An endocannabinoid found in brain and retina
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Labeled Version(s)
9001108Docosahexaenoyl Ethanolamide-d4
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Docosahexaenoyl Ethanolamide

Item No. 10007534

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-(2-hydroxyethyl)-4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenamide
CAS Number
162758-94-3
Synonyms
  • DEA
  • DHEA
  • Synaptamide
Molecular Formula
C24H37NO2
Formula Weight
371.6
Purity
≥98%
Formulation
A 50 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlEthanol: MisciblePBS (pH 7.2): .15 mg/ml
SMILES
OCCNC(=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-
InChi Key
GEEHOLRSGZPBSM-KUBAVDMBSA-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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    5 mg

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    50 mg

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    Product Description

    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 docosahexaenoic acid (DHA) compared to a control diet without DHA.3 DHEA binds to the rat brain CB1 receptor with a Ki of 324 nM, which is approximately 10-fold higher than the Ki for AEA.4 DHEA inhibits shaker-related voltage-gated potassium channels in brain slightly better than AEA, with an IC50 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

    Hartling, I., Cremonesi, A., Osuna, E., et al. Quantitative profiling of inflammatory and pro-resolving lipid mediators in human adolescents and mouse plasma using UHPLC-MS/MS. Clin. Chem. Lab. Med. 59(11), 1811-1823 (2021).

    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).