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| Names | |
|---|---|
| Preferred IUPAC name N-[2-(6-Hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide | |
| Other names 6-Oxymelatonin | |
| Identifiers | |
3D model (JSmol) | |
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.164.426 |
| KEGG | |
| UNII | |
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| Properties | |
| C13H16N2O3 | |
| Molar mass | 248.282 g·mol−1 |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
6-Hydroxymelatonin (6-OHM) is anaturally occurring,endogenous, majoractive metabolite ofmelatonin.[1] 6-Hydroxymelatonin is produced as a result of the enzymatic conversion of melatonin throughhydroxylation.[2] Similar to melatonin, 6-OHM is afull agonist of theMT1 andMT2 receptors.[3][4] It is also anantioxidant andneuroprotective, and is even more potent in this regard relative to melatonin.[5][6]
The determination of 6-OHM in human urine has been used to track the metabolism and excretion of melatonin usingLC-MS/MS, providing quantifiable insights intocircadian rhythm regulation and its oxidative role as abiomarker.[7] 6-OHM is one of four of the primary metabolic products of melatonin in the liver and is also a byproduct of its breakdown due to exposure to light. It is known to be very effective in protecting cells fromoxidative damage caused byultraviolet (UV) radiation.[8] Based on comparisons with other melatonin-related compounds, it is suggested that the protective effects of 6-OHM in mitigating oxidative stress are primarily attributed to their ability to scavengefree radicals.[9]
