6-Hydroxymelatonin

Chemical compound From Wikipedia, the free encyclopedia

6-Hydroxymelatonin (6-OHM) is a naturally occurring, endogenous, major active metabolite of melatonin.[1] 6-Hydroxymelatonin is produced as a result of the enzymatic conversion of melatonin through hydroxylation.[2] Similar to melatonin, 6-OHM is a full agonist of the MT1 and MT2 receptors.[3][4] It is also an antioxidant and neuroprotective, and is even more potent in this regard relative to melatonin.[5][6]

Quick facts Names, Identifiers ...
6-Hydroxymelatonin
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 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C13H16N2O3/c1-8(16)14-4-3-9-7-15-11-6-12(17)13(18-2)5-10(9)11/h5-7,15,17H,3-4H2,1-2H3,(H,14,16)
    Key: OMYMRCXOJJZYKE-UHFFFAOYSA-N
  • InChI=1/C13H16N2O3/c1-8(16)14-4-3-9-7-15-11-6-12(17)13(18-2)5-10(9)11/h5-7,15,17H,3-4H2,1-2H3,(H,14,16)
    Key: OMYMRCXOJJZYKE-UHFFFAOYAK
  • CC(=O)NCCC1=CNC2=CC(=C(C=C21)OC)O
Properties
C13H16N2O3
Molar mass 248.282 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Role in metabolism

The determination of 6-OHM in human urine has been used to track the metabolism and excretion of melatonin using LC-MS/MS, providing quantifiable insights into circadian rhythm regulation and its oxidative role as a biomarker.[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 from oxidative damage caused by ultraviolet (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 scavenge free radicals.[9]

See also

References

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