475-83-2

Basic information

• Product Name: NUCIFERINE
• Synonyms: (-)-nucipherine;(r)-1,2-dimethoxyaporphine;1,2-dimethoxy-6a-beta-aporphin;4H-Dibenzo[de,g]quinoline,5,6,6a,7-tetrahydro-1,2-diMethoxy-6-Methyl-, (6aR)-;Nuciferine 1,2-Dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline;6a;5,6,6a,7-tetrahydro-1,2-dimethoxy-6-methyl-g)quinolin(r)-4h-dibenzo(d;l-5,6-dimethoxyaporphine
• CAS NO: 475-83-2
• Molecular Formula: C₁₉H₂₁NO₂
• Molecular Weight: 295.38
• Product Categories: standardized herbal extract;Miscellaneous Natural Products;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).
• Mol File: 475-83-2.mol

Chemical Properties

• Melting Point: 165.5°C
• Boiling Point: 437.06°C (rough estimate)
• Flash Point: 151.9 °C
• Appearance: /
• Density: 1.1156 (rough estimate)
• Vapor Pressure: 1.27E-07mmHg at 25°C
• Refractive Index: 1.5000 (estimate)
• Storage Temp.: 2-8°C
• PKA: 7.87±0.20(Predicted)
• CAS DataBase Reference: NUCIFERINE(CAS DataBase Reference)
• NIST Chemistry Reference: NUCIFERINE(475-83-2)
• EPA Substance Registry System: NUCIFERINE(475-83-2)

Safety Data

• Safety Statements: 24/25
• RIDADR: UN 1544PSN1 6.1 / PGIII
• Hazardous Substances Data: 475-83-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Nuciferine is used as a bioactive compound for its potential weight loss and lipid reduction effects. It can be employed in the development of pharmaceutical products aimed at managing obesity and related metabolic disorders.
Used in Research and Development:
Nuciferine serves as a valuable subject for content determination, identification, and pharmacological experiments. Its unique properties and alkaloid structure make it an interesting candidate for further research in understanding its therapeutic potential and possible applications in medicine.

Safety Profile

Poison by ingestion andintraperitoneal routes. When heated to decomposition itemits toxic fumes of NOx.

References

Gulland, Haworth., J. Chern. Soc., 590 (1928)Yunusov, Konovalova, Orekhov., Bull. Soc. Chim. Fr., 70 (1940)Arthur, Cheung., J. Chern. Soc., 2306 (1959)Kupchan et al., Tetrahedron, 19, 227 (1963)

InChI:InChI=1/C19H21NO2/c1-20-9-8-13-11-16(21-2)19(22-3)18-14-7-5-4-6-12(14)10-15(20)17(13)18/h4-7,11,15H,8-10H2,1-3H3

Upstream product

• 186581-53-3 diazomethane 
• 6545-25-1 (-)-N-methylasimilobine 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 50-00-0 formaldehyd 
• 4846-19-9 (6aR)-1,2-dimethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline 
• 6275-29-2 N-[2-(3,4-dimethoxyphenyl)ethyl]acetamide 
• 4721-98-6 6,7-dimethoxy-1-methyl-3,4-dihydroisoquinoline 
• 6268-86-6 dimethoxy-6,7 methyl-1 dihydro-3,4 isoquinoleine chlorhydrate 

Downstream Products

• 5531-98-6 atherosperminine 
• 3175-79-9 (6aR)-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-1,2-diol 
• 7630-74-2 dehydronuciferine 
• 4846-19-9 (6aR)-1,2-dimethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline 
• 6899-64-5 caaverine 

Relevant articles and documents

Stereoselective total synthesis of (S)- and (R)-nuciferine using benzyne chemistry

Total syntheses of (S)- and (R)-nuciferine were accomplished through approach involving diastereoselective reaction between a chiral dihydroisoquinoline enamide and 2-(trimethylsilyl)phenyl trifluoromethanesulfonate promoted by CsF, affording a separable mixture of diastereoisomers, which provided (S)- and (R)-nuciferine via simple and efficient transformations.

Alkaloid constituents from flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) with melanogenesis inhibitory activity in B16 melanoma cells

Methanolic extracts from the flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) were found to show inhibitory effects on melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells. From the methanolic extracts, a new alkaloid, N-methylasimilobine N-oxide, was isolated together with eleven benzylisoquinoline alkaloids. The absolute stereostructure of the new alkaloid was determined from chemical and physicochemical evidence. Among the constituents isolated, nuciferine, N-methylasimilobine, (-)-lirinidine, and 2-hydroxy-1-methoxy-6a,7-dehydroaporphine showed potent inhibition of melanogenesis. Comparison of the inhibitory activities of synthetic related alkaloids facilitated characterization of the structure-activity relationships of aporphine- and benzylisoquinoline-type alkaloids. In addition, 3-30 μM nuciferine and N-methylasimilobine inhibited the expression of tyrosinase mRNA, 3-30 μM N-methylasimilobine inhibited the expression of TRP-1 mRNA, and 10-30 μM nuciferine inhibited the expression of TRP-2 mRNA.

Aporphine alkaloid synthesis and diversification via direct arylation

Palladium-catalyzed direct arylation of aryl chlorides, bromides and iodides has been applied to the preparation of new aporphine analogues including C2-substituted aporphines by reaction with benzodioxole, pyridine N-oxide and pyrazine N-oxide. Successful application of direct arylation in these diversification reactions highlights its utility not only in convergent, but also in divergent synthesis. We also describe enantioselective syntheses of (R)-nornuciferine and (R)-nuciferine employing a catalytic asymmetric transfer hydrogenation in high yield and excellent enantiomeric excess. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.