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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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Deepa S Maharaj et al.
Journal of neurochemistry, 96(1), 78-81 (2005-11-23)
Oxidative damage of biological macromolecules is a hallmark of most neurodegenerative disorders such as Alzheimer, Parkinson and diffuse Lewy body diseases. Another important phenomenon involved in these disorders is the alteration of iron homeostasis, with an increase in iron levels.
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
Katsuhisa Sakano et al.
Biochemical pharmacology, 68(9), 1869-1878 (2004-09-29)
Melatonin, an indolic pineal hormone, is produced primarily at night in mammals and is important in controlling biological rhythms. Although melatonin is known to be effective as a free radical scavenger and has an anti-cancer effect, carcinogenic properties have also
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
S Härtter et al.
Therapeutic drug monitoring, 23(3), 282-286 (2001-05-22)
Melatonin has recently garnered interest as a possible treatment for sleep disorders, and this has created a desire for appropriate pharmacokinetic studies. No method has yet been published that can measure the concentrations of both melatonin and its main metabolite
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