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(±)5(6)-EET Ethanolamide (CAS 0) LS-H22

CB2 agonist
LS-H22-25 / 25 µg / $215
LS-H22-50 / 50 µg / $255
LS-H22-100 / 100 µg / $345
USA Shipment Only
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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. Fatty acid amide hydrolase (FAAH) is the enzyme responsible for the hydrolysis and inactivation of AEA. Metabolism of AEA by cyclooxygenase-2, leading to formation of prostaglandin ethanolamides, and by lipoxygenases has also been documented. (±)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). H22_ChemicalStructureImage.png
N-(2-hydroxyethyl)-(±)5,6-epoxy-8Z,11Z,14Z-eicosatrienamide
(±)5,6-EpETrEEthanolamide
biochemical, chemical, agonist
LS-H22
0
C22H37NO3
≥95%
A solution in ethanol
0
CCCCC/C=C\C/C=C\C/C=C\C[C@@H](O1)[C@@H]1CCCC(N([H])CCO)=O
InChI=1S/C22H37NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-20-21(26-20)16-14-17-22(25)23-18-19-24/h6-7,9-10,12-13,20-21,24H,2-5,8,11,14-19H2,1H3,(H,23,25)/b7-6-,10-9-,13-12-/t20-,21+/m1/s1
RTDIKSCKKJORSI-ABYDBCJLSA-N
Shipped at 4°C, store at -20°C, ≥ 1 year shelf life.
This product is for research use only. Not for administration to humans, or for human or veterinary diagnostic or therapeutic use.
Data Sheet DataSheet    SDS SDS
Related Products: CNR2 / CB2 related products

Usage Information

(±)5(6)-EET ethanolamide is supplied as a solution in ethanol. To change the solvent, simply evaporate the ethanol under a gentle stream of nitrogen and immediately add the solvent of choice. Solvents such as DMSO and dimethyl formamide purged with an inert gas can be used. The solubility of (±)5(6)-EET ethanolamide in these solvents is approximately 20 mg/ml. (±)5(6)-EET ethanolamide is sparingly soluble in aqueous buffers. For maximum solubility in aqueous buffers, the ethanolic solution of (±)5(6)-EET ethanolamide should be diluted with the aqueous buffer of choice. (±)5(6)-EET ethanolamide has a solubility of approximately 0.5 mg/ml in a 1:6 solution of ethanol:PBS (pH 7.2) using this method. We do not recommend storing the aqueous solution for more than one day.

References:
  1. Felder, C.C., Briley, E.M., Axelrod, J., et al. Proc. Natl. Acad. Sci. USA 90, 7656-7660 (1993).
  2. Lambert, D.M. and Fowler, C.J. J. Med. Chem. 48(16), 5059-5087 (2005).
  3. Deutsch, D.G., Ueda, N., and Yamamoto, S. Prostaglandins Leukot. Essent. Fatty Acids 66(2&3), 201-210 (2002).
  4. Kozak, K.R. and Marnett, L.J. Prostaglandins Leukot. Essent. Fatty Acids 66(2&3), 211-220 (2002).
  5. Snider, N.T., Nast, J.A., Tesmer, L.A., et al. Mol. Pharmacol. 75(4), 965-972 (2009).

 


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