N-Arachidonoylserotonin (Arachidonyl serotonin; AA-5-HT) is a potent fatty acid amide hydrolase (FAAH) inhibitor with an IC50 value of 1~12 μM. N-Arachidonoylserotonin acts also as an antagonist of transient receptor potential vanilloid-type 1 (TRPV1) channels (IC50=70~100 nM). N-Arachidonoylserotonin is analgesic in rodents [1].
ChEBI: N-arachidonoylserotonin is an N-acylserotonin obtained by formal condensation of the carboxy group of arachidonic acid with the primary amino group of serotonin. It has a role as a human metabolite, a signalling molecule, an antioxidant, an anti-inflammatory agent, an anticonvulsant, a capsaicin receptor antagonist and an EC 3.5.1.99 (fatty acid amide hydrolase) inhibitor. It is a member of phenols and a N-acylserotonin. It is functionally related to an arachidonic acid.
Dual fatty acid amide hydrolase (FAAH) inhibitor/TRPV1 antagonist (IC 50 values are 5.6 μ M and 37-40 nM for FAAH and TRPV1 respectively). Inactive at cPLA 2 , CB 1 or 5-HT receptors. Displays strong analgesic activity against both acute and chronic peripheral pain.
[1] Ortar G, et al. New N-arachidonoylserotonin analogues with potential "dual" mechanism of action against pain. J Med Chem. 2007;50(26):6554-6569. DOI:
10.1021/jm070678q
