Extraction and Conversion Studies of the Antiaddictive Alkaloids Coronaridine, Ibogamine, Voacangine, and Ibogaine from Two Mexican Tabernaemontana Species (Apocynaceae).
Felix Krengel, Marco V Mijangos, Marisol Reyes-Lezama, Ricardo Reyes-Chilpa
Chemistry & Biodiversity July 1, 2019 DOI: 10.1002/cbdv.201900175 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Experimental study Qualitative Peer reviewed |
|---|---|
| Population | Root barks of Tabernaemontana alba and Tabernaemontana arborea |
| Interventions | acetone ethyl acetate dichloromethane chloroform |
| Topics | Ibogaine |
| Keywords | Tabernaemontana apocynaceae Alkaloids Phytochemistry: detailed phytochemistry Convert Methanol effectively extracts Simplifying the mixture Improved analysis Anti-addictive civi-complex Therapeutically important substances Mexican plants Promising sources Bulk production |
| Citations | 17 |
| Key findings | Methanol is the most suitable solvent for extracting the CIVI-complex from Mexican Tabernaemontana species, and a one-step demethoxycarbonylation process converts coronaridine and voacangine into ibogamine and ibogaine, simplifying analysis and enabling bulk production. |
Abstract
Several species from the Apocynaceae family, such as Tabernanthe iboga, Voacanga africana, and many Tabernaemontana species, produce ibogan type alkaloids, some of which present antiaddictive properties. In this study, we used gas chromatography/mass spectrometry (GC/MS) to examine the efficiency of methanol, acetone, ethyl acetate, dichloromethane, chloroform, and hydrochloric acid in extracting the antiaddictive compounds coronaridine, ibogamine, voacangine, and ibogaine (altogether the CIVI-complex) from the root barks of Tabernaemontana alba and Tabernaemontana arborea. These Mexican species have recently shown great potential as alternative natural sources of the aforementioned substances. Methanol proved to be the most suitable solvent. Furthermore, the crude methanolic extracts could be engaged in a one-step demethoxycarbonylation process that converted coronaridine and voacangine directly into its non-carboxylic counterparts ibogamine and ibogaine, respectively, without the intermediacy of their carboxylic acids. The established protocol straightforwardly simplifies the alkaloid mixture from four to two majority compounds. In summary, our findings facilitate and improve both the qualitative and quantitative analysis of CIVI-complex-containing plant material, as well as outlining a viable method for the bulk production of these scientifically and pharmaceutically important substances from Mexican Tabernaemontana species.
Comparable studies
Other experimental studies on ibogaine, most cited first.
| Study | Year | Design | Participants |
|---|---|---|---|
| Ibogaine, a noncompetitive inhibitor of serotonin transport, acts by stabilizing the cytoplasm-facing state of the transporter. In vitro (SERT) | 2007 | Laboratory study | |
| Mechanisms of action of ibogaine and harmaline congeners based on radioligand binding studies. | 1992 | Laboratory study | |
| The mechanistic basis for noncompetitive ibogaine inhibition of serotonin and dopamine transporters. | 2012 | Experimental study | |
| Identification of a primary metabolite of ibogaine that targets serotonin transporters and elevates serotonin. | 1995 | Experimental study | |
| Ibogaine and its congeners are sigma 2 receptor-selective ligands with moderate affinity. | 1995 | Laboratory study |
Citations in the library
Cited by 8
- Efficient Access to the Iboga Skeleton: Optimized Procedure to Obtain Voacangine from Voacanga africana Root Bark. ACS Omega July 6, 2021
- Tabernaemontana arborea and ibogaine induce paroxysmal EEG activity in freely moving mice: Involvement of serotonin 5-HT1A receptors. Neurotoxicology March 1, 2022
- A narrative review of the pharmacological, cultural and psychological literature on ibogaine Journal of Psychedelic Studies 2021
- Quantitative Evaluation of a Mexican and a Ghanaian Tabernaemontana Species as Alternatives to Voacanga africana for the Production of Antiaddictive Ibogan Type Alkaloids. Chemistry & Biodiversity May 1, 2020
- Central nervous system activity of a Tabernaemontana arborea alkaloid extract involves serotonergic and opioidergic neurotransmission in murine models. Fitoterapia September 1, 2023
and 3 more in the library
Cites 4
- Effects of iboga alkaloids on morphine and cocaine self-administration in rats: relationship to tremorigenic effects and to effects on dopamine release in nucleus accumbens and striatum. Brain Research September 19, 1994
- Extraction studies of Tabernanthe iboga and Voacanga africana. Natural product letters February 1, 2002
- Quantification of Anti-Addictive Alkaloids Ibogaine and Voacangine in In Vivo- and In Vitro-Grown Plants of Two Mexican Tabernaemontana Species. Chemistry & Biodiversity December 1, 2016
- Metabolite Profiling of Anti-Addictive Alkaloids from Four Mexican Tabernaemontana Species and the Entheogenic African Shrub Tabernanthe iboga (Apocynaceae). Chemistry & Biodiversity April 1, 2019