic blockade of endocannabinoid membrane transport.
Authors: Ronesi Et al.
J Neurosci 2004;24:1673
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The FGF receptor uses the endocannabinoid signaling system to couple to an axonal growth response.
Authors: Williams Et al.
Proc Natl Acad Sci U S A 2003;160:481
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