| Identification | Back Directory | [Name]
Palmitoyl Serotonin | [CAS]
212707-51-2 | [Synonyms]
Palmitoyl Serotonin
Palmitoyl Serotonin Exclusive
N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]hexadecanamide
Hexadecanamide, N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]- | [Molecular Formula]
C26H42N2O2 | [MDL Number]
MFCD18382130 | [MOL File]
212707-51-2.mol | [Molecular Weight]
414.62 |
| Hazard Information | Back Directory | [Definition]
ChEBI: N-palmitoylserotonin is an N-acylserotonin obtained by formal condensation of the carboxy group of hexadecanoic acid with the primary amino group of serotonin. It is functionally related to a hexadecanoic acid. | [Biological Activity]
palmitoyl serotonin is a trpv1 antagonist with ic50 value of 0.76 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].palmitoyl 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, palmitoyl serotonin inhibited anandamide hydrolysis mediated by faah and capsaicin-induced intracellular ca2+ elevation in hek293 cells overexpressing the human recombinant trpv1 receptor with ic50 values of > 50 μm and 0.76 μm, respectively. however, the effects of replacing the arachidonoyl portion with the saturated 16-carbon palmitoyl moiety had not been studied [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. |
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