WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 413361
CAS#: 3371-85-5
Description: Voacamine is a naturally occurring dimeric indole alkaloid of the secologanin type, found in a number of plants, including Voacanga africana and Tabernaemontana divaricata. It is approved for use as an antimalarial drug in several African countries.
MedKoo Cat#: 413361
Name: Voacamine
CAS#: 3371-85-5
Chemical Formula: C43H52N4O5
Exact Mass: 704.3938
Molecular Weight: 704.91
Elemental Analysis: C, 73.27; H, 7.44; N, 7.95; O, 11.35
Synonym: Voacamine; NSC82591; NSC-82591; NSC 82591
IUPAC/Chemical Name: methyl (6S,6aS,7S,9R)-7-ethyl-3-((2S,6R,Z)-5-ethylidene-14-(methoxycarbonyl)-3-methyl-2,3,4,5,6,7,8,9-octahydro-1H-2,6-methanoazecino[5,4-b]indol-8-yl)-2-methoxy-7,8,9,10,12,13-hexahydro-5H-6,9-methanopyrido[1',2':1,2]azepino[4,5-b]indole-6(6aH)-carboxylate
InChi Key: VCMIRXRRQJNZJT-MVVGXNPNSA-N
InChi Code: InChI=1S/C43H52N4O5/c1-7-24-15-23-20-43(42(49)52-6)39-27(13-14-47(21-23)40(24)43)29-19-36(50-4)30(17-34(29)45-39)31-16-28-25(8-2)22-46(3)35(37(28)41(48)51-5)18-32-26-11-9-10-12-33(26)44-38(31)32/h8-12,17,19,23-24,28,31,35,37,40,44-45H,7,13-16,18,20-22H2,1-6H3/t23-,24+,28+,31?,35+,37?,40+,43-/m1/s1
SMILES Code: CC[C@H]1C[C@H]2CN3CCc(c([C@]([C@H]13)(C(OC)=O)C2)[nH]4)c5c4cc(C6C[C@@H]7C(C(OC)=O)[C@@H](N(C/C7=C\C)C)Cc(c6[nH]8)c9c8cccc9)c(OC)c5
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 704.91 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
1: Condello M, Pellegrini E, Multari G, Gallo FR, Meschini S. Voacamine: Alkaloid with its essential dimeric units to reverse tumor multidrug resistance. Toxicol In Vitro. 2020 Jun;65:104819. doi: 10.1016/j.tiv.2020.104819. Epub 2020 Mar 2. PMID: 32135239.
2: Chowdhury SR, Kumar A, Godinho JLP, De Macedo Silva ST, Zuma AA, Saha S, Kumari N, Rodrigues JCF, Sundar S, Dujardin JC, Roy S, De Souza W, Mukhopadhyay S, Majumder HK. Voacamine alters Leishmania ultrastructure and kills parasite by poisoning unusual bi-subunit topoisomerase IB. Biochem Pharmacol. 2017 Aug 15;138:19-30. doi: 10.1016/j.bcp.2017.05.002. Epub 2017 May 5. PMID: 28483460.
3: Condello M, Cosentino D, Corinti S, Di Felice G, Multari G, Gallo FR, Arancia G, Meschini S. Voacamine modulates the sensitivity to doxorubicin of resistant osteosarcoma and melanoma cells and does not induce toxicity in normal fibroblasts. J Nat Prod. 2014 Apr 25;77(4):855-62. doi: 10.1021/np400950h. Epub 2014 Apr 10. PMID: 24720452; PMCID: PMC4010292.
4: Giansanti L, Condello M, Altieri B, Galantini L, Meschini S, Mancini G. Influence of lipid composition on the ability of liposome loaded voacamine to improve the reversion of doxorubicin resistant osteosarcoma cells. Chem Phys Lipids. 2019 Sep;223:104781. doi: 10.1016/j.chemphyslip.2019.05.006. Epub 2019 Jun 20. PMID: 31229409.
5: Wang YQ, Li HX, Liu XC, Zhao JS, Liu RQ, Huai WY, Ding WJ, Zhang TE, Deng Y. One bis-indole alkaloid-voacamine from Voacanga africana Stapf: biological activity evaluation of PTP1B in vitro utilizing enzymology method based on SPRi expriment. Nat Prod Res. 2019 Dec;33(23):3459-3463. doi: 10.1080/14786419.2018.1480623. Epub 2018 May 31. PMID: 29852800.
6: Meschini S, Marra M, Condello M, Calcabrini A, Federici E, Dupuis ML, Cianfriglia M, Arancia G. Voacamine, an alkaloid extracted from Peschiera fuchsiaefolia, inhibits P-glycoprotein action in multidrug-resistant tumor cells. Int J Oncol. 2005 Dec;27(6):1597-603. PMID: 16273216.
7: Meschini S, Marra M, Calcabrini A, Federici E, Galeffi C, Arancia G. Voacamine, a bisindolic alkaloid from Peschiera fuchsiaefolia, enhances the cytotoxic effect of doxorubicin on multidrug-resistant tumor cells. Int J Oncol. 2003 Dec;23(6):1505-13. doi: 10.3892/ijo.23.6.1505. PMID: 14612920.
8: BLANPIN O, QUEVAUVILLER A. Sur le camphosulfonate de voacamine [Voacamine camphosulfonate]. C R Seances Soc Biol Fil. 1956 Nov 18;150(6):1113-5. French. PMID: 13383906.
9: Condello M, Multari G, Gallo FR, Arancia G, Meschini S. High-performance thin-layer chromatography for the evaluation of voacamine intracellular concentration related to its cytotoxic effect. J Pharm Biomed Anal. 2015 Nov 10;115:467-74. doi: 10.1016/j.jpba.2015.08.012. Epub 2015 Aug 12. PMID: 26298394.
10: Meschini S, Condello M, Marra M, Formisano G, Federici E, Arancia G. Autophagy-mediated chemosensitizing effect of the plant alkaloid voacamine on multidrug resistant cells. Toxicol In Vitro. 2007 Mar;21(2):197-203. doi: 10.1016/j.tiv.2006.09.007. Epub 2006 Sep 16. PMID: 17070665.
