2468-21-5 Catharanthine AKSci R101
 
 
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  R101    
Catharanthine, 98% (HPLC)
 
(2alpha,5beta,6alpha,18beta)-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
IDENTITY
CAS Number:2468-21-5
MDL Number:MFCD01753356
MF:C21H24N2O2
MW:336.43
EINECS:219-586-6
SPECIFICATIONS & PROPERTIES
Min. Purity Spec:98% (HPLC)
Physical Form (at 20°C):Solid
Melting Point:126-128°C
Optical Rotation:+30 to +38° (c=0.5, CDCl3)
Long-Term Storage:Store long-term at -20°C
DOT/IATA TRANSPORT INFORMATION
Not hazardous material

BIOLOGICAL INFO
Solubility:DMSO: 5 mg/mL

REVIEW
 Catharanthine base is one of the many vinca alkaloids present in Catharanthus roseus. Can be used as a starting material for the synthesis of the anti-tumor drugs vinblastine and vincristine. It also binds to tubulin, with interaction of the indole part of catharanthine being common to its more potent vinca counterparts, Catharanthine inhibits nicotinic receptor mediated diaphragm contractions with IC50 of 59.6 uM. catharanthine . It has also shown to be an acetylcholineesterase receptor inhibitor and an voltage-operated calcium channels on vascular smooth muscle cells and cardiomyocytes. Catharanthine, was shown to stimulate release of amylase from pancreatic fragments and to cause extensive degranulation of pancreatic acinar cells with accumulation of membrane material in the Golgi region. It is indicated that catharanthine activates the physiological pathway controlling amylase release by causing a rise in cytoplasmic Ca2+.

REFERENCES
[1]Johann-Wolfgang-Goethe-Universitaet Catharanthine. Synform (1984), 2(1), 45-59.
[2] Kutney JP, Bylsma F. Studies on the synthesis of monomeric and dimeric vinca alkaloids. The total synthesis of isovelbanamine, velbanamine, cleavamine, 18 beta-carbomethoxycleavamine, and catharanthine. J Am Chem Soc. 1970 Oct 7;92(20):6090-2.
[3] Williams JA. Catharanthine: a novel stimulator of pancreatic enzyme release. Cell Tissue Res. 1978 Sep 5;192(2):277-84.
[4] Prakash V, Timasheff SN. Mechanism of interaction of vinca alkaloids with tubulin: catharanthine and vindoline. Biochemistry. 1991 Jan 22;30(3):873-80.

GLOBALLY HARMONIZED SYSTEM (GHS)

Pictograms

Signal Word
Warning

Hazard Statements
H315; H319; H335

Precautionary Statements
P261; P264; P271; P280; P302+P352; P304+P340; P305+P351+P338; P312; P321; P332+P313; P337+P313; P362; P403+P233; P405; P501

RELATED PRODUCTS
R101Catharanthine
V2290Catharanthine tartrate

Current as of April 20, 2024


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CATEGORIES
 APIs and Bioactives > Alkaloids, Chemotherapeutics


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