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Arachidonoyl serotonin

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Title: Arachidonoyl serotonin  
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Subject: Virodhamine, Oleoylethanolamide, Cannabipiperidiethanone, WIN 55,212-2, AM-2201
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Arachidonoyl serotonin

Arachidonoyl serotonin
IUPAC name

(5Z,8Z,11Z,14Z)-N-(2-(5-hydroxy-1H-indol-3-yl)ethyl)icosa-5,8,11,14-tetraenamide

Other names

N-arachidonoyl-serotonin

Identifiers
CAS number  N
PubChem
ChemSpider  YesY
ChEMBL  YesY
Jmol-3D images Image 1
Properties
Molecular formula C30H42N2O2
Molar mass 462.67 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N   YesY/N?)

Arachidonoyl serotonin (N-arachidonoyl-serotonin, AA-5-HT) is an endogenous lipid signaling molecule. It was first described in 1998 as being an inhibitor of fatty acid amide hydrolase (FAAH).[1] In 2007, it was shown to have analgesic properties and to act as an antagonist of the TRPV1 receptor.[2] In 2011, it was shown to be present in the ileum and jejunum of the gastrointestinal tract and modulate glucagon-like peptide-1 (GLP-1) secretion.[3]

References

  1. ^ Bisogno, T.; Melck, D.; De Petrocellis, L.; Bobrov, M. U.; Gretskaya, N. M.; Bezuglov, V. V.; Sitachitta, N.; Gerwick, W. H.; Di Marzo, V. (1998). "Arachidonoylserotonin and other novel inhibitors of fatty acid amide hydrolase". Biochemical and Biophysical Research Communications 248 (3): 515–522.  
  2. ^ Maione, S.; De Petrocellis, L.; De Novellis, V.; Moriello, A. S.; Petrosino, S.; Palazzo, E.; Rossi, F. S.; Woodward, D. F.; Di Marzo, V. (2007). "Analgesic actions of N-arachidonoyl-serotonin, a fatty acid amide hydrolase inhibitor with antagonistic activity at vanilloid TRPV1 receptors". British Journal of Pharmacology 150 (6): 766–781.  
  3. ^ Verhoeckx, K. C. M.; Voortman, T.; Balvers, M. G. J.; Hendriks, H. F. J.; m.Wortelboer, H.; Witkamp, R. F. (2011). "Presence, formation and putative biological activities of N-acyl serotonins, a novel class of fatty-acid derived mediators, in the intestinal tract". Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids 1811 (10): 578–586.  


Amino acid-derived
Lipid-derived
  • Neurosteroids: See instead.
Nucleobase-derived
Vitamin-derived
Miscellaneous

: PNS

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  • drug ()


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