H0627
6-Hydroxymelatonin
antioxidant
Synonym(s):
3-(N-Acetylaminoethyl)-6-hydroxy-5-methoxyindole
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About This Item
Empirical Formula (Hill Notation):
C13H16N2O3
CAS Number:
Molecular Weight:
248.28
UNSPSC Code:
41116107
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Product Name
6-Hydroxymelatonin,
SMILES string
COc1cc2c(CCNC(C)=O)c[nH]c2cc1O
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)
InChI key
OMYMRCXOJJZYKE-UHFFFAOYSA-N
solubility
alcohol: soluble
Quality Level
Gene Information
human ... MTNR1A(4543), MTNR1B(4544)
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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.
Application
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.
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).
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Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Carc. 2
Storage Class
11 - Combustible Solids
wgk
WGK 3
ppe
Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
Regulatory Information
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Herwig Frisch et al.
The Journal of clinical endocrinology and metabolism, 89(9), 4388-4390 (2004-09-10)
Melatonin (MLT), the pineal gland hormone involved in the regulation of circadian rhythms, shows characteristic diurnal variation. Its physiological role in humans is not clear. Exposure to high altitudes may disrupt the circadian rhythm and lead to various endocrine changes.
S Härtter et al.
Clinical pharmacology and therapeutics, 70(1), 10-16 (2001-07-14)
Melatonin is a hormone that is metabolized by cytochrome P450 (CYP) 1A2 to its main primary metabolite 6-hydroxymelatonin. We therefore evaluated the utility of oral melatonin as a marker of hepatic CYP1A2 activity. Twenty-five milligrams of melatonin was given at
Zorica Janjetovic et al.
Journal of pineal research, 57(1), 90-102 (2014-05-29)
We investigated the protective effects of melatonin and its metabolites: 6-hydroxymelatonin (6-OHM), N1-acetyl-N2-formyl-5-methoxykynuramine (AFMK), N-acetylserotonin (NAS), and 5-methoxytryptamine (5-MT) in human keratinocytes against a range of doses (25, 50, and 75 mJ/cm2) of ultraviolet B (UVB) radiation. There was significant
K N Ting et al.
British journal of pharmacology, 122(7), 1299-1306 (1998-01-08)
1. In this study we compared the vasoconstrictor activity of melatonin in rat isolated tail artery using two different recording systems, the Halpern pressure myograph and the Halpern-Mulvany wire myograph, with the view to determining a reliable method for obtaining
G Facciolá et al.
European journal of clinical pharmacology, 56(12), 881-888 (2001-04-25)
The present study was carried out to identify the cytochrome P450 enzyme(s) involved in the 6-hydroxylation and O-demethylation of melatonin. The formation kinetics of 6-hydroxymelatonin and N-acetylserotonin were determined using human liver microsomes and cDNA yeast-expressed human enzymes (CYP1A2, 2C9
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