Art. -Nr.: HY-W705415A

N-Methylcoclaurine

N-Methylcoclaurine is an orally active anticancer agent and PDI inhibitor with an IC₅₀ of 3.91 μM for the bovine-derived target. N-Methylcoclaurine selectively binds to κ opioid receptors with a K_i value of 0.9 μM. N-Methylcoclaurine inhibits tumor cell proliferation, migration, and invasion, and suppresses tumor growth in vivo. N-Methylcoclaurine inhibits iNOS expression and scavenges NO and DPPH radicals. N-Methylcoclaurine is a substrate of CyNMCH and an important branch intermediate in the biosynthesis of benzylisoquinoline alkaloids. N-Methylcoclaurine can be used in research related to hepatocellular carcinoma and neurological diseases.

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CAS. Nr.: 3423-07-2
Formel: C₁₈H₂₁NO₃
Molecular Weight:299.36

Speicherung:

Please store the product under the recommended conditions in the Certificate of Analysis.

Data Sheet (291 KB)

N-Methylcoclaurine Chemical Structure

CAS. Nr.: 3423-07-2

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Use of MCE Products

Strong Fluorescence Signal / Multi-Disciplinary Applications / High Fluorescence Specificity

Biologische Aktivität
- Beschreibung
- IC₅₀ & Target
- Cellular Effect
- In Vitro
- In Vivo
Chemical Information
Reinheit & Dokumentation
Verweise
Calculators
Help & FAQs
Classifications
Bioz

Biologische Aktivität

Beschreibung

IC₅₀ & Target

^[2]

human κ-opioid receptor (hKOR)

0.9 μM (Ki)

δ Opioid Receptor/DOR

20.1 μM (Ki)

human μ-opioid receptor

4.0 μM (Ki)

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Cellular Effect

Cell Line	Type	Value	Description	References
HepG2	CC₅₀	5.44 μM	Cytotoxicity against human HepG2 cells assessed as viability reduction after 24 hrs incubation with N-Methylcoclaurine by MTT assay. Cytotoxicity against human HepG2 cells assessed as viability reduction after 24 hrs incubation with N-Methylcoclaurine by MTT assay.	ijp.2025.464.474

In Vitro

Anti-cancerInnate ImmunityOxidative StressOthers

Anti-cancer

N-Methylcoclaurine (1-10 μM; 24-48 h) reduces HepG2 cell viability in the MTT assay with a CC₅₀ of 5.44 μM^[1].
N-Methylcoclaurine (1-10 μM; 24 h) reduces the number of HepG2 cells in crystal violet staining^[1].
N-Methylcoclaurine (1-10 μM; 24-48 h) inhibits HepG2 cell migration in the scratch assay^[1].
N-Methylcoclaurine (1-10 μM; 24 h) inhibits HepG2 cell invasion in the transwell assay^[1].

Innate Immunity

Oxidative Stress

N-methylcoclaurine (3.125-50 μM; 20 h) inhibits LPS (HY-D1056)-induced NO production in RAW 264.7 macrophages with an IC₅₀ of 6 μM, without reducing cell viability^[5].
N-methylcoclaurine (6.25-12.5 μM; 16 h) inhibits iNOS expression in LPS-induced RAW 264.7 macrophages^[5].

Oxidative Stress

N-methylcoclaurine (12.5-50 μM; 150 min) directly scavenges NO free radicals in SNP solution and shows moderate activity at high concentrations^[5].
N-methylcoclaurine (12.5-50 μM; 90 min in the dark) scavenges DPPH radicals with an IC₅₀ of 33.1 μM^[5].

Others

N-Methylcoclaurine (1-10 μM; 1 h) inhibits bovine PDI activity in an insulin turbidity assay with an IC₅₀ of 3.91 μM^[1].
N-Methylcoclaurine (1.7 nM-300 μM; 60-90 min) binds to κ opioid receptors expressed in HEK293 cell membranes with a K_i of 0.9 μM and shows weaker affinity for δ and μ opioid receptors, with K_i values of 20.1 and 4.0 μM, respectively^[2].
N-methylcoclaurine is an alkaloid among the TAs in lotus leaves, accounting for 275 mg/g (27.5%) as determined by HPLC^[5].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Cell Viability Assay^[1]

Cell Line:

HepG2 human hepatocellular carcinoma cells
Concentration:

1, 2, 3, 5 and 10 μM
Incubation Time:

24 and 48 h
Result:

Suppressed HepG2 proliferation, with survival rates of 79.46%, 60.32% and 17.06% for 1, 3 and 10 μM N-Methylcoclaurine, respectively.
CC₅₀ = 5.44 μM.

