54260-72-9

Basic information

• Product Name: 5,6-Dihydro-2,3-(methylenedioxy)-9,10-dimethoxy-13-methyldibenzo[a,g]quinolizinium
• Synonyms: 13-Methylberberine;2,3-(Methylenedioxy)-9,10-dimethoxy-13-methyl-5H,6H-dibenzo[a,g]quinolizin-7-ium;5,6-Dihydro-2,3-(methylenedioxy)-9,10-dimethoxy-13-methyldibenzo[a,g]quinolizinium;9,10-Dimethoxy-13-methyl-5,6-dihydrobenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium;13-Methylberberine (chloride)
• CAS NO: 54260-72-9
• Molecular Formula: C₂₁H₂₀NO₄*Cl
• Molecular Weight: 385.8408
• Mol File: 54260-72-9.mol
• Article Data: 9

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• CAS DataBase Reference: 5,6-Dihydro-2,3-(methylenedioxy)-9,10-dimethoxy-13-methyldibenzo[a,g]quinolizinium(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-Dihydro-2,3-(methylenedioxy)-9,10-dimethoxy-13-methyldibenzo[a,g]quinolizinium(54260-72-9)
• EPA Substance Registry System: 5,6-Dihydro-2,3-(methylenedioxy)-9,10-dimethoxy-13-methyldibenzo[a,g]quinolizinium(54260-72-9)

Safety Data

• Hazardous Substances Data: 54260-72-9(Hazardous Substances Data)

Usage

Description

13-Methylberberine (13-MB) (chloride) is a 13-methyl-substituted derivative of berberine . Berberine is a widely distributed berberidaceaen alkaloid found in plant tissues that has antibacterial, anti-inflammatory, antitumor, anti-obesity, and hypercholesterolemic activity. 13-MB has improved antibacterial activity against S. aureus (MIC = 125 μg/ml) and improved antitumor activity with a mean GI50 value of 11.7 μM, as compared to berberine. 13-MB also induces down-regulation of adipocyte differentiation transcription factors, reduces de novo lipid synthesis, and accumulates in murine 3T3-L1 adipocytes at higher levels than berberine, suggesting improved anti-obesity activity.

Uses

13-Methylberberinium Chloride can be used to treat and prevent immunoinflammatory dermal disorders. It can also be used in synthesis to result in derivatives that can be used to treat nerve diseases and anti-infective agents.

InChI:InChI=1/C21H20NO4.ClH/c1-12-14-4-5-17(23-2)21(24-3)16(14)10-22-7-6-13-8-18-19(26-11-25-18)9-15(13)20(12)22;/h4-5,8-10H,6-7,11H2,1-3H3;1H/q+1;/p-1

Upstream product

• 50-00-0 formaldehyd 
• 633-65-8 berberine chloride 
• 80665-65-2 9,10-dimethoxy-2,3-methylenedioxy-8,14-cycloberbin-13-one 
• 100986-33-2 9,10-dimethoxy-13-methylene-2,3-methylenedioxy-8,14-cycloberbine 
• 38699-81-9 9,10-dimethoxy-13ξ-methyl-5,6,8,13-tetrahydro-8r,13ac-propano-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-16-one 
• 483-15-8 7,8-dihydroberberine 
• 78-98-8 2-oxopropanal 

Relevant articles and documents

Synthesis method of 13-methyl berberine alkaloid

The invention belongs to the field of organic synthesis, and particularly relates to a synthesis method of 13-methyl berberine alkaloid. The method comprises the following steps: reaction a: taking arylethylamine and aryl formaldehyde as main starting raw materials, and reacting in the presence of other auxiliary materials to obtain secondary amine hydrochloride; and reaction b: taking secondary amine hydrochloride and pyruvic aldehyde as main raw materials, and reacting in the presence of other auxiliary materials to obtain the 13-methyl berberine alkaloid. According to the invention, aryl ethylamine and aryl formaldehyde are used as raw materials to synthesize secondary amine hydrochloride, and then the secondary amine hydrochloride and pyruvic aldehyde are subjected to Pickering-Schengger reaction/Friedel-Crafts hydroxyalkylation reaction/dehydration reaction/oxidation reaction in an anhydrous formic acid solution under the assistance of a dewatering agent and an oxidizing agent, so that the 13-methylberberine alkaloid is prepared at the yield of more than 80%, and the synthesis steps are simplified and easy to operate; and various expensive metal catalysts and excessive acid catalysis are not needed, the productivity is high, and the cost is low.

Berberine compounds and the use of a preparation method

The invention provides application of a compound with the structure as shown in the formula (I) in the specification, or a medical salt, a hydrate or a solvate, of the compound, in preparation of a medicine for treating nervous system diseases relevant to the dopamine receptor, and a preparation method of the compound with the structure as shown in the formula (I) in the specification or the medical salt, the hydrate or the solvate, of the compound. The compound has multiple pharmacologic functions such as mu-opioid receptor excitation and dopamine D2 receptor blocking, and has good physicochemical properties and oral bioavailability, and integral animal experiment shows that the compound has remarkable and long-lasting analgesia and calm activity and can be applied to treatment on pain and other mental diseases.

Berberine analogues as a novel class of the low-density-lipoprotein receptor up-regulators: Synthesis, structure-activity relationships, and cholesterol-lowering efficacy

Twenty-nine derivatives of berberine (1) or pseudoberberine (2) were designed, semisynthesized, and evaluated for their up-regulatory activity on the low-density-lipoprotein receptor (LDLR) expression. SAR analysis revealed that (i) the methylenedioxy group at the 2- and 3-position is an essential element to keep the activity, (ii) the 7-position quaternary ammonium and planar structure of the compound are activity-required, and (iii) addition of electron-donating groups at the 7- or 13-position reduced the activity. Of the compound 1 analogues, compound 2 exhibited an increased activity on LDLR expression compared to 1.Inthe hyperlipidemic rats, compound 2 (100 (mg/kg)/day) reduced blood CHO and LDL-c by 42.6% and 49.4%, respectively, more efficient than 1 did (p 50 of 2 in mice was over 5000 mg/kg (oral). We consider compound 2 a promising cholesterol- lowering drug candidate.