Docosahexaenoyl Ethanolamide-d4 Property

solubility 

DMF: 20 mg/ml; DMSO: 20 mg/ml; Ethanol: 5 mg/ml; PBS (pH 7.2): 0.15 mg/ml

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H225Highly Flammable liquid and vapour

H319Causes serious eye irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P240Ground/bond container and receiving equipment.

P241Use explosion-proof electrical/ventilating/lighting/…/equipment.

P242Use only non-sparking tools.

P243Take precautionary measures against static discharge.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P337+P313IF eye irritation persists: Get medical advice/attention.

P370+P378In case of fire: Use … for extinction.

P403+P235Store in a well-ventilated place. Keep cool.

P501Dispose of contents/container to..…

Docosahexaenoyl Ethanolamide-d4 Chemical Properties,Usage,Production

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 K_i value of 324 nM, which is approximately 10-fold higher than the K_i 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

Uses

Synaptamide-d4 is labelled Synaptamide (S910000) which is an endocannabinoid-like derivative of docosahexaenoic acid with cannabinoid-independent function. It has potent synaptogenic activity and structural similarity to anandamide. Synaptamide (S910000) is subjected to hydrolysis by fatty acid amide hydrolase, and can be oxygenated to bioactive metabolites.

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., Jr., et al. Anadamide, an endogenous cannabinoid, inhibits shaker-related voltage-gated K⁺ channels Neuropharmacology 35(7),983-991(1996).