기본 정보
- CAS
2208-41-5- 표준 SMILES
COc1cc2c(CCNC(C)=O)c[nH]c2cc1O- InChIKey
OMYMRCXOJJZYKE-UHFFFAOYSA-N- 분자식
- C13H16N2O3
- 평균 분자량
- 248.28 g/mol
- 단동위원소 질량
- 248.11609238
개요
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.
이름 및 식별자
- 우선 이름
- 6-Hydroxymelatonin
- IUPAC
- N-[2-(6-hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide
- 영어명
- 6-Hydroxymelatonin
- 분자식
- C13H16N2O3
- 분자량
- 248.28
이름 및 동의어
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
이름 더 보기
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
데이터베이스 식별자
물성
구조 계산 물성
- XLogP
- 1.2
- 극성 표면적
- 74.4 Ų
- 수소 결합 공여자 수
- 3
- 수소 결합 수용자 수
- 3
- 회전 가능 결합 수
- 4
- 무거운 원자 수
- 18
- 형식 전하
- 0
- 복잡도
- 298
실험 및 물리화학적 성질
Physical DescriptionSolid
물리화학적 성질
- 녹는점
- 172 · 172-175°C
- 끓는 점
- 564.7 · 564.7±50.0 °C(Predicted)
- 밀도
- 1.266 · 1.266±0.06 g/cm3(Predicted)
- 저장 조건
- Refrigerator
- 용해도
- 알코올: 용해 가능
- 산도 계수 (pKa)
- 10.12 · 10.12±0.40(Predicted)
- 물리적 상태
- 고체
- 색상
- 흰색에서 베이지색
- 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
화학적 성질
Off-White to Pale Beige Solid
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
GHS 분류
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.
유해성 정보
Hazard Classes and CategoriesAcute Tox. 4 (100%)
안전 데이터
- 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
- 스토리지 클래스
- 11 - Combustible Solids
화학 및 산업
약리 정보
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
응용 분야
개요6-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.
용도6-Hydroxymelatonin has been used as a melatonin derivative to test its protective effects in ultra violet B (UVB)-induced oxidative stress melanocytes and keratinocytes.
일반 설명6-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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