Docosahexaenoyl EthanolamideAn ethanolamine amide of DHA

Docosahexaenoyl Ethanolamide (CAS 162758-94-3)

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Synonym: DHEA; Synaptamide
Application: An ethanolamine amide of DHA
CAS Number: 162758-94-3
Molecular Weight: 371.60
Molecular Formula: C24H37NO2
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Docosahexaenoyl Ethanolamide (DHEA) is an ethanolamine amide of DHA that has been detected in both retina and brain at concentrations similar to those for arachidonoyl ethanolamide (AEA). Docosahexaenoic Acid (DHA) is an essential fatty acid and the most abundant ω-3 fatty acid in neural tissues, particularly in the retina and brain. A 9.5 fold increase of DHEA was observed in brain lipid extracts from piglets on a DHA-supplemented diet compared to a DHA-free control diet. DHEA binds rat brain CB1 receptor with a Ki of 324 nM, which is about 10-fold higher than the Ki for AEA. DHEA inhibits shaker-related voltage-gated potassium channels in the brain slightly better than AEA, with an IC50 of 1.5 μM.


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 40 659-667 (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).

Formulation :
A solution in ethanol
Appearance :
Solution
Physical State :
Liquid
Solubility :
Soluble in ethanol, DMSO (~20 mg/ml), DMF (~20 mg/ml), PBS (pH 7.2) (~0.15 mg/ml), and water (0.15 mg/ml at 25° C).
Storage :
Store at -20° C
Boiling Point :
78° C
Refractive Index :
n20D 1.52 (Predicted)
IC50 :
Shaker-related voltage-gated potassium channels: IC50 = 1.5 µM (brain)
Ki Data :
CB1: Ki= 324 nM (rat brain)
pK Values :
pKa: 15.45 (Predicted), pKb: -0.48 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
PubChem CID :
5283451
MDL Number :
MFCD12912674
SMILES :
CC/C=C\\C/C=C\\C/C=C\\C/C=C\\C/C=C\\C/C=C\\CCC(=O)NCCO

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Certificate of Analysis

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