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8(9)-EET Ethanolamide

Cayman Chemical Item Number 10008597

8(9)-EpETrE Ethanolamide

8(9)-EET Ethanolamide

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Description

Arachidonoyl ethanolamide (AEA) is an endogenous lipid neurotransmitter with cannabingeric 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 COX-2, lipoxygenases, and CYP450 enzymes has also been documented.4,5 8(9)-EET ethanolamide is a cytochrome P450 (CYP450) metabolite of AEA, although specific stereochemistry rather than a racemic mixture would likely ensue from enzymatic metabolism.5 Human liver microsomes metabolize AEA to 5,6-, 8,9-, 11,12-, and 14,15-EET ethanolamides in a time and protein concentration dependent manner.5 8(9)-EET reduces glomerular filtration rate through cyclooxygenase dependent preglomerular vasoconstriction.6 The physiological actions of 8(9)-EET ethanolamide have not been examined.

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., Kornilov, A.M., Kent, U.M., et al. Anandamide metabolism by human liver and kidney microsomal cytochrome P450 enzymes to form hydroxyeicosatetraenoic and epoxyeicosatrienoic acid ethanolamides. J Pharmacol Exp Ther 321(2) 590-597 (2007).

6 Katoh, T., Takahashi, K., Capdevila, J., et al. Glomerular stereospecific synthesis and hemodynamic actions of 8,9-epoxyeicosatrienoic acid in rat kidney. Am J Physiol 261 F578-F586 (1991).

Synonyms
  • 8(9)-EpETrE Ethanolamide
Formal Name N-​(2-​hydroxyethyl)-​(±)8(9)-​epoxy-​5Z,​11Z,​14Z-​eicosatrienoic amide
Molecular Formula C22H37NO3
Formula Weight 363.5
Formulation A solution in ethanol
Purity ≥98%
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@H]​1O[C@H]​1C/C=C\CCCC(=O)​NCCO

Background Reading

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).

Katoh, T., Takahashi, K., Capdevila, J., et al. Glomerular stereospecific synthesis and hemodynamic actions of 8,9-epoxyeicosatrienoic acid in rat kidney. Am J Physiol 261 F578-F586 (1991).

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).

Snider, N.T., Kornilov, A.M., Kent, U.M., et al. Anandamide metabolism by human liver and kidney microsomal cytochrome P450 enzymes to form hydroxyeicosatetraenoic and epoxyeicosatrienoic acid ethanolamides. J Pharmacol Exp Ther 321(2) 590-597 (2007).

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

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8(9)-EET Ethanolamide is available in the following screening library:

Size Price Quantity Subtotal
25 µg $72.00 $0.00
50 µg $137.00 $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.

Related Products

8(9)-EET
8(9)-EET-d11
8(9)-EET methyl ester
Arachidonoyl Ethanolamide
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