71266-78-9

Basic information

• Product Name: 8,8-diethyl-9,10-dimethoxy-5,8-dihydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline
• CAS NO: 71266-78-9
• Molecular Formula: C₂₄H₂₇NO₄
• Molecular Weight: 393.4755
• Mol File: 71266-78-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 570.5°C at 760 mmHg
• Flash Point: 164.1°C
• Density: 1.26g/cm³
• Vapor Pressure: 4.99E-13mmHg at 25°C
• Refractive Index: 1.635
• CAS DataBase Reference: 8,8-diethyl-9,10-dimethoxy-5,8-dihydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 8,8-diethyl-9,10-dimethoxy-5,8-dihydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline(71266-78-9)
• EPA Substance Registry System: 8,8-diethyl-9,10-dimethoxy-5,8-dihydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline(71266-78-9)

Safety Data

• Hazardous Substances Data: 71266-78-9(Hazardous Substances Data)

Upstream product

• 925-90-6 ethylmagnesium bromide 
• 549-21-3 oxyberberine 
• 2386-64-3 ethylmagnesium chloride 
• 316-41-6 berberine hemisulfate 

Relevant articles and documents

8,8-Dimethyldihydroberberine with improved bioavailability and oral efficacy on obese and diabetic mouse models

The clinical use of the natural alkaloid berberine (BBR) as an antidiabetic reagent is limited by its poor bioavailability. Our previous work demonstrated that dihydroberberine (dhBBR) has enhanced bioavailability and in vivo efficacy compared with berberine. Here we synthesized the 8,8-dimethyldihydroberberine (Di-Me) with improved stability, and bioavailability over dhBBR. Similar to BBR and dhBBR, Di-Me inhibited mitochondria respiration, increased AMP:ATP ratio, activated AMPK and stimulated glucose uptake in L6 myotubes. In diet-induced obese (DIO) mice, Di-Me counteracted the increased adiposity, tissue triglyceride accumulation and insulin resistance, and improved glucose tolerance at a dosage of 15 mg/kg. Administered to db/db mice with a dosage of 50 mg/kg, Di-Me effectively reduced random fed and fasting blood glucose, improved glucose tolerance, alleviated insulin resistance and reduced plasma triglycerides, with better efficacy than dhBBR at the same dosage. Our work highlights the importance of dihydroberberine analogs as potential therapeutic reagents for type 2 diabetes treatment.

NOVEL ISOQUINOLINE DERIVATIVES

A compound of formula (I) or a pharmaceutically acceptable salt thereof, wherein R1 to R7 have the significance given in claim 1, can be used in the form of a pharmaceutical composition.

Chemistry of 8-chloroberberine

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