Stereo structural formula of voacangine
Ball-and-stick model of the voacangine molecule
IUPAC name
12-Methoxyibogamine-18-carboxylic acid, methyl ester
Systematic IUPAC name
Methyl 17-ethyl-7-methoxy-3,13-diazapentacyclo[,10.04,9.013,18] nonadeca-2(10),4,6,8-tetraene-1-carboxylate[1]
Other names
Methyl 12-methoxyibogamine-18-carboxylate
3D model (JSmol)
ECHA InfoCard 100.214.137 Edit this at Wikidata
MeSH Voacangine
  • InChI=1S/C22H28N2O3/c1-4-14-9-13-11-22(21(25)27-3)19-16(7-8-24(12-13)20(14)22)17-10-15(26-2)5-6-18(17)23-19/h5-6,10,13-14,20,23H,4,7-9,11-12H2,1-3H3/t13-,14+,20+,22-/m1/s1 ☒N
  • O=C(OC)[C@@]43c2[nH]c1ccc(OC)cc1c2CCN5[C@H]3[C@H](C[C@H](C4)C5)CC
Molar mass 368.477 g·mol−1
Melting point 136 to 137 °C (277 to 279 °F; 409 to 410 K)
log P 3.748
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Voacangine (12-methoxyibogamine-18-carboxylic acid methyl ester) is an alkaloid found predominantly in the root bark of the Voacanga africana tree, as well as in other plants such as Tabernanthe iboga, Tabernaemontana africana, Trachelospermum jasminoides, Tabernaemontana divaricata and Ervatamia yunnanensis.[2][3][4][5] It is an iboga alkaloid which commonly serves as a precursor for the semi-synthesis of ibogaine.[6] It has been demonstrated in animals to have similar anti-addictive properties to ibogaine itself.[7] It also potentiates the effects of barbiturates.[8] Under UV-A and UV-B light its crystals fluoresce blue-green, and it is soluble in ethanol.



Voacangine exhibits AChE inhibitory activity.[9][10] Docking simulation reveals that it has inhibitory effect on VEGF2 kinase[11] and reduces angiogenesis.[12] Like ibogaine, its a potent HERG blocker in vitro.[13] It also acts as antagonist to TRPM8 and TRPV1 receptor but agonist of TRPA1.[14][15]


The absolute bioavailability of voacangine is around 11-13%.[13]

Side effects

High doses of voacangine produce convulsions and asphyxia.[16]

See also


  1. ^ "Compound Report Card CHEMBL182120 - Voacangine". ChEMBL.
  2. ^ Patel, M. B.; Miet, C.; Poisson, J. (1967). "Alkaloids of some African Tabernaemontana". Annales Pharmaceutiques Françaises. 25 (5): 379–384. PMID 5611538.
  3. ^ Fatima, T.; Ijaz, S.; Crank, G.; Wasti, S. (1987). "Indole Alkaloids from Trachelospermum jasminoides". Planta Medica. 53 (1): 57–59. doi:10.1055/s-2006-962620. PMID 17268963.
  4. ^ Liu, G.; Liu, X.; Feng, X. Z. (1988). "Ervayunine: A New Indole Alkaloid from Ervatamia yunnanensis". Planta Medica. 54 (6): 519–521. doi:10.1055/s-2006-962535. PMID 3212080.
  5. ^ Jenks, C. W. (2002). "Extraction Studies of Tabernanthe iboga and Voacanga africana". Natural Product Letters. 16 (1): 71–76. doi:10.1080/1057563029001/4881. PMID 11942686. S2CID 23390825.
  6. ^ US patent 2813873, "Derivatives of the Ibogaine Alkaloids", issued 1957-11-19 
  7. ^ Tsing Hua (January 28, 2006). "Antiaddictive Indole Alkaloids in Ervatamia yunnanensis and their Bioactivity". Academic Journal of Second Military Medical University.
  8. ^ http://medind.nic.in/iby/t08/i4/ibyt08i4p317.pdf[bare URL PDF]
  9. ^ VIEIRA I, MEDEIROS W, MONNERAT C, SOUZA J, MATHIAS L, BRAZ-FILHO R, PINTO A, SOUSA P, REZENDE C, EPIFANIO R (2008). "Two fast screening methods (GC-MS and TLC-ChEI assay) for rapid evaluation of potential anticholinesterasic indole alkaloids in complex mixtures" (PDF). Annals of the Brazilian Academy of Sciences. 80 (3): 419–426. doi:10.1590/s0001-37652008000300003. ISSN 0001-3765. PMID 18797794. Archived from the original (PDF) on 2020-02-19.
  10. ^ Andrade MT, Lima JA, Pinto AC, Rezende CM, Carvalho MP, Epifanio RA (June 2005). "Indole alkaloids from Tabernaemontana australis (Muell. Arg) Miers that inhibit acetylcholinesterase enzyme". Bioorganic & Medicinal Chemistry. 13 (12): 4092–5. doi:10.1016/j.bmc.2005.03.045. PMID 15911323.
  11. ^ Kim Y, Sugihara Y, Kim TY, Cho SM, Kim JY, Lee JY, Yoo JS, Song D, Han G, Rezeli M, Welinder C, Appelqvist R, Marko-Varga G, Kwon HJ (March 2020). "Identification and Validation of VEGFR2 Kinase as a Target of Voacangine by a Systematic Combination of DARTS and MSI". Biomolecules. 10 (4): 508. doi:10.3390/biom10040508. PMC 7226133. PMID 32230857.
  12. ^ Kim Y, Jung HJ, Kwon HJ (January 2012). "A natural small molecule voacangine inhibits angiogenesis both in vitro and in vivo". Biochemical and Biophysical Research Communications. 417 (1): 330–4. doi:10.1016/j.bbrc.2011.11.109. PMID 22155252.
  13. ^ a b Mair CE, de Miranda Silva C, Grienke U, Kratz JM, Carreño F, Zimmermann ES, de Araújo BV, Dalla Costa T, Rollinger JM (July 2016). "Pharmacokinetics of hERG Channel Blocking Voacangine in Wistar Rats Applying a Validated LC-ESI-MS/MS Method". Planta Medica. 82 (11–12): 1030–8. doi:10.1055/s-0042-107800. PMID 27257769.
  14. ^ Terada Y, Horie S, Takayama H, Uchida K, Tominaga M, Watanabe T (February 2014). "Activation and inhibition of thermosensitive TRP channels by voacangine, an alkaloid present in Voacanga africana, an African tree". Journal of Natural Products. 77 (2): 285–97. doi:10.1021/np400885u. PMID 24484240.
  15. ^ Lo MW, Matsumoto K, Iwai M, Tashima K, Kitajima M, Horie S, Takayama H (January 2011). "Inhibitory effect of Iboga-type indole alkaloids on capsaicin-induced contraction in isolated mouse rectum". Journal of Natural Medicines. 65 (1): 157–65. doi:10.1007/s11418-010-0478-6. PMID 21042867. S2CID 25706616.
  16. ^ "Erowid Voacanga africana Vault : Info #1".