2-Arachidonyl glyceryl ether
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| 2-Arachidonyl glyceryl ether | |
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| 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 | [222723-55-9] |
| 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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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]
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[edit] 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,[2] two other research groups successfully detected it in animal tissues.[3] [4]
[edit] Pharmacology
Noladin binds with a Ki of 21 nM to the CB1 receptor[1] and 480 nM to the CB2 receptor.[5] It shows agonistic behaviour on both receptors and is a partial agonist for the TRPV1 channel.[6] After binding to CB2 receptors it inhibits adenylate cyclase and stimulates ERK-MAPK and regulates calcium transients.[7]
In comparison to 2-arachidonoyl glycerol noladin is metabolically more stable resulting in a longer half-life time.[8]
It lowers intraocular pressure,[8] increases the uptake of GABA in the globus pallidus of rats[9] and is neuroprotective by binding to and activation of PPARα.[10]
[edit] References
- ^ a b Hanus L, Abu-Lafi S, Fride E, et al (2001). "2-arachidonyl glyceryl ether, an endogenous agonist of the cannabinoid CB1 receptor". Proc. Natl. Acad. Sci. U.S.A. 98 (7): 3662–5. doi:. PMID 11259648.
- ^ Oka S, Tsuchie A, Tokumura A, et al (2003). "Ether-linked analogue of 2-arachidonoylglycerol (noladin ether) was not detected in the brains of various mammalian species". J. Neurochem. 85 (6): 1374–81. PMID 12787057.
- ^ Fezza F, Bisogno T, Minassi A, Appendino G, Mechoulam R, Di Marzo V (2002). "Noladin ether, a putative novel endocannabinoid: inactivation mechanisms and a sensitive method for its quantification in rat tissues". FEBS Lett. 513 (2-3): 294–8. PMID 11904167.
- ^ Richardson D, Ortori CA, Chapman V, Kendall DA, Barrett DA (2007). "Quantitative profiling of endocannabinoids and related compounds in rat brain using liquid chromatography-tandem electrospray ionization mass spectrometry". Anal. Biochem. 360 (2): 216–26. doi:. PMID 17141174.
- ^ Shoemaker JL, Joseph BK, Ruckle MB, Mayeux PR, Prather PL (2005). "The endocannabinoid noladin ether acts as a full agonist at human CB2 cannabinoid receptors". J. Pharmacol. Exp. Ther. 314 (2): 868–75. doi:. PMID 15901805.
- ^ Duncan M, Millns P, Smart D, Wright JE, Kendall DA, Ralevic V (2004). "Noladin ether, a putative endocannabinoid, attenuates sensory neurotransmission in the rat isolated mesenteric arterial bed via a non-CB1/CB2 G(i/o) linked receptor". Br. J. Pharmacol. 142 (3): 509–18. doi:. PMID 15148262.
- ^ Shoemaker JL, Ruckle MB, Mayeux PR, Prather PL (2005). "Agonist-directed trafficking of response by endocannabinoids acting at CB2 receptors". J. Pharmacol. Exp. Ther. 315 (2): 828–38. doi:. PMID 16081674.
- ^ a b Laine K, Järvinen K, Mechoulam R, Breuer A, Järvinen T (2002). "Comparison of the enzymatic stability and intraocular pressure effects of 2-arachidonylglycerol and noladin ether, a novel putative endocannabinoid". Invest. Ophthalmol. Vis. Sci. 43 (10): 3216–22. PMID 12356827.
- ^ Venderova K, Brown TM, Brotchie JM (2005). "Differential effects of endocannabinoids on [(3)H]-GABA uptake in the rat globus pallidus". Exp. Neurol. 194 (1): 284–7. doi:. PMID 15899265.
- ^ Sun Y, Alexander SP, Garle MJ, et al (2007). "Cannabinoid activation of PPARalpha; a novel neuroprotective mechanism". Br. J. Pharmacol. 152 (5): 734–43. doi:. PMID 17906680.
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