19-Epivoacristine

19-Epivoacristine
Names
	IUPAC name Methyl (20R)-20-hydroxy-12-methoxyibogamine-18-carboxylate
	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
	Other names 20-Epivoacangarine; 19-Epi-voacangarine
Identifiers
CAS Number	6883-77-8;
3D model (JSmol)	Interactive image;
PubChem CID	56842093;
CompTox Dashboard (EPA)	DTXSID70218938 ;
	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/s1 Key: OYMQKBZMKFJPMH-MDIKWQLESA-N;
	SMILES 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
Chemical formula	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). Infobox references

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]

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

^ 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.
^ "Tabernaemontana dichotoma Roxb.ex Wall". PhytoChemical Interactions DB (PCIDB).
^ 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.
^ Manske RH (12 May 2014). The Alkaloids: Chemistry and Physiology. Elsevier. p. 83. ISBN 9781483221960.

Names

IUPAC name Methyl (20R)-20-hydroxy-12-methoxyibogamine-18-carboxylate
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
Other names 20-Epivoacangarine; 19-Epi-voacangarine
Identifiers
CAS Number	6883-77-8
3D model (JSmol)	Interactive image
PubChem CID	56842093
CompTox Dashboard (EPA)	DTXSID70218938
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/s1 Key: OYMQKBZMKFJPMH-MDIKWQLESA-N
SMILES 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
Chemical formula	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). Infobox references