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Docosahexaenoyl Ethanolamide Exclusive

Cayman Chemical Item Number 10007534

DHEA; DEA (CAS 162758-94-3)

Docosahexaenoyl Ethanolamide (CAS 162758-94-3)

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Description

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 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

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 40 659-667 (1997).

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

Synonyms
  • DHEA
  • DEA
Formal Name N-​(2-​hydroxyethyl)-​4Z,​7Z,​10Z,​13Z,​16Z,​19Z-​docosahexaenamide
CAS Number 162758-94-3
Molecular Formula C24H37NO2
Formula Weight 371.6
Formulation A solution in ethanol
Purity ≥98%
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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OCCNC(=O)​CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC

Background Reading

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).

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

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).

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

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).

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Docosahexaenoyl Ethanolamide is available in the following screening library:

Size Price Quantity Subtotal
5 mg $33.00 $0.00
10 mg $63.00 $0.00
25 mg $149.00 $0.00
50 mg $264.00 $0.00
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Cart Total $0.00

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Pricing updated 2012-05-26. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

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