19-Epivoacristine

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19-Epivoacristine
19-Epivoacristine.png
Names
Preferred IUPAC name
Methyl (6S,6aS,7S,9R)-7-[(1R)-1-hydroxyethyl]-2-methoxy-7,8,9,10,12,13-hexahydro-5H-6,9-methanopyrido[1′,2′:1,2]azepino[4,5-b]indole-6(6aH)-carboxylate
Other names
20-Epivoacangarine; 19-Epi-voacangarine
Identifiers
3D model (JSmol)
  • 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/s1
    Key: OYMQKBZMKFJPMH-MDIKWQLESA-N
  • C[C@H]([C@H]1C[C@@H]2C[C@@]3([C@H]1N(C2)CCC4=C3NC5=C4C=C(C=C5)OC)C(=O)OC)O
Properties
C22H28N2O4
Molar mass 384.476 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

19-Epivoacristine is an indole alkaloid found in different species of Tabernaemontana, such as Tabernaemontana dichotoma, as well as in Peschiera affinis.[1] It is also known as 20-epivoacangarine and 19-epi-voacangarine.[2]

Potential pharmacology[edit]

19-Epivoacristine may be a selective acetylcholinesterase (AChE) inhibitor in vitro.[3]

Chemistry[edit]

19-Epivoacristine can be prepared by potassium borohydride reduction of voacryptine.[4]

See also[edit]

References[edit]

  1. ^ Lemos TL, Andrade CH, Guimarães AM, Wolter-Filho W, Braz-Filho RF (1996). "19-Epivoacristine, an iboga alkaloid isolated from Peschiera affinis". 7 (2): 123–126. {{cite journal}}: Cite journal requires |journal= (help)
  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. p. 83. ISBN 9781483221960.