5083-88-5

Basic information

• Product Name: thaliporphine
• Synonyms: thaliporphine;(6aS)-5,6,6a,7-Tetrahydro-2,9,10-trimethoxy-6-methyl-4H-dibenzo[de,g]quinolin-1-ol;Thalicmidine
• CAS NO: 5083-88-5
• Molecular Formula: C₂₀H₂₃NO₄
• Molecular Weight: 341.4
• Mol File: 5083-88-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 505.7°C at 760 mmHg
• Flash Point: 259.7°C
• Appearance: /
• Density: 1.222g/cm³
• Vapor Pressure: 7.51E-11mmHg at 25°C
• Refractive Index: 1.603
• PKA: 9.58±0.20(Predicted)
• CAS DataBase Reference: thaliporphine(CAS DataBase Reference)
• NIST Chemistry Reference: thaliporphine(5083-88-5)
• EPA Substance Registry System: thaliporphine(5083-88-5)

Safety Data

• Hazardous Substances Data: 5083-88-5(Hazardous Substances Data)

Usage

General Description

Thaliporphine is a natural alkaloid compound that is isolated from a variety of plants, including some species of the family Papaveraceae. It has been identified as a potent antioxidant and has demonstrated potential anti-inflammatory and analgesic properties in experimental studies. Thaliporphine has also shown promise in inhibiting the growth of cancer cells and could potentially be developed into a novel anti-cancer agent. Additionally, it has been found to possess vasorelaxant effects, which could make it useful in the treatment of cardiovascular diseases. Overall, thaliporphine is a versatile chemical with a wide range of potential therapeutic applications.

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

Upstream product

• 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 
• 35587-63-4 O-acetylthaliporphine 

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.

LIPASE-CATALYZED RESOLUTION OF ACETATES OF RACEMIC PHENOLIC APORPHINES AND HOMOAPORPHINES IN ORGANIC SOLVENT

Enzymatic resolution of (+/-)-1-acetoxy-2,9,10-trimethoxyaporphine (O-acetylthaliporphine) (3), (+/-)-2-acetoxy-1,9,10-trimethoxyaporphine (O-acetylpredicentrine) (4), and (+/-)-3-acetoxy-2,9,10-trimethoxyaporphines (5) by use of immobilized lipase in organic solvent gave resolved 3-5 and the corresponding hydroxyaporphines (9-11) in fair to good chemical and optical yields.Analogous reaction of (+/-)-1-acetoxy-2,10,11-trimethoxyhomoaporphine (6) did not take place, whereas that of (+/-)-2-acetoxy-1,10,11-trimethoxy- and (+/-)-3-acetoxy-1,10,11-trimethoxyhomoaporhines (7 and 8) produced optical active 7, 8 and hydroxyhomoaporphines (13,14).