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19-Epivoacristine

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19-Epivoacristine
Names
IUPAC name Methyl (20R)-20-hydroxy-12-methoxyibogamine-18-carboxylate
Systematic IUPAC name Methyl (6S,6aS,7S,9R)-7--2-methoxy-7,8,9,10,12,13-hexahydro-5H-6,9-methanopyridoazepinoindole-6(6aH)-carboxylate
Other names 20-Epivoacangarine; 19-Epi-voacangarine
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C22H28N2O4/c1-12(25)16-8-13-10-22(21(26)28-3)19-15(6-7-24(11-13)20(16)22)17-9-14(27-2)4-5-18(17)23-19/h4-5,9,12-13,16,20,23,25H,6-8,10-11H2,1-3H3/t12-,13-,16-,20+,22-/m1/s1Key: OYMQKBZMKFJPMH-MDIKWQLESA-N
SMILES
  • C(1C2C3(1N(C2)CCC4=C3NC5=C4C=C(C=C5)OC)C(=O)OC)O
Properties
Chemical formula C22H28N2O4
Molar mass 384.476 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

19-Epivoacristine is an indole alkaloid found in different species of Tabernaemontana, such as Tabernaemontana dichotoma, as well as in Peschiera affinis. It is also known as 20-epivoacangarine and 19-epi-voacangarine.

Potential pharmacology

19-Epivoacristine may be a selective acetylcholinesterase (AChE) inhibitor in vitro.

Chemistry

19-Epivoacristine can be prepared by potassium borohydride reduction of voacryptine.

See also

References

  1. Lemos TL, Andrade CH, Guimarães AM, Wolter-Filho W, Braz-Filho RF (1996). "19-Epivoacristine, an Iboga Alkaloid Isolated from Peschiera affinis". Journal of the Brazilian Chemical Society. 7 (2): 123–126. doi:10.5935/0103-5053.19960018.
  2. "Tabernaemontana dichotoma Roxb.ex Wall". PhytoChemical Interactions DB (PCIDB).
  3. Vieira IJ, Medeiros WL, Monnerat CS, Souza JJ, Mathias L, Braz-Filho R, Pinto AC, Sousa PM, Rezende CM, Epifanio Rde A (September 2008). "Two fast screening methods (GC-MS and TLC-ChEI assay) for rapid evaluation of potential anticholinesterasic indole alkaloids in complex mixtures" (PDF). Anais da Academia Brasileira de Ciências. 80 (3): 419–26. doi:10.1590/s0001-37652008000300003. PMID 18797794.
  4. Manske RH (12 May 2014). The Alkaloids: Chemistry and Physiology. Elsevier. p. 83. ISBN 9781483221960.
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