19-Epivoacristine

19-Epivoacristine
Identifiers
	IUPAC name methyl (1S,15R,17S,18S)-17-[(1R)-1-hydroxyethyl]-7-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4(9),5,7-tetraene-1-carboxylate;
CAS Number	6883-77-8;
PubChem CID	56842093;
Chemical and physical data
3D model (JSmol)	Interactive image;
	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;
	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;

19-Epivoacristine is a indole alkaloid found in different species of Tabernaemontana such as Tabernaemontana dichotoma as well as in Peschiera affinis.[1] Its also known as 20-Epivoacangarine and 19-epi-Voacangarine. [2]

Uses

Pharmacology

It appears to be selective AChE inhibitor.[3]

Chemistry

Synthesis

It's prepared from potassium borohydride reduction of voacryptine.[4]

References

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 requires |journal= (help)
"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 Ciencias. 80 (3): 419–26. doi:10.1590/s0001-37652008000300003. PMID 18797794.
Manske RH (12 May 2014). The Alkaloids: Chemistry and Physiology. p. 83. ISBN 9781483221960.

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[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 requires |journal= (help)

[2] "Tabernaemontana dichotoma Roxb.ex Wall". PhytoChemical Interactions DB (PCIDB).

[pmid18797794-3] 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 Ciencias. 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.