39945-43-2

Basic information

• Product Name: (±)-wilsonirine
• Synonyms: (±)-wilsonirine
• CAS NO: 39945-43-2
• Molecular Weight: 327.38
• Mol File: 39945-43-2.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (±)-wilsonirine(CAS DataBase Reference)
• NIST Chemistry Reference: (±)-wilsonirine(39945-43-2)
• EPA Substance Registry System: (±)-wilsonirine(39945-43-2)

Safety Data

• Hazardous Substances Data: 39945-43-2(Hazardous Substances Data)

Upstream product

• 39945-40-9 (+/-)-norglaucine 
• 50722-33-3 6-formyl-1,2,9,10-tetramethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline 
• 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 
• 128957-80-2 Acetic acid 1-(3,4-dimethoxy-benzyl)-6-methoxy-7-oxo-2-(2,2,2-trifluoro-acetyl)-1,2,3,4,6,7-hexahydro-isoquinolin-6-yl ester 
• 61659-86-7 (+/-)-N-trifluoroacetylnorcodamine 
• 85011-55-8 pancorynine 
• 39945-37-4 oxoaporphine 
• 61659-87-8 (+/-)-N-trifluoroacetylwilsonirine 

Downstream Products

• 17807-64-6 (R)-(-)-wilsonirine 
• 17807-64-6 wilsonirine 
• 371196-20-2 N-[2-(2-methoxyphenoxyl)]ethylnorthaliporphine 

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.

A NOVEL SYNTHESIS OF (+/-)-NORAPORPHINE ALKALOIDS, (+/-)-WILSONIRINE AND (+/-)-NORDOMESTICINE

(+/-)-Wilsonirine (1a) and (+/-)-nordomesticine (1b) were synthesized in moderate yields on acid treatment, followed by alkaline hydrolysis of o-quinolacetates (o-QAs) (3) readily obtained by lead tetraacetate oxidation of (+/-)-N-trifluoroacetyltetrahydr

THE DEMETHYLATION OF APORPHINES WITH SULFURIC ACID

Sulfuric acid at room temperature has been found a useful reagent for interconverting aporphine alkaloids by selective O-demethylation.This was controlled by electronic or steric effects.