H0627

6-Hydroxymelatonin

antioxidant

• Synonym(s): 3-(N-Acetylaminoethyl)-6-hydroxy-5-methoxyindole
• Empirical Formula (Hill Notation): C₁₃H₁₆N₂O₃
• CAS Number: 2208-41-5
• Molecular Weight: 248.28
• UNSPSC Code: 41116107
• PubChem Substance ID: 24278458
• NACRES: NA.77
• MDL number: MFCD00037971

Properties

• Product Name: 6-Hydroxymelatonin,
• solubility: alcohol: soluble
• Quality Segment: 100
• 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)

Description

General description

6-Hydroxymelatonin (6-OHM) is a melatonin metabolite.[1] It is produced in the liver by the action of cytochrome P450 enzyme[2] as well as by photodegradation of melatonin. In the central nervous system, it exists as a sulfated form.[2] 6-OHM is a partial melatonin receptor MT2 agonist.[3]

Application

6-Hydroxymelatonin has been used as a melatonin derivative to test its protective effects in ultra violet B (UVB)-induced oxidative stress melanocytes[1] and keratinocytes.[4]

Biochem/physiol Actions

6-Hydroxymelatonin (6-OHM) is an antioxidant with a free radical scavenging role.[2] Like melatonin, it reduces the impact of UVB-induced oxidative stress in melanocytes.[1] It also aids protection during iron (Fe²⁺)-induced neurotoxicity. 6-OHM effectively reduces lipid peroxidation and superoxide anion production induced by potassium cyanide (KCN).[2]

Safety Information

• pictograms: GHS08,GHS07
• signalword: Warning
• hcodes: H302,H351
• pcodes: P201 - P301 + P312 + P330 - P308 + P313
• Hazard Classifications: Acute Tox. 4 Oral - Carc. 2
• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• ppe: Eyeshields, Gloves, type P3 (EN 143) respirator cartridges