Catalog Number: 1298
Alternate Names: 2-AG, Arachidonoylglycerol
Chemical Name: (5Z,8Z,11Z,14Z)-5,8,11,14-Eicosatetraenoic acid, 2-hydroxy-1-(hydroxymethyl)ethyl ester
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
  • Solubility:
    Soluble to 100 mM in ethanol and to 100 mM in DMSO
  • Storage:
    Store at -80°C
  • CAS No:
    53847-30-6
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.
Background References
  1. The orphan receptor GPR55 is a novel cannabinoid receptor.
    Ryberg et al.
    Br.J.Pharmacol., 2007;152:1092
  2. Evidence that the cannabinoid CB1 receptor is a 2-arachidonoylglycerol receptor.
    Sugiura et al.
    J.Biol.Chem., 1999;274:2794
  3. Identification of an endogenous 2-monoglyceride, present in canine gut, that binds to cannabinoid receptors.
    Mechoulam et al.
    Biochem.Pharmacol., 1995;50:83
  4. 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
Citations:

The citations listed below are publications that use Tocris products. Selected citations for 2-Arachidonylglycerol include:

12 Citations: Showing 1 - 10
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  1. 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
  2. Ligand-specific endocytic dwell times control functional selectivity of the cannabinoid receptor 1.
    Authors: Flores-Otero Et al.
    Nat Commun 2014;5:4589
  3. 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
  4. Differential modulation of nociceptive versus non-nociceptive synapses by endocannabinoids.
    Authors: Higgins Et al.
    Mol Pain 2013;9:26
  5. 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
  6. 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.
    Authors: Chanda Et al.
    J Cell Biol 2012;287:38041
  7. 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
  8. Endocannabinoid-dependent LTD in a nociceptive synapse requires activation of a presynaptic TRPV-like receptor.
    Authors: Yuan and Burrell
    J Neurophysiol 2010;104:2766
  9. Cannabinoid regulation of nitric oxide synthase I (nNOS) in neuronal cells.
    Authors: Carney Et al.
    J Neuroimmune Pharmacol 2009;4:338
  10. Pretreatment with electroacupuncture induces rapid tolerance to focal cerebral ischemia through regulation of endocannabinoid system.
    Authors: Wang Et al.
    Stroke 2009;40:2157
  11. Endothelium-dependent metabolism by endocannabinoid hydrolases and cyclooxygenases limits vasorelaxation to anandamide and 2-arachidonoylglycerol.
    Authors: Ho and Randall
    Exp Neurol 2007;150:641
  12. 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
Expand to show all 12 Citations
Tocris Small Molecules
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2-Palmitoylglycerol

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