Basic information Safety Supplier Related

2-AG

Basic information Safety Supplier Related

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
More
Less

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)
More
Less

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

More
Less

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

J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Email
jkinfo@jkchemical.com
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Email
3bsc@sina.com
Ascent Scientific
Tel
4401179829988
Email
customerservice@ascentscientific.co.uk
Chemsky(shanghai)International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Shanghai T&W Pharmaceutical Co., Ltd.
Tel
+86 21 61551611