Abbreviated Ibogaine Congeners. Synthesis and Reactions of Tropan-3-yl-2- and -3-indoles. Investigation of an Unusual Isomerization of 2-Substituted Indoles Using Computational and Spectroscopic Techniques

Abstract

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(±)‐18‐Methoxycoronaridine: A Novel Iboga Alkaloid Congener Having Potential Anti‐Addictive Efficacy

“…Consistent with previous studies (4,6,18,20,30,32,34,(39)(40)(41), ibogaine and noribogaine have low micromolar affinities for several sites, including kappa and mu opioid receptors, NMDA receptors, 5HT 3 receptors, sigma 2 sites, sodium channels and the serotonin transporter; functional studies (2,38) have also shown ibogaine to behave as a noncompetitive antagonist at nicotinic receptors, acting perhaps as an open channel blocker that is not revealed in binding studies.…”

“…5, No. 1, 1999 34 S. D. GLICK ET AL. ceptors but no affinity at NMDA receptors or the serotonin transporter.…”

Syntheses of chiral 1,3-disubstituted tetrahydro-β-carbolines via CIAT process: highly stereoselective Pictet–Spengler reaction of d-tryptophan ester hydrochlorides with various aldehydes

“…There are three reasonable pathways 10,11,[47][48][49] for the CIAT process. Path A involves double migration of the double bond catalyzed by acid.…”

Ibogaine and the inhibition of acetylcholinesterase

“…Both ibogaine and noribogaine bind weakly to M1 or M2 muscarinic cholinergic receptors (mAChRs) with reported affinities generally in the range of approximately 5-30 M (Repke et al, 1994;Sweetnam et al, 1995;Staley et al, 1996;Glick et al, 2001), although the functional effect of this interaction has not apparently been investigated. The association of ibogaine with an atropine-sensitive EEG rhythm is not necessarily conclusive evidence for an agonist effect at mAChRs per se, because some electrical or pharmacological manipulations of the ARAS can produce an atropine-sensitive EEG rhythm without the administration of cholinergic agents (Bradley and Key, 1958;White and Daigneault, 1959).…”