Ibogaine and Noribogaine: Structural Analysis and Stability Studies. Use of LC‐MS to Determine Alkaloid Contents of the Root Bark of Tabernanthe Iboga

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, 208C) 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 þ H) þ 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.

Fatalities Temporally Associated with the Ingestion of Ibogaine

“…The total alkaloid content of the root bark is c . 2–8% of the dry weight of the root bark, about half of which is iboga alkaloids, 80% of which is ibogaine (157,158). Utilization of water‐soluble extractants yields an extract with an alkaloid fraction composed of c .…”

“…40% ibogaine, 10% related iboga alkaloids, and 50% other alkaloids, whereas utilization of an organic solvent such as acetone or methanol yields a total alkaloid fraction with relatively less non‐iboga alkaloid content (157). Other iboga alkaloids that co‐occur with ibogaine in T. iboga root bark include ibogamine, ibogaine, tabernanthine, and voacangine (157–159) (see Fig. 1).…”