12-Methoxyibogamine-18-carboxylic acid, methyl ester
|Systematic IUPAC name
Methyl 17-ethyl-7-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18] nonadeca-2(10),4,6,8-tetraene-1-carboxylate
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||368.477 g·mol−1|
|Melting point||136 to 137 °C (277 to 279 °F; 409 to 410 K)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
what is ?)(
Voacangine (12-methoxyibogamine-18-carboxylic acid methyl ester) is an alkaloid found predominantly in the root bark of the Voacanga africana tree, as well as in other plants such as Tabernanthe iboga, Tabernaemontana africana, Trachelospermum jasminoides, Tabernaemontana divaricata and Ervatamia yunnanensis. It is an iboga alkaloid which commonly serves as a precursor for the semi-synthesis of ibogaine. It has been demonstrated in animals to have similar anti-addictive properties to ibogaine itself. It also potentiates the effects of barbiturates. Under UV-A and UV-B light its crystals fluoresce blue-green, and it is soluble in ethanol.
Voacangine exhibits AChE inhibitory activity. Docking simulation reveals that it has inhibitory effect on VEGF2 kinase and reduces angiogenesis. Like ibogaine, its a potent HERG blocker in vitro. It also acts as antagonist to TRPM8 and TRPV1 receptor but agonist of TRPA1.
The absolute bioavailability of voacangine is around 11-13%.
High doses of voacangine produce convulsions and asphyxia.