An alkaloid with diverse biological activities
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N-Methylcytisine

Item No. 34752

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1R,5S)-1,2,3,4,5,6-hexahydro-3-methyl-1,5-methano-8H-pyrido[1,2-a][1,5]diazocin-8-one
CAS Number
486-86-2
Synonyms
  • Caulophylline
  • N-Me-cy
Molecular Formula
C12H16N2O
Formula Weight
204.3
Purity
≥95%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 15 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
234, 311 nm
SMILES
CN1C[C@H]2C[C@H](CN3C2=CC=CC3=O)C1
InChi Code
InChI=1S/C12H16N2O/c1-13-6-9-5-10(8-13)11-3-2-4-12(15)14(11)7-9/h2-4,9-10H,5-8H2,1H3/t9-,10+/m0/s1
InChi Key
CULUKMPMGVXCEI-VHSXEESVSA-N
Origin
Plant/Sophora flavescens
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    N-Methylcytisine is an alkaloid that has been found in L. albus and has diverse biological activities.1,2,3,4,5 It is an agonist of nicotinic acetylcholine receptors (nAChRs) and selectively binds to nAChRs over muscarinic acetylcholine receptors (mAChRs; IC50s = 0.05 and 417 µM, respectively).1,2 It elicits whole-cell currents in Xenopus oocytes expressing α4β2, α4β4, and α7 subunit-containing nAChRs (EC50s = 13, 13, and 340 µM, respectively, for the human receptors).2 N-Methylcytisine is nematocidal against B. xylophilus.3 It inhibits LPS-induced production of nitric oxide (NO) in RAW 264.7 macrophages (IC50 = 33.3 µM) and proliferation of SMMC-7721 cells when used at a concentration of 4 mg/ml.4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Schmeller, T., Sauerwein, M., Sporer, F., et al. Binding of quinolizidine alkaloids to nicotinic and muscarinic acetylcholine receptors. J. Nat. Prod. 57(9), 1316-1319 (1994).

    2. Slater, Y.E., Houlihan, L.M., Maskell, P.D., et al. Halogenated cytisine derivatives as agonists at human neuronal nicotinic acetylcholine receptor subtypes. Neuropharmacology 44(4), 503-515 (2003).

    3. Matsuda, K., Yamada, K., Kimura, M., et al. Nematicidal activity of matrine and its derivatives against pine wood nematodes. J. Agric. Food Chem. 39(1), 189-191 (1991).

    4. Li, J.-C., Dai, W.-F., Liu, D., et al. Quinolizidine alkaloids from Sophora alopecuroides with anti-inflammatory and anti-tumor properties. Bioorg. Chem. 110, 104781 (2021).

    5. Gao, L., Wang, K.-x., Zhou, Y.-z., et al. Uncovering the anticancer mechanism of Compound Kushen Injection against HCC by integrating quantitative analysis, network analysis and experimental validation. Sci. Rep. 8(1), 624 (2018).