An alkaloid with diverse biological activities
Technical Support & Resources

Information provided in the product description is from published literature. Due to the nature of scientific experimentation, your results (e.g., selectivity and effective concentrations) or specific application for this product may differ. If you have questions about how this product fits your application, please contact our technical support staff.

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

Voacamine

Item No. 25204

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
12-methoxy-13-[(3α)-17-methoxy-17-oxovobasan-3-yl]-ibogamine-18-carboxylic acid, methyl ester
CAS Number
3371-85-5
Synonyms
  • NSC 82591
Molecular Formula
C43H52N4O5
Formula Weight
704.9
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 20 mg/mlEthanol: 5 mg/ml
λmax
226, 295 nm
SMILES
C/C=C1CN(C)[C@@]2([H])CC3=C(NC4=C3C=CC=C4)[C@](C5=CC(NC6=C7CC[N@@](C8)[C@]9([H])[C@@]6(C(OC)=O)C[C@@]8([H])C[C@@H]9CC)=C7C=C5OC)([H])C[C@]\1([H])[C@]2([H])C(OC)=O
InChi Code
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-/m1/s1
InChi Key
VCMIRXRRQJNZJT-KANKAIPDSA-N
Origin
Plant/Voacanga africana
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    1 mg

    $90

    Add

    5 mg

    $241

    Add

    10 mg

    $436

    Add
    Cayman Chemical
    Visit Our Cancer Resource Center
    Find Tools & Resources to Study the Hallmarks of Cancer
    • Cancer cell signaling & regulation
    • Cancer metabolism
    • Tumor microenvironment
    EXPLORE NOW
    Product Description

    Voacamine is an alkaloid originally isolated from Voacanga that has diverse biological activities.1 It is a cannabinoid receptor 1 (CB1) antagonist (IC50 = 41 nM).2 Voacamine (1-10 µg/ml) time- and dose-dependently decreases survival of U2OS and multi-drug resistant U2OS (U2OS/DX) osteosarcoma cells and induces autophagy but not apoptosis.3 It also has antimalarial activity, inhibiting growth of P. falciparum in vitro at the trophozoite and schizont stages and reducing parasitemia in mice infected with P. yoelii when administered at doses of 2.5, 5, and 10 mg/kg.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Quevauviller, A., Goutarel, R., and Janot, M.M. Pharmacology of the alkaloids of Voacanga species. Ann. Pharm. Fr. 13, 423-424 (1955).

    2. Kitajima, M., Iwai, M., Kikura-Hanajiri, R., et al. Discovery of indole alkaloids with cannabinoid CB1 receptor antagonistic activity. Bioorg. Med. Chem. Lett. 21(7), 1962-1964 (2011).

    3. Meschini, S., Condello, M., Calcabrini, A., et al. The plant alkaloid voacamine induces apoptosis-independent autophagic cell death on both sensitive and multidrug resistant human osteosarcoma cells. Autophagy 4(8), 1020-1033 (2008).

    4. Ramanitrahasimbola, D., Rasoanaivo, P., Ratsimamanga-Urverg, S., et al. Biological activities of the plant-derived bisindole voacamine with reference to malaria. Phytother. Res. 15(1), 30-33 (2001).