Ibogaline

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]

Ibogaline
Names
IUPAC name
(1R,17S)-17-Ethyl-6,7-dimethoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4,6,8-tetraene
Other names
12,13-Dimethoxyibogamine
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C18H21ClN2/c19-17-7-4-8-18(15-17)21-13-11-20(12-14-21)10-9-16-5-2-1-3-6-16/h1-8,15H,9-14H2
    Key: NKMGWZZAFWDLFG-UHFFFAOYSA-N
  • CC[C@H]1C[C@@H]2C[C@@H]3[C@H]1N(C2)CCC4=C3NC5=CC(=C(C=C45)OC)OC
Properties
C21H28N2O2
Molar mass 340.467 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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]

A subsequent study confirmed these findings.[6]

See also

References
  1. Andrade MT, Lima JA, Pinto AC, Rezende CM, Carvalho MP, Epifanio RA (June 2005). "Indole alkaloids from Tabernaemontana australis (Muell. Arg) Miers that inhibit acetylcholinesterase enzyme". Bioorganic & Medicinal Chemistry. 13 (12): 4092–5. doi:10.1016/j.bmc.2005.03.045. PMID 15911323.
  2. Piotr Popik, Phil Skolnick (1998). Pharmacology of Ibogaine and Ibogaine-Related Alkaloids. {{cite book}}: |work= ignored (help)CS1 maint: location missing publisher (link)
  3. 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.
  4. 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. ISSN 0022-3263.
  5. Zetler G, Singbartl G, Schlosser L (1972). "Cerebral Phamacokinetics of Tremor-producing Harmala and Iboga Alkaloids". Pharmacology. 7 (4): 237–248. doi:10.1159/000136294. PMID 5077309.
  6. 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. PMID 7820611. S2CID 1940631.
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