53847-30-6 Usage
Description
2-Arachidonoylglycerol (2-AG) is a major endocannabinoid, a type of lipid molecule that acts as a neurotransmitter in the endocannabinoid system. It is synthesized and released on demand and is involved in various physiological processes, including pain, appetite, mood, and memory.
Used in Pharmaceutical Industry:
2-AG is used as a therapeutic agent for its potential role in treating various conditions such as pain, inflammation, anxiety, and neurological disorders. Its ability to modulate synaptic transmission through the activation of presynaptic cannabinoid CB1 receptors makes it a promising candidate for the development of new drugs.
Used in Research Applications:
2-AG is used as a research tool for studying the endocannabinoid system and its role in various physiological and pathological processes. It helps researchers understand the mechanisms of action of cannabinoids and develop new therapeutic strategies targeting the endocannabinoid system.
Used in Nutraceutical Industry:
2-AG is used as a dietary supplement for its potential health benefits, including its role in maintaining homeostasis, reducing inflammation, and promoting overall well-being. It can be found in various nutraceutical products, such as capsules, oils, and edibles, and is marketed for its potential to support cognitive function, mood regulation, and pain relief.
Used in Cosmetic Industry:
2-AG is used as an ingredient in cosmetic products for its potential anti-aging and skin health benefits. Its anti-inflammatory and antioxidant properties may help improve skin appearance, reduce signs of aging, and promote skin health.
Overall, 2-AG is a versatile molecule with a wide range of applications in various industries, including pharmaceutical, research, nutraceutical, and cosmetic. Its ability to modulate various physiological processes and its potential therapeutic effects make it an important molecule for further research and development.
Biological Activity
Endogenous cannabinoid ligand that acts as a potent agonist at GPR55 (EC 50 values are 3, 519 and 618 nM at GPR55, CB 1 and CB 2 respectively; K i values are 472 and 1400 nM at CB 1 and CB 2 respectively). Found in the brain at concentrations 1000-fold higher than that of anandamide.
Biochem/physiol Actions
Endogenous cannabinoid receptor agonist.
Enzyme inhibitor
This potent endocannabinoid (FW = 378.30 g/mol; CAS 53847-30-6; Symbol: 2-AG), also known as 1,3-dihydroxy-2-propanyl (5Z,8Z,11Z,14Z)- 5,8,11,14-eicosatetraenoate, is an endogenous agonist of the CB1, the G- protein-coupled Cannabinoid receptor type-1 found primarily in the central and peripheral nervous system. 2-AG is found at highest concentrations in the CNS, where it exerts its cannabinoid-like neuromodulatory effects. Found in milk, 2-AG plays a role in sustaining infant suckling, and the selective CB1 receptor antagonist SR141617A (N-(piperidin-1-yl)-5-(4- chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3- carboxamide) permanently prevents milk ingestion in a dose-dependent manner, when administered to mouse pups, within 1 day of birth. 2-AG is formed by phospholipase C (PLC) and diacylglycerol lipase (DAGL) from arachidonic acid-containing diacylglycerol (DAG). In the CNS, three serine-hydrolases, monoacylglycerol lipase (MAGL), a,b-hydrolase- domain-6 (ABHD6) and a,b-hydrolase-domain 12 (ABHD12) are responsible for inactivation of the primary 2-arachidonoylglycerol. Irreversible ABHD6 inhibitors show exceptional potency and selectivity in cells (<5 nM) and, at equivalent doses in mice (1 mg/kg), acting as systemic and peripherally restricted inhibitors, respectively. Indeed, selective knockdown of ABHD6 in metabolic tissues protects mice from high-fat-diet-induced obesity, hepatic steatosis, and systemic insulin resistance.
Check Digit Verification of cas no
The CAS Registry Mumber 53847-30-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,3,8,4 and 7 respectively; the second part has 2 digits, 3 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 53847-30:
(7*5)+(6*3)+(5*8)+(4*4)+(3*7)+(2*3)+(1*0)=136
136 % 10 = 6
So 53847-30-6 is a valid CAS Registry Number.
InChI:InChI=1/C23H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(26)27-22(20-24)21-25/h6-7,9-10,12-13,15-16,22,24-25H,2-5,8,11,14,17-21H2,1H3/b7-6-,10-9-,13-12-,16-15-
53847-30-6Relevant articles and documents
Novel, regioselective transformation of an oxirane system. An efficient approach to the synthesis of endocannabinoid 2-arachidonoylglycerol
Stamatov, Stephan D.,Stawinski, Jacek
, p. 1759 - 1761 (2002)
A trifluoroacetic anhydride-catalysed opening of the oxirane system of glycidyl arachidonate with a simultaneous migration of the acyl group provides a new, efficient entry to 2-arachidonoylglycerol.
