2-Arachidonyl glyceryl ether
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| 2-Arachidonyl glyceryl ether | |
|---|---|
| Image:2-AGE.png | |
| IUPAC name | 2-[(5Z,8Z,11Z,14Z)-5,8,11,14- Icosatetraen- 1-yloxy]-1,3-propanediol |
| Other names | 2-AGE, 2-arachidonylglyceryl ether, Noladin ether, Noladin |
| Identifiers | |
| CAS number | |
| PubChem | |
| SMILES | OCC(CO)OCCCC\C=C/C\C =C/C/C=C\C/C=C\CCCCC |
| Properties | |
| Molecular formula | C23H40O3 |
| Molar mass | 364.5619 g/mol |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references | |
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Overview
2-Arachidonyl glyceryl ether (2-AGE, Noladin ether) is a putative endocannabinoid discovered by Lumír Hanuš at the Hebrew University of Jerusalem, Israel. Its isolation from porcine brain and its structural elucidation and synthesis were described in 2001.[1]
Detection
The presence of noladin 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,[1] two other research groups successfully detected it in animal tissues.[1] [1]
Pharmacology
Noladin binds with a Ki of 21 nM to the CB1 receptor[1] and 480 nM to the CB2 receptor.[1] It shows agonistic behaviour on both receptors and is a partial agonist for the TRPV1 channel.[1] After binding to CB2 receptors it inhibits adenylate cyclase and stimulates ERK-MAPK and regulates calcium transients.[1]
In comparison to 2-arachidonoyl glycerol noladin is metabolically more stable resulting in a longer half-life time.[1]
It lowers intraocular pressure,[1] increases the uptake of GABA in the globus pallidus of rats[1] and is neuroprotective by binding to and activation of PPARα.[1]
References
External links
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Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
