6-Hydroxymelatonin

Last updated
6-Hydroxymelatonin
6-Hydroxymelatonin structure.svg
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 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
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).

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]

Contents

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

  1. ↑ Hardeland R (2010). "Melatonin metabolism in the central nervous system". Curr Neuropharmacol. 8 (3): 168–81. doi:10.2174/157015910792246164. PMC   3001211 . PMID   21358968.
  2. ↑ Magliocco, G.; Le Bloc'h, F.; Thomas, A.; Desmeules, J.; Daali, Y. (2021-09-01). "Simultaneous determination of melatonin and 6-hydroxymelatonin in human overnight urine by LC-MS/MS". Journal of Chromatography. 1181 122938. doi:10.1016/j.jchromb.2021.122938. PMID   34521018.
  3. ↑ Dubocovich ML (1988). "Pharmacology and function of melatonin receptors". FASEB J. 2 (12): 2765–73. doi: 10.1096/fasebj.2.12.2842214 . PMID   2842214. S2CID   45788574.
  4. ↑ Browning, Christopher; Beresford, Isabel; Fraser, Neil; Giles, Heather (2000). "Pharmacological characterization of human recombinant melatonin mt1and MT2receptors". British Journal of Pharmacology. 129 (5): 877–886. doi:10.1038/sj.bjp.0703130. ISSN   0007-1188. PMC   1571913 . PMID   10696085.
  5. ↑ Maharaj DS, Glass BD, Daya S (2007). "Melatonin: new places in therapy". Biosci. Rep. 27 (6): 299–320. doi:10.1007/s10540-007-9052-1. PMID   17828452. S2CID   32437175.
  6. ↑ Álvarez-Diduk R, Galano A, Tan DX, Reiter RJ (2015). "N-Acetylserotonin and 6-Hydroxymelatonin against Oxidative Stress: Implications for the Overall Protection Exerted by Melatonin". J Phys Chem B. 119 (27): 8535–43. doi: 10.1021/acs.jpcb.5b04920 . PMID   26079042.
  7. ↑ Magliocco, G.; Le Bloc'h, F.; Thomas, A.; Desmeules, J.; Daali, Y. (2021-09-01). "Simultaneous determination of melatonin and 6-hydroxymelatonin in human overnight urine by LC-MS/MS". Journal of Chromatography B. 1181 122938. doi:10.1016/j.jchromb.2021.122938. PMID   34521018.
  8. ↑ Maharaj, Deepa S.; Anoopkumar-Dukie, Shailendra; Glass, Beverley D.; Antunes, Edith M.; Lack, Barbara; Walker, Roderick B.; Daya, Santy (2002-04-30). "The identification of the UV degradants of melatonin and their ability to scavenge free radicals" . Journal of Pineal Research. 32 (4): 257–261. doi:10.1034/j.1600-079x.2002.01866.x. ISSN   0742-3098. PMID   11982796.
  9. ↑ Álvarez-Diduk, Ruslán; Galano, Annia; Tan, Dun Xian; Reiter, Russel J. (2015-07-09). "N -Acetylserotonin and 6-Hydroxymelatonin against Oxidative Stress: Implications for the Overall Protection Exerted by Melatonin" . The Journal of Physical Chemistry B. 119 (27): 8535–8543. doi:10.1021/acs.jpcb.5b04920. ISSN   1520-6106. PMID   26079042.