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Merck
CN

54274

Chelidonine

≥97.0% (HPLC)

Synonym(s):

Stylophorin

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About This Item

Empirical Formula (Hill Notation):
C20H19NO5
CAS Number:
476-32-4
Molecular Weight:
353.37
NACRES:
NA.77
PubChem Substance ID:
329758025
UNSPSC Code:
12352202
EC Number:
207-504-1
MDL number:
MFCD00069660

Key Documents

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Product Name

Chelidonine, ≥97.0% (HPLC)

InChI key

GHKISGDRQRSCII-ZOCIIQOWSA-N

InChI

1S/C20H19NO5/c1-21-7-13-11(2-3-15-20(13)26-9-23-15)18-14(22)4-10-5-16-17(25-8-24-16)6-12(10)19(18)21/h2-3,5-6,14,18-19,22H,4,7-9H2,1H3/t14-,18-,19+/m0/s1

SMILES string

[H][C@]12[C@@H](O)Cc3cc4OCOc4cc3[C@@]1([H])N(C)Cc5c6OCOc6ccc25

assay

≥97.0% (HPLC)

form

solid

impurities

~5% water

storage temp.

2-8°C

Quality Level

100

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Related Categories

Biochem/physiol Actions

Inhibits tubulin polymerisation (IC50=24 μM), thereby disrupting microtubule structure in cells and inducing a G2/M mitotic arrest.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCCD7509
BCBZ6536
BCBF0551V
BCBV3780
BCBQ5285V

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Z Kleinrok et al.
Polish journal of pharmacology and pharmacy, 42(5), 417-424 (1990-09-01)
Chelidonine administered to rats in doses of 25, 50, 100 and 200 mg/kg ip exerted an inhibitory effect on the dopaminergic structures in the rat. It was shown that chelidonine decreased amphetamine- and apomorphine-induced hyperactivity and inhibited amphetamine and apomorphine
Matthew J Fleming et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 14(7), 2112-2124 (2008-01-18)
New enantioselective syntheses of the B/C hexahydrobenzo[c]phenanthridine alkaloids (+)-homochelidonine, (+)-chelamidine, (+)-chelidonine, (+)-chelamine, and (+)-norchelidonine are described. Our rapid and convergent route to this class of natural products involved the development and application of a Pd II-catalyzed asymmetric ring-opening reaction of
Zhi-Xiong Ma et al.
Organic letters, 14(11), 2742-2745 (2012-05-12)
Total syntheses of chelidonine and norchelidonine featuring an enamide-benzyne-[2 + 2] cycloaddition initiated cascade is described. The cascade includes a pericyclic ring-opening and intramolecular Diels-Alder reaction.
Maria Emilia Isolani et al.
European journal of pharmacology, 686(1-3), 1-7 (2012-04-17)
The presence of adult pluripotent stem cells and the amazing regenerative capabilities make planarian flatworms an extraordinary experimental model to assess in vivo the effects of substances of both natural and synthetic origin on stem cell dynamics. This study focuses
Vitaliy Kaminskyy et al.
Toxicology letters, 177(3), 168-181 (2008-03-08)
Sanguinarine, chelerythrine and chelidonine possess prominent apoptotic effects towards cancer cells. In this study, we found that sanguinarine and chelerythrine induce apoptosis in human CEM T-leukemia cells, and that is accompanied by an early increase in cytosolic cytochrome c that
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