38291-33-7

Basic information

• Product Name: (6aR)-10,11-Dimethoxy-4,5,6a,7-tetrahydro-6-methyl-6H-dibenzo[de,g]quinoline
• Synonyms: (6aR)-10,11-Dimethoxy-4,5,6a,7-tetrahydro-6-methyl-6H-dibenzo[de,g]quinoline;(6aR)-5,6,6a,7-Tetrahydro-10,11-dimethoxy-6-methyl-4H-dibenzo[de,g]quinoline
• CAS NO: 38291-33-7
• Molecular Formula: C₁₉H₂₁NO₂
• Molecular Weight: 0
• Mol File: 38291-33-7.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (6aR)-10,11-Dimethoxy-4,5,6a,7-tetrahydro-6-methyl-6H-dibenzo[de,g]quinoline(CAS DataBase Reference)
• NIST Chemistry Reference: (6aR)-10,11-Dimethoxy-4,5,6a,7-tetrahydro-6-methyl-6H-dibenzo[de,g]quinoline(38291-33-7)
• EPA Substance Registry System: (6aR)-10,11-Dimethoxy-4,5,6a,7-tetrahydro-6-methyl-6H-dibenzo[de,g]quinoline(38291-33-7)

Safety Data

• Hazardous Substances Data: 38291-33-7(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 314-19-2 apomorphine hydrochloride 
• 18605-43-1 10,11-dimethoxy-6-methyl-5,6-dihydro-4H-dibenzo[de,g]quinoline 
• 39478-63-2 10,11-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline 
• 58-00-4 apomorphin 
• 65185-58-2 2-(2-bromophenyl)ethanamine 
• 74315-08-5 N-acetyl-2-(2-bromophenyl)ethylamine 
• 2033-89-8 3,4-dimethoxyphenol 
• 18605-42-0 10,11-dimethoxy-6-methyl-aporphane 
• 641-36-1 Apocodeine 
• 74-88-4 methyl iodide 
• 76-57-3 codeine 

Downstream Products

• 119597-07-8 N-[2-(5,6-dimethoxy-[1]phenanthryl)-ethyl]-N-methyl-benzamide 
• 18605-43-1 10,11-dimethoxy-6-methyl-5,6-dihydro-4H-dibenzo[de,g]quinoline 
• 58-00-4 apomorphin 
• 41035-30-7 (S)-(+)-apomorphine hydrochloride 
• 61013-20-5 10,11-dimethoxy-6-methyl-6H-dibenzo[de,g]quinoline 

Relevant articles and documents

Regio- and stereoselective derivatisation of an aporphine scaffold

Treatment of 10,11-dimethoxyaporphine with chromium hexacarbonyl was found to give two diastereoisomeric products on regioselective co-ordination of the chromium tricarbonyl fragment to the A ring. For one of the diastereoisomeric complexes, alkylation was found to proceed with high regio- and diastereoselectivity at C(4), whereas regio- and diastereoselective alkylation was observed at C(6a) for the other diastereoisomer. In the case of the C(4)- and C(6a)-methylated products, these substrates were decomplexed in high yield to give the corresponding enantiopure, C(4)- and C(6a)-methyl substituted aporphines.

PHARMACEUTICAL COMPOSITION FOR USE IN THE TREATMENT OF NEUROLOGICAL DISEASES

The present invention relates to pharmaceutical compositions for administration to mammals that include (6aS)-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-10,11-diol or a pharmaceutically acceptable salt thereof and at least one pharmaceutically acceptable excipient that provides pharmacokinetic profiles useful for the treatment of neurodegenerative diseases.

Racemization of (S)-(+)-10,11-dimethoxyaporphine and (S)-(+)-aporphine: efficient preparations of (R)-(-)-apomorphine and (R)-(-)-aporphine via a recycle process of resolution

Efficient preparations of (R)-(-)-apomorphine (R)-1 and (R)-(-)-aporphine (R)-2 based on a recycle process of resolution are described. In this recycle process of resolution, (RS)-(±)-10,11-dimethoxyaporphine 3 as the precursor of 1, and (RS)-(±)-aporphine 2 were successfully resolved into both enantiomers with (+)-dibenzoyltartaric acid (DBTA). The desired (R)-3 and (R)-2 were obtained and then, respectively, transformed to compound (R)-1, the hydrochloride salt of (R)-1, diacetate compound 4 and the hydrochloride salt of (R)-2; while the undesired (S)-3 and (S)-2 were racemized to obtain a racemate, which was suitable for further resolution. A method for the racemization of the undesired (S)-3 and (S)-2 was extensively studied, in order to obtain high-yielding racemization conditions. A plausible mechanism for the racemization of (S)-3 and (S)-2 was also proposed.