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Ibogaine and the Inhibition of Acetylcholinesterase

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Ibogaine and the Inhibition of Acetylcholinesterase See discussions, stats, and author profiles for this publication at: https://www.researchgate.net/publication/51894894 Ibogaine and the inhibition of acetylcholinesterase Article in Journal of ethnopharmacology · December 2011 DOI: 10.1016/j.jep.2011.12.006 · Source: PubMed CITATIONS READS 5 40 3 authors, including: Kenneth Alper Henry Sershen NYU Langone Medical Center Nathan Kline Institute 76 PUBLICATIONS 2,547 CITATIONS 202 PUBLICATIONS 5,322 CITATIONS SEE PROFILE SEE PROFILE All content following this page was uploaded by Kenneth Alper on 29 June 2015. The user has requested enhancement of the downloaded file. All in-text references underlined in blue are added to the original document and are linked to publications on ResearchGate, letting you access and read them immediately. Journal of Ethnopharmacology 139 (2012) 879–882 Contents lists available at SciVerse ScienceDirect Journal of Ethnopharmacology journa l homepage: www.elsevier.com/locate/jethpharm Ethnopharmacological communication Ibogaine and the inhibition of acetylcholinesterase a,∗ b c,d Kenneth Alper , Maarten E.A. Reith , Henry Sershen a Departments of Psychiatry and Neurology, New York University School of Medicine, New York, NY 10016, USA b Departments of Psychiatry and Pharmacology, New York University School of Medicine, New York, NY 10016, USA c Department of Neurochemistry, Nathan S. Kline Institute for Psychiatric Research, Orangeburg, NY 10962, USA d Department of Psychiatry, New York University School of Medicine, New York, NY 10016, USA a r t i c l e i n f o a b s t r a c t Article history: Ethnopharmacological relevance: Ibogaine is a psychoactive monoterpine indole alkaloid extracted from Received 24 August 2011 the root bark of Tabernanthe iboga Baill. that is used globally in medical and nonmedical settings to Received in revised form treat drug and alcohol addiction, and is of interest as an ethnopharmacological prototype for exper- 29 November 2011 imental investigation and pharmaceutical development. The question of whether ibogaine inhibits Accepted 2 December 2011 acetylcholinesterase (AChE) is of pharmacological and toxicological significance. Available online 19 December 2011 Materials and methods: AChE activity was evaluated utilizing reaction with Ellman’s reagent with physostigmine as a control. Keywords: ± ␮ Ibogaine Results: Ibogaine inhibited AChE with an IC50 of 520 40 M. Conclusions: Ibogaine’s inhibition of AChE is physiologically negligible, and does not appear to account Iboga alkaloid Acetylcholinesterase for observations of functional effects in animals and humans that might otherwise suggest the possible Addiction involvement of pathways linked to muscarinic acetylcholine transmission. Muscarinic cholinergic © 2011 Elsevier Ireland Ltd. All rights reserved. Toxicology 1. Introduction the potentiation of morphine analgesia by ibogaine. Bradycardia, which can result from increased muscarinic cholinergic transmis- The iboga alkaloids are a group of naturally occurring and syn- sion among a variety of other causes, was observed in 6 of a series of thetic monoterpine indole alkaloids, some of which reportedly 39 patients following single oral dose administrations of ibogaine reduce the self-administration of drugs of abuse and opiate with- (Mash et al., 1998), and has been reported anecdotally in medi- drawal symptoms in animal models and humans (Alper, 2001; Glick cal (Kamlet, 2009) and nonmedical (Samorini, 1998) settings and et al., 2001; Alper et al., 2008). Ibogaine (Fig. 1) is the most abundant in some preclinical studies (Schneider and Rinehart, 1957; Dhahir, iboga alkaloid in the root bark of Tabernanthe iboga Baill., which 1971; Glick et al., 1999; Binienda et al., 2002). The apparently sig- grows in West Africa where eboga, the shavings of T. iboga root nificant role of pre-existing cardiovascular medical comorbidities bark, has been used as a psychopharmacological sacrament in the in deaths temporally associated with the use of ibogaine (Alper Bwiti religion for several centuries (Fernandez, 1982). Outside of et al., in press) indicates the medical and toxicological relevance Africa ibogaine has been used with increasing frequency over the of bradycardia, which heightens the risk for fatal cardiac arrhyth- last 25 years, most often for detoxification from opiates (Alper et al., mia (Cubeddu, 2009). Ibogaine produces an atropine-sensitive EEG 1999, 2008). rhythm in animals (Depoortere, 1987; Schneider and Sigg, 1957) The inhibition of acetylcholinesterase (AChE) could explain that has been attributed to muscarinic cholinergic input from the some functional effects of ibogaine that appear consistent with ascending reticular activating