Ibogaline
   HOME

TheInfoList



OR:

Ibogaline is an
alkaloid Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar ...
found in ''
Tabernanthe iboga ''Tabernanthe iboga'' (iboga) is an evergreen rainforest shrub native to Central Africa. A member of the Apocynaceae family indigenous to Gabon, the Democratic Republic of Congo, and the Republic of Congo, it is cultivated across Central Africa ...
'' along with the related chemical compounds
ibogaine Ibogaine is a naturally occurring psychoactive substance found in plants in the family Apocynaceae such as ''Tabernanthe iboga'', ''Voacanga africana'', and ''Tabernaemontana undulata''. It is a psychedelic with dissociative properties. Prel ...
,
ibogamine Ibogamine is an anti-convulsant, anti-addictive, CNS stimulant alkaloid found in ''Tabernanthe iboga'' and Crepe Jasmine (''Tabernaemontana divaricata''). Basic research related to how addiction affects the brain has used this chemical. Ibogamin ...
, and other minor alkaloids. It is a relatively smaller component of ''Tabernanthe iboga'' root bark total alkaloids (TA) content. It is also present in ''
Tabernaemontana ''Tabernaemontana'' is a genus of flowering plants in the family Apocynaceae. It has a pan-tropical distribution, found in Asia, Africa, Australia, North America, South America, and a wide assortment of oceanic islands. These plants are evergreen ...
'' species such as '' Tabernaemontana australis'' which shares similar ibogan-biosynthetic pathways. The percentage of ibogaline in ''T. iboga'' root bark is up to 15% TA with ibogaine constituting 80% of the alkaloids and ibogamine up to 5%.


Chemistry


Derivatives

Kisantine and Gabonine are thought to be ibogaline's oxidation byproducts.


Adverse effect

In rodents, ibogaline induces more body
tremor A tremor is an involuntary, somewhat rhythmic, muscle contraction and relaxation involving oscillations or twitching movements of one or more body parts. It is the most common of all involuntary movements and can affect the hands, arms, eyes, fa ...
and
ataxia Ataxia is a neurological sign consisting of lack of voluntary coordination of muscle movements that can include gait abnormality, speech changes, and abnormalities in eye movements. Ataxia is a clinical manifestation indicating dysfunction of ...
compared to ibogaine and ibogamine. Among a series of iboga and
harmala alkaloids Several alkaloids that function as monoamine oxidase inhibitors (MAOIs) are found in the seeds of ''Peganum harmala'' (also known as ''Harmal'' or ''Syrian Rue''), as well as tobacco leaves including harmine, harmaline, and harmalol, which are me ...
evaluated in rats, the study authors found the following order of potency in causing tremors: * ED50 (μmol/kg, sc):
tabernanthine Tabernanthine is an alkaloid found in ''Tabernanthe iboga''. It has been used in laboratory experiments to study how addiction affects the brain. Tabernanthine persistently reduced the self-administration of cocaine and morphine in rats. Phar ...
(4.5) > ibogaline (7.6) >
harmaline Harmaline is a fluorescent indole alkaloid from the group of harmala alkaloids and beta-carbolines. It is the partly hydrogenated form of harmine. Occurrence in nature Various plants contain harmaline including ''Peganum harmala'' (Syrian rue) ...
(12.8) >
harmine Harmine is a beta-carboline and a harmala alkaloid. It occurs in a number of different plants, most notably the Syrian rue and ''Banisteriopsis caapi''. Harmine reversibly inhibits monoamine oxidase A (MAO-A), an enzyme which breaks down monoamin ...
(13.7) > ibogaine (34.8) >
noribogaine Noribogaine (actually O-desmethylibogaine), or 12-hydroxyibogamine, is the principal psychoactive metabolite of the oneirogen ibogaine. It is thought to be involved in the antiaddictive effects of ibogaine-containing plant extracts, such as '' ...
(176.0) A subsequent study confirmed these findings.


See also

*
Coronaridine Coronaridine, also known as 18-carbomethoxyibogamine, is an alkaloid found in ''Tabernanthe iboga'' and related species, including ''Tabernaemontana divaricata'' for which (under the now obsolete synonym ''Ervatamia coronaria'') it was named. Li ...
*
Voacangine Voacangine (12-methoxyibogamine-18-carboxylic acid methyl ester) is an alkaloid found predominantly in the root bark of the ''Voacanga africana'' tree, as well as in other plants such as ''Tabernanthe iboga'', ''Tabernaemontana africana'', ''Trach ...


References

{{reflist Alkaloids found in Iboga Indole alkaloids