Ibogaline is an
alkaloid found in Tabernanthe iboga along with the related chemical compounds
ibogaine,
ibogamine, 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 species such as Tabernaemontana australis[1] 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%.[2][3]
Chemistry
Derivatives
Kisantine and Gabonine are thought to be ibogaline's oxidation byproducts.[4]
Adverse effect
In rodents, ibogaline induces more body
tremor and
ataxia compared to ibogaine and ibogamine.[5] Among a series of iboga and
harmala alkaloids evaluated in rats, the study authors found the following order of potency in causing tremors:[5]
^Piotr Popik, Phil Skolnick (1998). Pharmacology of Ibogaine and Ibogaine-Related Alkaloids. Vol. 52. San Diego. {{
cite book}}: |work= ignored (
help)CS1 maint: location missing publisher (
link)
^Norbert Neuss (1959). "Notes- Alkaloids from Apocynaceae II. Ibogaline, A New Alkaloid From Tabernanthe Iboga Baill". J. Org. Chem. 24 (12): 2047–2048.
doi:
10.1021/jo01094a622.
^Taylor, W. I. (2002). "The Alkaloids of Tabernanthe iboga. IX.1 The Structures of the Ibogaline Derivatives, Kisantine and Gabonine". The Journal of Organic Chemistry. 30 (1): 309–310.
doi:
10.1021/jo01012a515.
ISSN0022-3263.
^
abZetler G, Singbartl G, Schlosser L (1972). "Cerebral Phamacokinetics of Tremor-producing Harmala and Iboga Alkaloids". Pharmacology. 7 (4): 237–248.
doi:
10.1159/000136294.
PMID5077309.
^Glick SD, Kuehne ME, Raucci J, Wilson TE, Larson D, Keller RW Jr, Carlson JN (1994). "Effects of iboga alkaloids on morphine and cocaine self-administration in rats: relationship to tremorigenic effects and to effects on dopamine release in nucleus accumbens and striatum". Brain Res. 657 (1–2): 14–22.
doi:
10.1016/0006-8993(94)90948-2.
PMID7820611.
S2CID1940631.