Voacamine

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 and Tabernaemontana divaricata. It is approved for use as an antimalarial drug in several African countries.^[1] Voacamine exhibits cannabinoid CB1 receptor antagonistic activity.^[2]

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 N
PubChem CID	11953931
DrugBank	DB04877 N
ChemSpider	30808559 N
UNII	2Z504YT5AG
ChEMBL	ChEMBL445022 N
CompTox Dashboard (EPA)	DTXSID20863159
ECHA InfoCard	100.020.139
Chemical and physical data
Formula	C43H52N4O5
Molar mass	704.912 g·mol−1
3D model (JSmol)	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 N Key:VCMIRXRRQJNZJT-XBBWQDJOSA-N N
NY (what is this?)  (verify)

Chemistry

Structure

There is considerable confusion about the absolute stereochemical configuration of voacamine and the originally published absolute structure had to be later revised.^[3][4] It has an ibogaine unit joined with vobasine unit.

Adverse Effect

Voacamine can cause hypertension in high dose.^[5]

See also

• Vincamine
• Voacangine
• Vobtusine