ARACHIDONOYL SERINOL Chemical Properties

Boiling point:

569.9±50.0 °C(Predicted)

Density 

0.983±0.06 g/cm3(Predicted)

storage temp. 

Store at -20°C

solubility 

≤10mg/ml in ethanol;10mg/ml in DMSO;10mg/ml in dimethyl formamide

form 

solution in ethanol.

pka

13.97±0.10(Predicted)

color 

Off-white to light yellow

ARACHIDONOYL SERINOL Usage And Synthesis

Uses

Arachidonoyl Serinol, an endogenous cannabimimetic metabolite, is an inhibitor of monoacylglycerol lipase (MAGL). Arachidonoyl Serinol inhibits the hydrolysis of [3H]2-oleoylglycerol and [3H]anandamide with IC50s of ～70 μM[1][2][3].

Definition

ChEBI: N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-(1,3-dihydroxy-propyl-2-amine) is a fatty amide.

Biological Activity

arachidonoyl serinol is an amide bond-containing analogue of 2-arachidonoylglycerol, exhibited only weak cb1 receptor agonistic activity. 2-arachidonoyl glycerol (2-ag), a product of increased inositol phospholipid metabolism, is the natural endocannabinoid ligand for the cb1 receptor [1][2][3].cannabinoid receptor (cb1) was first identified in rat brain in 1988. n-arachidonoylethanolamine (anandamide) binds to the cannabinoid receptor and exhibits various cannabimimetic activities. anandamide inhibits calcium currents in n18 neuroblastoma cells, inhibits forskolin-stimulated adenylase cyclase activity, electrically evokes twitch response of the mouse vas deferens, and causes analgesia, hypothermia, hypoactivity, and catalepsy [3]. anandamide acts as a weak agonist and 2-arachidonoylglycerol may be an endogenous cannabinoid receptor agonist in nervous tissues [1].replacement of the sn-2 oxygen in the glycerol moiety of 2-ag with a nitrogen atom produces arachidonoyl serinol. in ng108-15 cells, arachidonoyl serinol induced a weak elevation of [ca2+]i [1][2].

References

[1] Khanolkar AD, et, al. Head group analogs of arachidonylethanolamide, the endogenous cannabinoid ligand. J Med Chem. 1996 Oct 25;39(22):4515-9. DOI:10.1021/jm960152y
[2] Fowler CJ, et, al. Cyclooxygenation of the arachidonoyl side chain of 1-arachidonoylglycerol and related compounds block their ability to prevent anandamide and 2-oleoylglycerol metabolism by rat brain in vitro. Biochem Pharmacol. 2005 Apr 15;69(8):1241-5. DOI:10.1016/j.bcp.2005.01.016
[3] Ghafouri N, et, al. Inhibition of monoacylglycerol lipase and fatty acid amide hydrolase by analogues of 2-arachidonoylglycerol. Br J Pharmacol. 2004 Nov;143(6):774-84. DOI:10.1038/sj.bjp.0705948

ARACHIDONOYL SERINOL(183718-70-9)Related Product Information

• O-(2-AMINOETHYL)-5Z,8Z,11Z,14Z-EICOSATETRAENOATE
• ARACHIDONOYL SERINOL