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H0627

Sigma-Aldrich

6-Hydroxymelatonin

Synonym(s):

3-(N-Acetylaminoethyl)-6-hydroxy-5-methoxyindole

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About This Item

Empirical Formula (Hill Notation):
C13H16N2O3
CAS Number:
2208-41-5
Molecular Weight:
248.28
MDL number:
MFCD00037971
UNSPSC Code:
41116107
PubChem Substance ID:
24278458
NACRES:
NA.77

solubility

alcohol: soluble

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

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).

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H302,H351

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
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
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
James B Burch et al.
Journal of occupational and environmental medicine, 47(9), 893-901 (2005-09-13)
Night work is associated with disrupted circadian rhythms, fatigue, accidents, and chronic disease. Melatonin secretion helps regulate sleep and circadian rhythms. Melatonin, sleep disturbances, and symptoms (sleep, fatigue, mental) were compared among workers on permanent day, swing, and night shifts.
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