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H0627

Sigma-Aldrich

6-Hydroxymelatonin

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C13H16N2O3
Numéro CAS:
2208-41-5
Poids moléculaire :
248.28
Numéro MDL:
MFCD00037971
Code UNSPSC :
41116107
ID de substance PubChem :
24278458
Nomenclature NACRES :
NA.77

Solubilité

alcohol: soluble

Chaîne 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)

Clé InChI

OMYMRCXOJJZYKE-UHFFFAOYSA-N

Informations sur le gène

human ... MTNR1A(4543) , MTNR1B(4544)

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Description générale

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.

Actions biochimiques/physiologiques

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).

Pictogrammes

Health hazardExclamation mark
GHS08,GHS07

Mention d'avertissement

Warning

Mentions de danger

H302,H351

Classification des risques

Acute Tox. 4 Oral - Carc. 2

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Équipement de protection individuelle

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

Certificats d'analyse (COA)

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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
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
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
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
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