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5(6)-EET Ethanolamide

Cayman Chemical Item Number 10008596

5(6)-EpETrE Ethanolamide

5(6)-EET Ethanolamide

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Description

Arachidonyl ethanolamide (AEA) is an endogenous lipid neurotransmitter with cannabinergic activity, binding to both the central cannabinoid (CB1) and peripheral cannabinoid (CB2) receptors.1,2 Fatty acid amide hydrolase (FAAH) is the enzyme responsible for the hydrolysis and inactivation of AEA.3 Metabolism of AEA by cyclooxygenase-2, leading to formation of prostaglandin ethanolamides, and by lipoxygenases has also been documented.4 5(6)-EET ethanolamide is a cytochrome P450 (CYP450) metabolite of AEA, although specific stereochemistry rather than a racemic mixture ensues from enzymatic metabolism. 5(6)-EET ethanolamide is a potent and selective agonist of CB2 (Ki = 8.9 nM for CB2, 11.4 μM for CB1), effectively suppressing forskolin-stimulated accumulation of cAMP through this Gi-coupled receptor (IC50 = 9.8 nM).5

1 Felder, C.C., Briley, E.M., Axelrod, J., et al. Anandamide, an endogenous cannabimimetic eicosanoid, binds to the cloned human cannabinoid receptor and stimulates receptor-mediated signal transduction. Proc Natl Acad Sci USA 90 7656-7660 (1993).

2 Lambert, D.M., and Fowler, C.J. The endocannabinoid system: Drug targets, lead compounds, and potential therapeutic applications. J Med Chem 48(16) 5059-5087 (2005).

3 Deutsch, D.G., Ueda, N., and Yamamoto, S. The fatty acid amide hydrolase (FAAH). Prostaglandins Leukot Essent Fatty Acids 66(2&3) 201-210 (2002).

4 Kozak, K.R., and Marnett, L.J. Oxidative metabolism of endocannabinoids. Prostaglandins Leukot Essent Fatty Acids 66(2&3) 211-220 (2002).

5 Snider, N.T., Nast, J.A., Tesmer, L.A., et al. A cytochrome P450-derived epoxygenated metabolite of anandamide is a potent cannabinoid receptor 2-selective agonist. Mol Pharmacol 75(4) 965-972 (2009).

Synonyms
  • 5(6)-EpETrE Ethanolamide
Formal Name N-​(2-​hydroxyethyl)-​(±)5(6)-​epoxy-​8Z,​11Z,​14Z-​eicosatrienamide
Molecular Formula C22H37NO3
Formula Weight 363.5
Formulation A solution in ethanol
Purity ≥95%
Stability 1 year
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
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CCCCC/C=C\C/C=C\C/C=C\C[C@H]​1O[C@H]​1CCCC(=O)​NCCO

Background Reading

Felder, C.C., Briley, E.M., Axelrod, J., et al. Anandamide, an endogenous cannabimimetic eicosanoid, binds to the cloned human cannabinoid receptor and stimulates receptor-mediated signal transduction. Proc Natl Acad Sci USA 90 7656-7660 (1993).

Kozak, K.R., and Marnett, L.J. Oxidative metabolism of endocannabinoids. Prostaglandins Leukot Essent Fatty Acids 66(2&3) 211-220 (2002).

Deutsch, D.G., Ueda, N., and Yamamoto, S. The fatty acid amide hydrolase (FAAH). Prostaglandins Leukot Essent Fatty Acids 66(2&3) 201-210 (2002).

Lambert, D.M., and Fowler, C.J. The endocannabinoid system: Drug targets, lead compounds, and potential therapeutic applications. J Med Chem 48(16) 5059-5087 (2005).

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5(6)-EET Ethanolamide is available in the following screening library:

Size Price Quantity Subtotal
25 µg $72.00 $0.00
50 µg $132.00 $0.00
100 µg $259.00 $0.00
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

Please contact our Sales Department for a quote or to purchase.

Pricing updated 2012-05-25. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

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