R101 Catharanthine - AK Scientific
 
 
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  Catalog ID # R101
Catharanthine
, 98%
 
(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 Registry #:[2468-21-5]
MDL Number:MFCD01753356
MF:C21H24N2O2
MW:336.4275
SPECIFICATIONS & PROPERTIES
Purity:98%
Physical Form:White to off-white powder or crystalline powder
Melting Point:126-128 °C
Optical Rotation:+30 to +38° (c=0.5, CDCl3)
Long-Term Storage:Store at -20°C
Shipping:Normal Temperature

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.
[5] Lev?que D, Wihlm J, Jehl F Pharmacology of Catharanthus alkaloids. Bull Cancer. 1996 Mar;83(3):176-86.
[6] Moisan L, Thu?ry P, Nicolas M, Doris E, Rousseau B Formal synthesis of (+)-catharanthine+Angew Chem Int Ed Engl. 2006 Aug 11;45(32):5334-6.
[7] Ishikawa H, Colby DA, Boger DL. Direct coupling of catharanthine and vindoline to provide vinblastine: total synthesis of (+)- and ent-(-)-vinblastine. J Am Chem Soc. 2008 Jan 16;130(2):420-1.
[8] Arias HR, Feuerbach D, Targowska-Duda KM, Jozwiak KCatharanthine alkaloids are noncompetitive antagonists of muscle-type nicotinic acetylcholine receptors. Neurochem Int. 2010 Sep;57(2):153-61. doi: 10.1016/j.neuint.2010.05.007. Epub 2010 May 20.
[9] Jadhav A, Liang W, Papageorgiou PC, Shoker A, Kanthan SC, Balsevich J, Levy AS, Heximer S, Backx PH, Gopalakrishnan VCatharanthine dilates small mesenteric arteries and decreases heart rate and cardiac contractility by inhibition of voltage-operated calcium channels on vascular smooth muscle cells and cardiomyocytes. J Pharmacol Exp Ther. 2013 Jun;345(3):383-92.

Risk Description(s)
R36/37/38:Irritating to eyes, respiratory system and skin

Safety Description(s)
S24/25:Avoid contact with skin and eyes.


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RELATED PRODUCTS
R101Catharanthine
V2290Catharanthine tartrate

CATEGORIES

 APIs and Bioactives > Alkaloids, Chemotherapeutics

USEFUL LINKS

  PubChem