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.
^^^^^^
Found this on google
and this
Analysis of T. iboga root bark using silica TLC, eluting twice with ethyl acetate followed by staining with iodine
vapor, showed ibogaine as a dark brown spot (Rf = 0.16) with a trail (depending on concentration), a red spot
(Rf = 0.07) belonging to ibogaline below it, and a small brown spot (Rf = 0.21), assumed to be ibogamine,
slightly above it. The percentages of ibogaine, ibogaline, and ibogamine appear to be 80%, 15%, and 5%
respectively judging by the size and density of the stained spots. The spot for ibogaline gave a red stain using
Keller’s reagent (12), confirming its identity (9). Occasionally a batch of root would contain ibogaine and
ibogamine but little or no ibogaline, and perhaps this was a related Tabernanthe species (9). TLC analysis of root
wood, stem bark or leaves of the T. iboga plant showed negligible ibogaine.
....
Recrystallization of PTA HCl from 95% ethanol gave ibogaine HCl with a significant amount of ibogaline still
present. Each successive recrystallization removed about half of the remaining ibogaline, but at a cost in yield.
Ibogaine HCl crystals dissolved slowly in the boiling ethanol while the solution darkened. Recrystallization from
water or mixtures of water and ethanol seemed to remove a larger proportion of ibogaline but also darkened.
Recrystallization from 95% ethanol gave greater purification and yield for the base (2) than for the ibogaine
HCl, but the base was less stable for both handling in solution and storage, unless melted and solidified into a
solid chunk. Chromatography using activity III basic alumina, eluting with cyclohexane followed by benzene or
toluene, separated ibogaine (490 mg) and ibogaline (109 mg) from TA, but this method was costly and laborious
on a large scale.
and this
"This material, named ibogaline, gave analytical results compatible with a C21H28N2O2 formulation"
http://pubs.acs.org/cgi-bin/abstract.cgi/joceah/1959/24/i12/f-pdf/f_jo01094a622.pdf?sessid=6006l3
"The scarcity of the material did not allow any degradative studies to prove the tentative assignment of the structure of ibogaline as 12,13-dimethoxy ibogamine"
Whatever the hell that all means. BTW these are from '59 and '65 I believe..
edit: apparently ibogaline oxidizes into
kisantine and gabonine
