| Identification | Back Directory | [Name]
Oleoyl Serotonin | [CAS]
1002100-44-8 | [Synonyms]
Oleoyl Serotonin
Oleoyl Serotonin Exclusive
(Z)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]octadec-9-enamide
9-Octadecenamide, N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-, (9Z)- | [Molecular Formula]
C28H44N2O2 | [MDL Number]
MFCD18428060 | [MOL File]
1002100-44-8.mol | [Molecular Weight]
440.66 |
| Chemical Properties | Back Directory | [storage temp. ]
Store at -20°C | [solubility ]
≤15mg/ml in DMSO;15mg/ml in dimethyl formamide | [form ]
solution in ethanol. | [color ]
Colorless to light yellow |
| Hazard Information | Back Directory | [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. |
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