Voacamine | CAS# 3371-85-5 | antimalarial

Voacamine
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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.

Chemical Structure

Voacamine

CAS# 3371-85-5

Instruction

Theoretical Analysis

MedKoo Cat#: 413361
Name: Voacamine
CAS#: 3371-85-5
Chemical Formula: C43H52N4O5
Exact Mass: 704.39
Molecular Weight: 704.910
Elemental Analysis: C, 73.27; H, 7.44; N, 7.95; O, 11.35

Price and Availability

Size	Price	Availability
1mg	USD 245	2 Weeks
5mg	USD 469	2 Weeks
10mg	USD 775	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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

More Info:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	Soluble in DMSO	0.0	100.00

Preparing Stock Solutions

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

Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.

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