6-Hydroxymelatonin

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]

6-Hydroxymelatonin

Names
IUPAC name N-[2-(6-Hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide
Other names 6-Oxymelatonin
Identifiers
CAS Number	2208-41-5^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:198
ChemSpider	1794
ECHA InfoCard	100.164.426
KEGG	C05643
PubChem CID	1864
UNII	TV437T5077^Y
CompTox Dashboard (EPA)	DTXSID00176577
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
SMILES 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

See also

• N-Acetylserotonin (normelatonin)
• 5-Methoxytryptamine

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.
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.
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.