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| Names | |
|---|---|
| Preferred 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 | |
3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
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| Properties | |
| C30H42N2O2 | |
| Molar mass | 462.678 g·mol−1 |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Arachidonoyl serotonin (N-arachidonoyl-serotonin, AA-5-HT) is an endogenous lipid signaling molecule. It was first described in 1998 as being an inhibitor offatty acid amide hydrolase (FAAH).[1] In 2007, it was shown to haveanalgesic properties and to act as anantagonist of theTRPV1 receptor.[2] In 2011, it was shown to be present in theileum andjejunum of thegastrointestinal tract and modulateglucagon-like peptide-1 (GLP-1) secretion.[3] In addition to this, in 2016, AA-5-HT was also found to affect the signaling mechanisms responsible for anxiety, by inhibitingdopamine release from theBasolateral amygdala following fear behavior.[4] In 2017, AA-5-HT was tested in its effects on the sleep wake cycle, where it was found to affect the sleep homeostasis when used in conjunction with molecules and chemicals that affect wake-related neurotransmitters.[5]
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