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Merck
CN

H0627

Sigma-Aldrich

6-Hydroxymelatonin

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别名:
3-(N-Acetylaminoethyl)-6-hydroxy-5-methoxyindole
经验公式(希尔记法):
C13H16N2O3
CAS号:
分子量:
248.28
MDL编号:
UNSPSC代码:
12352200
PubChem化学物质编号:
NACRES:
NA.77

溶解性

alcohol: soluble

质量水平

SMILES字符串

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

基因信息

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一般描述

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.

应用

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.

生化/生理作用

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).

象形图

Health hazardExclamation mark

警示用语:

Warning

危险声明

危险分类

Acute Tox. 4 Oral - Carc. 2

WGK

WGK 3

个人防护装备

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

法规信息

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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.
Zorica Janjetovic et al.
Scientific reports, 7(1), 1274-1274 (2017-04-30)
Ultraviolet light (UV) is an inducer of reactive oxygen species (ROS) as well as 6-4-photoproducts and cyclobutane pyrimidine dimers (CPD) in the skin, which further cause damage to the skin cells. Irradiation of cultured human melanocytes with UVB stimulated ROS
Xuwan Liu et al.
American journal of physiology. Heart and circulatory physiology, 283(1), H254-H263 (2002-06-14)
The present study was designed to explore the protective effects of melatonin and its analogs, 6-hydroxymelatonin and 8-methoxy-2-propionamidotetralin, on the survival of doxorubicin-treated mice and on doxorubicin-induced cardiac dysfunction, ultrastructural alterations, and apoptosis in mouse hearts. Whereas 60% of the
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.

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