| Identification | Back Directory | [Name]
6-HYDROXYMELATONIN | [CAS]
2208-41-5 | [Synonyms]
Sutan (Butylate)
6-HYDROXYMELATONIN
6-Hydroxymelatonine
MELATONIN, 6-HYDROXY
Melatonin 6-Hydroxy Impurity
6-HYDROXY-N-ACETYL-5-METHOXYTRYPTAMINE
N-ACETYL-6-HYDROXY-5-METHOXYTRYPTAMINE
Melatonin Impurity 3 (6-Hydroxy Melatonin)
3-[N-ACETYLAMINOETHYL]-6-HYDROXY-5-METHOXYINDOLE
3-[2-(Acetylamino)ethyl]-5-methoxy-1H-indole-6-ol
N-Acetyl-5-methoxy-6-hydroxy-1H-indole-3-ethanamine
n-(2-(6-hydroxy-5-methoxyindol-3-yl)ethyl)-acetamid
N-[2-(6-hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide
N-[2-(6-hydroxy-5-methoxy-1H-indol-3-yl)ethyl]ethanamide
N-[2-(5-Methoxy-6-hydroxy-1H-indole-3-yl)ethyl]acetamide
Acetamide, N-[2-(6-hydroxy-5-methoxy-1H-indol-3-yl)ethyl]- | [EINECS(EC#)]
636-648-1 | [Molecular Formula]
C13H16N2O3 | [MDL Number]
MFCD00037971 | [MOL File]
2208-41-5.mol | [Molecular Weight]
248.28 |
| Chemical Properties | Back Directory | [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
| [form ]
Solid | [pka]
10.12±0.40(Predicted) | [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 |
| Hazard Information | Back Directory | [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 (MT1A), MT1B, 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 major human metabolite of Melatonin | [Uses]
A metabolite of Melatonin (M215000). | [Uses]
A metabolite of Melatonin (S689050). | [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 |
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