Description
6-hydroxy Melatonin is an active metabolite of melatonin . It is formed from melatonin by the cytochrome P450 (CYP) isoform CYP1A2 in human liver microsomes. 6-hydroxy Melatonin is a melatonin 1A (MT
1A), MT
1B, and MT
2 receptor agonist. It inhibits dopamine release from isolated rabbit retina (IC
50 = 0.0016 μM). 6-hydroxy Melatonin (10 and 100 μM) reduces increases in the levels of NF-κB, IL-6, and IL-8 and decreases in glutathione (GSH) levels in LPS- and peptidoglycan G-stimulated human umbilical vein endothelial cells (HUVECs) in an
in vitro model of sepsis. It reduces iron-induced lipid oxidation in rat hippocampal homogenate when administered at a dose of 10 mg/kg.
Chemical Properties
Off-White to Pale Beige Solid
Uses
A metabolite of Melatonin (M215000).
Uses
A metabolite of Melatonin (S689050).
Uses
A major human metabolite of Melatonin
Uses
6-Hydroxymelatonin has been used as a melatonin derivative to test its protective effects in ultra violet B (UVB)-induced oxidative stress melanocytes and keratinocytes.
Definition
ChEBI: A member of the class of tryptamines that is melatonin with a hydroxy group substituent at position 6.
General Description
6-Hydroxymelatonin (6-OHM) is a melatonin metabolite. It is produced in the liver by the action of cytochrome P450 enzyme as well as by photodegradation of melatonin. In the central nervous system, it exists as a sulfated form. 6-OHM is a partial melatonin receptor MT2 agonist.
Biochem/physiol Actions
6-Hydroxymelatonin (6-OHM) is an antioxidant with a free radical scavenging role. Like melatonin, it reduces the impact of UVB-induced oxidative stress in melanocytes. It also aids protection during iron (Fe2+)-induced neurotoxicity. 6-OHM effectively reduces lipid peroxidation and superoxide anion production induced by potassium cyanide (KCN).
References
[1] M L DUBOCOVICH. Melatonin receptor antagonists that differentiate between the human Mel1a and Mel1b recombinant subtypes are used to assess the pharmacological profile of the rabbit retina ML1 presynaptic heteroreceptor.[J]. Naunyn-Schmiedeberg’s archives of pharmacology, 1997, 355 3: 365-375. DOI:
10.1007/pl00004956[2] DUBOCOVICH M L. Melatonin receptors: are there multiple subtypes[J]. Trends in pharmacological sciences, 1995, 16 2: 50-56. DOI:
10.1016/s0165-6147(00)88978-6[3] DUBOCOVICH M L. Characterization of a retinal melatonin receptor.[J]. Journal of Pharmacology and Experimental Therapeutics, 1985, 234 2: 395-401.
[4] D.A. LOWES . Melatonin and structurally similar compounds have differing effects on inflammation and mitochondrial function in endothelial cells under conditions mimicking sepsis[J]. British journal of anaesthesia, 2011, 107 2: Pages 193-201. DOI:
10.1093/bja/aer149[5] DEEPA S. MAHARAJ. Melatonin and 6-hydroxymelatonin protect against iron-induced neurotoxicity[J]. Journal of Neurochemistry, 2005, 96 1: 78-81. DOI:
10.1111/j.1471-4159.2005.03532.x[6] S. HRTTER. Differential Effects of Fluvoxamine and Other Antidepressants on the Biotransformation of Melatonin[J]. Journal of Clinical Psychopharmacology, 2001, 123 1 1: 167-174. DOI:
10.1097/00004714-200104000-00008
