An isoquinoline alkaloid with diverse biological activities
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Tetrahydroberberine

Item No. 33157

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5,8,13,13a-tetrahydro-9,10-dimethoxy-6H-benzo[g]-1,3-benzodioxolo[5,6-a]quinolizine
CAS Number
522-97-4
Synonyms
  • Canadine
  • NSC 36351
  • NSC 94918
  • (±)-Tetrahydroberberine
  • Xanthopuccine
Molecular Formula
C20H21NO4
Formula Weight
339.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 1 mg/mlDMSO: 1 mg/mlDMSO:PBS (pH 7.2) (1:3): 0.25 mg/ml
SMILES
COC1=C(CN2CCC3=CC4=C(C=C3C2C5)OCO4)C5=CC=C1OC
InChi Code
InChI=1S/C20H21NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4,8-9,16H,5-7,10-11H2,1-2H3
InChi Key
VZTUIEROBZXUFA-UHFFFAOYSA-N
Origin
Plant/Phellodendron chinense
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $37

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    5 mg

    $132

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    10 mg

    $194

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    25 mg

    $436

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    Product Description

    Tetrahydroberberine is an isoquinoline alkaloid that has been found in C. turtschaninovii and has diverse biological activities.1,2,3,4 It inhibits iron- and ascorbate-induced lipid peroxidation in rat liver microsomes (IC50 = 13.7 µM).1 Tetrahydroberberine binds to dopamine D2 receptors and the serotonin (5-HT) receptor subtype 5-HT1A (Kis = 0.83 and 4.2 µM, respectively).2 It inhibits potassium currents induced by acetylcholine (Item No. 23829) in primary rat hippocampal CA1 pyramidal neurons (IC50 = 13 µM).3 Tetrahydroberberine stimulates mouse C12C12 myoblast differentiation in a concentration-dependent manner.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ubeda, A., Montesinos, C., Payá, M., et al. Antioxidant action of benzylisoquinoline alkaloids. Free Radic. Res. Commun. 18(3), 167-175 (1993).

    2. Lee, T.H., Kim, K.H., Lee, S.O., et al. Tetrahydroberberine, an isoquinoline alkaloid isolated from corydalis tuber, enhances gastrointestinal motor function. J. Pharmacol. Exp. Ther. 338(3), 917-924 (2011).

    3. Wu, J., and Jin, G.Z. Tetrahydroberberine inhibits acetylcholine-induced K+ current in acutely dissociated rat hippocampal CA1 pyramidal neurons. Neurosci. Lett. 222(2), 115-118 (1997).

    4. Lee, H., Lee, S.-J., Bae, G.-U., et al. Canadine from Corydalis turtschaninovii stimulates myoblast differentiation and protects against myotube atrophy. Int. J. Mol. Sci. 18(12), 2748 (2017).