Ibogaine Analogs

The usual...

names?

I read somewhere something about somones partner backin out and patenting a bunch of 'more potent' ibogaine analogs behind partners back... any names for these?? Potencies?

18-Methoxycoronaridine

It appears that the best known of ibogaine's analogs is 18-Methoxycoronaridine, which is a bit more potent than Ibogaine when measured in terms of its anti-addictive effects.

http://www.ibogaine.org/18-mc/


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Ibogaine's anti-addictive effects seem mostly to stem from its alpha3-beta4 nicotinic receptor antagonism.

(±)-18-Methoxycoronaridine: A Novel Iboga Alkaloid Congener Having Potential Anti-Addictive Efficacy.
Stanley D. Glick, Isabelle M. Maisonneuve, Lindsay B. Hough, Martin E. Kuehne and Upul K. Bandarage
CNS Drug Reviews. 5: 27-42 (1999)
http://www.nevapress.com/cnsdr/full/5/1/27.pdf


18-Methoxycoronaridine (18-MC) and Ibogaine: Comparison of Antiaddictive Efficacy, Toxicity, and Mechanisms of Action.
Stanley D. Glick, Isabelle M. Maisonneuve and Karen K. Szumlinski
Annals of the New York Academy of Sciences. 914: 369-386 (2000)
http://tinyurl.com/bghb3


Ibogaine Analogues. Synthesis and Preliminary Pharmacological Evaluation of 7-Heteroaryl-2-azabicyclo[2.2.2]oct-7-enes
Daniele Passarella, Raffaele Favia, Alessandra Giardini, Giordano Lesma, Marisa Martinelli, Alessandra Silvani, Bruno Danieli, Simon M. N. Efangeb and Deborah C. Mashc
Bioorganic & Medicinal Chemistry. 11: 1007–1014 (2003)
http://tinyurl.com/cuvxh


Antagonism of alpha3 beta4 nicotinic receptors as a strategy to reduce opioid and stimulant self-administration
Stanley D. Glick, Isabelle M. Maisonneuve, Barbara A. Kitchen and Mark W. Fleck
European Journal of Pharmacology. 438: 99–105 (2002)
http://tinyurl.com/d57o9


Novel iboga alkaloid congeners block nicotinic receptors and reduce drug self-administration
Christopher J. Pace, Stanley D. Glick, Isabelle M. Maisonneuve, Li-Wen He, Patrick A. Jokiel, Martin E. Kuehne and Mark W. Fleck
European Journal of Pharmacology. 492: 159–167 (2004)
http://tinyurl.com/a7j6g


Synthesis and Biological Evaluation of 18-Methoxycoronaridine Congeners. Potential Antiaddiction Agents
Martin E. Kuehne, Li-Wen He, Patrick A. Jokiel, C. J. Pace, Mark W. Fleck, Isabelle M. Maisonneuve, Stanley D. Glick and Jean M. Bidlack
J. Med. Chem. 46: 2716–2730 (2004)
http://tinyurl.com/cz5ov


Anti-addictive actions of an iboga alkaloid congener: a novel mechanism for a novel treatment
Isabelle M. Maisonneuve, Stanley D. Glick
Pharmacology, Biochemistry and Behavior. 75: 607-618 (2003)
http://tinyurl.com/cpffn


Synthesis of Enantiomerically Pure (+)- and (-)-18-Methoxycoronaridine Hydrochloride and Their Preliminary Assessment as Anti-Addictive Agents
Chi-Hsin R. King, Harold Meckler, R. Jason Herr, Michael P. Trova, Stanley D. Glick and Isabelle M. Maisonneuve
Bioorganic & Medicinal Chemistry Letters. 10: 473-476 (2000)
http://tinyurl.com/cs6ok

Perhaps I should have specified I was seeking the pyschedelic effects, not anti-addictive. I beleive psychedelic dosages are lower than those used for the treatments?? Somewhere I read Ibogaine was 200mg for rec and around 1000mg for other.

Bumpity bump...using the Heck reaction from a substituted tryptamine you should apparently be able to make some interesting modifications of ibogaine, a more potent and less toxic version would be ideal for something like psychotherapy.

Yeah ibogaine is an interesting one...apparantly very difficult to work with synthetically but sure someone out there could do it.

Such a messy drug though...combines mu-opioid agonist, NMDA antagonist, 5HT2A agonist and DAT inhibition effects in a single molecule, not to mention that alpha3beta4 nicotinic acetylcholine antagonist activity that seems to produce the anti-addictive action.

Most research has been to maximise the anti-addictive effects, and 18-MC is both less hallucinogenic and less opioid effects than ibogaine itself. Seeing as ibogaine already has a 12-methoxy group at the equivalent of the tryptamine 5-position, im not sure what you would put on there to increase the psychadelic effects...maybe an OH at the equivalent of the 4-position, but the nitrogen is all saturated and the other free sites on the benzene ring always produce inactive compounds with the 6- and 7- substituted tryptamine analogues.

http://www.ncbi.nlm.nih.gov/entrez/..._uids=16753910&query_hl=1&itool=pubmed_docsum

Nature-inspired indolyl-2-azabicyclo[2.2.2]oct-7-ene derivatives as promising agents for the attenuation of withdrawal symptoms: synthesis of 20-desethyl-20-hydroxymethyl-11-demethoxyibogaine.

Here is my ChemDraw Professional 17 version of 18MC, modified from the program-generated structure of ibogaine.