6-Hydroxymelatonin
Grundinformationen
- CAS
2208-41-5- Standard-SMILES
COc1cc2c(CCNC(C)=O)c[nH]c2cc1O- InChIKey
OMYMRCXOJJZYKE-UHFFFAOYSA-N- Summenformel
- C13H16N2O3
- Durchschnittliche Molmasse
- 248,28 g/mol
- Monoisotopische Masse
- 248,11609238
Überblick
6-hydroxymelatonin is a member of the class of tryptamines that is melatonin with a hydroxy group substituent at position 6. It has a role as a metabolite and a mouse metabolite. It is a member of acetamides and a member of tryptamines. It is functionally related to a melatonin.
Namen und Bezeichner
- Bevorzugter Name
- 6-Hydroxymelatonin
- IUPAC
- N-[2-(6-hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide
- Englischer Name
- 6-Hydroxymelatonin
- Summenformel
- C13H16N2O3
- Molmasse
- 248.28
Namen und Synonyme
6-HYDROXYMELATONIN2208-41-5N-[2-(6-Hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamideN-(2-(6-Hydroxy-5-methoxy-1H-indol-3-yl)ethyl)acetamideTV437T5077CHEBI:2198Acetamide, N-(2-(6-hydroxy-5-methoxy-1H-indol-3-yl)ethyl)-DTXSID00176577Acetamide, N-[2-(6-hydroxy-5-methoxy-1H-indol-3-yl)ethyl]-RefChem:104818DTXCID1099068636-648-1
Weitere Namen anzeigen
Sutan (Butylate)6-HydroxymelatonineMelatonin 6-Hydroxy Impurity6Hydroxymelatonin,6 HydroxymelatoninN-ACETYL-6-HYDROXY-5-METHOXYTRYPTAMINE6-HYDROXY-N-ACETYL-5-METHOXYTRYPTAMINEMelatonin Impurity 3 (6-Hydroxy Melatonin)3-[N-ACETYLAMINOETHYL]-6-HYDROXY-5-METHOXYINDOLE
N-(2(6-Hydroxy-5-methoxy-1H-indol-3-yl)ethyl)acetamide6-hydroxy melatoninLopac-H-0627melatonin, 6-HydroxyMFCD00037971ACETAMIDE, N-(2-(6-HYDROXY-5-METHOXYINDOL-3-YL)ETHYL)-6-OH-melatonin6-OH-MLT
Datenbank-Bezeichner
- CAS
2208-41-5- PubChem CID
- 1864
- DTXSID
DTXSID00176577- ChEMBL
CHEMBL127421- ChEBI
CHEBI:2198- UNII
- TV437T5077
- EC Number
- 636-648-1
- Nikkaji
- J102.947I
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,2
- Polarare Oberfläche (TPSA)
- 74,4 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 4
- Schwere Atome
- 18
- Formalladung
- 0
- Komplexität
- 298
Experimentelle und physikochemische Eigenschaften
Physical DescriptionSolid
Physikochemische Eigenschaften
- Schmelzpunkt
- 172 · 172-175°C
- Siedepunkt
- 564.7 · 564.7±50.0 °C(Predicted)
- Dichte
- 1.266 · 1.266±0.06 g/cm3(Predicted)
- storage temp.
- Refrigerator
- Löslichkeit
- alcohol: soluble
- pka
- 10.12 · 10.12±0.40(Predicted)
- Aggregatzustand
- Solid
- Farbe
- 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
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P264, P270, P280, P301+P317, P318, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Sicherheitsdaten
- wgk
- 3
- RTECS-Nr.
- AC3607000
- risk_code
- 22-40-51/53-20
- hazard_code
- Xn,N
- safety_code
- 36/37-60
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Acute Tox. 4 OralCarc. 2
Chemie und Industrie
Pharmakologische Informationen
Metabolism/Metabolites6-Hydroxymelatonin has known human metabolites that include 6-[[3-(2-Acetamidoethyl)-5-methoxy-1H-indol-6-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid.
MeSH Pharmacological Classification
Agents that have a strengthening effect on the heart or that can increase cardiac output. They may be CARDIAC GLYCOSIDES; SYMPATHOMIMETICS; or other drugs. They are used after MYOCARDIAL INFARCT; CARDIAC SURGICAL PROCEDURES; in SHOCK; or in congestive heart failure (HEART FAILURE).
Tissue LocationsAdrenal Medulla
Cellular LocationsCytoplasm
Metabolite PathwaysTryptophan metabolism
Anwendungen
Beschreibung6-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.
Verwenden6-Hydroxymelatonin has been used as a melatonin derivative to test its protective effects in ultra violet B (UVB)-induced oxidative stress melanocytes and keratinocytes.
Vor- und nachgelagerte Produkte
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Ergänzende Hinweise
DefinitionChEBI: A member of the class of tryptamines that is melatonin with a hydroxy group substituent at position 6.
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