A potential cytochrome P450 metabolite of AEA
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(±)5(6)-EET Ethanolamide

Item No. 10008596

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-(2-hydroxyethyl)-(±)5,6-epoxy-8Z,11Z,14Z-eicosatrienamide
Synonyms
  • (±)5,6-EpETrE Ethanolamide
Molecular Formula
C22H37NO3
Formula Weight
363.5
Purity
≥95%
Formulation
A 100 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 20 mg/mlEthanol: 30 mg/mlEthanol:PBS (pH 7.2)(1:6): 0.5 mg/ml
SMILES
CCCCC/C=C\C/C=C\C/C=C\C[C@@H](O1)[C@@H]1CCCC(N([H])CCO)=O
InChi Code
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
InChi Key
RTDIKSCKKJORSI-ABYDBCJLSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    25 µg

    $98

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    50 µg

    $179

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    100 µg

    $347

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    Product Description

    (±)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).1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. 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).