Voacamine | CAS# 3371-85-5 | antimalarial

MedKoo Cat#: 413361 | Name: Voacamine

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Theoretical Analysis

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

Price and Availability

Size	Price	Availability
1mg	USD 245.00	2 Weeks
5mg	USD 469.00	2 Weeks
10mg	USD 775.00	2 Weeks

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Related CAS #

No Data

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

	Solvent	mg/mL	mM
Solubility
	Soluble in DMSO	0.0	100.00

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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

1: Soares Ribeiro Nogueira T, Gonçalves Curcino Vieira M, Rodrigues da Silva Robaina R, Braz-Filho R, da Costa Gontijo D, Braga de Oliveira A, Curcino Vieira IJ. An update review on monoterpene indole alkaloids and biological activities of Tabernaemontana species occurring in Brazil. J Ethnopharmacol. 2024 Jun 28;328:117921. doi: 10.1016/j.jep.2024.117921. Epub 2024 Feb 16. PMID: 38369065. 2: Hassan AA, Khalid HE, Abdalla AH, Mukhtar MM, Osman WJ, Efferth T. Antileishmanial Activities of Medicinal Herbs and Phytochemicals In Vitro and In Vivo: An Update for the Years 2015 to 2021. Molecules. 2022 Nov 4;27(21):7579. doi: 10.3390/molecules27217579. PMID: 36364404; PMCID: PMC9656935. 3: Chen Y, Yang J, Zuo Y, Zhang C, Pu Y, Ren Q, Li X, Huang Y, Huang H, Yang H, You O, Xia X, Lu A, Shi S, Deng Y, Lu J. Voacamine is a novel inhibitor of EGFR exerting oncogenic activity against colorectal cancer through the mitochondrial pathway. Pharmacol Res. 2022 Oct;184:106415. doi: 10.1016/j.phrs.2022.106415. Epub 2022 Aug 25. PMID: 36029932. 4: Zuo Y, Zhang CZ, Ren Q, Chen Y, Li X, Yang JR, Li HX, Tang WT, Ho HM, Sun C, Li MM, Ren B, Deng Y, Wang ML, Lu J. Activation of mitochondrial-associated apoptosis signaling pathway and inhibition of PI3K/Akt/mTOR signaling pathway by voacamine suppress breast cancer progression. Phytomedicine. 2022 May;99:154015. doi: 10.1016/j.phymed.2022.154015. Epub 2022 Mar 3. PMID: 35278901. 5: Singh L, Roy S, Kumar A, Rastogi S, Kumar D, Ansari MN, Saeedan AS, Singh M, Kaithwas G. Repurposing Combination Therapy of Voacamine With Vincristine for Downregulation of Hypoxia-Inducible Factor-1α/Fatty Acid Synthase Co-axis and Prolyl Hydroxylase-2 Activation in ER+ Mammary Neoplasia. Front Cell Dev Biol. 2021 Nov 18;9:736910. doi: 10.3389/fcell.2021.736910. PMID: 34869321; PMCID: PMC8637442. 6: Pellegrini E, Multari G, Gallo FR, Vecchiotti D, Zazzeroni F, Condello M, Meschini S. A natural product, voacamine, sensitizes paclitaxel-resistant human ovarian cancer cells. Toxicol Appl Pharmacol. 2022 Jan 1;434:115816. doi: 10.1016/j.taap.2021.115816. Epub 2021 Nov 29. PMID: 34856211. 7: González B, Fagúndez C, Peixoto de Abreu Lima A, Suescun L, Sellanes D, Seoane GA, Carrera I. Efficient Access to the Iboga Skeleton: Optimized Procedure to Obtain Voacangine from Voacanga africana Root Bark. ACS Omega. 2021 Jun 24;6(26):16755-16762. doi: 10.1021/acsomega.1c00745. PMID: 34250335; PMCID: PMC8264847. 8: Singh L, Singh M, Rastogi S, Choudhary A, Kumar D, Raj R, Ansari MN, Saeedan AS, Kaithwas G. Effect of Voacamine upon inhibition of hypoxia induced fatty acid synthesis in a rat model of methyln-nitrosourea induced mammary gland carcinoma. BMC Mol Cell Biol. 2021 Jun 5;22(1):33. doi: 10.1186/s12860-021-00371-9. PMID: 34090331; PMCID: PMC8180083. 9: Babiaka SB, Simoben CV, Abuga KO, Mbah JA, Karpoormath R, Ongarora D, Mugo H, Monya E, Cho-Ngwa F, Sippl W, Loveridge EJ, Ntie-Kang F. Alkaloids with Anti- Onchocercal Activity from Voacanga africana Stapf (Apocynaceae): Identification and Molecular Modeling. Molecules. 2020 Dec 25;26(1):70. doi: 10.3390/molecules26010070. PMID: 33375687; PMCID: PMC7795662. 10: Guzmán-Gutiérrez SL, Silva-Miranda M, Krengel F, Huerta-Salazar E, León- Santiago M, Díaz-Cantón JK, Espitia Pinzón C, Reyes-Chilpa R. Antimycobacterial Activity of Alkaloids and Extracts from Tabernaemontana alba and T. arborea. Planta Med. 2022 Jan;88(1):53-61. doi: 10.1055/a-1157-1732. Epub 2020 May 11. Erratum in: Planta Med. 2022 Jan;88(1):e1. doi: 10.1055/a-1177-3691. PMID: 32392600. 11: 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. 12: 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. 13: Ndjonka D, Djafsia B, Liebau E. Review on medicinal plants and natural compounds as anti-Onchocerca agents. Parasitol Res. 2018 Sep;117(9):2697-2713. doi: 10.1007/s00436-018-6003-7. Epub 2018 Jul 15. PMID: 30008135. 14: 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. 15: 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. 16: Kumar A, Banerjee N, Singamaneni V, K Dokuparthi S, Chakrabarti T, Mukhopadhyay S. Phytochemical investigations and evaluation of antimutagenic activity of the alcoholic extract of Glycosmis pentaphylla and Tabernaemontana coronaria by Ames test. Nat Prod Res. 2018 Mar;32(5):582-587. doi: 10.1080/14786419.2017.1318384. Epub 2017 Apr 20. PMID: 28423921. 17: 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. 18: Chen HM, Yang YT, Li HX, Cao ZX, Dan XM, Mei L, Guo DL, Song CX, Dai Y, Hu J, Deng Y. Cytotoxic monoterpenoid indole alkaloids isolated from the barks of Voacanga africana Staph. Nat Prod Res. 2016;30(10):1144-9. doi: 10.1080/14786419.2015.1046132. Epub 2015 Jul 3. PMID: 26140390. 19: Currais A, Chiruta C, Goujon-Svrzic M, Costa G, Santos T, Batista MT, Paiva J, do Céu Madureira M, Maher P. Screening and identification of neuroprotective compounds relevant to Alzheimer׳s disease from medicinal plants of S. Tomé e Príncipe. J Ethnopharmacol. 2014 Aug 8;155(1):830-40. doi: 10.1016/j.jep.2014.06.046. Epub 2014 Jun 24. PMID: 24971794. 20: 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.