Molecular structure of Eicosapentaenoyl Serotonin, CAS Number: 199875-71-3
Eicosapentaenoyl Serotonin (CAS 199875-71-3)
Alternate Names:
N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-5Z,8Z,11Z,14Z,17Z-eicosapentaenamide
Application:
Eicosapentaenoyl Serotonin is a dual fatty acid amide hydrolase and TRPV1 antagonist
CAS Number:
199875-71-3
Molecular Weight:
460.66
Molecular Formula:
C30H40N2O2
Supplemental Information:
This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.
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SDS & Certificate of Analysis
Eicosapentaenoyl serotonin is a hybrid molecule patterned after arachidonoyl serotonin (sc-201460). 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. The effects of replacing the arachidonoyl portion with eicosapentaenoic acid 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).
Eicosapentaenoyl Serotonin (CAS 199875-71-3) References
- Analgesic actions of N-arachidonoyl-serotonin, a fatty acid amide hydrolase inhibitor with antagonistic activity at vanilloid TRPV1 receptors. | Maione, S., et al. 2007. Br J Pharmacol. 150: 766-81. PMID: 17279090
- New N-arachidonoylserotonin analogues with potential 'dual' mechanism of action against pain. | Ortar, G., et al. 2007. J Med Chem. 50: 6554-69. PMID: 18027904
- Presence, formation and putative biological activities of N-acyl serotonins, a novel class of fatty-acid derived mediators, in the intestinal tract. | Verhoeckx, KC., et al. 2011. Biochim Biophys Acta. 1811: 578-86. PMID: 21798367
- Docosahexaenoyl serotonin, an endogenously formed n-3 fatty acid-serotonin conjugate has anti-inflammatory properties by attenuating IL-23-IL-17 signaling in macrophages. | Poland, M., et al. 2016. Biochim Biophys Acta. 1861: 2020-2028. PMID: 27663185
- Docosahexaenoyl serotonin emerges as most potent inhibitor of IL-17 and CCL-20 released by blood mononuclear cells from a series of N-acyl serotonins identified in human intestinal tissue. | Wang, Y., et al. 2017. Biochim Biophys Acta Mol Cell Biol Lipids. 1862: 823-831. PMID: 28526351
- The Intestinal Fatty Acid-Enteroendocrine Interplay, Emerging Roles for Olfactory Signaling and Serotonin Conjugates. | Meijerink, J. 2021. Molecules. 26: PMID: 33807994
- Arachidonoylserotonin and other novel inhibitors of fatty acid amide hydrolase. | Bisogno, T., et al. 1998. Biochem Biophys Res Commun. 248: 515-22. PMID: 9703957
Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
Eicosapentaenoyl Serotonin, 1 mg | sc-358802 | 1 mg | $80.00 | |||
Eicosapentaenoyl Serotonin, 5 mg | sc-358802A | 5 mg | $360.00 |