| Identification | Back Directory | [Name]
NOLADIN ETHER | [CAS]
222723-55-9 | [Synonyms]
HU 310
2-AG ETHER
NOLADIN ETHER
Noladineether
2-O-arachidonylglycerol
2-ARACHIDONYL GLYCERYL ETHER
2-ARACHIDONYL GLYCEROL ETHER
5Z,8Z,11Z,14Z-EICOSATETRAEN-2-GLYCERYL ETHER
2-[(5Z,8Z,11Z,14Z)-EICOSATETRAENYLOXY]-1,3-PROPANEDIOL
2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoxy]propane-1,3-diol
2-[(5Z,8Z,11Z,14Z)-5,8,11,14-Eicosatetraen-1-yloxy]-1,3-propanediol
1,3-Propanediol, 2-[(5Z,8Z,11Z,14Z)-5,8,11,14-eicosatetraen-1-yloxy]- | [EINECS(EC#)]
200-578-6 | [Molecular Formula]
C23H40O3 | [MDL Number]
MFCD05865095 | [MOL File]
222723-55-9.mol | [Molecular Weight]
364.56 |
| Chemical Properties | Back Directory | [Boiling point ]
488.9±45.0 °C(Predicted) | [density ]
0.948±0.06 g/cm3(Predicted) | [Fp ]
14℃ | [storage temp. ]
Desiccate at -20°C | [solubility ]
DMF: 20 mg/ml; DMSO: 15 mg/ml; Ethanol: 25 mg/ml; Ethanol:PBS(pH 7.2) (1:1): 500 μg/ml | [form ]
ethanol solution (10 mg/mL (1% w/v)) | [pka]
13.92±0.10(Predicted) | [color ]
colorless to light yellow |
| Hazard Information | Back Directory | [Description]
2-Arachidonyl glycerol ether (2-AG ether) selectively binds to cannabinoid (CB) receptor 1 (Kis = 21.2 and >3,000 nM for CB1 and CB2, respectively, in a radioligand binding assay). It is a potent and selective agonist of CB1 and GPR55 with EC50 values of 10, 37, and >30,000 nM for CB1, GPR55, and CB2, respectively. 2-AG ether displays the typical tetrad of CB activities in mice. It is more chemically stable than 2-AG , with an endogenous half-life of hours rather than minutes. However, it is at least 10-fold less potent than 2-AG in eliciting typical CB1-mediated responses. 2-AG ether elicits modest reductions in intraocular pressure in rabbits when administered at doses exceeding 50 μg per eye. It increases aqueous humor outflow via the CB1 receptor in the trabecular meshwork. Administration of 2-AG ether to the nucleus accumbens (0.0625-1 μg) increases dietary intake and enhances fat consumption in rats given access to both high-carbohydrate and high-fat diets. | [Uses]
HU 310 is an endogenous GPR55 and CB1 receptors agonist. HU 310 has been shown to induce hyperglycia in rats. HU 310 can be used to investigate the biological roles of GPR55 and CB1 receptors. | [Definition]
ChEBI: A monoalkylglycerol that is the 2-O-arachidonyl derivative of glycerol. | [Biological Activity]
Endogenous agonist for the GPR55 and CB 1 receptors (EC 50 values are 10 and 37 nM respectively) that displays selectivity over CB 2 receptors (K i values are 21.2 nM and > 3mM at CB 1 and CB 2 respectively). Causes sedation, hypothermia, intestinal immobility and mild antinociception in vivo . Attenuates sensory neurotransmission in rat mesenteric arteries via GPR55. Also available as part of the Endocannabinoid Tocriset™ . | [IC 50]
CB1: 21.2 nM (Ki); CB2: >3 mM (Ki) | [References]
[1] L. HANU?. 2-Arachidonyl glyceryl ether, an endogenous agonist of the cannabinoid CB1 receptor[J]. Proceedings of the National Academy of Sciences of the United States of America, 2001, 98 1: 3662-3665. DOI: 10.1073/pnas.061029898
[2] E RYBERG. The orphan receptor GPR55 is a novel cannabinoid receptor[J]. British Journal of Pharmacology, 2009, 152 7: 1092-1101. DOI: 10.1038/sj.bjp.0707460
[3] KRISTA LAINE. Comparison of the enzymatic stability and intraocular pressure effects of 2-arachidonylglycerol and noladin ether, a novel putative endocannabinoid.[J]. Investigative ophthalmology & visual science, 2002, 43 10: 3216-3222.
[4] T SUGIURA. Evidence that the cannabinoid CB1 receptor is a 2-arachidonoylglycerol receptor. Structure-activity relationship of 2-arachidonoylglycerol, ether-linked analogues, and related compounds.[J]. The Journal of Biological Chemistry, 1999, 274 5: 2794-2801. DOI: 10.1074/jbc.274.5.2794
[5] YA FATOU NJIE. Noladin ether acts on trabecular meshwork cannabinoid (CB1) receptors to enhance aqueous humor outflow facility.[J]. Investigative ophthalmology & visual science, 2006, 47 5: 1999-2005. DOI: 10.1167/iovs.05-0729
[6] RAHUL R. DESHMUKH P. L S. Stimulation of accumbens shell cannabinoid CB1 receptors by noladin ether, a putative endocannabinoid, modulates food intake and dietary selection in rats[J]. Pharmacological research, 2012, 66 3: Pages 276-282. DOI: 10.1016/j.phrs.2012.06.004 |
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| Company Name: |
Enzo Biochem Inc
|
| Tel: |
Enzo Biochem Inc. 13797054060 |
| Website: |
www.enzo.com |
| Company Name: |
Merck KGaA
|
| Tel: |
21-20338288 |
| Website: |
www.sigmaaldrich.cn |
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