An isoquinoline alkaloid and metabolite of L-THP with diverse biological activities
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(−)-Isocorypalmine

Item No. 29886

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(13aS)-5,8,13,13a-tetrahydro-3,9,10-trimethoxy-6H-dibenzo[a,g]quinolizin-2-ol
CAS Number
483-34-1
Synonyms
  • L-Isocorypalmine
  • Isocorypalmine
Molecular Formula
C20H23NO4
Formula Weight
341.4
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Methanol: Soluble
SMILES
COC1=CC=C2C(CN(CCC3=C4C=C(O)C(OC)=C3)[C@@]4([H])C2)=C1OC
InChi Code
InChI=1S/C20H23NO4/c1-23-18-5-4-12-8-16-14-10-17(22)19(24-2)9-13(14)6-7-21(16)11-15(12)20(18)25-3/h4-5,9-10,16,22H,6-8,11H2,1-3H3/t16-/m0/s1
InChi Key
KDFKJOFJHSVROC-INIZCTEOSA-N
Origin
Plant/Mahoniae Caulis
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $107

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    5 mg

    $396

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    Product Description

    (–)-Isocorypalmine is an isoquinoline alkaloid and a metabolite of L-tetrahydropalmitine (L-THP; Item No. 20535) that has been found in Corydalis and has diverse biological activities.1,2,3,4,5 It binds to human dopamine D1-5 receptors with Ki values of 6.2, 41.8, 37.3, 77.4, and 9.5 nM, respectively.2 (–)-Isocorypalmine inhibits Epstein-Barr virus-early antigen (EBV-EA) activation induced by phorbol 12-myristate 13-acetate (TPA; Item No. 10008014) in Raji cells (IC50 = 300 mol ratio/32 pmol TPA), which is predictive for anti-tumor activity.3 It is cytotoxic to A549, SKOV3, SK-MEL-2, and HCT15 cancer cells (IC50s = 67.32, 47.37, 47.66, and 67.32 μM, respectively).4 (–)-Isocorypalmine is active against clinical strains of C. albicans, C. glabratas, C. krusei, C. parapsilosis, and C. neoformans (MICs = 40-320 μg/ml).5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Xiao, W., Zhuang, X., Shen, G., et al. Simultaneous quantification of ?-tetrahydropalmatine and its urine metabolites by ultra high performance liquid chromatography with tandem mass spectrometry. J. Sep. Sci. 37(6), 696-703 (2014).

    2. Lee, D.Y.W., Liu, J., Zhang, S., et al. Asymmetric total synthesis of tetrahydroprotoberberine derivatives and evaluation of their binding affinities at dopamine receptors. Bioorg. Med. Chem. Lett. 27(6), 1437-1440 (2017).

    3. Ito, C., Itoigawa, M., Tokuda, H., et al. Chemopreventive activity of isoquinoline alkaloids from Corydalis plants. Planta Med. 67(5), 473-475 (2001).

    4. Kim, K.H., Piao, C., J., Choi, S.U., et al. New cytotoxic tetrahydroprotoberberine-aporphine dimeric and aporphine alkaloids from Corydalis turtschaninovii. Planta Med. 76(15), 1732-1738 (2010).

    5. Rao, G.-X., Zhang, S., Wang, H.-M., et al. Antifungal alkaloids from the fresh rattan stem of Fibraurea recisa Pierre. J. Ethnopharmacol. 123(1), 1-5 (2009).