Oleoyl Serotonin

Definition

ChEBI: N-oleoylserotonin is an N-acylserotonin obtained by formal condensation of the carboxy group of oleoic acid with the primary amino group of serotonin. It is functionally related to an oleic acid.

Biological Activity

oleoyl serotonin is a trpv1 antagonist with ic50 value of 2.57 μm for human trpv1 [1].the transient receptor potential vanilloid-type 1 (trpv1) channel is a nonselective cation channel that may be activated by a variety of exogenous and endogenous physical and chemical stimuli. trpv1 is decreased in the injured nerve fibers but increased in those proximal to the site damage. trpv1 is a potential new target for the development of analgesic and anti-inflammatory drugs [1].oleoyl serotonin is a hybrid molecule patterned after arachidonoyl serotonin. arachidonoyl serotonin is a dual antagonist of trpv1 and fatty acid amide hydrolase (faah) with ic50 values of 0.27 and 8 μm, respectively. arachidonoyl serotonin was highly effective against both acute and chronic peripheral pain [1][2]. in trpv1 and faah assays, oleoyl serotonin inhibited anandamide hydrolysis by faah and capsaicin-induced intracellular ca2+ elevation in hek293 cells overexpressing the human recombinant trpv1 receptor with ic50 values of > 50 μm and 2.57 μm, respectively [1].

References

[1]. ortar g, cascio mg, de petrocellis l, et al. new n-arachidonoylserotonin analogues with potential "dual" mechanism of action against pain. j med chem. 2007 dec 27;50(26):6554-69.
[2]. maione s, de petrocellis l, de novellis v, et al. analgesic actions of n-arachidonoyl-serotonin, a fatty acid amide hydrolase inhibitor with antagonistic activity at vanilloid trpv1 receptors. br j pharmacol. 2007 mar;150(6):766-81.