Ibogaline

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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).

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]

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. Vol. 52. San Diego. {{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. ^ a b 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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