478-57-9

Basic information

• Product Name: aporphine
• Synonyms: aporphine;4,5,6,6a-Tetrahydro-6-methyl-7H-dibenzo[de,g]quinoline;5,6,6a,7-Tetrahydro-6-methyl-4H-dibenzo[de,g]quinoline
• CAS NO: 478-57-9
• Molecular Formula: C17H17N
• Molecular Weight: 235.32
• Mol File: 478-57-9.mol

Chemical Properties

• Boiling Point: 371.3°Cat760mmHg
• Flash Point: 160.5°C
• Appearance: /
• Density: 1.127g/cm³
• Vapor Pressure: 1.04E-05mmHg at 25°C
• Refractive Index: 1.628
• PKA: 8.28±0.20(Predicted)
• CAS DataBase Reference: aporphine(CAS DataBase Reference)
• NIST Chemistry Reference: aporphine(478-57-9)
• EPA Substance Registry System: aporphine(478-57-9)

Safety Data

• Hazardous Substances Data: 478-57-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Aporphine is used as a pharmaceutical compound for its potential therapeutic properties. It has been found to have various biological activities, such as anti-inflammatory, analgesic, and antipyretic effects. Additionally, it has been studied for its potential use in the treatment of neurological disorders, such as Parkinson's disease, due to its ability to modulate dopaminergic pathways.
Used in Cosmetic Industry:
Aporphine is used as a cosmetic ingredient for its potential skin-soothing and anti-aging properties. It has been found to have antioxidant and anti-inflammatory effects, which can help protect the skin from environmental stressors and promote a more youthful appearance.
Used in Agrochemical Industry:
Aporphine is used as an agrochemical compound for its potential insecticidal and pesticidal properties. It has been found to have neurotoxic effects on certain insects, making it a potential candidate for use in pest control strategies.
Used in Research and Development:
Aporphine is used as a research compound for the development of new drugs and therapies. Its unique chemical structure and biological activities make it an interesting target for further investigation and potential application in various fields, such as medicine, agriculture, and cosmetics.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 6, p. 91, 1963 DOI: 10.1021/jm00338a001

InChI:InChI=1/C17H17N/c1-18-10-9-12-6-4-8-15-14-7-3-2-5-13(14)11-16(18)17(12)15/h2-8,16H,9-11H2,1H3

Upstream product

• 51-67-2 tyrosamine 
• 259263-97-3 4-methyl-N-[2-(4-hydroxyphenyl)ethyl]benzenesulfonamide 
• 2412-58-0 1-methyl-3,4,dihydroisoquinoline 
• 877-95-2 methyl-N-(benzyl-methyl)-formamide 
• 64-04-0 phenethylamine 
• 4965-16-6 1-(1-methylene-3,4-dihydroisoquinolin-2(1H)-yl)ethanone 
• 14528-29-1 6-acetyl-5,6,6a,7-tetrahydro-4H-dibenzo(de,g)quinoline 
• 100-44-7 benzyl chloride 
• 74-88-4 methyl iodide 
• 1418222-47-5 5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-6-carboxaldehyde 
• 1418222-45-3 1-[(2-bromophenyl)methyl]-3,4-dihydro-1H-isoquinoline-2-carboxaldehyde 
• 78774-88-6 1-[(2-bromophenyl)methyl]-1,2,3,4-tetrahydroisoquinoline 
• 839673-85-7 2-(bromophenyl)-N-(2-phenylethyl)acetamide 
• 729572-41-2 6-tosyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-1-yl trifluoromethanesulfonate 

Relevant articles and documents

Synthesis of Aporphine Analogues via Palladium-Catalyzed Intramolecular Aryl-Aryl Dehydrogenative Coupling

Reported herein is an intramolecular dehydrogenative coupling of two inert aryl C-H bonds for the synthesis of aporphine analogues. The process represents a novel tool for the preparation of aporphines via palladiun-catalyzed C-H bond activation. The present reaction is compatible with various functional groups, and the coupling products have been further applied for the synthesis of natural products aporphine and zenkerine.

A convenient formation of aporphine core via benzyne chemistry: Conformational analysis and synthesis of (R)-aporphine

Total synthesis of (R)-aporphine has been accomplished by an approach that employs in the key step a sequence of transformations involving a [4+2] cycloaddition reaction followed by a hydrogen migration, leading to aporphine core in good yield, which was subjected to a 1D gradient NOE experiment, conformational analysis, and simple transformations, including a small scale resolution process, to afford enantiomerically enriched aporphine alkaloid.

Phenanthrene derivatives for use as medicaments

Phenanthrene derivatives of formula I for use as medicaments. The present invention refers to phenanthrene derivatives for use as medicaments, mainly in the prevention and/or treatment of DM1, HDL2, SCA8, DM2, SCA3, FXTAS, FTD/ALS, and SCA31. In a preferred embodiment, phenanthrene derivatives of the invention are also used as antimyotonic agents.

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.

Synthesis of (±)-aporphine utilizing Pictet-Spengler and intramolecular phenol ortho-arylation reactions

A synthesis of the alkaloid (±)-aporphine is reported. The initial key step of the synthesis involves a Pictet-Spengler cyclization of N-tosyl tyramine with 2-bromophenylacetaldehyde in trifluoroacetic acid. This step was followed by the second strategic

Preparation and Pharmacological Evaluation of Enantiomers of Certain Nonoxygenated Aporphines: (+)- and (-)-Aporphine and (+)- and (-)-10-Methylaporphine

The subject compounds were prepared as a part of a continuing structure-activity study of the contrasting actions (agonism-antagonism) of (+)- and (-)-11-hydroxy-10-methylaporphine at serotonin (5-HT1A) receptors. None of the targeted nonoxygen