21848-62-4

Basic information

• Product Name: [6aS,(+)]-5,6,6a,7-Tetrahydro-1,2,9,10-tetramethoxy-4H-dibenzo[de,g]quinoline
• Synonyms: (+)-N-Norglaucine;(6aS)-5,6,6a,7-Tetrahydro-1,2,9,10-tetramethoxy-4H-dibenzo[de,g]quinoline;[6aS,(+)]-5,6,6a,7-Tetrahydro-1,2,9,10-tetramethoxy-4H-dibenzo[de,g]quinoline;d-N-Norglaucine;Norglaucin;Norglaucine
• CAS NO: 21848-62-4
• Molecular Formula: C₂₀H₂₃NO₄
• Molecular Weight: 341.44
• Mol File: 21848-62-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 477.03°C (rough estimate)
• Flash Point: 208.5°C
• Appearance: /
• Density: 1.2064 (rough estimate)
• Vapor Pressure: 3.53E-10mmHg at 25°C
• Refractive Index: 1.5614 (estimate)
• PKA: 7.14±0.20(Predicted)
• CAS DataBase Reference: [6aS,(+)]-5,6,6a,7-Tetrahydro-1,2,9,10-tetramethoxy-4H-dibenzo[de,g]quinoline(CAS DataBase Reference)
• NIST Chemistry Reference: [6aS,(+)]-5,6,6a,7-Tetrahydro-1,2,9,10-tetramethoxy-4H-dibenzo[de,g]quinoline(21848-62-4)
• EPA Substance Registry System: [6aS,(+)]-5,6,6a,7-Tetrahydro-1,2,9,10-tetramethoxy-4H-dibenzo[de,g]quinoline(21848-62-4)

Safety Data

• Hazardous Substances Data: 21848-62-4(Hazardous Substances Data)

Usage

Safety Profile

Poison by intravenous andintraperitoneal routes. Moderately toxic by ingestion. When heated to decomposition it emits toxic fumes ofNOx.

InChI:InChI=1/C20H23NO4/c1-22-15-9-12-7-14-18-11(5-6-21-14)8-17(24-3)20(25-4)19(18)13(12)10-16(15)23-2/h8-10,14,21H,5-7H2,1-4H3/t14-/m0/s1

Upstream product

• 476-70-0 boldine 
• 475-81-0 glaucine 
• 371196-16-6 (6aS)-4,5,6a,7-tetrahydro-1,2,9,10-tetramethoxy-6H-dibenzo[de,g]quinoline-6-carbaldehyde 
• 5890-18-6 (+)-norboldine 
• 371196-15-5 N-formyl-laurolitsine 
• 186581-53-3 diazomethane 
• 72498-23-8 glaucine N-oxide 

Relevant articles and documents

Semisynthesis and myocardial activity of thaliporphine N-homologues

The N-homologues and optical isomers of thaliporphine (5a), a potent antiarrhythmic agent, were prepared starting from laurolitsine (1), an abundant aporphine present in Phoebe formosana. Treating N-propylnorglaucine with 90% H2SO4 yielded one additional product, an 11-sulfonyl-1,11-anhydroaporphine. Reaction of N-formylnorglaucine (3a) with 90% H2SO4, however, yielded the 9-sulfonyl-seco product as a major product. Treatment of 3a with 98% H2SO4 yielded pancordine (10), which, upon catalytic hydrogenation, yielded (±)-wilsonirine. 1H NMR spectroscopic analysis was applied successfully to monitor the optical purity of the crystalline salt while undertaking optical resolution. Thaliporphine (5a) was demonstrated to possess better positive inotropic and less negative chronotropic effects than the left-hand optical isomer and showed the best activity on rat cardiac tissue among the N-homologues prepared.

Uses of thaliporphine or its derivatives in treatment of cardiac diseases and preparation of same

The present invention discloses thaliporphine and its derivatives for the treatment and/or prophylaxis of cardiac diseases, including cardiac arrhythmia, myocardial ischemia or myocardial infarction, and sudden death caused by cardiac arrhythmia or acute myocardial infarction.