Skip to Content
Merck
All Photos(1)

Documents

363960

Sigma-Aldrich

(S,R)-Noscapine

97%

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C22H23NO7
CAS Number:
128-62-1
Molecular Weight:
413.42
EC Number:
204-899-2
MDL number:
MFCD00069316
UNSPSC Code:
12352005
PubChem Substance ID:
24862408
NACRES:
NA.22

Assay

97%

form

solid

optical activity

[α]20/D −200°, c = 1 in chloroform

mp

174-176 °C (lit.)

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

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
GHS07

Signal Word

Warning

Hazard Statements

H302,H336

Precautionary Statements

P301 + P312 + P330

Hazard Classifications

Acute Tox. 4 Oral - STOT SE 3

Target Organs

Central nervous system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 2

1 of 2

Colchicine ≥95% (HPLC), powder

Sigma-Aldrich

C9754

Colchicine

Denatonium benzoate ≥98%

Sigma-Aldrich

D5765

Denatonium benzoate

V Pannu et al.
Cell death & disease, 3, e346-e346 (2012-07-13)
Centrosome amplification (CA) and resultant chromosomal instability have long been associated with tumorigenesis. However, exacerbation of CA and relentless centrosome declustering engender robust spindle multipolarity (SM) during mitosis and may induce cell death. Recently, we demonstrated that a noscapinoid member
Zhong-Ze Fang et al.
British journal of pharmacology, 167(6), 1271-1286 (2012-06-08)
Noscapine is a promising anti-tumour agent. The purpose of the present study was to describe the metabolic map and investigate the bioactivation of noscapine. Ultra-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight mass spectrometry-based metabolomics was used to analyse
Pradeep K Naik et al.
Journal of computer-aided molecular design, 25(5), 443-454 (2011-05-06)
Noscapine and its derivatives are important microtubule-interfering agents shown to have potent anti-tumor activity. The binding free energies (ΔG (bind)) of noscapinoids computed using linear interaction energy (LIE) method with a surface generalized Born (SGB) continuum solvation model were in
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
Jitender Madan et al.
Molecular pharmaceutics, 9(5), 1470-1480 (2012-05-01)
We have previously shown that a novel microtubule-modulating noscapinoid, EM011 (9-Br-Nos), displays potent anticancer activity by inhibition of cellular proliferation and induction of apoptosis in prostate cancer cells and preclinical mice models. However, physicochemical and cellular barriers encumber the development
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service