2-Arachidonylglycerol

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Cat.No. 1298 - 2-Arachidonylglycerol | C23H38O4 | CAS No. 53847-30-6
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
Datasheet
Citations (18)
Reviews
Literature

Biological Activity

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.

Technical Data

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

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
ethanol 37.85 100
DMSO 37.85 100

Preparing Stock Solutions

The following data is based on the product molecular weight 378.55. Batch specific molecular weights may vary from batch to batch due to solvent 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

Certificate of Analysis / Product Datasheet
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References

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


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Keywords: 2-Arachidonylglycerol, 2-Arachidonylglycerol supplier, endogenous, cannabinoids, ligand, agonists, non-selective, receptors, cb2r, cb1r, GBR55, CB1, CB2, endocannabinoids, 2-AG, Arachidonoylglycerol, Non-selective, Cannabinoids, 1298, Tocris Bioscience

18 Citations for 2-Arachidonylglycerol

Citations are publications that use Tocris products. Selected citations for 2-Arachidonylglycerol include:

Higgins et al (2013) Differential modulation of nociceptive versus non-nociceptive synapses by endocannabinoids. Mol Pain 9 26 PMID: 23725095

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

Nogueras-Ortiz (2017) Retromer stops beta-arrestin 1 mediated signaling from internalized cannabinoid 2 receptors. Mol Biol Cell 28 3554 PMID: 28954865

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

Chanda et al (2012) Activation of cannabinoid receptor type 1 (Cb1r) disrupts hepatic insulin 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

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

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

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

Won et al (2009) Molecular reconstruction of mGluR5a-mediated endocannabinoid signaling cascade in single rat sympathetic neurons. J Neurosci 29 13603 PMID: 19864572

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

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

Carney et al (2009) Cannabinoid regulation of nitric oxide synthase I (nNOS) in neuronal cells. J Neuroimmune Pharmacol 4 338 PMID: 19365734

Wang et al (2009) Pretreatment with electroacupuncture induces rapid tolerance to focal cerebral ischemia through regulation of endocannabinoid system. Stroke 40 2157 PMID: 19372445


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