Voacamine

Voacamine
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
ChEMBL
ECHA InfoCard 100.020.139 Edit this at Wikidata
Chemical and physical data
Formula C43H52N4O5
Molar mass 704.91 g·mol−1
3D model (JSmol)
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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.

It is approved for use as an antimalarial drug in several African countries.[1]

Voacamine exhibits cannabinoid CB1 receptor antagonistic activity.[2]

Chemical 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]

References

  1. ↑ "Voacamine". DrugBank. Canadian Institutes of Health Research.
  2. ↑ Kitajima, Mariko; Iwai, Masumi; Kikura-Hanajiri, Ruri; Goda, Yukihiro; Iida, Mitsuru; Yabushita, Hisatoshi; Takayama, Hiromitsu (2011-04-01). "Discovery of indole alkaloids with cannabinoid CB1 receptor antagonistic activity". Bioorganic & Medicinal Chemistry Letters. 21 (7): 1962–1964. doi:10.1016/j.bmcl.2011.02.036. ISSN 0960-894X.
  3. ↑ 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.
  4. ↑ 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.
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