6-HYDROXYMELATONIN Chemical Properties

Melting point:

172-175°C

Boiling point:

564.7±50.0 °C(Predicted)

Density 

1.266±0.06 g/cm3(Predicted)

storage temp. 

Refrigerator

solubility 

alcohol: soluble

pka

10.12±0.40(Predicted)

form 

Solid

color 

White to Beige

InChIKey

OMYMRCXOJJZYKE-UHFFFAOYSA-N

Safety Information

Hazard Codes 

Xn,N

Risk Statements 

22-40-51/53-20

Safety Statements 

36/37-60

WGK Germany 

3

RTECS 

AC3607000

MSDS

• Language:English Provider:SigmaAldrich

6-HYDROXYMELATONIN Usage And Synthesis

Description

6-hydroxy Melatonin is an active metabolite of melatonin . It is formed from melatonin by the cytochrome P450 (CYP) isoform CYP1A2 in human liver microsomes. 6-hydroxy Melatonin is a melatonin 1A (MT_1A), MT_1B, and MT₂ receptor agonist. It inhibits dopamine release from isolated rabbit retina (IC₅₀ = 0.0016 μM). 6-hydroxy Melatonin (10 and 100 μM) reduces increases in the levels of NF-κB, IL-6, and IL-8 and decreases in glutathione (GSH) levels in LPS- and peptidoglycan G-stimulated human umbilical vein endothelial cells (HUVECs) in an in vitro model of sepsis. It reduces iron-induced lipid oxidation in rat hippocampal homogenate when administered at a dose of 10 mg/kg.

Chemical Properties

Off-White to Pale Beige Solid

Uses

A metabolite of Melatonin (M215000).

Uses

A major human metabolite of Melatonin

Uses

A metabolite of Melatonin (S689050).

Uses

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.

Definition

ChEBI: A member of the class of tryptamines that is melatonin with a hydroxy group substituent at position 6.

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.

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).

6-HYDROXYMELATONIN(2208-41-5)Related Product Information

• Sodium carbonate
• 6-hydroxymelatonin sulfotransferase
• 6-hydroxymelatonin glucuronide
• 5-Hydroxymelatonin
• Melatonine
• 5-Methoxytryptamine
• 3-(2-methylaminoethyl)-1H-indol-5-ol
• 5-Hydroxytryptamine
• 6-HYDROXYMELATONIN
• 6-HYDROXYMELATONIN SULFATE
• 6-hydroxytryptamine
• 5,6-DIHYDROXYINDOLE