Voacamine

Voacamine

Identifiers
IUPAC name (6R,6aR,7R,11S)-methyl 7-ethyl-3-((2R,6S,8R,14S,E)-5-ethylidene-14-(methoxycarbonyl)-3-methyl-2,3,4,5,6,7,8,9-octahydro-1H-2,6-methanoazecino[5,4-b]indol-8-yl)-2-methoxy-6,6a,7,8,9,10,12,13-octahydro-5H-6,9-methanopyrido[1',2':1,2]azepino[4,5-b]indole-6-carboxylate
CAS Number	3371-85-5
PubChem (CID)	11953931
DrugBank	DB04877
ChemSpider	30808559
ChEMBL	CHEMBL445022
ECHA InfoCard	100.020.139
Chemical and physical data
Formula	C43H52N4O5
Molar mass	704.90 g/mol
3D model (Jmol)	Interactive image
SMILES CCC1CC2CC3(C1N(C2)CCC4=C3NC5=CC(=C(C=C45)OC)C6CC\7C(C(CC8=C6NC9=CC=CC=C89)N(C/C7=C/C)C)C(=O)OC)C(=O)OC
InChI InChI=1S/C43H52N4O5/c1-7-24-15-23-20-43(42(49)52-6)39-27(13-14-47(21-23)40(24)43)29-19-36(50-4)30(17-34(29)45-39)31-16-28-25(8-2)22-46(3)35(37(28)41(48)51-5)18-32-26-11-9-10-12-33(26)44-38(31)32/h8-12,17,19,23-24,28,31,35,37,40,44-45H,7,13-16,18,20-22H2,1-6H3/b25-8-/t23-,24+,28-,31+,35-,37-,40-,43-/m0/s1 Key:VCMIRXRRQJNZJT-XBBWQDJOSA-N
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Voacamine, also known under the older names voacanginine and vocamine, is a naturally occurring dimeric indole alkaloid of the secologanin type, found in a number of plants, including Voacanga africana.

Chemical structure

There is considerable confusion about the absolute stereochemical conformation of voacamine and the originally published absolute structure had to be later revised.^[1][2]

See also

• Voacanga africana
• Indole alkaloid

References

1. James P. Kutney; Richard T. Brown & Edward Piers (1966). "The absolute configuration of the iboga alkaloids". Can. J. Chem. 44 (5): 637–639. doi:10.1139/v66-087.
2. J. P. Kutney, Kaoru Fuji, Adi M. Treasurywala, Jose Fayos, Jon Clardy, A. Ian Scott, C. C. Wei (1973). "Structure and Absolute Configuration of (+)-Coronaridine Hydrobromide. A Comment on the Absolute Configuration of the Iboga Alkaloids". J. Am. Chem. Soc. 95 (16): 5407–5409. doi:10.1021/ja00797a049.