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363960

Sigma-Aldrich

(S,R)-Noscapine

97%

Synonyme(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

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About This Item

Formule empirique (notation de Hill):
C22H23NO7
Numéro CAS:
128-62-1
Poids moléculaire :
413.42
Numéro CE :
204-899-2
Numéro MDL:
MFCD00069316
Code UNSPSC :
12352005
ID de substance PubChem :
24862408
Nomenclature NACRES :
NA.22

Niveau de qualité

100

Pureté

97%

Forme

solid

Activité optique

[α]20/D −200°, c = 1 in chloroform

Pf

174-176 °C (lit.)

Chaîne SMILES 

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

Clé InChI

AKNNEGZIBPJZJG-MSOLQXFVSA-N

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Catégories apparentées

Description générale

(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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302 - H336

Conseils de prudence

P301 + P312 + P330

Classification des risques

Acute Tox. 4 Oral - STOT SE 3

Organes cibles

Central nervous system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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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
Aaron J DeBono et al.
ChemMedChem, 7(12), 2122-2133 (2012-10-12)
Noscapine is a phthalideisoquinoline alkaloid isolated from the opium poppy Papaver somniferum. It has long been used as an antitussive agent, but has more recently been found to possess microtubule-modulating properties and anticancer activity. Herein we report the synthesis and
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
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