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Submit Review2-Arachidonylglycerol
Description: Endogenous and non-selective CB agonist; potent GPR55 agonist
Alternative Names: 2-AG,Arachidonoylglycerol
Chemical Name: (5Z,8Z,11Z,14Z)-5,8,11,14-Eicosatetraenoic acid, 2-hydroxy-1-(hydroxymethyl)ethyl ester
Biological Activity for 2-Arachidonylglycerol
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 for 2-Arachidonylglycerol
| M. Wt | 378.55 |
| Formula | C23H38O4 |
| Storage | Store at -80°C |
| CAS Number | 53847-30-6 |
| PubChem ID | 5282280 |
| InChI Key | RCRCTBLIHCHWDZ-DOFZRALJSA-N |
| Smiles | O=C(OC(CO)CO)CCC\C=C/C\C=C/C/C=C\C/C=C\CCCCC |
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 2-Arachidonylglycerol
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| ethanol | 37.85 | 100 | |
| DMSO | 37.85 | 100 |
Preparing Stock Solutions for 2-Arachidonylglycerol
The following data is based on the product molecular weight 378.55. 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 | 2.64 mL | 13.21 mL | 26.42 mL |
| 5 mM | 0.53 mL | 2.64 mL | 5.28 mL |
| 10 mM | 0.26 mL | 1.32 mL | 2.64 mL |
| 50 mM | 0.05 mL | 0.26 mL | 0.53 mL |
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Product Datasheets for 2-Arachidonylglycerol
References for 2-Arachidonylglycerol
References are publications that support the biological activity of the product.
Mechoulam et al (1995) Identification of an endogenous 2-monoglyceride, present in canine gut, that binds to cannabinoid receptors. Biochem.Pharmacol. 50 83 PMID: 7605349
Ryberg et al (2007) The orphan receptor GPR55 is a novel cannabinoid receptor. Br.J.Pharmacol. 152 1092 PMID: 17876302
Sugiura et al (1999) Evidence that the cannabinoid CB1 receptor is a 2-arachidonoylglycerol receptor. J.Biol.Chem. 274 2794 PMID: 9915812
Sugiura et al (2000) Evidence that 2-arachidonoylglycerol but not N-palmitoylethanolamine or anandamide is the physiological ligand for the cannabinoid CB2 receptor. J.Biol.Chem. 275 605 PMID: 10617657
Ellermann et al (2020) Endocannabinoids inhibit the induction of virulence in enteric pathogens. Cell PMID: 33031742
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Keywords: 2-Arachidonylglycerol, 2-Arachidonylglycerol supplier, endogenous, cannabinoids, ligand, agonists, non-selective, receptors, cb2r, cb1r, GBR55, CB1, CB2, endocannabinoids, quorum, sensing, QSeC, bacterial, virulence, 2-AG, Arachidonoylglycerol, Non-selective, Cannabinoids, 1298, Tocris Bioscience
22 Citations for 2-Arachidonylglycerol
Citations are publications that use Tocris products. Selected citations for 2-Arachidonylglycerol include:
Lin et al (2014) Diacylglycerol lipase regulates lifespan and oxidative stress response by inversely modulating TOR signaling in Drosophila and C. elegans. Aging Cell 13 755 PMID: 24889782
Flores-Otero et al (2014) Ligand-specific endocytic dwell times control functional selectivity of the cannabinoid receptor 1. Nat Commun 5 4589 PMID: 25081814
Valdeolivas et al (2013) 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. Br J Pharmacol 4 e862 PMID: 24136226
Ellermann et al (2020) Endocannabinoids inhibit the induction of virulence in enteric pathogens. Cell PMID: 33031742
Nogueras-Ortiz (2017) Retromer stops beta-arrestin 1 mediated signaling from internalized cannabinoid 2 receptors. Mol Biol Cell 28 3554 PMID: 28954865
Wu and Tasker (2017) Nongenomic Glucocorticoid Suppression of a Postsynaptic Potassium Current via Emergent Autocrine Endocannabinoid Signaling in Hypothalamic Neuroendocrine Cells following Chronic Dehydration. Eneuro 4 PMID: 28966975
Higgins et al (2013) Differential modulation of nociceptive versus non-nociceptive synapses by endocannabinoids. Mol Pain 9 26 PMID: 23725095
Wang et al (2009) Pretreatment with electroacupuncture induces rapid tolerance to focal cerebral ischemia through regulation of endocannabinoid system. Stroke 40 2157 PMID: 19372445
Guindon et al (2011) Peripheral antinociceptive effects of inhibitors of monoacylglycerol lipase in a rat model of inflammatory pain. Br J Pharmacol 163 1464 PMID: 21198549
Hu et al (2019) Endocannabinoid Signaling Mediates Local Dendritic Coordination between Excitatory and Inhibitory Synapses. Cell Rep 27 666 PMID: 30995465
Won et al (2009) Molecular reconstruction of mGluR5a-mediated endocannabinoid signaling cascade in single rat sympathetic neurons. J Neurosci 29 13603 PMID: 19864572
Yuan and Burrell (2010) Endocannabinoid-dependent LTD in a nociceptive synapse requires activation of a presynaptic TRPV-like receptor. J Neurophysiol 104 2766 PMID: 20884761
Petrosino et al (2016) The anti-inflammatory mediator palmitoylethanolamide enhances the levels of 2-arachidonoyl-glycerol and potentiates its actions at TRPV1 cation channels. Br J Pharmacol 173 1154 PMID: 25598150
Mounsey et al (2015) 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. Pharmacol Res 273 36 PMID: 26244281
Chanda et al (2012) 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. J Cell Biol 287 38041 PMID: 22989885
Khasabova et al (2011) Increasing 2-arachidonoyl glycerol signaling in the periphery attenuates mechanical hyperalgesia in a model of bone cancer pain. J Biol Chem 64 60 PMID: 21440630
Nieri et al (2006) Modulation of P-glycoprotein activity by cannabinoid molecules in HK-2 renal cells. Br J Pharmacol 148 682 PMID: 16715117
Okada et al (2005) Biophysical properties of voltage-gated Na+ channels in frog parathyroid cells and their modulation by cannabinoids. J Exp Biol 208 4747 PMID: 16326956
Ho and Randall (2007) Endothelium-dependent metabolism by endocannabinoid hydrolases and cyclooxygenases limits vasorelaxation to anandamide and 2-arachidonoylglycerol. Exp Neurol 150 641 PMID: 17245358
Carney et al (2009) Cannabinoid regulation of nitric oxide synthase I (nNOS) in neuronal cells. J Neuroimmune Pharmacol 4 338 PMID: 19365734
Ronesi et al (2004) Disruption of endocannabinoid release and striatal long-term depression by postsynaptic blockade of endocannabinoid membrane transport. J Neurosci 24 1673 PMID: 14973237
Williams et al (2003) The FGF receptor uses the endocannabinoid signaling system to couple to an axonal growth response. Proc Natl Acad Sci U S A 160 481 PMID: 12578907
Do you know of a great paper that uses 2-Arachidonylglycerol from Tocris? Please let us know.
Reviews for 2-Arachidonylglycerol
Average Rating: 4 (Based on 1 Review.)
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Great product.
By
Kevin Lorch on 10/05/2022
Assay Type: In Vivo
Species: Other
Used in a bacterial signaling assay to screen for potential sensors of 2-arachidonylglycerol. Very easy to work with, non-toxic to E. coli even at concentrations up to 1 mg/mL. Planning to reorder for some follow-up experiments. Only downside is having to store at -80C.
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.