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363960

Sigma-Aldrich

(S,R)-Noscapine

97%

Synonyma:

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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About This Item

Empirický vzorec (Hillův zápis):
C22H23NO7
Číslo CAS:
128-62-1
Molekulová hmotnost:
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

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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

signalword

Warning

hcodes

H302,H336

Hazard Classifications

Acute Tox. 4 Oral - STOT SE 3

target_organs

Central nervous system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Osvědčení o analýze (COA)

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Thu-Thuy T Dang et al.
Plant physiology, 159(2), 618-631 (2012-04-27)
Noscapine is a benzylisoquinoline alkaloid produced in opium poppy (Papaver somniferum) and other members of the Papaveraceae. It has been used as a cough suppressant and more recently was shown to possess anticancer activity. However, the biosynthesis of noscapine in
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
Niyati Jhaveri et al.
Cancer letters, 312(2), 245-252 (2011-09-20)
Noscapine, a common oral antitussive agent, has been shown to have potent antitumor activity in a variety of cancers. Treatment of glioblastoma multiforme (GBM) with temozolomide (TMZ), its current standard of care, is problematic because the tumor generally recurs and
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