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| Product Name: | 2-AG | | Synonyms: | 5Z,8Z,11Z,14Z-EICOSATETRAENOIC ACID, 2-GLYCERYL ESTER;(5Z,8Z,11Z,14Z)-5,8,11,14-EICOSATETRAENOIC ACID, 2-HYDROXY-1-(HYDROXYMETHYL)ETHYL ESTER;2-ARACHIDONOYLGLYCEROL;2-ARACHIDONYLGLYCEROL;2-AG;NOLADIN;(5Z,8Z,11Z,14Z)-5,8,11,14-Eicosatetraenoicacid;2-Hydroxy-1-(hydroxymethyl)ethylester | | CAS: | 53847-30-6 | | MF: | C23H38O4 | | MW: | 378.55 | | EINECS: | 200-835-2 | | Product Categories: | Cannabinoid;Fatty Acid Derivatives & Lipids;Cannabinoid receptor;Glycerols;Intermediates & Fine Chemicals;Pharmaceuticals | | Mol File: | 53847-30-6.mol |
| Boiling point | 508.6±50.0 °C(Predicted) | | density | 0.992±0.06 g/cm3(Predicted) | | Fp | 2 °C | | storage temp. | -20°C | | form | acetonitrile solution | | pka | 13.54±0.10(Predicted) | | CAS DataBase Reference | 53847-30-6(CAS DataBase Reference) |
| Uses | 2-Arachidonoylglycerol is a major endocannabinoid, which can inhibit synaptic transmission by presynaptic cannabinoid CB1 receptors. It plays an inhibitory role in the bombesin-induced activation of central adrenomedullary outflow in rats. | | Definition | ChEBI: An endocannabinoid and an endogenous agonist of the cannabinoid receptors (CB1 and CB2). It is an ester formed from omega-6-arachidonic acid and glycerol. | | General Description | 2-Arachidonoylglycerol (2-AG), is an endocannabinoid, an endogenous agonist of the CB1 receptor. 2-AG, unlike anandamide, is present at relatively high levels in the central nervous system; it is the most abundant molecular species of monoacylglycerol found in mouse and rat brain (~5-10 nmol/g tissue). Detection of 2-AG in brain tissue is complicated by the relative ease of its isomerization to 1-AG during standard lipid extraction conditions. Unlike anandamide, formation of 2-AG is calcium-dependent and is mediated by the activities of phospholipase C (PLC) and diacylglycerol lipase (DAGL). 2-AG acts as a full agonist at the CB1 receptor. At a concentration of 0.3nM, 2-AG induces a rapid, transient increase in intracellular free calcium in NG108-15 neuroblastoma X glioma cells through a CB1 receptor-dependent mechanism. 2-AG is hydrolyzed in vitro by monoacylglycerol lipase (MAGL), fatty acid amide hydrolase (FAAH), and the uncharacterized serine hydrolase enzymes ABHD6 and ABHD12. | | 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. |
| 2-AG Preparation Products And Raw materials |
| Raw materials | 5,8,11,14-Eicosatetraenoic acid, 2-[(2,2,2-trifluoroacetyl)oxy]-1-[[(2,2,2-trifluoroacetyl)oxy]methyl]ethyl ester, (5Z,8Z,11Z,14Z)--->O-ARACHIDONOYL GLYCIDOL-->1-STEAROYL-2-ARACHIDONOYL-SN-GLYCEROL-->(5Z,8Z,11Z,14Z)-2-[[Tris(1-Methylethyl)silyl]oxy]-5,8,11,14-eicosatetraenoic Acid 1-[[[Tris(1-Methylethyl)silyl]oxy]Methyl]ethyl Ester-->Arachidonic acid | | Preparation Products | 1-MONOARACHIDIN |
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