芦竹碱

芦竹碱用途

Gramine (Donaxine) 是从芦竹中得到的生物碱[2],为有效的脂联素受体 (adiponectin receptor (AdipoR)) 激动剂,对 AdipoR2 和 AdipoR1 的 IC50 值分别为 3.2 和 4.2 µM[1]。Gramine 同时为小鼠和人 β2-Adrenergic receptor (β2-AR) 激动剂[2]。Gramine 具有抗肿瘤、抗炎和抗病毒作用[1]。

芦竹碱作用

【用途一】
该品是合成色氨酸的中间体。

芦竹碱名称

[ CAS 号 ]:
87-52-5

[ 中文名 ]:
芦竹碱

[ 英文名 ]:
Gramine

[中文别名 ]:

[英文别名 ]:

1H-Indole-3-methanamine, N,N-dimethyl-
Gramin
Donaxine
Indole, 3-[(dimethylamino)methyl]-
Indole,3-[(dimethylamino)methyl]
Gramine
MFCD00005629
3-(Dimethylaminomethyl)indole
Indol-3-ylmethyldimethylamine
EINECS 201-749-8

芦竹碱生物活性

[ 描述 ]:

[ 相关类别 ]:

信号通路 >> G 蛋白偶联受体/G 蛋白 >> 脂联素受体

信号通路 >> G 蛋白偶联受体/G 蛋白 >> 肾上腺素能受体

研究领域 >> 癌症

研究领域 >> 感染

研究领域 >> 代谢疾病

天然产物 >> 生物碱

[ 靶点 ]

IC50: 3.2 µM (AdipoR2), 4.2 µM (AdipoR1)[1]

[体外研究]

Gramine是一种活跃的脂联素受体(AdipoR)激动剂,AdipoR2和AdipoR1的IC50分别为3.2和4.2μM[1]。 Gramine是一种潜在的β2-AR激动剂[2]。 Gramine(20μM至1.2 nM)剂量依赖性地抑制AdipoR1/adipoR2阳性癌细胞系(MDA-MB-231和MCF-7细胞)的生长,IC50分别为9.6±0.9和0.1±0.1μM[ 1]。

[参考文献]

[1]. Sun Y, et al. Identification of adiponectin receptor agonist utilizing a fluorescence polarization based high throughput assay. PLoS One. 2013 May 14;8(5):e63354.

[2]. Chikazawa M, et al. Identification of Functional Food Factors as β2-Adrenergic Receptor Agonists and Their Potential Roles in Skeletal Muscle. J Nutr Sci Vitaminol (Tokyo). 2018;64(1):68-74.

[相关活性小分子]

芦竹碱物理化学性质

[ 密度 ]:
1.1±0.1 g/cm3

[ 沸点 ]:
293.9±15.0 °C at 760 mmHg

[ 熔点 ]:
132-134 °C(lit.)

[ 分子式 ]:
C₁₁H₁₄N₂

[ 分子量 ]:
174.242

[ 闪点 ]:
131.5±20.4 °C

[ 精确质量 ]:
174.115692

[ PSA ]:
19.03000

[ LogP ]:
1.90

[ 外观性状 ]:
白色结晶粉末

[ 蒸汽压 ]:
0.0±0.6 mmHg at 25°C

[ 折射率 ]:
1.631

[ 储存条件 ]:
Refrigerator (+4°C)

[ 水溶解性 ]:
PRACTICALLY INSOLUBLE

芦竹碱MSDS

详细MSDS(安全技术说明书)

芦竹碱毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NL7525000

CHEMICAL NAME :: Indole, 3-((dimethylamino)methyl)-

CAS REGISTRY NUMBER :: 87-52-5

LAST UPDATED :: 199712

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C11-H14-N2

MOLECULAR WEIGHT :: 174.27

WISWESSER LINE NOTATION :: T56 BMJ D1N1&1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 250 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NCNSA6 National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. (Washington, DC) Volume(issue)/page/year: 5,11,1953

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 122 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: PSYPAG Psychopharmacologia (Berlin). (Berlin, Ger.) V.1-46, 1959-76. For publisher information, see PSCHDL. Volume(issue)/page/year: 16,385,1970

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 46 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - excitement

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 105,130,1952 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - species unspecified

DOSE/DURATION :: 127 gm/kg/3W-C

TOXIC EFFECTS :: Kidney, Ureter, Bladder - changes in both tubules and glomeruli Endocrine - changes in spleen weight Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - phosphatases

REFERENCE :: TXCYAC Toxicology. (Elsevier Scientific Pub. Ireland, Ltd., POB 85, Limerick, Ireland) V.1- 1973- Volume(issue)/page/year: 18,125,1980

芦竹碱安全信息

[ 危害码 (欧洲) ]:
Xi:Irritant;

[ 风险声明 (欧洲) ]:
R36

[ 安全声明 (欧洲) ]:
S45-S36/37/39-S26

[ 危险品运输编码 ]:
NONH for all modes of transport

[ WGK德国 ]:
3

[ RTECS号 ]:
NL7525000

[ 海关编码 ]:
2933990090

芦竹碱合成路线

详细合成路线

芦竹碱上下游产品

芦竹碱上游产品

芦竹碱下游产品

芦竹碱制备

由吲哚与甲醛、二甲胺缩合而得。将二甲胺冷至-5℃，加至冰醋酸中。在温度不超过5℃的条件下，加入甲醛、吲哚，在30-40℃反应8h，冷至5℃，用40%氢氧化钠调节pH等于1，冷却出芦竹碱结晶。过滤，水洗，抽干后将此粗品用丙酮加热溶解，冷却、析出结晶、过滤、干燥，得成品。

芦竹碱海关

[ 海关编码 ]: 2933990090

[ 中文概述 ]:
2933990090. 其他仅含氮杂原子的杂环化合物. 增值税率:17.0%. 退税率:13.0%. 监管条件:无. 最惠国关税:6.5%. 普通关税:20.0%

[ 申报要素 ]: 品名, 成分含量, 用途, 乌洛托品请注明外观, 6－己内酰胺请注明外观, 签约日期

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

芦竹碱文献

A retro-biosynthetic approach to the prediction of biosynthetic pathways from position-specific isotope analysis as shown for tramadol.

Proc. Natl. Acad. Sci. U. S. A. 112 , 8296-301, (2015)

Tramadol, previously only known as a synthetic analgesic, has now been found in the bark and wood of roots of the African medicinal tree Nauclea latifolia. At present, no direct evidence is available ...

NMR-titrations with complexes between ds-DNA and indole derivatives including tryptophane containing peptides.

FEBS Lett. 374(3) , 387-92, (1995)

It is shown that NMR titrations can be used on a quantitative basis to derive binding constants and binding modes of ds-DNA ligand complexes from several signals. The results are partially at variance...

Response of animals to dietary gramine. I. Performance and selected hematological, biochemical and histological parameters in growing chicken, rats and pigs.

Arch. Tierernahr. 55(1) , 1-16, (2001)

The effects of feeding varied levels of low- and high-gramine yellow lupin seeds (LG and HG, respectively), and of synthetic gramine added to the diets in amounts ranging from 0.15 to 1.2 g per kg wer...

更多文献

芦竹碱