An ω-3 endocannabinoid epoxide and CB receptor agonist
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(±)10(11)-EDP Ethanolamide

Item No. 25878

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-(2-hydroxyethyl)-9-[3-(2Z,5Z,8Z)-2,5,8-undecatrien-1-yl-2-oxiranyl]-4Z,7Z-nonadienamide
CAS Number
2123484-71-7
Synonyms
  • 10,11-EDP-EA
  • 10,11-EDP epoxide
  • 10,11-epoxy Docosapentaenoic Ethanolamide
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
λmax
242 nm
SMILES
CC/C=C\C/C=C\C/C=C\CC1C(O1)C/C=C\C/C=C\CCC(NCCO)=O
InChi Code
InChI=1S/C24H37NO3/c1-2-3-4-5-6-7-8-11-14-17-22-23(28-22)18-15-12-9-10-13-16-19-24(27)25-20-21-26/h3-4,6-7,10-15,22-23,26H,2,5,8-9,16-21H2,1H3,(H,25,27)/b4-3-,7-6-,13-10-,14-11-,15-12-
InChi Key
OZFSRFILTKLOCC-UQZHZJRSSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    25 µg

    $98

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    50 µg

    $185

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    100 µg

    $347

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    Product Description

    (±)10(11)-EDP ethanolamide is an ω-3 endocannabinoid epoxide and cannabinoid (CB) receptor agonist (EC50s = 0.43 and 22.5 nM for CB1 and CB2 receptors, respectively).1 It is produced though direct epoxygenation of docosahexaenoyl ethanolamide (DHEA; Item No. 10007534) by cytochrome P450 (CYP) epoxygenases.1,2 10,11-EDP epoxide (12.5 and 25 μM) reduces the viability of 143B metastatic osteosarcoma cells.1 It induces apoptosis and inhibits cell migration in a wound-healing assay in 143B, MG63, and HOS osteosarcoma cells. (±)10(11)-EDP ethanolamide also reduces tube formation by human umbilical vein endothelial cells (HUVECs) in a Matrigel™ assay.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. 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).

    2. 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).