641-36-1

Usage

Purification Methods

Crystallise apocodeine from absolute EtOH by boiling and allowing to stand at 0o to give the alcoholate, m 104.5-106.5o; EtOH is lost slowly at 25o/2mm but readily at 78o/2mm, and the anhydrous base has m 122.5-124.5o. It is soluble in Et2O. [Folkers J Am Chem Soc 58 1814 1936.] It has also been crystallised from MeOH or MeOH with a little CH2Cl2 as a waxy solid and dried at 80o/2mm. It softens above 100o before melting and is sensitive to air and light. The hydrochloride, which is formed from the base in EtOH containing an equivalent amount of HCl followed by addition of Et2O, is recrystallised from 95% EtOH and adding Et2O until crystals separate. It melts at 260-263o (dec, with softening at 140o) and has [] D -41.3o to -43.3o (c 0.81, H2O). [Neumyer et al. J Med Chem 16 1223 1973.]

InChI:InChI=1/C18H19NO2/c1-19-9-8-11-4-3-5-13-16(11)14(19)10-12-6-7-15(21-2)18(20)17(12)13/h3-7,14,20H,8-10H2,1-2H3/t14-/m1/s1

Upstream product

• 76-57-3 codeine 
• 76-57-3 codeine 
• 73378-07-1 Codeine-6-(2-phenyltetrazole) Ether 

Downstream Products

• 38291-33-7 (R)-10,11-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline 
• 61013-20-5 10,11-dimethoxy-6-methyl-6H-dibenzo[de,g]quinoline 
• 18605-43-1 10,11-dimethoxy-6-methyl-5,6-dihydro-4H-dibenzo[de,g]quinoline 
• 41035-30-7 (S)-(+)-apomorphine hydrochloride 
• 58-00-4 apomorphin 

Relevant academic research and scientific papers

PHARMACEUTICAL COMPOSITIONS OF (6AS)-6-METHYL-5,6,6A,7-TETRAHYDRO-4H-DIBENZO[DE,G]QUINOLINE-10,11-DIOL

This invention relates to pharmaceutical compositions for enhancing the solubility of (6aS)-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-10,11-diol and salt forms thereof.

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.

FACILE 'ONE POT' PROCESS FOR APOMORPHINE FROM CODEINE

An improved method for producing apomorphine and derivatives thereof is provided. The method is a convenient 'one-pot' process, comprising the conversion of codeine into apomorphine without isolating the apocodeine intermediate. Use of water reactive scavengers, reagents that will react irreversibly with water, decreases side product formation and allows the use of milder reaction conditions. This one-pot synthesis of apomorphine from codeine provides a faster reaction with improved yields at temperatures lower as compared to conventional methods. The lower operating temperatures and less volatile reactants make the method particularly useful for large-scale manufacturing.

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.

PROCESS FOR MAKING APOMORPHINE AND APOCODEINE

There is provided an improved and convenient process for the synthesis of aporphines, such as apomorphine and apocodeine, by the rearrangement of the corresponding morphine or codeine derivatives. The use of a suitable water scavenger in an acid catalyzed rearrangement of the morphine derivatives unexpectedly results in a reaction temperature convenient for plant operation without sacrificing product. The method of the present invention also alleviates the cumbersome operations that were employed in the prior art to eliminate water from the reaction mixture at the elevated temperatures. This process is adaptable for the general preparation of other aporphines from the corresponding morphine congeners.

Aporphines. 27. Mechanistic Aspects of the Rearrangement of Thebaine and Codeine Analogues in Methanesulfonic Acid. Improved Method for Synthesis of N-Alkylated Aporphines

The rearrangement of thebaine (1a), northebaine (1b), and N-(2-hydroxyethyl)northebaine (1c) in methanesulfonic acid leading to the formation of novel N-alkylated-2-O-methylated normorphothebaine derivatives 4a-c was investigated.We have observed that a s