H0627
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:
Molecular Weight:
248.28
MDL number:
UNSPSC Code:
41116107
PubChem Substance ID:
NACRES:
NA.77
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solubility
alcohol: soluble
Quality Level
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).
Signal Word
Warning
Hazard Statements
Precautionary Statements
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
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