Ibogaine and Noribogaine: Structural Analysis and Stability Studies. Use of LC‐MS to Determine Alkaloid Contents of the Root Bark of Tabernanthe Iboga
Violeta Kontrimavičiūtė, Olivier Mathieu, Laurence Balas, Roger Escale, Jean Pierre Blayac, Françoise Bressolle
Journal of Liquid Chromatography & Related Technologies March 1, 2007 Peer reviewed DOI: 10.1080/10826070601128451 via OpenAlex
Summary
The study analyzed ibogaine and noribogaine, identifying oxidation products formed when exposed to light. Two new compounds were detected after daylight exposure, and another potential compound was observed under UV light. Additionally, seven alkaloids were identified in the root bark of the Tabernanthe iboga shrub using mass spectrometry, with ibogaine being the most abundant at concentrations between 1.8 and 5.93 mg/g, while other alkaloids made up smaller percentages of ibogaine's peak area.
Study at a glance
| Population | root bark of the Tabernanthe iboga shrub |
|---|---|
| Key finding | Ibogaine was the principal alkaloid in the root bark, with concentrations ranging from 1.8 to 5.93 mg/g. |
Abstract
Abstract The aim of this study was: i) to carry out a structural analysis of ibogaine and noribogaine, ii) to identify products formed under light exposure (daylight or 254 nm, 20°C) of the two drugs in methanolic solutions, and iii) to examine the alkaloid contents of a specimen of root bark of the Tabernanthe iboga shrub using liquid chromatography‐electrospray mass spectrometry. After daylight exposure, two oxidation products were detected: ibochine and iboluteine from ibogaine, and desmethoxyibochine and desmethoxyiboluteine from noribogaine. After exposure to 254 nm of the ibogaine solution, another compound that could possibly be the analogous lactam of iboluteine was detected. From the liquid chromatography electrospray‐mass spectrometry analysis of the root barks of a specimen of the Tabernanthe iboga shrub, seven alkaloids were detected: ibochine (m/z 325), ibogaline (m/z 341), iboluteine (m/z 327), ibogaine (m/z 311), ibogamine (m/z 281) and voacangine (m/z 369). The last compound characterized by the protonated species (M+H)+ at m/z 309 has not been identified. In all samples, ibogaine was the principal alkaloid observed; its concentration ranged from 1.8 to 5.93 mg/g. For the other indole alkaloids, the peak areas of ibogaline, ibogamine and voacangine represent 11.9, 21.5, and 30.5% of that of ibogaine, respectively.