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
More
Less

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
More
Less

Safety

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

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.

More
Less

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
More
Less

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 (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 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

More
Less

6-HYDROXYMELATONIN Suppliers

Canada 1 China 58 Germany 2 India 2 Switzerland 2 United Kingdom 1 United States 13 Global 79
J & K SCIENTIFIC LTD.
Tel
18210857532; 18210857532
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15838
Advantage
69
Chemsky（shanghai）International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
32321
Advantage
50
Daicel Chiral Technologies (China)CO.,LTD
Tel
021-50460086-9 15921403865
Fax
+86-21-50462321
Email
han_yajun@dctc.daicel.com
Country
China
ProdList
7471
Advantage
65
Shanghai Aladdin Bio-Chem Technology Co.,LTD
Tel
400-6206333 13167063860
Fax
021-50323701
Email
anhua.mao@aladdin-e.com
Country
China
ProdList
25003
Advantage
65
Sigma-Aldrich
Tel
021-61415566 800-8193336
Email
orderCN@merckgroup.com
Country
China
ProdList
51395
Advantage
80
Alta Scientific Co., Ltd.
Tel
022-6537-8550 15522853686
Fax
022-2532-9655
Email
sales@altasci.com.cn
Country
China
ProdList
4511
Advantage
55
BOC Sciences
Tel
16314854226
Email
info@bocsci.com
Country
United States
ProdList
9923
Advantage
65
Shanghai YuanYe Biotechnology Co., Ltd.
Tel
021-61312847; 18021002903
Fax
QQ:3008007432
Email
3008007409@qq.com
Country
China
ProdList
71826
Advantage
60
Chengdu Huachun Technology Co., Ltd
Tel
400-1166-196 15982826727
Fax
QQ：800101999
Email
cdhxsj@163.com
Country
China
ProdList
14603
Advantage
60

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