An alkaloid with diverse biological activities
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Protopine (hydrochloride)

Item No. 23366

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4,6,7,14-tetrahydro-5-methyl-bis[1,3]benzodioxolo[4,5-c:5',6'-g]azecin-13(5H)-one, monohydrochloride
CAS Number
6164-47-2
Molecular Formula
C20H19NO5 • HCl
Formula Weight
389.8
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 0.1 mg/mlDMSO: 0.1 mg/ml
λmax
206 nm
SMILES
O=C1CC2=C(C(OCO3)=C3C=C2)CN(C)CCC4=CC5=C(OCO5)C=C41.Cl
InChi Code
InChI=1S/C20H19NO5.ClH/c1-21-5-4-13-7-18-19(25-10-24-18)8-14(13)16(22)6-12-2-3-17-20(15(12)9-21)26-11-23-17;/h2-3,7-8H,4-6,9-11H2,1H3;1H
InChi Key
NWNVDSJZGYDVQW-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $103

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    1 mg

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    Product Description

    Protopine is an alkaloid found in Berberidaceae, Ranunculaceae, Rutaceae, Fumariaceae, and Papaveraceae with diverse biological activities.1 It inhibits platelet aggregation induced by ADP, arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607), platelet-activating factor (PAF), and collagen in rabbit platelet-rich plasma at a concentration of 100 μM.2 Protopine inhibits contraction of isolated rat thoracic aorta induced by norepinephrine (Item No. 16673) and is a non-selective inhibitor of ICa, IK, IK1, and INa in guinea pig ventricular myocytes.3,4 Protopine inhibits the growth of H. pylori with an MIC50 value of 100 μg/ml.5 It reduces growth of PC3 and DU145 prostate cancer cells in a dose-dependent manner via induction of mitotic cell cycle arrest.6 Protopine (0.005 mg/kg) increases latency to first seizure in a mouse model induced by pentylenetetrazole (Item No. 18682).7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Üstünes, L., Laekeman, G.M., Gözler, B., et al. In vitro study of the anticholinergic and antihistaminic activities of protopine and some derivatives. J. Nat. Prod. 51(5), 1021-1022 (1988).

    2. Ko, F.N., Wu, T.S., Lu, S.T., et al. Antiplatelet effects of protopine isolated from Corydalis tubers. Thromb. Res. 56(2), 289-298 (1989).

    3. Ko, F.-N., Wu, T.-S., Lu, S.-T., et al. Ca2+-channel blockade in rat thoracic aorta by protopine isolated from Corydalis tubers. Jpn. J. Pharmacol. 58(1), 1-9 (1992).

    4. Song, L.-S., Ren, G.-J., Chen, Z.-L., et al. Electrophysiological effects of protopine in cardiac myocytes: Inhibition of multiple cation channel currents. Br. J. Pharmac. 129(5), 893-900 (2000).

    5. Mahady, G.B., Pendland, S.L., Stoia, A., et al. In vitro susceptibility of Helicobacter pylori to isoquinoline alkaloids from Sanguinaria canadensis and Hydrastis canadensis. Phytother. Res. 17(3), 217-221 (2003).

    6. Chen, C.-H., Liao, C.-H., Chang, Y.-L., et al. Protopine, a novel microtubule-stabilizing agent, causes mitotic arrest and apoptotic cell death in human hormone-refractory prostate cancer cell lines. Cancer Lett. 315(1), 1-11 (2012).

    7. Prokopenko, Y., Tsyvunin, V., Shtrygol, S., et al. In Vivo Anticonvulsant Activity of Extracts and Protopine from the Fumaria schleicheri Herb. Sci. Pharm. 84(3), 547-554 (2015).