2-AG
2-AG Basic information
- 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
2-AG Chemical Properties
- Boiling point:
- 508.6±50.0 °C(Predicted)
- Density
- 0.992±0.06 g/cm3(Predicted)
- Flash point:
- 2 °C
- storage temp.
- -20°C
- solubility
- DMSO: 10 mg/ml; Ethanol: Miscible; PBS (pH 7.2): ~150 μg/ml
- pka
- 13.54±0.10(Predicted)
- form
- acetonitrile solution
- color
- Colorless to light yellow
- CAS DataBase Reference
- 53847-30-6(CAS DataBase Reference)
Safety Information
- Hazard Codes
- F,Xn
- Risk Statements
- 11-20/21/22-36
- Safety Statements
- 26-36/37-16
- RIDADR
- UN 1648 3/PG 2
- WGK Germany
- 2
MSDS
- Language:English Provider:SigmaAldrich
2-AG Usage And Synthesis
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.
storage
Store at -80°C
2-AGSupplier
- Tel
- 010-82848833 400-666-7788
- jkinfo@jkchemical.com
- Tel
- 821-50328103-801 18930552037
- 3bsc@sina.com
- Tel
- 4401179829988
- customerservice@ascentscientific.co.uk
- Tel
- 021-50135380
- shchemsky@sina.com
- Tel
- +86 21 61551611
2-AG(53847-30-6)Related Product Information
- 1-OCTADECANOYL-2-[(CIS,CIS,CIS,CIS)-5,8,11,14-EICOSATETRAENOYL]-SN-GLYCERO-3-PHOSPHOCHOLINE
- 1,2-DI5,8,11,14(ALL-CIS)EICOSATETRAENOYL-SN-GLYCERO-3-PHOSPHOCHOLINE
- SPECS AG-205/15424553
- 1-AG
- 17-AAG
- SPECS AG-205/25005652
- 1-STEAROYL-2-ARACHIDONOYL-PHOSPHATIDYLINOSITOL 3,4,5-TRIPHOSPHATE, (NA+ SALT)
- 2-AG-D5
- 2-AG
- 1-O-HEXADECYL-2-ARACHIDONYL-SN-GLYCERO-3-PHOSPHOCHOLINE
- 1-STEAROYL-2-ARACHIDONOYL-SN-GLYCEROL
- 2-AG-D8
- TRIARACHIDONIN
- SPECS AG-205/25006771
- 2-ARACHIDONYL GLYCEROL, [GLYCEROL 1,3-3H]
- PHOSPHATIDYLCHOLINE, L-ALPHA-1-O HEXADECYL-1-2-ARACHIDONYL, [ARACHIDONYL-5,6,8,9,11,12,14,15-3H(N)]
- PHOSPHATIDYLCHOLINE, L-ALPHA-1-PALMITOYL-, 2-ARACHIDONYL, [ARACHIDONYL-1-14C]
- PHOSPHATIDYLETHANOLAMINE, L-ALPHA-1-PALMITOYL, 2-ARACHIDONYL, [ARACHIDONYL-1-14C]