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The Iboga Alkaloids

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Progress in the Chemistry of Organic Natural Products 105

Part of the book series: Progress in the Chemistry of Organic Natural Products ((POGRCHEM,volume 105))

Abstract

Iboga alkaloids are a particular class of indolomonoterpenes most often characterized by an isoquinuclidine nucleus. Their first occurrence was detected in the roots of Tabernanthe iboga, a sacred plant to the people of Gabon, which made it cult object. Ibogaine is the main representative of this class of alkaloids and its psychoactive properties are well documented. It has been proposed as a drug cessation treatment and has a wide range of activities in targeting opioids, cocaine, and alcohol. The purpose of this chapter is to provide a background on this molecule and related compounds and to update knowledge on the most recent advances made. Difficulties linked to the status of ibogaine as a drug in several countries have hampered its development, but 18-methoxycoronaridine is currently under evaluation for the same purposes and for the treatment of leishmaniasis. The chapter is divided into six parts: an introduction aiming at defining what is called an iboga alkaloid, and this is followed by current knowledge on their biosynthesis, which unfortunately remains a “black box” as far as the key construction step is concerned. Many of these alkaloids are still being discovered and the third and fourth parts of the chapter discuss the analytical tools in use for this purpose and give lists of new monomeric and dimeric alkaloids belonging to this class. When necessary, the structures are discussed especially with regard to absolute configuration determinations, which remain a point of weakness in their assignments. Part V gives an account of progress made in the synthesis, partial and total, which the authors believe is key to providing solid solutions to the industrial development of the most promising molecules. The last part of the chapter is devoted to the biological properties of iboga alkaloids, with particular emphasis on ibogaine and 18-methoxycoronaridine.

Dedicated to the memory of Howard J Lotsof

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Acknowledgments

It is our pleasure to thank the many individuals with whom we were able to exchange correspondence during the writing of this review: Ken Alper, Laurence Balas, Françoise Bressolle, Geoffrey Cordell, Mohammed Damak, Françoise Guéritte, Toh Seok Kam, Muriel Le Roux, Dalibor Sames, Surajit Sinha, and Hiromitsu Takayama. For pictures of plants, we are indebted to Philomène Akoua Kouassi, University of Cocody (Ivory Coast) and Bruno David, Pierre Fabre Laboratories, Toulouse (France).

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  1. Faculty of Pharmacy, Université de Reims Champagne-Ardenne, Institut de Chimie Moléculaire de Reims, UMR CNRS 7312, Case postale 44, UFR des Sciences Exactes et Naturelles, BP 1039, 51687, Reims, Cedex 2, France

    Catherine Lavaud

  2. Université de Reims Champagne-Ardenne, Institut de Chimie Moléculaire de Reims, UMR CNRS 7312, Case postale 44, UFR des Sciences Exactes et Naturelles, BP 1039, 51687, Reims, Cedex 2, France

    Georges Massiot

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  1. Catherine Lavaud
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  2. Georges Massiot
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Correspondence to Catherine Lavaud .

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Editors and Affiliations

  1. Division of Medicinal Chemistry & Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, Ohio, USA

    A. Douglas Kinghorn

  2. Institute of Organic Chemistry, Johannes Kepler University Linz, Linz, Austria

    Heinz Falk

  3. Research Department of Pharmaceutical and Biological Chemistry, UCL School of Pharmacy, London, United Kingdom

    Simon Gibbons

  4. Graduate School of Pharmaceutical Science, Hokkaido University, Sapporo, Japan

    Jun'ichi Kobayashi

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© 2017 Springer International Publishing AG

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Lavaud, C., Massiot, G. (2017). The Iboga Alkaloids. In: Kinghorn, A., Falk, H., Gibbons, S., Kobayashi, J. (eds) Progress in the Chemistry of Organic Natural Products 105. Progress in the Chemistry of Organic Natural Products, vol 105. Springer, Cham. https://doi.org/10.1007/978-3-319-49712-9_2

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