LIPID MAPS

Structure Database (LMSD)

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Common Name

Palmitoyl Serotonin

Systematic Name

N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-hexadecanamide

Synonyms

PA-5HT
Palmitoyl 5HT

LM ID

LMFA08020302

Formula

C₂₆H₄₂N₂O₂

Exact Mass

Calculate m/z

414.324628

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

Palmitoyl serotonin is a hybrid molecule patterned after arachidonoyl serotonin (Catalog No. 70665). Arachidonoyl serotonin is a dual antagonist of fatty acid amide hydrolase (FAAH) and the transient receptor potential vanilloid-type 1 (TRPV1) channel, reducing both acute and chronic peripheral pain.^1,2 The effects of replacing the arachidonoyl portion with the saturated 16-carbon palmitoyl moiety have not been studied. However, replacement of arachidonate with saturated 11- or 12-carbon fatty acids produces compounds that potently inhibit capsaicin-induced TRPV1 channel activation (IC50 = 0.76 μM) without blocking FAAH-mediated hydrolysis of arachidonoyl ethanolamine (IC50 > 50 μM).¹

This information has been provided by Cayman Chemical

References

1. Ortar, G., Cascio, M.G., De Petrocellis, L., et al. New N-arachidonoylserotonin analogues with potential "dual" mechanism of action against pain. J. Med. Chem. 50(26), 6554-6569 (2007).

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. 150(6), 766-781 (2007).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Sus scrofa (#9823)

Mammalia (#40674)

Presence, formation and putative biological activities of N-acyl serotonins, a novel class of fatty-acid derived mediators, in the intestinal tract.,
Biochim Biophys Acta, 2011

Pubmed ID: 21798367

DOI: 10.1016/j.bbalip.2011.07.008

String Representations

InChiKey (Click to copy)

AKQOZSXOPVLUHA-UHFFFAOYSA-N

InChi (Click to copy)

InChI=1S/C26H42N2O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-26(30)27-19-18-22-21-28-25-17-16-23(29)20-24(22)25/h16-17,20-21,28-29H,2-15,18-19H2,1H3,(H,27,30)

SMILES (Click to copy)

C(NCCC1=CNC2=CC=C(O)C=C12)(=O)CCCCCCCCCCCCCCC