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

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)

InChIKey

OMYMRCXOJJZYKE-UHFFFAOYSA-N

SMILES

COc1cc2c(CCNC(C)=O)c[nH]c2cc1O

Safety Information

Hazard Codes 

Xn,N

Risk Statements 

22-40-51/53-20

Safety Statements 

36/37-60

WGK Germany 

3

RTECS 

AC3607000

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Oral
Carc. 2

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).

References

[1] M L DUBOCOVICH. Melatonin receptor antagonists that differentiate between the human Mel1a and Mel1b recombinant subtypes are used to assess the pharmacological profile of the rabbit retina ML1 presynaptic heteroreceptor.[J]. Naunyn-Schmiedeberg’s archives of pharmacology, 1997, 355 3: 365-375. DOI: 10.1007/pl00004956
[2] DUBOCOVICH M L. Melatonin receptors: are there multiple subtypes?[J]. Trends in pharmacological sciences, 1995, 16 2: 50-56. DOI: 10.1016/s0165-6147(00)88978-6
[3] DUBOCOVICH M L. Characterization of a retinal melatonin receptor.[J]. Journal of Pharmacology and Experimental Therapeutics, 1985, 234 2: 395-401.
[4] D.A. LOWES . Melatonin and structurally similar compounds have differing effects on inflammation and mitochondrial function in endothelial cells under conditions mimicking sepsis[J]. British journal of anaesthesia, 2011, 107 2: Pages 193-201. DOI: 10.1093/bja/aer149
[5] DEEPA S. MAHARAJ. Melatonin and 6-hydroxymelatonin protect against iron-induced neurotoxicity[J]. Journal of Neurochemistry, 2005, 96 1: 78-81. DOI: 10.1111/j.1471-4159.2005.03532.x
[6] S. H?RTTER. Differential Effects of Fluvoxamine and Other Antidepressants on the Biotransformation of Melatonin[J]. Journal of Clinical Psychopharmacology, 2001, 123 1 1: 167-174. DOI: 10.1097/00004714-200104000-00008

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

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• 3-(2-methylaminoethyl)-1H-indol-5-ol
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• 6-HYDROXYMELATONIN SULFATE
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