Cell Proliferation Assay^[1]

Cell Line:

HepG2 cells
Concentration:

1 and 10 μM
Incubation Time:

24 h
Result:

Reduced the cell number index to 0.76 and 0.22 at 1 and 10 μM, respectively.

Cell Migration Assay ^[1]

Cell Line:

HepG2 cells
Concentration:

1, 3, 5, 10 μM
Incubation Time:

24 and 48 h
Result:

Control migration rates were 65.15% at 24 h and 86.93% at 48 h.
N-Methylcoclaurine-exposed low-, medium- and high-dose groups had migration rates of 47.76%, 42.02% and 34.45% at 24 h, and 53.97%, 46.57% and 35.96% at 48 h, respectively, showing reduced migration versus control.

Cell Invasion Assay^[1]

Cell Line:

HepG2 cells
Concentration:

1, 5, 10 μM
Incubation Time:

24 h
Result:

Effectively inhibited HepG2 cell invasion at 1-10 μM in a concentration-dependent manner.

Western Blot Analysis^[5]

Cell Line:

RAW 264.7 murine macrophages
Concentration:

6.25 and 12.5 μM
Incubation Time:

16 h (with 1 μg/mL LPS)
Result:

The results illustrated that compound 5 significantly inhibited iNOS expression in a concentration-dependent manner.

In Vivo

Anti-cancer

N-Methylcoclaurine (10-40 mg/kg/day; intragastrically; daily; 2 weeks) suppresses H22 tumor growth in ICR mice dose-dependently, with tumor inhibition rates reaching 63.67% at 40 mg/kg/day^[1].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:

ICR (6 weeks old, 18-22 g)^[1]
Dosage:

10 mg/kg/day, 20 mg/kg/day, and 40 mg/kg/day
Administration:

intragastrically; daily; 2 weeks
Result:

Compared with the saline group, N-Methylcoclaurine dose-dependently inhibited H22 tumor growth, with tumor inhibition rates of 42.27%, 54.63%, and 63.67% at 10, 20, and 40 mg/kg/day, respectively.
H&E staining showed various degrees of cell loss and white vacuoles in tumors from N-Methylcoclaurine groups, and the remaining cell number index decreased in all N-Methylcoclaurine groups.

Related Protocols :

Chemical Information

CAS. Nr. 3423-07-2
Molecular Weight 299.36
Formel C₁₈H₂₁NO₃
SMILES

OC1=CC2=C(C=C1OC)CCN(C)[C@H]2CC3=CC=C(O)C=C3
Versand

Room temperature in continental US; may vary elsewhere.
Speicherung

Please store the product under the recommended conditions in the Certificate of Analysis.

Reinheit & Dokumentation

Select Batch:

Reinheit: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (291 KB)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

Verweise

[1]. Fu Y, et al. N-Methylcoclaurine Suppresses Hepatocellular Carcinoma by Inhibiting Protein Disulfide Isomerase in vitro and in vivo. International Journal of Pharmacology. 2025 Jan 1;21(3):464-74.

[2]. Kumarihamy M, et al. In vitro opioid receptor affinity and in vivo behavioral studies of Nelumbo nucifera flower. Journal of ethnopharmacology. 2015 Nov 4;174:57-65.

[3]. Liu X, et al. Functional characterization of (S)-N-methylcoclaurine 3'-hydroxylase (NMCH) involved in the biosynthesis of benzylisoquinoline alkaloids in Corydalis yanhusuo. Plant physiology and biochemistry : PPB. 2021 Nov;168:507-515. [Content Brief]

[4]. Loeffler S, et al. S-adenosyl-l-methionine:(S)-coclaurine-N-methyltransferase from Tinospora cordifolia[J]. Phytochemistry, 1995, 38(6): 1387-1395.

[5]. Lin HY, et al. Anti-inflammatory alkaloids from lotus (Nelumbo nucifera Gaertn.) leaves. European Food Research and Technology. 2023 Mar;249(3):739-48.

Calculators

Molaritätsrechner

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass Mass

Konzentration Konzentration

Volumen Volumen

Molecular Weight Molecular Weight

Verdünnungsrechner

Konzentration _{(Stammlösung)} × Volumen _{(Stammlösung)} = Konzentration _{(Ziellösung)} × Volumen _{(Ziellösung)}

Konzentration _{(Stammlösung)} Konzentration _{(Stammlösung)}

Volumen _{(Stammlösung)} Volumen _{(Stammlösung)}

Konzentration _{(Ziellösung)} Konzentration _{(Ziellösung)}

Volumen _{(Ziellösung)} Volumen _{(Ziellösung)}

Help & FAQs

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1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

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N-Methylcoclaurine

Alle Opioid Receptor Isoform-spezifische Produkte anzeigen