From Wikipedia, the free encyclopedia
19-Epivoacristine
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Names
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IUPAC name
Methyl (20R)-20-hydroxy-12-methoxyibogamine-18-carboxylate
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Systematic 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
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Other names
20-Epivoacangarine; 19-Epi-voacangarine
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Identifiers
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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
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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
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Properties
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C22H28N2O4
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Molar mass
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384.476 g·mol−1
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Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
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
19-Epivoacristine may be a selective
acetylcholinesterase (AChE)
inhibitor
in vitro.
[3]
Chemistry
19-Epivoacristine can be prepared by
potassium borohydride reduction of
voacryptine.
[4]
See also
References
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^ 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.
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^
"Tabernaemontana dichotoma Roxb.ex Wall". PhytoChemical Interactions DB (PCIDB).
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^ 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.
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^ Manske RH (12 May 2014).
The Alkaloids: Chemistry and Physiology. Elsevier. p. 83.
ISBN
9781483221960.