Cyclic 3-hydroxymelatonin

Cyclic 3-hydroxymelatonin
Names
	IUPAC name 1-[(3aS,8bR)-8b-Hydroxy-7-methoxy-1,2,3a,4-tetrahydropyrrolo[2,3-b]indol-3-yl]ethanone
Identifiers
CAS Number	220890-80-2;
3D model (JSmol)	Interactive image;
ChemSpider	35031688;
PubChem CID	100952227;
UNII	YCG9VDC7QG;
	InChI InChI=1S/C13H16N2O3/c1-8(16)15-6-5-13(17)10-7-9(18-2)3-4-11(10)14-12(13)15/h3-4,7,12,14,17H,5-6H2,1-2H3/t12-,13+/m0/s1 Key: VADOSKJWFKUPQF-QWHCGFSZSA-N;
	SMILES CC(=O)N1CC[C@@]2([C@H]1NC3=C2C=C(C=C3)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

Cyclic 3-hydroxymelatonin (3-OHM) is a metabolite of melatonin and an antioxidant more potent than melatonin.^[1] It is a non-radical species and does not further propagate the radical chain reaction

It is a footprint product of the reaction between melatonin and hydroxyl radical.^[2]

^ Tan, Dun-Xian; Hardeland, R.; Manchester, L. C.; Galano, A.; Reiter, R. J. (May 11, 2014). "Cyclic-3-hydroxymelatonin (C3HOM), a potent antioxidant, scavenges free radicals and suppresses oxidative reactions". Current Medicinal Chemistry. 21 (13): 1557–1565. doi:10.2174/0929867321666131129113146. PMID 24304286 – via PubMed.
^ Tan, Dun-Xian; Manchester, LucienC.; Reiter, RusselJ.; Plummer, BenjaminF. (March 19, 1999). "Cyclic 3-Hydroxymelatonin: A Melatonin Metabolite Generated as a Result of Hydroxyl Radical Scavenging". Biological Signals and Receptors. 8 (1–2): 70–74. doi:10.1159/000014571 (inactive 1 November 2024). PMID 10085465 – via Silverchair.{{cite journal}}: CS1 maint: DOI inactive as of November 2024 (link)

[1] Tan, Dun-Xian; Hardeland, R.; Manchester, L. C.; Galano, A.; Reiter, R. J. (May 11, 2014). "Cyclic-3-hydroxymelatonin (C3HOM), a potent antioxidant, scavenges free radicals and suppresses oxidative reactions". Current Medicinal Chemistry. 21 (13): 1557–1565. doi:10.2174/0929867321666131129113146. PMID 24304286 – via PubMed.

[2] Tan, Dun-Xian; Manchester, LucienC.; Reiter, RusselJ.; Plummer, BenjaminF. (March 19, 1999). "Cyclic 3-Hydroxymelatonin: A Melatonin Metabolite Generated as a Result of Hydroxyl Radical Scavenging". Biological Signals and Receptors. 8 (1–2): 70–74. doi:10.1159/000014571 (inactive 1 November 2024). PMID 10085465 – via Silverchair.{{cite journal}}: CS1 maint: DOI inactive as of November 2024 (link)

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