ChemicalBook > CAS DataBase List > 6-HYDROXYMELATONIN

6-HYDROXYMELATONIN

Product Name: 6-HYDROXYMELATONIN
CAS No.: 2208-41-5
Chemical Name: 6-HYDROXYMELATONIN
Synonyms: Sutan (Butylate);6-HYDROXYMELATONIN;6-Hydroxymelatonine;MELATONIN, 6-HYDROXY;Melatonin 6-Hydroxy Impurity;6Hydroxymelatonin,6 Hydroxymelatonin;N-ACETYL-6-HYDROXY-5-METHOXYTRYPTAMINE;6-HYDROXY-N-ACETYL-5-METHOXYTRYPTAMINE;Melatonin Impurity 3 (6-Hydroxy Melatonin);3-[N-ACETYLAMINOETHYL]-6-HYDROXY-5-METHOXYINDOLE
CBNumber: CB4436858
Molecular Formula: C13H16N2O3
Formula Weight: 248.28
MOL File: 2208-41-5.mol

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6-HYDROXYMELATONIN Property

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

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Safety

Hazard Codes: Xn,N
Risk Statements: 22-40-51/53-20
Safety Statements: 36/37-60
WGK Germany: 3
RTECS: AC3607000

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H351Suspected of causing cancer

Precautionary statements

P201Obtain special instructions before use.

P308+P313IF exposed or concerned: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: H0627
Product name: 6-Hydroxymelatonin
Packaging: 50mg
Price: $804
Updated: 2025/07/31

Cayman Chemical

Product number: 21857
Product name: 6-hydroxy Melatonin
Purity: ≥95%
Packaging: 1mg
Price: $81
Updated: 2024/03/01

Cayman Chemical

Product number: 21857
Product name: 6-hydroxy Melatonin
Purity: ≥95%
Packaging: 5mg
Price: $238
Updated: 2024/03/01

Cayman Chemical

Product number: 21857
Product name: 6-hydroxy Melatonin
Purity: ≥95%
Packaging: 10mg
Price: $380
Updated: 2024/03/01

TRC

Product number: H944625
Product name: 6-HydroxyMelatonin
Packaging: 5mg
Price: $165
Updated: 2021/12/16

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6-HYDROXYMELATONIN Chemical Properties,Usage,Production

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 Preparation Products And Raw materials

Raw materials

Diisobutylamine Ethanethiol

Preparation Products

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6-HYDROXYMELATONIN Suppliers

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2208-41-5, 6-HYDROXYMELATONINRelated Search:

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

3-[N-ACETYLAMINOETHYL]-6-HYDROXY-5-METHOXYINDOLE

6-HYDROXYMELATONIN

6-HYDROXY-N-ACETYL-5-METHOXYTRYPTAMINE

N-ACETYL-6-HYDROXY-5-METHOXYTRYPTAMINE

n-(2-(6-hydroxy-5-methoxyindol-3-yl)ethyl)-acetamid

N-[2-(6-hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide

3-[2-(Acetylamino)ethyl]-5-methoxy-1H-indole-6-ol

N-[2-(5-Methoxy-6-hydroxy-1H-indole-3-yl)ethyl]acetamide

N-Acetyl-5-methoxy-6-hydroxy-1H-indole-3-ethanamine

N-[2-(6-hydroxy-5-methoxy-1H-indol-3-yl)ethyl]ethanamide

Sutan (Butylate)

MELATONIN, 6-HYDROXY

Melatonin 6-Hydroxy Impurity

Acetamide, N-[2-(6-hydroxy-5-methoxy-1H-indol-3-yl)ethyl]-

Melatonin Impurity 3 (6-Hydroxy Melatonin)

6-Hydroxymelatonine

6Hydroxymelatonin,6 Hydroxymelatonin

2208-41-5

Aromatics

Heterocycles

Intermediates & Fine Chemicals

Metabolites & Impurities

Pharmaceuticals

Sulfur & Selenium Compounds

Various Metabolites and Impurities

Metabolites