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

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

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. 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. doi:10.1021/jo01094a622
    .
  4. ISSN 0022-3263
    .
  5. ^
    PMID 5077309
    .
  6. S2CID 1940631
    .
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