system (ARAS) on the basis of abla- increased muscarinic cholinergic transmission. Ciba Pharmaceu- tion experiments and suggested to involve the inhibition of AChE tical patented ibogaine for the indication of reducing tolerance to (Schneider and Sigg, 1957). The enhancement of spatial memory opioid analgesics (Schneider and McArthur, 1956; Schneider, 1957) by ibogaine in preclinical models (Popik, 1996; Helsley et al., 1997) and specifically suggested that AChE inhibition might mediate is another functional effect that could possibly relate to the inhibi- tion of AChE in view of the use of AChE inhibitors to treat memory impairment in dementias (Birks, 2009). Studies performed in the 1940s found that ibogaine obtained by ∗ Corresponding author at: Departments of Psychiatry and Neurology, New York crystallization from extract of T. iboga root bark inhibited AChE from University School of Medicine, Brain Research Laboratories, 8th Floor Old Bellevue horse serum, sheep brain, and dog pancreas with an IC50 of approx- Administration Building, 462 First Avenue, New York, NY 10016, USA. imately 150 ␮M (Vincent and Sero, 1942; Vincent and Lagreu, Tel.: +1 212 263 6287; fax: +1 212 409 8902. E-mail address: [email protected] (K. Alper). 1949). These early studies utilized a manometer for gasometric 0378-8741/$ – see front matter © 2011 Elsevier Ireland Ltd. All rights reserved. doi:10.1016/j.jep.2011.12.006 880 K. Alper et al. / Journal of Ethnopharmacology 139 (2012) 879–882 Fig. 1. Chemical structures of ibogaine (top) and physostigmine (bottom). Fig. 2. Inhibitory effects of physostigmine and ibogaine on cholinesterase activity determination of rates of AChE inhibition, which predated the con- measured in vitro utilizing the acetylcholine pseudo-substrate ACTI and Ellman’s reagent in the presence of enzyme (AChE, 0.19 U). temporary colorimetric approach (Ellman et al., 1961; Järvinen et al., 2010), and raises questions regarding the accuracy of their estimates. In these early studies T. iboga root bark extract produced recordings were taken for 6 min. Ibogaine and physostigmine were a greater degree of AChE inhibition than the crystallisate, suggest- ␮ initially tested at 1, 10, and 100 M concentrations to determine ing an effect due to additional alkaloids other than ibogaine in the inhibition–dose range; subsequent assays were conducted at the root bark. Other studies have evaluated the inhibition of AChE by dose–inhibition range shown in Fig. 2. Two control curves were col- crude extracts that included various iboga alkaloids from Taber- lected in the absence of inhibiting compound, one at the beginning naemontana australis (Müell. Arg) Miers (Andrade et al., 2005) or of the experiment prior to testing varying concentrations of com- Tabernaemontana divaricata R.Br. ex Roem. & Schult (Ingkaninan pound, and a second at the end after compound testing. The two et al., 2006; Chattipakorn et al., 2007; Nakdook et al., 2010; control curves were almost identical and were averaged for subse- Pratchayasakul et al., 2010). In view of the need for a contempo- quent analysis. AChE activity per minute was computed for control rary laboratory investigation focused specifically on ibogaine with and drug concentrations, and IC50 values were estimated by non- its purity established by current chemical analytical techniques, linear computer curve-fitting procedures. Specifically, the ALLFIT this present study utilized ibogaine in the HCl form, and an assay equation for drug inhibition (DeLean et al., 1978) was used, which based on reaction with Ellman’s reagent to evaluate the inhibition equals the logistic model in the Origin software (Origin-Lab Corp., of AChE (Ellman et al., 1961; Järvinen et al., 2010). Northampton, MA, USA). Analysis of the multiple drug concentra- tion inhibition data by computer fitting with the ALLFIT equation 2. Methods provided the standard deviations given in the text. 2.1. Materials 3. Results and discussion Chemicals were purchased from Sigma–Aldrich (St. Louis, The IC for the inhibition of AChE by ibogaine was 520 ± 40 ␮M 50 MO): 5,5 -dithiobis(2-nitrobenzoic acid) (DTNB – D218200), (Fig. 2). The IC50 of physostigmine at a substrate concentration of acetylthiocholine iodide (ACTI – A5751), – acetylcholinesterase 2.7 nM ACTI with AChE from electric eel was 18.4 ± 1.8 nM, which from Electrophorus electricus, (AChE – C3389-2KU, ∼236 U/mg), is comparable to recently reported values for IC50 for inhibition physostigmine (Fig. 1) (E8375). Ibogaine HCl was obtained from of AChE by physostigmine of 40 nM with AChE from electric eel Slater & Frith Ltd, UK (assay analysis 95%) (Slater and Frith LTD., (Järvinen et al., 2010), and 40 nM and 20 nM in rat and human neo- 2008). Most of the remaining 5% was ibogamine with lesser cortex respectively (Jackisch et al., 2009). In this study the activity
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