An alkaloid
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Nitidine (chloride)

Item No. 29223

Technical Information
Formal Name
2,3-dimethoxy-12-methyl-[1,3]benzodioxolo[5,6-c]phenanthridinium, monochloride
CAS Number
13063-04-2
Synonyms
  • NSC 146397
Molecular Formula
C21H18NO4 • Cl
Formula Weight
Purity
≥98%
A solid
DMF: 0.25 mg/mlDMSO: 0.5 mg/ml
λmax
221, 236, 271, 293, 329, 384 nm
SMILES
COC1=C(OC)C=C2C(C=[N+](C)C3=C(C=C(OCO4)C4=C5)C5=CC=C32)=C1.[Cl-]
InChi Code
InChI=1S/C21H18NO4.ClH/c1-22-10-13-7-17(23-2)18(24-3)8-15(13)14-5-4-12-6-19-20(26-11-25-19)9-16(12)21(14)22;/h4-10H,11H2,1-3H3;1H/q+1;/p-1
InChi Key
QLDAACVSUMUMOR-UHFFFAOYSA-M
Origin
Plant/Zanthoxylum nitidum
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Nitidine is an alkaloid originally isolated from Z. nitidium that has antimalarial, anti-inflammatory, and anticancer activities.1,2,3,4,5 It is active against the F32 chloroquine-sensitive and FcB1 and FcM2 chloroquine-resistant strains of P. falciparum (IC50s = 0.52, 0.8, and 0.49 µM, respectively) and reduces parasitemia in a mouse model of P. vinckei infection with an ED50 value of 18.9 mg/kg per day.1 It decreases LPS-induced increases in TNF-α, IL-1β, and IL-6 levels and p65 nuclear translocation in RAW 264.7 cells when used at a concentration of 5 µM.3 Nitidine (5 mg/kg) decreases serum levels of IL-10, TNF-α, and IL-6 and reduces mortality in a mouse model of LPS-induced endotoxemia.4 It inhibits proliferation of B16 melanoma, MCF-7 and Hs 578T breast, and DU145 and MPC3 prostate cancer cells with IC50 values ranging from 2.65 to 370 ng/ml.2 Nitidine (0.1-10 µM) induces apoptosis and decreases STAT3 phosphorylation in HSC-3 and HSC-4 oral cancer cells, as well as reduces tumor growth in an HSC-3 mouse xenograft model when administered at a dose of 10 mg/kg per day for 24 days.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bouquet, J., Rivaud, M., Chevalley, S., et alBiological activities of nitidine, a potential anti-malarial lead compound. Malar. J. 11, 67 (2012).

    2. Del Poeta, M., Chen, S.-F., Von Hoff, D., et alComparison of in vitro activities of camptothecin and nitidine derivatives against fungal and cancer cells. Antimicrob. Agents Chemother. 43(12), 2862-2868 (1999).

    3. Wang, Z., Jiang, W., Zhang, Z., et alNitidine chloride inhibits LPS-induced inflammatory cytokines production via MAPK and NF-kappaB pathway in RAW 264.7 cells. J. Ethnopharmacol. 144(1), 145-150 (2012).

    4. Yang, N., Yue, R., Ma, J., et alNitidine chloride exerts anti-inflammatory action by targeting Topoisomerase I and enhancing IL-10 production. Pharmacol. Res. 148, 104368 (2019).

    5. Kim, L.-H., Khadka, S., Shin, J.-A., et alNitidine chloride acts as an apoptosis inducer in human oral cancer cells and a nude mouse xenograft model via inhibition of STAT3. Oncotarget 8(53), 91306-91315 (2017).