Date: Thu, 20 Mar 1997 22:50:16 -0500 (EST)
From: Chris Jenks <jenks>
To: Multiple recipients of list <email@example.com>
Subject: Re: Ibogaline
At 08:02 PM 3/20/97 -0500, you wrote:
> Is Ibogaline known by another name generally, from perusing the
>phytochemical and research articles I've seen never seen or heard of a
>report of an alkaloid with this name, are there any synonyms?
> Is there any further references on it's structure and or relationship to
I haven't read much about ibogaline either, which is strange because the
Schmid article says it is isolated from T. iboga, and it would have to be
present in substantial amount. An article by Dickel et al. describes a
thorough extraction and analysis of T. iboga root - 100 kg of it - but no
ibogaline is mentioned, although ibogamine and tabernanthine, and other
alkaloids, are. I have to conclude that the composition of what is taken to
be Tabernanthe iboga root varies greatly.
Ibogaline has only one name, as far as I know. For the structure of
ibogaine, check out http://www.ibogaine.org. The "-O" group on the left
side of the molecule is called a "methoxy" group, and is an abbreviation
for "CH3O". The rest of the molecule, without the methoxy, is called
"ibogamine". The position on ibogamine that the methoxy is attached to is
#12, and the position below that, currently bearing an unshown hydrogen, is
#13. Another name for ibogaine is 12-methoxyibogamine. A metabolite of
ibogaine currently being compared to ibogaine for addiction treatment is
12-hydroxyibogamine, which has an "OH" or "hydroxy" group instead of a
methoxy group on the 12 position of ibogaine. Position #18 is two carbons
to the right of the "NH".
Common name Position 12 Position 13 Position 18
Ibogamine H H H
Ibogaine OCH3 H H
Tabernanthine H OCH3 H
Ibogaline OCH3 OCH3 H
Coronaridine H H COOCH3
Voacangine OCH3 H COOCH3
Isovoacangine H OCH3 COOCH3
Conopharyngine OCH3 OCH3 COOCH3
The "COOCH3" group is a carboxylic ester, which can be removed easily in
a laboratory. As a result, each of the first four entries in the above
table can be manufactured from the corresponding last four. This is how
ibogaine is "synthesized" from voacangine, without becoming racemic.
The information in this table was transferred from the following article,
which thoroughly describes the structure determination for each of the
alkaloids. Physical constants are given, but no extraction, pharmacology,
or relative abundances are mentioned.
Taylor, W. I. "Review: "The Iboga and Voacanga Alkaloids".", The Alkaloids,
Chemistry and Physiology, (1965), Vol. 8, R. H. F. Manske, Ed. (Academic
Press, New York) pp203-235.