A natural indole alkaloid
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Voacangine

Item No. 24692

Product Insert (PDF)GC-MS (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
12-methoxy-ibogamine-18-carboxylic acid, methyl ester
CAS Number
510-22-5
Synonyms
  • 10-methoxy Coronaridine
Molecular Formula
C22H28N2O3
Formula Weight
368.5
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 16 mg/mlDMSO: 16 mg/mlDMSO:PBS(pH 7.2) (1:3): 0.33 mg/ml
λmax
226, 288 nm
SMILES
[H][C@]12[C@@H](CC)C[C@]3([H])C[C@@]1(C(OC)=O)C4=C(C(C=C(OC)C=C5)=C5N4)CC[N@]2C3
InChi Code
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
InChi Key
MMAYTCMMKJYIAM-PHKAQXKASA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    Voacangine is an indole alkaloid that has been found in T. citrifolia, V. africana, V. obtusa, and T. iboga with diverse biological activities.1,2 It inhibits the growth of M. tuberculosis, M. avium, and M. kansasii with MIC values of 50, >200, and 100 μg/mL, respectively.2 Voacangine (0.01-100 μM) dose-dependently reduces membrane currents in HEK293 cells expressing the hERG potassium channel and displaces the hERG ligand dofetilide (Item No. 15045) with a Ki value of 3.9 μM.3 Voacangine suppresses agonist-induced activation of transient receptor potential (TRP) channels with IC50 values of 50 and 9 μM for activation induced by the TRPV1 agonist capsaicin (Item No. 92350) and the TRPM8 agonist menthol, respectively.4 It also activates TRPA1 channels and stimulates calcium influx (IC50 = 8 μM in HEK293 cells expressing TRPA1), an effect that is blocked by the TRPA1 blocker HC-030031 (Item No. 11923). In vivo, voacangine (2 and 4 μg per egg) inhibits angiogenesis in chick embryo chorioallantoic membranes without apparent cytotoxicity.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bartlett, M.F., Dickel, D.F., and Taylor, W.I. The alkaloids of Tabernanthe iboga. Part IV. The structures of ibogamine, ibogaine, tabernanthine and voacangine. J. Am. Chem. Soc. 80(1), 126-136 (1958).

    2. Rastogi, N., Abaul, J., Goh, K.S., et al. Antimycobacterial activity of chemically defined natural substances from the Caribbean flora in Guadeloupe. FEMS Immunol. Med. Microbiol. 20(4), 267-273 (1998).

    3. Alper, K., Bai, R., Liu, N., et al. hERG Blockade by iboga alkaloids. Cardiovasc. Toxicol. 16(1), 14-22 (2016).

    4. Terada, Y., Horie, S., Takayama, H., et al. Activation and inhibition of thermosensitive TRP channels by voacangine, an alkaloid present in Voacanga africana, an African tree. J. Nat. Prod. 77(2), 285-297 (2014).

    5. Kim, Y., Jung, H.J., and Kwon, H.J. A natural small molecule voacangine inhibits angiogenesis both in vitro and in vivo. Biochem. Biophys. Res. Commun. 417(1), 330-334 (2012).