2208-41-5 Usage
Description
6-Hydroxymelatonin (6-OHM), also known as 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-OHM is a melatonin receptor agonist, specifically for the MT1A, MT1B, and MT2 receptors. It is a member of the class of tryptamines and is characterized by its off-white to pale beige solid appearance.
Uses
Used in Antioxidant Applications:
6-Hydroxymelatonin is used as an antioxidant for its protective effects against oxidative stress. It has been utilized in testing its protective effects in ultraviolet B (UVB)-induced oxidative stress in melanocytes and keratinocytes.
Used in the Pharmaceutical Industry:
6-Hydroxymelatonin is used as a melatonin derivative in the pharmaceutical industry for its potential therapeutic applications. It has demonstrated neuroprotective properties, such as inhibiting dopamine release from isolated rabbit retina and reducing iron-induced lipid oxidation in rat hippocampal homogenate.
Used in the Research and Development Industry:
6-Hydroxymelatonin is used as a research compound for studying its effects on various cellular processes and its potential as a therapeutic agent. It has shown to reduce increases in the levels of NF-κB, IL-6, and IL-8 and decrease in glutathione (GSH) levels in LPSand peptidoglycan G-stimulated human umbilical vein endothelial cells (HUVECs) in an in vitro model of sepsis.
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).
Check Digit Verification of cas no
The CAS Registry Mumber 2208-41-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,2,0 and 8 respectively; the second part has 2 digits, 4 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 2208-41:
(6*2)+(5*2)+(4*0)+(3*8)+(2*4)+(1*1)=55
55 % 10 = 5
So 2208-41-5 is a valid CAS Registry Number.
InChI:InChI=1/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)
2208-41-5Relevant articles and documents
Further insights into the reaction of melatonin with hydroxyl radical
Horstman, Joseph A.,Wrona, Monika Z.,Dryhurst, Glenn
, p. 371 - 382 (2002)
Recent interest has focused on the use of exogenous melatonin as an antioxidant, particularly to scavenge the highly cytotoxic hydroxyl radical (HO?) which may be generated in many pathological conditions. However, in vitro and in vivo studies aimed at assessing the antioxidant properties of melatonin have produced conflicting results. While it is known that HO? reacts with melatonin at a diffusion limited rate, very little is known about the products of this reaction. In this investigation it is shown that incubation of melatonin with a Fenton-type HO?-generating system at pH 7.4 forms a complex mixture of primary products. These include 2-hydroxymelatonin, which was isolated as its more stable oxindole tautomer, 4- and 6-hydroxymelatonin, N-acetyl-N2-formyl-5-methoxykynurenine and 7,7′-bi-(5-methoxy-N-acetyltryptamine-4-one). Reaction pathways that might lead to these products are described. The differing biological effects of these products, while currently incompletely understood, might account for the controversy concerning the antioxidant properties of melatonin.
An efficient synthesis of 6-hydroxymelatonin, a human metabolite of melatonin
Karam, Omar,Zunino, Fabien,Chagnaut, Vincent,Jouannetaud, Marie Paule,Jacquesy, Jean Claude
, p. 1511 - 1513 (2007/10/03)
A four-step synthesis of 6-hydroxymelatonin 5, major human metabolite of melatonin 1, is reported starting from melatonin. The synthesis involves in the keys steps a regioselective Friedel-Crafts acylation followed by a Baeyer-Villiger oxidation. The overall yield is 48%.
