Oleoyl Serotonin
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.
Physical Appearance | A solution in ethanol. To change the solvent, simply evaporate the ethanol under a gentle stream of nitrogen and immediately add the solvent of choice. |
Storage | Store at -20°C |
M.Wt | 440.1 |
Cas No. | 1002100-44-8 |
Formula | C28H44N2O2 |
Solubility | ≤15mg/ml in DMSO;15mg/ml in dimethyl formamide |
Chemical Name | N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-9Z-octadecenamide |
SDF | Download SDF |
Canonical SMILES | O=C(NCCC1=CNC2=CC=C(O)C=C12)CCCCCCC/C=C\CCCCCCCC |
Shipping Condition | Small Molecules with Blue Ice, Modified Nucleotides with Dry Ice. |
General tips | We do not recommend long-term storage for the solution, please use it up soon. |
Quality Control & MSDS
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Purity = 98.00%
- COA (Certificate Of Analysis)
- MSDS (Material Safety Data Sheet)
- Datasheet
Chemical structure
