An isoquinoline alkaloid with diverse biological properties
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Active Metabolite(s)
344728-Oxycoptisine
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Coptisine (chloride)

Item No. 28424

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
6,7-dihydro-bis[1,3]benzodioxolo[5,6-a:4′,5′-g]quinolizinium, monochloride
CAS Number
6020-18-4
Molecular Formula
C19H14NO4 • Cl
Formula Weight
355.8
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
PBS (pH 7.2): insolube
λmax
229, 241, 266, 360, 462 nm
SMILES
C1(OCO2)=C2C=C(CC[N+]3=CC4=C(OCO5)C5=CC=C4C=C36)C6=C1.[Cl-]
InChi Code
InChI=1S/C19H14NO4.ClH/c1-2-16-19(24-10-21-16)14-8-20-4-3-12-6-17-18(23-9-22-17)7-13(12)15(20)5-11(1)14;/h1-2,5-8H,3-4,9-10H2;1H/q+1;/p-1
InChi Key
LUXPUVKJHVUJAV-UHFFFAOYSA-M
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 mg

    $134

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    25 mg

    $316

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    50 mg

    $598

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    100 mg

    $1,058

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    Cayman Chemical
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    OBESITY RESEARCH SOLUTIONS
    Product Description

    Coptisine is an isoquinoline alkaloid that has been found in Coptis chinensis and has diverse biological activities, including antioxidant, enzyme inhibitory, antiproliferative, and anti‑hypercholesterolemic properties.1,2,3,4,5 It inhibits the production of reactive oxygen species (ROS) in isolated kidney mitochondria in a 2,7-dichlorodihydrofluorescein diacetate (DCFH-DA; Item No. 85155) assay (IC50 = 48.93 μM).1 Coptisine inhibits acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) but not β-secretase 1 (BACE1) in cell-free enzyme assays (IC50s = 0.8, 5.81, and >100 μM, respectively). It also inhibits indoleamine 2,3-dioxygenase (IDO) in vitro (IC50 = 6.3 μM), as well as organic cation transporter 1 (OCT1), OCT2, and OCT3 in MDCK cells (IC50s = 0.931, 2.27, and 2.27 μM, respectively, for the human transporters).2,3 It inhibits proliferation of A549, H460, and H2170 human lung cancer cells with IC50 values of 18.09, 29.5, and 21.6 μM, respectively.4 Coptisine (70.05 mg/kg) decreases total serum cholesterol, triglyceride, and LDL-cholesterol levels and increases serum HDL-cholesterol levels in Syrian golden hamsters fed a high-fat and high-cholesterol diet.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Jung, H.A., Min, B.S., Yokozawa, T., et al. Anti-Alzheimer and antioxidant activities of Coptidis Rhizoma alkaloids. Biol. Pharm. Bull. 32(8), 1433-1438 (2009).

    2. Yu, D., Tao, B.-B., Yang, Y.-Y., et al. The IDO inhibitor coptisine ameliorates cognitive impairment in a mouse model of Alzheimer’s disease. J. Alzheimers Dis. 43(1), 291-302 (2015).

    3. Li, L., Sun, S., Weng, Y., et al. Interaction of six protoberberine alkaloids with human organic cation transporters 1, 2 and 3. Xenobiotica 46(2), 175-183 (2016).

    4. Rao, P.C., Begum, S., Sahai, M., et al. Coptisine-induced cell cycle arrest at G2/M phase and ractive oxygen species-dependent mitochondria-mediated apoptosis in non-small-cell lung cancer A549 cells. Tumour Biol. 39(3), 1-13 (2017).

    5. He, K., Ye, X., Wu, H., et al. The safety and anti-hypercholesterolemic effect of coptisine in syrian golden hamsters. Lipids 50(2), 185-194 (2015).