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Merck
CN
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安全信息

SML0259

Sigma-Aldrich

长春质碱

≥95% (HPLC)

别名:

(+)-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

经验公式（希尔记法）:
C21H24N2O2
CAS号:
2468-21-5
分子量:
336.43
MDL编号:
MFCD01753356
UNSPSC代码:
12352200
PubChem化学物质编号:
329825267
NACRES:
NA.77

方案

≥95% (HPLC)

表单

powder

旋光性

[α]/D +30 to +38° (c=0.5, CDCl3)

颜色

white to beige

溶解性

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

运输

wet ice

储存温度

−20°C

SMILES字符串

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

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生化/生理作用

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.

象形图

Exclamation mark
GHS07

警示用语：

Warning

危险声明

H302

预防措施声明

P301 + P312 + P330

危险分类

Acute Tox. 4 Oral

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

法规信息

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分析证书(COA)

Lot/Batch Number
0000035668
0000035103
116M4718V
082M4725V

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Hiroaki Gotoh et al.
Journal of the American Chemical Society, 134(32), 13240-13243 (2012-08-04)
A definition of the scope of aromatic substrates that participate with catharanthine in an Fe(III)-mediated coupling reaction, an examination of the key structural features of catharanthine required for participation in the reaction, and the development of a generalized indole functionalization
Hugo R Arias et al.
Neurochemistry international, 57(2), 153-161 (2010-05-25)
We compared the interaction of several catharanthine alkaloids including, ibogaine, vincristine, and vinblastine, with that for the noncompetitive antagonist phencyclidine (PCP) at muscle nicotinic acetylcholine receptors (AChRs) in different conformational states. The results established that catharanthine alkaloids: (a) inhibit, in
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
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 microbiology and biotechnology, 91(4), 1095-1105 (2011-05-19)
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. Production of catharanthine in cell cultures or in hairy roots established by transformation with
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