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SML0259

Catharanthine

≥95% (HPLC)

Synonym(s):

(+)-3,4-Didehydrocoronaridine, (2α,5β,6α,18β)-3,4-Didehydroibogamine-18-carboxylic acid methyl ester, 7-Ethyl-9,10,12,13-tetrahydro-6,9-methano-5H-pyrido[1′,2′:1,2]azepino[4,5-b]indole-6(6aH)-carboxylic acid methyl ester

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About This Item

Empirical Formula (Hill Notation):
C21H24N2O2
CAS Number:
2468-21-5
Molecular Weight:
336.43
NACRES:
NA.77
PubChem Substance ID:
329825267
UNSPSC Code:
12352200
MDL number:
MFCD01753356
Assay:
≥95% (HPLC)
Form:
powder
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assay

≥95% (HPLC)

form

powder

optical activity

[α]/D +30 to +38° (c=0.5, CDCl3)

color

white to beige

solubility

DMSO: 5 mg/mL (clear solution; warmed)

shipped in

wet ice

storage temp.

−20°C

SMILES string

CCC1=C[C@@H]2C[N@H]3CCc4c([nH]c5ccccc45)[C@@](C2)([C@@H]13)C(=O)OC

InChI

1S/C21H24N2O2/c1-3-14-10-13-11-21(20(24)25-2)18-16(8-9-23(12-13)19(14)21)15-6-4-5-7-17(15)22-18/h4-7,10,13,19,22H,3,8-9,11-12H2,1-2H3/t13-,19+,21-/m0/s1

InChI key

CMKFQVZJOWHHDV-NQZBTDCJSA-N

Biochem/physiol Actions

Catharanthine is a precursor of the anti-tumor drugs vinblastine and vincristine, formed by dimerization of catharanthine with vindoline. Catharanthine itself is an inhibitor of tubulin self-assembly into microtubules, although not so potent as vinblastine or vincristine. Catharanthine also has anticholinergic activity. It showed muscarinic antagonism at 10 microM and fully inhibited nicotinic receptor mediated diaphragm contractions with an IC50 of 59.6 microM.
Catharanthine is a precursor of the anti-tumor drugs vinblastine and vincristine..Catharanthine is an inhibitor of tubulin self-assembly into microtubules.

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pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000035668
0000035103
116M4718V
082M4725V

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Mei-Liang Zhou et al.
Applied microbiology and biotechnology, 88(3), 737-750 (2010-08-18)
Jasmonates and nitric oxide (NO) play important roles in the regulation of the signaling network leading to the biosynthesis of plant secondary metabolites. In this work, we explore the effect of constitutive overexpression of CrORCA3 (octadecanoid-responsive Catharanthus AP2/ERF domain), methyl
Xiaofen Sun et al.
Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 34(2), 128-131 (2009-04-24)
Catharanthine content and agronomic traits in major Catharanthus roseus varieties were analyzed. It was found that there existed great difference in catharanthine content and agronomic traits among the varieties. Catharanthine content was the highest in variety Pacifica Polka Dot (PPD)
Mei-Liang Zhou et al.
Applied biochemistry and biotechnology, 166(7), 1674-1684 (2012-02-14)
Catharanthus roseus (L.) G. Don is a plant species known for its production of a variety of terpenoid indole alkaloids, many of which have pharmacological activities. Catharanthine can be chemically coupled to the abundant leaf alkaloid vindoline to form the
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Global Trade Item Number

SKUGTIN
SML0259-50MG04061833222348
SML0259-10MG04061833222331