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Palmitoyl Serotonin TRPV1 channel inhibitor

Catalog No.C4169
Size Price Stock Qty
1mg
$64.00
In stock
5mg
$287.00
In stock
10mg
$509.00
In stock
25mg
$1,114.00
In stock

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Sample solution is provided at 25 µL, 10mM.

Quality Control

Quality Control & MSDS

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Chemical structure

Palmitoyl Serotonin

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Chemical Properties

Cas No. 212707-51-2 SDF Download SDF
Chemical Name N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-hexadecanamide
Canonical SMILES CCCCCCCCCCCCCCCC(NCCC1=CNC2=CC=C(O)C=C12)=O
Formula C26H42N2O2 M.Wt 414.6
Solubility ≤30mg/ml in ethanol;15mg/ml in DMSO;30mg/ml in dimethyl formamide Storage Store at -20°C
Physical Appearance A neat solid Shipping Condition Evaluation sample solution : ship with blue ice.All other available size: ship with RT , or blue ice upon request
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.

Background

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.