Voacamine Explained

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.^{[3] [4]} It has an ibogaine unit joined with vobasine unit.

Adverse Effect

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

See also

• Vincamine
• Vobtusine

Notes and References

1. Web site: Voacamine . DrugBank . Canadian Institutes of Health Research .
2. Kitajima M, Iwai M, Kikura-Hanajiri R, Goda Y, Iida M, Yabushita H, Takayama H . Discovery of indole alkaloids with cannabinoid CB1 receptor antagonistic activity . Bioorganic & Medicinal Chemistry Letters . 21 . 7 . 1962–4 . April 2011 . 21376588 . 10.1016/j.bmcl.2011.02.036 .
3. Kutney JP, Brown RT, Piers E . The absolute configuration of the Iboga alkaloids. . Canadian Journal of Chemistry . March 1966 . 44 . 5 . 637–9 . 10.1139/v66-087 .
4. Kutney JP, Fuji K, Treasurywala AM, Fayos J, Clardy J, Scott AI, Wei CC . Jon Clardy . 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 . 10.1021/ja00797a049 .
5. Web site: Leeuwenberg AJ . oacanga, (Apocynaceae), a review of its taxonomy, phytochemistry, ethnobotany and pharmacology. . Agric. Univ. Wagenigen . 85–3 . 1985 .