Home>>Synaptamide (Dehydroepiandrosteron(DHEA))
Synaptamide (Dehydroepiandrosteron(DHEA)) Catalog No.GC30815

An endocannabinoid found in brain and retina

Size Price Stock Qty
5mg
$43.00
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10mg
$81.00
In stock
25mg
$194.00
In stock
50mg
$343.00
In stock

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Sample solution is provided at 25 µL, 10mM.

Quality Control

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Chemical Properties

Cas No. 162758-94-3 SDF Download SDF
Synonyms N/A
Chemical Name N-(2-hydroxyethyl)-4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenamide
Canonical SMILES CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(NCCO)=O
Formula C24H37NO2 M.Wt 371.56
Solubility 20mg/mL in DMSO or DMF Storage Store at -20°C
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
Shipping Condition Evaluation sample solution : ship with blue ice
All other available size: ship with RT , or blue ice upon request
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Background

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 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]

Reference:
[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. European Journal of Biochemistry 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. Archives of Biochemistry and Biophysics 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. Proceedings of the National Academy of Sciences of the United States of America 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. Journal of Medicinal Chemistry 40, 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).