基本情報
- CAS
2208-41-5- 標準SMILES
COc1cc2c(CCNC(C)=O)c[nH]c2cc1O- InChIKey
OMYMRCXOJJZYKE-UHFFFAOYSA-N- 分子式
- C13H16N2O3
- 平均分子量
- 248.28 g/mol
- 単同位体質量
- 248.11609238
概要
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.
名称と識別子
- 優先名称
- 6-Hydroxymelatonin
- IUPAC
- N-[2-(6-hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide
- 現地名
- N-アセチル-5-メトキシ-6-ヒドロキシ-1H-インドール-3-エタンアミン
- 英語名
- 6-Hydroxymelatonin
- 分子式
- C13H16N2O3
- 分子量
- 248.28
名称と別名
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
名称をさらに表示
N-[2-(5-メトキシ-6-ヒドロキシ-1H-インドール-3-イル)エチル]アセトアミドN-アセチル-6-ヒドロキシ-5-メトキシトリプタミン6-ヒドロキシメラトニンN-[2-(6-ヒドロキシ-5-メトキシ-1H-インドール-3-イル)エチル]アセトアミドN-アセチル-5-メトキシ-6-ヒドロキシ-1H-インドール-3-エタンアミン3-[2-(アセチルアミノ)エチル]-5-メトキシ-1H-インドール-6-オール5-メトキシ-6-ヒドロキシ-3-[2-(アセチルアミノ)エチル]-1H-インドールSutan (Butylate)6-HydroxymelatonineMelatonin 6-Hydroxy Impurity6Hydroxymelatonin,6 HydroxymelatoninN-ACETYL-6-HYDROXY-5-METHOXYTRYPTAMINE6-HYDROXY-N-ACETYL-5-METHOXYTRYPTAMINEMelatonin Impurity 3 (6-Hydroxy Melatonin)
物性
構造計算による物性
- XLogP
- 1.2
- 極性表面積
- 74.4 Ų
- 水素結合供与体数
- 3
- 水素結合受容体数
- 3
- 回転可能結合数
- 4
- 重原子数
- 18
- 形式電荷
- 0
- 複雑度
- 298
実験および物理化学的性質
Physical DescriptionSolid
物理化学的性質
- 融点
- 172 · 172-175°C
- 沸点
- 564.7 · 564.7±50.0 °C(Predicted)
- 比重(密度)
- 1.266 · 1.266±0.06 g/cm3(Predicted)
- 貯蔵温度
- Refrigerator
- 溶解性
- アルコール：可溶
- 酸解離定数(Pka)
- 10.12 · 10.12±0.40(Predicted)
- 外見
- 個体
- 色
- 白からベージュ
- 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
化学的性質
化学的特性Off-White to Pale Beige Solid
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
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.
危険有害性情報
Hazard Classes and CategoriesAcute Tox. 4 (100%)
安全データ
- wgk
- 3
- rtecs
- AC3607000
- risk_code
- 22-40-51/53-20
- hazard_code
- Xn,N
- safety_code
- 36/37-60
- Hazard Classifications
- Acute Tox. 4 OralCarc. 2
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
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
応用分野
説明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.
使用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.
一般的な説明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.
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