Article · Wikipedia archive · Last revised Jul 23, 2026

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. Voacamine exhibits cannabinoid CB1 receptor antagonistic activity.

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Jul 23, 2026
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Voacamine
Identifiers
  • (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
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.020.139
Chemical and physical data
FormulaC43H52N4O5
Molar mass704.912 g·mol−1
3D model (JSmol)
  • 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=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
 ☒NcheckY (what is this?)  (verify)

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

Chemistry

Structure

There is considerable confusion about the absolute stereochemical configuration of voacamine and the originally published absolute structure had to be later revised.34 It has an ibogaine unit joined with vobasine unit.

Adverse Effect

Voacamine can cause hypertension in high dose.5

See also

See also

References

References

  1. "Voacamine". DrugBank. Canadian Institutes of Health Research.
  2. Kitajima M, Iwai M, Kikura-Hanajiri R, Goda Y, Iida M, Yabushita H, Takayama H (April 2011). "Discovery of indole alkaloids with cannabinoid CB1 receptor antagonistic activity". Bioorganic & Medicinal Chemistry Letters. 21 (7): 1962–4. doi:10.1016/j.bmcl.2011.02.036. PMID 21376588.
  3. Kutney JP, Brown RT, Piers E (March 1966). "The absolute configuration of the Iboga alkaloids". Canadian Journal of Chemistry. 44 (5): 637–9. doi:10.1139/v66-087.
  4. Kutney JP, Fuji K, Treasurywala AM, Fayos J, Clardy J, Scott AI, Wei CC (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.
  5. Leeuwenberg AJ (1985). "oacanga, (Apocynaceae), a review of its taxonomy, phytochemistry, ethnobotany and pharmacology". Agric. Univ. Wagenigen. pp. 85–3.