60716-41-8

Basic information

• Product Name: N-benzylberberine chloride
• Synonyms: N-benzylberberine chloride
• CAS NO: 60716-41-8
• Molecular Weight: 446.933
• Mol File: 60716-41-8.mol

Chemical Properties

• CAS DataBase Reference: N-benzylberberine chloride(CAS DataBase Reference)
• NIST Chemistry Reference: N-benzylberberine chloride(60716-41-8)
• EPA Substance Registry System: N-benzylberberine chloride(60716-41-8)

Safety Data

• Hazardous Substances Data: 60716-41-8(Hazardous Substances Data)

Upstream product

• 633-65-8 berberine chloride 
• 100-46-9 benzylamine 

Relevant articles and documents

Experimental and quantum-chemical study of nucleophilic substitution mechanism in berberine

Principal differences in the interaction mechanisms of alkaloid berberine with primary and secondary amines were investigated experimentally and by quantum-chemical calculations according to density functional theory (DFT/B3LYP) with 6-31G** basis set. The nucleophilic substitution of 9-metoxy group with primary amine was shown to proceed through a stage of σ-complex formation and led to 9-alkylamino derivatives of berberine. Analogous substitution with a secondary amine did not occur due to unfavorable thermodynamic parameters. The secondary amine participated in this reaction not as the attacking nucleophile, but rather as a bifunctional catalyst of berberine hydrolysis to berberrubine. The driving force for all these processes was the stabilization of products by hydrogen bonding. Based on the obtained results, we developed a new effective method for the preparation of berberrubine, one of the key intermediates in synthetic transformations of berberine. New 9-monoalkylamino derivatives of berberine containing indole moieties were synthesized.

Synthesis, biological evaluation of 9-N-substituted berberine derivatives as multi-functional agents of antioxidant, inhibitors of acetylcholinesterase, butyrylcholinesterase and amyloid-β aggregation

A series of 9-N-substituted berberine derivatives were synthesized and biologically evaluated as antioxidant and inhibitors of acetylcholinesterase (AChE), butyrylcholinesterase and amyloid-β aggregation. Most of these compounds exhibited very good antioxidant activities, inhibitive activities of AChE and amyloid-β aggregation. Among them, compound 8d, (o-methylphenethyl)amino linked at the 9-position of berberine, was found to be a good antioxidant (with 4.05 μM of Trolox equivalents), potent inhibitor of AChE (an IC50 value of 0.027 μM), and high active inhibitor of amyloid-β aggregation (an IC50 value of 2.73 μM).