Ibogaine and Noribogaine: Structural Analysis and Stability Studies. Use of LC‐MS to Determine Alkaloid Contents of the Root Bark of Tabernanthe Iboga
Violeta Kontrimaviciūte, Olivier Mathieu, Laurence Balas, Roger Escale, Jean Pierre Blayac, Françoise M M Bressolle
Journal of Liquid Chromatography & Related Technologies March 1, 2007 DOI: 10.1080/10826070601128451 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Observational study Peer reviewed |
|---|---|
| Population | Root bark of one Tabernanthe iboga shrub specimen |
| Topics | Ibogaine |
| Keywords | Bark sound Chromatography Indole alkaloid Mass spectrometry Stereochemistry Alkaloids |
| Citations | 7 |
| Key findings | Ibogaine is the principal alkaloid in the root bark, and both ibogaine and noribogaine produce specific oxidation products under light exposure. |
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.
Comparable studies
Other observational and cohort studies on ibogaine, most cited first.
| Study | Year | Design | Participants |
|---|---|---|---|
| Treatment of opioid use disorder with ibogaine: detoxification and drug use outcomes. Adults with DSM-IV opioid dependence | 2018 | Observational study | n = 30 |
| Ibogaine treatment outcomes for opioid dependence from a twelve-month follow-up observational study. Individuals receiving legal ibogaine treatment for opioid dependence in New Zealand | 2018 | Observational study | n = 14 |
| Ibogaine: complex pharmacokinetics, concerns for safety, and preliminary efficacy measures. Drug-dependent persons undergoing inpatient detoxification | 2000 | Observational study | |
| Treating drug dependence with the aid of ibogaine: a retrospective study. Former alcohol, cannabis, cocaine and crack users (72% poly-drug users) | 2014 | Retrospective analysis | n = 75 |
| Magnesium-ibogaine therapy in veterans with traumatic brain injuries. Male Special Operations Forces veterans with predominantly mild traumatic brain injury | 2024 | Prospective observational study | n = 30 |
Citations in the library
Cited by 4
- Ibogaine, an anti-addictive drug: pharmacology and time to go further in development. A narrative review. Human & Experimental Toxicology March 1, 2008
- Fatalities temporally associated with the ingestion of ibogaine. Journal of Forensic Sciences March 1, 2012
- Psychoactive natural products: overview of recent developments. Annali dell'Istituto superiore di sanita 2014
- The Iboga Alkaloids. Progress in the chemistry of organic natural products 2017
Cites 7
- Ibogaine: complex pharmacokinetics, concerns for safety, and preliminary efficacy measures. Annals of the New York Academy of Sciences September 1, 2000
- Medication Development of Ibogaine as a Pharmacotherapy for Drug Dependencea. Annals of the New York Academy of Sciences May 1, 1998
- Extraction studies of Tabernanthe iboga and Voacanga africana. Natural product letters February 1, 2002
- 13C‐NMR. Spectroscopy of Naturally Occurring Substances. XLV. Iboga Alkaloids Helvetica Chimica Acta November 3, 1976
- Distribution of ibogaine and noribogaine in a man following a poisoning involving root bark of the Tabernanthe iboga shrub. Journal of Analytical Toxicology September 1, 2006
and 2 more in the library