An indole alkaloid with diverse biological activities
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Catharanthine (tartrate)

Item No. 11695

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2α,5β,6α)-3,4-didehydro-ibogamine-18β-carboxylic acid, methyl ester, 2R,3R-dihydroxybutanedioate (2:1)
CAS Number
4168-17-6
Synonyms
  • (+)-3,4-Didehydrocoronaridine
Molecular Formula
C21H24N2O2 • 1/2C4H6O6
Formula Weight
486.5
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS(pH7.2) (1:1): 0.5 mg/ml
λmax
224, 283 nm
SMILES
CCC1=C[C@H]2C[C@]([C@]1([H])[N@@](C2)CC3)(C(OC)=O)C4=C3C5=C(N4)C=CC=C5.OC([C@@H]([C@@H](O)C(O)=O)O)=O.CCC6=C[C@H]7C[C@]([C@]6([H])[N@@](C7)CC8)(C(OC)=O)C9=C8C%10=C(N9)C=CC=C%10
InChi Code
InChI=1S/2C21H24N2O2.C4H6O6/c2*1-3-14-10-13-11-21(20(24)25-2)18-16(8-9-23(12-13)19(14)21)15-6-4-5-7-17(15)22-18;5-1(3(7)8)2(6)4(9)10/h2*4-7,10,13,19,22H,3,8-9,11-12H2,1-2H3;1-2,5-6H,(H,7,8)(H,9,10)/t2*13-,19+,21-;1-,2-/m001/s1
InChi Key
OXIDCVCPXUNSCI-DWGLLIDUSA-N
Origin
Plant/Vinca rosea
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    50 mg

    $42

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    100 mg

    $79

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    500 mg

    $363

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    Cayman Chemical
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    Product Description

    Catharanthine is an indole alkaloid that has been found in C. roseus and has diverse biological activities.1,2,3,4,5 It is a precursor in the biosynthesis of the antimitotic agents vinblastine (Item No. 11762) and vincristine (Item No. 11764).1 Catharanthine (320 µM) inhibits microtubule assembly and the proliferation of HCT116 colon cancer cells (IC50 = 60 µg/ml).2,3 It induces the release of amylase from mouse pancreas preparations when used at a concentration of 100 µM.4 Catharanthine (0.5-20 mg/kg) decreases blood pressure and heart rate in anesthetized normotensive rats.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Gupta, M.M., Singh, D.V., Tripathi, A.K., et al. Simultaneous determination of vincristine, vinblastine, catharanthine, and vindoline in leaves of Catharanthus roseus by high-performance liquid chromatography. J. Chromatogr. Sci. 43(9), 450-453 (2005).

    2. Prakash, V., and Timasheff, S.N. Mechanism of interaction of vinca alkaloids with tubulin: Catharanthine and vindoline. Biochemistry 30(3), 873-880 (1991).

    3. Siddiqui, M.J., Ismail, Z., Aisha, A.F.A., et al. Cytotoxic activity of Catharanthus roseus (apocynaceae) crude extracts and pure compounds against human colorectal carcinoma cell line. Int. J. Pharmacol. 6(1), 43-47 (2010).

    4. Williams, J.A. Catharanthine: A novel stimulator of pancreatic enzyme release. Cell Tissue Res. 192(2), 277-284 (1978).

    5. Jadhav, A., Liang, W., Papageorgiou, P.C., et al. Catharanthine 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. 345(3), 383-392 (2013).