478-53-5

Basic information

• Product Name: (6aR)-5,6,6a,7-Tetrahydro-10-methoxy-6-methyl-4H-dibenzo[de,g]quinoline-2,11-diol
• Synonyms: (6aR)-5,6,6a,7-Tetrahydro-10-methoxy-6-methyl-4H-dibenzo[de,g]quinoline-2,11-diol;Morphothebaine
• CAS NO: 478-53-5
• Molecular Formula: C₁₈H₁₉NO₃
• Molecular Weight: 297.3484
• Mol File: 478-53-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 515.3°Cat760mmHg
• Flash Point: 265.4°C
• Appearance: /
• Density: 1.294g/cm³
• Vapor Pressure: 3.07E-11mmHg at 25°C
• Refractive Index: 1.657
• CAS DataBase Reference: (6aR)-5,6,6a,7-Tetrahydro-10-methoxy-6-methyl-4H-dibenzo[de,g]quinoline-2,11-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (6aR)-5,6,6a,7-Tetrahydro-10-methoxy-6-methyl-4H-dibenzo[de,g]quinoline-2,11-diol(478-53-5)
• EPA Substance Registry System: (6aR)-5,6,6a,7-Tetrahydro-10-methoxy-6-methyl-4H-dibenzo[de,g]quinoline-2,11-diol(478-53-5)

Safety Data

• Hazardous Substances Data: 478-53-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C18H19NO3/c1-19-6-5-11-7-12(20)9-13-16(11)14(19)8-10-3-4-15(22-2)18(21)17(10)13/h3-4,7,9,14,20-21H,5-6,8H2,1-2H3

Upstream product

• 3271-79-2 (7S)-salutaridinol 
• 2392-98-5 salutaridinol 
• 115-37-7 thebaine 
• 76-57-3 codeine 
• 467-13-0 codeinone 

Downstream Products

• 77630-01-4 (-)-2,10,11-trihydroxyaporphine 

Relevant articles and documents

Microwave-promoted acid-catalyzed rearrangement of morphinans - A high-yield synthesis of R(-)-apomorphine

The microwave-promoted acid-catalyzed rearrangement of morphine (1), codeine (2), and thebaine (3) was investigated. In all cases, a significant improvement in the yields were achieved compared to the traditional techniques. R(-)-Apomorphine (4), which is a clinically important dopamine agonist, was synthesized from morphine (1) in 75% yield. Copyright Taylor & Francis Group, LLC.

Synthesis and binding studies of 2-arylapomorphines

From codeine, four different 2-aryl substituted apomorphines were synthesised in 6 steps each. Oxidation of codeine with IBX followed by acid catalysed rearrangement gave morphothebaine, which was selectively triflylated at the 2-position and subsequently O-acetylated at the 11-position. The resulting triflate was coupled in a Suzuki-Miyaura type reaction with a series of 4-substituted arylboronic esters which, after deprotection, gave the desired 2-aryl apomorphines. The analogues were tested for affinity towards a range of dopaminergic, serotonergic and adrenergic receptors. 2-(4-Hydroxyphenyl)- apomorphine exhibited high affinity for the dopamine D2 receptor. A putative ligand-receptor interaction was put forward. The Royal Society of Chemistry 2005.