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2-Arachidonyl glyceryl ether

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2-Arachidonyl glyceryl ether
Names
IUPAC names
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
3D model (JSmol)
  • OCC(CO)OCCCC\C=C/C\C =C/C/C=C\C/C=C\CCCCC
Properties
C23H40O3
Molar mass 364.5619 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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,[2] two other research groups successfully detected it in animal tissues.[3] [4]

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]

References

  1. ^ 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:10.1073/pnas.061029898. PMID 11259648. {{cite journal}}: Explicit use of et al. in: |author= (help)CS1 maint: multiple names: authors list (link) Cite error: The named reference "pmid11259648" was defined multiple times with different content (see the help page).
  2. ^ 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. {{cite journal}}: Explicit use of et al. in: |author= (help)CS1 maint: multiple names: authors list (link)
  3. ^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. ^ 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:10.1016/j.ab.2006.10.039. PMID 17141174.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  5. ^ 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:10.1124/jpet.105.085282. PMID 15901805.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  6. ^ 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:10.1038/sj.bjp.0705789. PMID 15148262.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  7. ^ 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:10.1124/jpet.105.089474. PMID 16081674.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  8. ^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  9. ^ 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:10.1016/j.expneurol.2005.02.012. PMID 15899265.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  10. ^ 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:10.1038/sj.bjp.0707478. PMID 17906680. {{cite journal}}: Explicit use of et al. in: |author= (help)CS1 maint: multiple names: authors list (link)
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