Facile synthesis and stabilization of 2-arachidonylglycerol via its 1,3- phenylboronate ester
Seltzman, Herbert H.,Fleming, Denise N.,Hawkins, Gregory D.,Carroll, F. Ivy
, p. 3589 - 3592 (2000)
2-Arachidonylglycerol (2-Ara-Gl) was synthesized via the intermediacy of its 1,3-phenylboronic acid ester. The boronate ester is easily stable enough to enable chromatographic resolution from the corresponding 1-Ara-Gl boronate ester on normal phase elution yet immediately and completely hydrolyzes to 2- Ara-G1 and phenylboronic acid, without isomerization, by simple solution in aqueous-organic solvents. The phenylboronate ester of this 2-acylglycerol has the added advantage of being markedly more stable to both isomerization and oxidation upon storage than the labile 2-Ara-Gl. (C) 2000 Elsevier Science Ltd.
Highly Selective, Reversible Inhibitor Identified by Comparative Chemoproteomics Modulates Diacylglycerol Lipase Activity in Neurons
Baggelaar, Marc P.,Chameau, Pascal J. P.,Kantae, Vasudev,Hummel, Jessica,Hsu, Ku-Lung,Janssen, Freek,Van Der Wel, Tom,Soethoudt, Marjolein,Deng, Hui,Den Dulk, Hans,Allarà, Marco,Florea, Bogdan I.,Di Marzo, Vincenzo,Wadman, Wytse J.,Kruse, Chris G.,Overkleeft, Herman S.,Hankemeier, Thomas,Werkman, Taco R.,Cravatt, Benjamin F.,Van Der Stelt, Mario
supporting information, p. 8851 - 8857 (2015/07/27)
Diacylglycerol lipase (DAGL)-α and -β are enzymes responsible for the biosynthesis of the endocannabinoid 2-arachidonoylglycerol (2-AG). Selective and reversible inhibitors are required to study the function of DAGLs in neuronal cells in an acute and temporal fashion, but they are currently lacking. Here, we describe the identification of a highly selective DAGL inhibitor using structure-guided and a chemoproteomics strategy to characterize the selectivity of the inhibitor in complex proteomes. Key to the success of this approach is the use of comparative and competitive activity-based proteome profiling (ABPP), in which broad-spectrum and tailor-made activity-based probes are combined to report on the inhibition of a protein family in its native environment. Competitive ABPP with broad-spectrum fluorophosphonate-based probes and specific β-lactone-based probes led to the discovery of α-ketoheterocycle LEI105 as a potent, highly selective, and reversible dual DAGL-α/DAGL-β inhibitor. LEI105 did not affect other enzymes involved in endocannabinoid metabolism including abhydrolase domain-containing protein 6, abhydrolase domain-containing protein 12, monoacylglycerol lipase, and fatty acid amide hydrolase and did not display affinity for the cannabinoid CB1 receptor. Targeted lipidomics revealed that LEI105 concentration-dependently reduced 2-AG levels, but not anandamide levels, in Neuro2A cells. We show that cannabinoid CB1-receptor-mediated short-term synaptic plasticity in a mouse hippocampal slice model can be reduced by LEI105. Thus, we have developed a highly selective DAGL inhibitor and provide new pharmacological evidence to support the hypothesis that "on demand biosynthesis" of 2-AG is responsible for retrograde signaling.
Mild acetal cleavage using B-chlorocatecholborane in the synthesis of rearrangement-sensitive 2-arachidonoylglycerol
Roche, Michael J.,Madren, Seth M.,Tallent, C. Ray,Carroll, F. Ivy,Seltzman, Herbert H.
experimental part, p. 3825 - 3827 (2012/08/28)
A mild method for the cleavage of an acetal to afford a rearrangement sensitive diol using B-chlorocatecholborane was developed for the synthesis of the endogenous cannabinoid neurochemical messenger 2-arachidonoylglycerol. The tendency for rearrangement of 2-arachidonoylglycerol to the corresponding 1-arachidonoylglycerol was precluded with this reagent. Features of the partial recyclization to an isomeric acetal provide mechanistic detail.
