872094-33-2

Basic information

• Product Name: (R)-(-)-11-acetoxy-2-(4-tolyl)-10-methoxyapomorphine
• Synonyms: (R)-(-)-11-acetoxy-2-(4-tolyl)-10-methoxyapomorphine
• CAS NO: 872094-33-2
• Molecular Weight: 413.516
• Mol File: 872094-33-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (R)-(-)-11-acetoxy-2-(4-tolyl)-10-methoxyapomorphine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-11-acetoxy-2-(4-tolyl)-10-methoxyapomorphine(872094-33-2)
• EPA Substance Registry System: (R)-(-)-11-acetoxy-2-(4-tolyl)-10-methoxyapomorphine(872094-33-2)

Safety Data

• Hazardous Substances Data: 872094-33-2(Hazardous Substances Data)

Upstream product

• 76-57-3 codeine 
• 872094-27-4 (R)-(-)-11-acetoxy-10-methoxy-2-(trifluoromethanesulfonyloxy)-N-methylapomorphine 
• 380481-66-3 5,5-dimethyl-2-(4-methylphenyl)-1,3,2-dioxaborinane 

Relevant articles and documents

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.