2-Arachidonyl glyceryl ether
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| Names | |
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| IUPAC names
2-[(5Z,8Z,11Z,14Z)-5,8,11,14- Icosatetraen-
1-yloxy]-1,3-propanediol |
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| Other names
2-AGE, 2-arachidonylglyceryl ether, Noladin ether, Noladin
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| Identifiers | |
222723-55-9  |
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| ChEBI | CHEBI:75913 |
| ChEMBL | ChEMBL146346  |
| ChemSpider | 4983515 |
| 5545 | |
| Jmol 3D model | Interactive image |
| PubChem | 6483057 |
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| Properties | |
| C23H40O3 | |
| Molar mass | 364.56 g/mol |
| Vapor pressure | {{{value}}} |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 verify (what is ?) |
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| Infobox references | |
2-Arachidonyl glyceryl ether (2-AGE, Noladin ether) is a putative endocannabinoid discovered by Lumír Hanuš and colleagues at the Hebrew University of Jerusalem, Israel. Its isolation from porcine brain and its structural elucidation and synthesis were described in 2001.[1]
Discovery
Lumír Hanuš, Saleh Abu-Lafi, Ester Fride, Aviva Breuer, Zvi Vogel, Deborah E. Shalev, Irina Kustanovich, and Raphael Mechoulam found the endogenous agonist of the cannabinoid receptor type 1 (CB1) in 2000. The discovery was 100 gram of porcine brain, (approximately a single brain) was added to a mixture of 200 mL of chloroform and 200 mL of methanol and mixed in a laboratory blender for 2 minutes. 100 mL of Water was then added, and the mixing process continued for another minute. After this, the mixture was filtered. Two layers then formed and the layer of water-methanol was separated and evaporated when pressure was reduced. Synaptosomal membranes were prepared from 250g of the brains of Sabra male rats. A Hewlett Packard G 1800B GCD system that has a HP-5971 GC with electron ionization detector was used.[1]
Production
The production of the endocannabinoid is enhanced in normal, but not in endothelium-denuded rat aorta on reacting with carbachol, an parasympathomimetic drug. It potently reduces blood pressure in rats and may represent an endothelium-derived hypotension factor.[1]
2-Arachidonyl glyceryl ether's structure can be determined by mass spectrometry and Rutherford backscattering spectrometry. It was confirmed by comparison with a synthetic sample of the endocannabinoid. It binds to the Cannabinoid receptor type 1 (Ki = 21.2 ± 0.5 nM), which causes sedation, hypothermia, intestinal immobility, and mild antinociception in mice.[1] The endocannabinoid exhibits Ki values of 21.2 nM and >3 µM at the Cannabinoid receptor type 1 and the peripheral cannabinoid receptors.[2]
The presence of 2-AGE in body tissue is disputed. Although a research group from Teikyo University, Kanagawa, Japan could not detect it in the brains of mice, hamsters, guinea-pigs or pigs,[3] two other research groups successfully detected it in animal tissues.[4][5]
Pharmacology
2-AGE binds with a Ki of 21 nM to the CB1 receptor[1] and 480 nM to the CB2 receptor.[6] It shows agonistic behaviour on both receptors and is a partial agonist for the TRPV1 channel.[7] After binding to CB2 receptors it inhibits adenylate cyclase and stimulates ERK-MAPK and regulates calcium transients.[8] In comparison to 2-arachidonoyl glycerol, noladin is metabolically more stable resulting in a longer half-life.[9] It lowers Intraocular pressure,[9] increases the uptake of GABA in the globus pallidus of rats[10] and is neuroprotective by binding to and activation of PPARα.[11]
See also
References
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- ↑ "2-Arachidonyl Glycerol ether · Noladin; 2-AG ether (CAS 222723-55-9) || Cayman Chemical". Cayman Chemical. Retrieved 2011-05-29.
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