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Merck
CN

363960

(S,R)-诺司卡品

97%

别名:

α-Narcotine, (3S)-6,7-Dimethoxy-3-[(5R)-5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]-1(3H)-isobenzofuranone

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关于此项目

经验公式(希尔记法):
C22H23NO7
化学文摘社编号:
分子量:
413.42
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352005
EC Number:
204-899-2
MDL number:
Assay:
97%
Form:
solid
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assay

97%

form

solid

optical activity

[α]20/D −200°, c = 1 in chloroform

mp

174-176 °C (lit.)

functional group

ester

SMILES string

COc1ccc2C(OC(=O)c2c1OC)C3N(C)CCc4cc5OCOc5c(OC)c34

InChI

1S/C22H23NO7/c1-23-8-7-11-9-14-20(29-10-28-14)21(27-4)15(11)17(23)18-12-5-6-13(25-2)19(26-3)16(12)22(24)30-18/h5-6,9,17-18H,7-8,10H2,1-4H3/t17-,18+/m1/s1

InChI key

AKNNEGZIBPJZJG-MSOLQXFVSA-N

General description

(S,R)-Noscapine is a phthalideisoquinoline alkaloid found in opium. It is an antimicrotubule agent that also shows potent antitumor activity.

Application

Noscapine may be used as a source to synthesize its bromo-derivatives, which has higher tubulin binding activity when compared to noscapine. Its 3,4,5-trimethoxybenzyl analog is a potential antitumor agent.


pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral - STOT SE 3

target_organs

Central nervous system

存储类别

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

法规信息

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历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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Pradeep K Naik et al.
Journal of computer-aided molecular design, 26(2), 233-247 (2011-12-16)
Our screen for tubulin-binding small molecules that do not depolymerize bulk cellular microtubules, but based upon structural features of well known microtubule-depolymerizing colchicine and podophyllotoxin, revealed tubulin binding anti-cancer property of noscapine (Ye et al. in Proc Natl Acad Sci
Brominated derivatives of noscapine are potent microtubule-interfering agents that perturb mitosis and inhibit cell proliferation.
Zhou J, et al.
Molecular Pharmacology, 63(4), 799-807 (2003)
Thilo Winzer et al.
Science (New York, N.Y.), 336(6089), 1704-1708 (2012-06-02)
Noscapine is an antitumor alkaloid from opium poppy that binds tubulin, arrests metaphase, and induces apoptosis in dividing human cells. Elucidation of the biosynthetic pathway will enable improvement in the commercial production of noscapine and related bioactive molecules. Transcriptomic analysis



全球贸易项目编号

货号GTIN
363960-5G04061831825213