6-Hydroxymelatonin

6-Hydroxymelatonin
Names
Preferred IUPAC name
N-[2-(6-Hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide
Other names
6-Oxymelatonin
Identifiers
CAS Number
  • 2208-41-5 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:198
ChemSpider
  • 1794
ECHA InfoCard 100.164.426 Edit this at Wikidata
KEGG
  • C05643
PubChem CID
  • 1864
UNII
  • TV437T5077 checkY
CompTox Dashboard (EPA)
  • DTXSID00176577 Edit this at Wikidata
InChI
  • 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
Chemical formula
 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).
Infobox references
Chemical compound

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

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. ^ 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.
  3. ^ 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.
  4. ^ 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.
  5. ^ 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.
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MT1Tooltip Melatonin receptor 1
MT2Tooltip Melatonin receptor 2
Unsorted
  • Agonists: 2-Phenylmelatonin
  • 5-Methoxyluzindole
  • 6-Chloromelatonin
  • 6-Fluoromelatonin
  • 6-Methoxymelatonin
  • 6,7-Dichloro-2-methylmelatonin
  • 8-M-PDOT
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  • GR-135,531 (of MT3Tooltip melatonin receptor 1C)
  • N-Acetyltryptamine
  • N-Butanoylmelatonin
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  • S-24268
  • S-25150
  • See also: Receptor/signaling modulators
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