那可汀

中文名称:

那可汀

中文同义词:

那可汀;(S,R)-诺司卡品;诺司卡品;诺斯卡品;(S,R)-那可汀;纳可丁;那可汀[鹼];那可丁 USP标准品

英文名称:

Narcotine

英文同义词:

,2,3,4-tetrahydroisoquinaline;[S-(R*,S*)]-6,7-Dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-1(3H)-Isobenzofuranone;1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-, [S-(R*,S*)]-;1-alpha-Narcotine;5-g)isoquinolin-5-yl)-,(s-(r*,s*))-3-dioxolo(4;5-g]isoquinolin-5-yl)-,[s-(theta,s)]-3-dioxolo[4;6,7-Dimethoxy-3-(4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-2-benzofuran-1(3H)-one;nsc5366

CAS号:

128-62-1

分子式:

C22H23NO7

分子量:

413.42

EINECS号:

204-899-2

相关类别:

镇咳药物;标准品;Intermediates Fine Chemicals;Pharmaceuticals;Asymmetric Synthesis;Chiral Building Blocks;Complex Molecules;FINACEAE

Mol文件:

128-62-1.mol

熔点 

174-176 °C(lit.)

比旋光度 

-200 º (c=1 in chloroform)

沸点 

532.6°C (rough estimate)

密度 

1.395

折射率 

1.5614 (estimate)

储存条件 

-20°C Freezer, Under Inert Atmosphere

溶解度 

Practically insoluble in water, soluble in acetone, slightly soluble in ethanol (96 per cent). It dissolves in strong acids; on dilution of the solution with water, the base may be precipitated.

酸度系数(pKa)

7.8(at 25℃)

形态

neat

颜色

Orthorhombic prisms or stout needles from alc

旋光性 (optical activity)

[α]20/D 200°, c = 1 in chloroform

水溶解性 

302.9mg/L(25 ºC)

Merck 

13,6752

NIST化学物质信息

Narcotine alkaloid(128-62-1)

EPA化学物质信息

1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-[(5R)-5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]-, (3S)- (128-62-1)

生物活性

Noscapine ((S,R)-Noscapine) 是一种具有口服活性的苯酞异喹啉生物碱，具有强效镇咳作用。Noscapine 通过激活 sigma 阿片类受体 (sigma opioid receptors) 发挥镇咳作用，是一种非竞争性 Bradykinin 抑制剂。Noscapine 破坏微管动力学，诱导细胞有丝分裂停滞和凋亡 (apoptosis) 以及活性。Noscapine 具有抗癌，神经保护，抗炎活性，并且可以穿越血脑屏障。

靶点

Sigma opioid receptors Bradykinin Apoptosis

体外研究

Noscapine (0-1000 μM; 0-96 hours; rat C6 glioma cells) treatment inhibits cell viability of rat C6 glioma in vitro in a dose- and time-dependent manner. Noscapine inhibits the viability of rat C6 glioma cells with an IC 50 of 250 μM at 72 hours. Noscapine exposure causes abnormal S-phase reentry, increases mitotic arrest and results in excessive DNA accumulation. Cylindromatosis increases the ability of noscapine to induce mitotic arrest and apoptosis. Cylindromatosis enhances the effect of noscapine on microtubule polymerization and promotes noscapine binding to microtubules. Cell Viability Assay Cell Line: Rat C6 glioma cells Concentration: 0 μM, 0.1 μM, 1 μM, 2 μM, 10 μM, 50 μM, 100 μM, 1000 μM Incubation Time: 0 hours, 12 hours, 24 hours, 48 hours, 72 hours, 96 hours Result: Inhibited cell viability of rat C6 glioma in vitro in a dose- and time-dependent manner.

Cell Line:

Rat C6 glioma cells

Concentration:

0 μM, 0.1 μM, 1 μM, 2 μM, 10 μM, 50 μM, 100 μM, 1000 μM

Incubation Time:

0 hours, 12 hours, 24 hours, 48 hours, 72 hours, 96 hours

Result:

Inhibited cell viability of rat C6 glioma in vitro in a dose- and time-dependent manner.

体内研究

Noscapine (300 mg/kg; oral gavage; daily; for 15 days; athymic female mice) treatment reduces tumor growth in mice. Animal Model: Athymic female mice (nu/nu) (8-week-old) injected with rat C6 glioma cells Dosage: 300 mg/kg Administration: Oral gavage; daily; for 15 days Result: Revealed a significant reduction of tumor volume.

Animal Model:

Athymic female mice (nu/nu) (8-week-old) injected with rat C6 glioma cells

Dosage:

300 mg/kg

Administration:

Oral gavage; daily; for 15 days

Result:

Revealed a significant reduction of tumor volume.

化学性质 

无色结晶性粉末或有光泽的棱柱状或片状结晶；无臭，无味。几乎不溶于水，微溶于乙醇与乙醚，溶于氯仿。

用途 

支气管解痉性镇咳药。

危险品标志 

Xn

危险类别码 

22

安全说明 

24/25

危险品运输编号 

1544

WGK Germany 

3

RTECS号

RD2625000

HazardClass 

6.1(b)

PackingGroup 

III

海关编码 

29329990

毒害物质数据

128-62-1(Hazardous Substances Data)

毒性

cyt-ham:lng 100 mg/L ATSUDG (4),41,80