Voacangine

Catalog Number	ACM510225
CAS Number	510-22-5
Synonyms	12-Methoxyibogamine-18-carboxylic acid methyl ester
Molecular Weight	368.5
InChI	InChI=1S/C22H28N2O3/c1-4-14-9-13-11-22(21(25)27-3)19-16(7-8-24(12-13)20(14)22)17-10-15(26-2)5-6-18(17)23-19/h5-6,10,13-14,20,23H,4,7-9,11-12H2,1-3H3/t13-,14-,20-,22+/m0/s1
InChI Key	MMAYTCMMKJYIAM-RUGRQLENSA-N
Melting Point	223-224 °C
Complexity	598
Covalently-Bonded Unit Count	1
Defined Atom Stereocenter Count	4
Exact Mass	368.20999276
Heavy Atom Count	27
Hydrogen Bond Acceptor Count	4
Hydrogen Bond Donor Count	1
Isomeric SMILES	CC[C@H]1C[C@H]2C[C@@]3([C@H]1N(C2)CCC4=C3NC5=C4C=C(C=C5)OC)C(=O)OC
Monoisotopic Mass	368.20999276
PhysicalState	Powder
Rotatable Bond Count	4
Topological Polar Surface Area	54.6 Ų

Case Study

Evaluation of Antiviral Activity of Voacangine and Its Structural Analogs

Monsalve-Escudero, Laura Milena, et al. Plants, 2021, 10(7), 1280.

This work evaluates the in vitro antiviral effects of voacangine and its three structural analogs (voacangine-7-hydroxyindole, rupicoline, and 3-oxo-voacangine) against different dengue virus (DENV) strains. Results indicate that the antiviral effects of these indole alkaloids depend on serotype and viral strain and are promising molecules for the development of anti-DENV drugs.
Assessment methods and results
· The in vitro antiviral effect evaluation strategy involved in this work includes 4 methods: compounds added before infection (Pre), at the same time with the virus (Trans), and after infection (Post) or compounds present at all times during the experiment (Pre- Trans-Post, combination therapy).
· During the Pre-treatment stage, only voacangine-7-hydroxyindolenine and rupicoline were effective in inhibiting the infection caused by the DENV-2/NG strain, with infection rates of 16.4% and 29.6% respectively.
· On the other hand, in the Trans-treatment approach, voacangine, voacangine-7-hydroxyindolenine, and rupicoline showed inhibition against both DENV-2/NG and DENV-2/16681 infection models, with varying infection rates. Notably, 3-oxo-voacangine was highly effective against the DENV-2/16681 strain, with 82.8% inhibition. Voacangine was identified as the most potent virucidal agent, displaying effective inhibition against DENV-1/WestPac/74 and DENV-2/S16803 strains.
· Conversely, the post-treatment approach did not yield any inhibition.
· The combined approach demonstrated that voacangine, voacangine-7-hydroxyindolenine, and rupicoline collectively inhibited over 90% of infections in both DENV-2/NG and DENV-2/16681 strains.

The Potential of Voacangine as An Anti-Angiogenic Agent

Yonghyo Kim, et al. Biochemical and Biophysical Research Communications, 2012, 417(1), 330-334.

This work investigated the anti-angiogenic activity of the natural small molecule voacangine. The results indicate that voacangine inhibits tumor-induced angiogenesis in a dose-dependent manner by inhibiting HIF-1α. This means that voacangine could serve as a basis for the development of new anti-angiogenic drugs.
Anti-angiogenic activity assessment of voacangine
· It was observed that voacangine had a stronger inhibitory effect on HUVECs compared to other normal and cancer cell lines. Various concentrations of voacangine (1 to 20 μM) were tested on HUVECs to determine the optimal dose that had no harmful effects on cell viability, as assessed by the trypan blue exclusion method. Results showed that voacangine did not exhibit any cytotoxicity on HUVECs at doses up to 20 μM over a 3-day period.
· In vitro experiments were conducted to evaluate the impact of voacangine on HUVEC angiogenic characteristics, specifically tube formation and chemical invasion. The findings revealed that voacangine inhibited VEGF-induced tube formation in a dose-dependent manner without causing any cytotoxic effects. Additionally, voacangine displayed a dose-dependent inhibition of VEGF-induced enhanced invasiveness of HUVECs.
· The anti-angiogenic properties of voacangine were further confirmed through in vivo testing using a chick embryo chorioallantoic membrane (CAM) assay. Voacangine demonstrated a dose-dependent inhibition of capillary formation during CAM development, with no observable thrombosis or hemorrhage.

Custom Q&A

What is the chemical formula of Voacangine?

The chemical formula of Voacangine is C22H28N2O3.

What is the molecular weight of Voacangine?

The molecular weight of Voacangine is 368.47.

At what temperature does Voacangine melt?

Voacangine melts at 223-224℃.

What is the density of Voacangine at 20°C and 760 Torr?

The density of Voacangine at 20°C and 760 Torr is 1.25±0.1 g/cm3.

How should Voacangine be stored?

Voacangine should be stored at -20°C and protected from light.

In which solvents is Voacangine soluble?

Voacangine is soluble in DMF, DMSO, and DMSO:PBS(pH 7.2) (1:3).

What is the chemical structure of Voacangine?

The chemical structure of Voacangine is a monoterpenoid indole alkaloid.

What is the role of Voacangine?

Voacangine has a role as an angiogenesis inhibitor, an antineoplastic agent, and a plant metabolite.

What is the activity of (-)-Voacangine in vitro?

(-)-Voacangine is a bisindole alkaloid with ether-?a-?go-?go-?related gene channel blocker activity in vitro.

How is Ibogaine obtained from Voacangine?

Hydrolysis with KOH followed by acidification with HCl yields Ibogaine from Voacangine.

※ Please kindly note that our products are for research use only.