An internal standard for the quantification of docosahexaenoyl ethanolamide
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Unlabeled Version(s)
10007534Docosahexaenoyl Ethanolamide
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Docosahexaenoyl Ethanolamide-d4

Item No. 9001108

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-(2-hydroxyethyl-1,1',2,2'-d4)-4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenamide
CAS Number
946524-43-2
Synonyms
  • DEA-d4
  • DHEA-d4
Molecular Formula
C24H33D4NO2
Formula Weight
375.6
Purity
≥99% deuterated forms (d1-d4)
Formulation
A 1 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlEthanol: 5 mg/mlPBS (pH 7.2): 0.15 mg/ml
SMILES
O=C(NC([2H])([2H])C([2H])([2H])O)CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC
InChi Code
InChI=1S/C24H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-24(27)25-22-23-26/h3-4,6-7,9-10,12-13,15-16,18-19,26H,2,5,8,11,14,17,20-23H2,1H3,(H,25,27)/b4-3-,7-6-,10-9-,13-12-,16-15-,19-18-/i22D2,23D2
InChi Key
GEEHOLRSGZPBSM-DXYZWJMHSA-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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    100 µg

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    Product Description

    Docosahexaenoyl ethanolamide-d4 contains four deuterium atoms at the 1, 1', 2, and 2' positions. It is intended for use as an internal standard for the quantification of docosahexaenoyl ethanolamide by GC- or LC-mass spectrometry (MS). Docosahexaenoic Acid (DHA) is an essential fatty acid and the most abundant ω-3 fatty acid in neural tissues, especially in the retina and brain. Docosahexaenoyl ethanolamide (DHEA) is the ethanolamine amide of DHA that has been detected in both brain and retina at concentrations similar to those for arachidonoyl ethanolamide (AEA).1,2 A 9.5 fold increase of DHEA was observed in brain lipid extracts from piglets fed a diet supplemented with DHA compared to a control diet without DHA.3 DHEA binds to the rat brain CB1 receptor with a Ki value of 324 nM, which is approximately 10-fold higher than the Ki value for AEA.4 DHEA inhibits shaker-related voltage-gated potassium channels in brain slightly better than AEA, with an IC50 value of 1.5 µM.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sugiura, T., Kondo, S., Sukagawa, A., et al. Transacylase-mediated and phosphodiesterase-mediated synthesis of N-arachidonoylethanolamine, an endogenous cannabinoid-receptor ligand, in rat brain microsomes. Comparison with synthesis from free arachidonic acid and ethanolamine. Eur. J. Biochem. 240, 53-62 (1996).

    2. Bisogno, T., Delton-Vandenbroucke, I., Milone, A., et al. Biosynthesis and inactivation of N-Arachidonoylethanolamine (Ananadamide) and N-Docosahexaenoylethanolamine in bovine retina. Arch. Biochem. Biophys. 370(2), 300-307 (1999).

    3. Berger, A., Crozier, G., Bisogno, T., et al. Anandamide and diet: Inclusion of dietary arachidonate and docosahexaenoate leads to increased brain levels of the corresponding N-acylethanolamines in piglets. Proc. Natl. Acad. Sci. USA 98(11), 6402-6406 (2001).

    4. Sheskin, T., Hanus, L., Slager, J., et al. Structural requirements for binding of anandamide-type compounds to the brain cannabinoid receptor. J. Med. Chem. 40(5), 659-667 (1997).

    5. Poling, J.S., Rogawski, M.A., Salem, N., Jr., et al. Anadamide, an endogenous cannabinoid, inhibits shaker-related voltage-gated K+ channels. Neuropharmacology 35(7), 983-991 (1996).

    Product Citations

    Kantae, V., Ogino, S., Noga, M., et al. Quantitative profiling of endocannabinoids and related N-acylethanolamines in human CSF using nano LC-MS/MS. J. Lipid. Res. 58(3), 615-624 (2017).