An ω-3 endocannabinoid epoxide and CB receptor agonist
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(±)19(20)-EDP Ethanolamide

Item No. 25917

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
18-(3-ethyl-2-oxiranyl)-N-(2-hydroxyethyl)-4Z,7Z,10Z,13Z,16Z-octadecapentaenamide
CAS Number
2123485-34-5
Synonyms
  • 19,20-DHEA epoxide
  • 19,20-epoxy Docosapentaenoic Acid Ethanolamide
  • 19,20-EDP-EA
  • 19,20-EDP epoxide
Molecular Formula
C24H37NO3
Formula Weight
387.6
Purity
≥98%
Formulation
A 100 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 50 mg/mlDMSO: 50 mg/mlEthanol: 50 mg/mlEthanol:PBS(pH 7.2) (1:1): 0.5 mg/ml
SMILES
CCC1C(O1)C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(NCCO)=O
InChi Code
InChI=1S/C24H37NO3/c1-2-22-23(28-22)18-16-14-12-10-8-6-4-3-5-7-9-11-13-15-17-19-24(27)25-20-21-26/h3-4,7-10,13-16,22-23,26H,2,5-6,11-12,17-21H2,1H3,(H,25,27)/b4-3-,9-7-,10-8-,15-13-,16-14-
InChi Key
HQRHKQCFLLFLJV-MBYQGORISA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    25 µg

    $46

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    50 µg

    $86

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    100 µg

    $160

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    500 µg

    $707

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    Product Description

    (±)19(20)-EDP ethanolamide is an ω-3 endocannabinoid epoxide and cannabinoid (CB) receptor agonist (EC50s = 108 and 280 nM for CB1 and CB2, respectively). It is produced through direct epoxygenation of docosahexaenoyl ethanolamide (DHEA; Item No. 10007534) by cytochrome P450 (CYP) epoxygenases.1,2 (±)19(20)-EDP ethanolamide (25 µM) reduces the viability of 143B metastatic osteosarcoma cells.2 It decreases the production of IL-6 and increases the production of IL-10 when used at concentrations ranging from 2.5 to 10 µM in BV-2 microglia stimulated by LPS and decreases LPS-induced cytotoxicity when used at concentrations ranging from 5 to 10 µM. It also decreases nitrite production when used at a concentration of 7.5 µM, an effect that can be partially reversed by the CB2 receptor antagonist AM630 (Item No. 10006974) and the PPARγ antagonist GW 9662 (Item No. 70785). (±)19(20)-EDP ethanolamide induces vasodilation of isolated preconstricted bovine coronary arteries (ED50 = 1.9 µM) and reduces tube formation by human microvascular endothelial cells (HMVECs) in a Matrigel™ assay.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. McDougle, D.R., Watson, J.E., Abdeen, A.A., et al. Anti-inflammatory ω-3 endocannabinoid epoxides. Proc. Natl. Acad. Sci. USA 114(30), E6034-E6043 (2017).

    2. Roy, J., Watson, J.E., Hong, I.S., et al. Antitumorigenic properties of omega-3 endocannabinoid epoxides. J. Med. Chem. 61(13), 5569-5579 (2018).