H0627
6-Hydroxymelatonin
Sinónimos:
3-(N-Acetylaminoethyl)-6-hydroxy-5-methoxyindole
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About This Item
Fórmula empírica (notación de Hill):
C13H16N2O3
Número de CAS:
Peso molecular:
248.28
Número MDL:
Código UNSPSC:
41116107
ID de la sustancia en PubChem:
NACRES:
NA.77
Productos recomendados
solubilidad
alcohol: soluble
Nivel de calidad
cadena SMILES
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)
Clave InChI
OMYMRCXOJJZYKE-UHFFFAOYSA-N
Información sobre el gen
human ... MTNR1A(4543) , MTNR1B(4544)
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Descripción general
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.
Aplicación
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.
Acciones bioquímicas o fisiológicas
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).
Palabra de señalización
Warning
Frases de peligro
Consejos de prudencia
Clasificaciones de peligro
Acute Tox. 4 Oral - Carc. 2
Código de clase de almacenamiento
11 - Combustible Solids
Clase de riesgo para el agua (WGK)
WGK 3
Equipo de protección personal
Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
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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.
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
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
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
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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