A benzylisoquinoline alkaloid with nAChR inhibitory and insecticidal activities
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Coclaurine

Item No. 35716

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1S)-1,2,3,4-tetrahydro-1-[(4-hydroxyphenyl)methyl]-6-methoxy-7-isoquinolinol
CAS Number
486-39-5
Synonyms
  • (S)-Coclaurine
  • (–)-Coclaurine
Molecular Formula
C17H19NO3
Formula Weight
285.3
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Acetone: solubleChloroform: solubleDichloromethane: solubleDMSO: soluble
λmax
227 nm
SMILES
COC(C=C(CCN1)C([C@@H]1CC2=CC=C(C=C2)O)=C3)=C3O
InChi Code
InChI=1S/C17H19NO3/c1-21-17-9-12-6-7-18-15(14(12)10-16(17)20)8-11-2-4-13(19)5-3-11/h2-5,9-10,15,18-20H,6-8H2,1H3/t15-/m0/s1
InChi Key
LVVKXRQZSRUVPY-HNNXBMFYSA-N
Origin
Plant/Lindera aggregata (Sims) Kosterm.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Coclaurine is a benzylisoquinoline alkaloid that has been found in T. quinquenervia and has nicotinic acetylcholine receptor (nAChR) inhibitory and insecticidal activities.1,2 It inhibits ACh-induced currents in Xenopus oocytes expressing human α4β2 or α4β4 subunit-containing nAChRs (IC50s = 49 and 18 µM, respectively).1 Coclaurine induces mortality in D. melanogaster and C. pomonella larvae (LD50s = 78.2 and 35.4 µg/ml, respectively).2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Exley, R., Iturriaga-Vásquez, P., Lukas, R.J., et al. Evaluation of benzyltetrahydroisoquinolines as ligands for neuronal nicotinic acetylcholine receptors. Br. J. Pharmacol. 146(1), 15-24 (2005).

    2. Quiroz-Carreño, S., Pastene-Navarrete, E., Espinoza-Pinochet, C., et al. Assessment of insecticidal activity of benzylisoquinoline alkaloids from Chilean Rhamnaceae plants against fruit-fly Drosophila melanogaster and the lepidopteran crop pest Cydia pomonella. Molecules 25(21), 5094 (2020).