641-36-1

Basic information

• Product Name: R(-)-APOCODEINE HYDROCHLORIDE
• Synonyms: (6aR)-5,6,6a,7-Tetrahydro-10-methoxy-6-methyl-4H-dibenzo[de,g]quinolin-11-ol;R(-)-10-Methoxy-11-hydroxyaporphine;(-)-apocodeine;10-methoxy-6a-beta-aporphin-11-o;apocodein;g)quinolin-11-ol,5,6,6a,7-tetrahydro-10-methoxy-6-methyl-4h-dibenzo(d(r);R(-)-APOCODEINE HYDROCHLORIDE DOPAMINE A GONIST
• CAS NO: 641-36-1
• Molecular Formula: C₁₈H₁₉NO₂
• Molecular Weight: 281.353
• Mol File: 641-36-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: 124° (dry)
• Boiling Point: 424.01°C (rough estimate)
• Flash Point: 228.4°C
• Appearance: off-white/solid
• Density: 1.1236 (rough estimate)
• Vapor Pressure: 7.32E-09mmHg at 25°C
• Refractive Index: 1.5100 (estimate)
• Storage Temp.: 2-8°C
• Solubility: H2O: soluble
• PKA: 9.60±0.20(Predicted)
• CAS DataBase Reference: R(-)-APOCODEINE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: R(-)-APOCODEINE HYDROCHLORIDE(641-36-1)
• EPA Substance Registry System: R(-)-APOCODEINE HYDROCHLORIDE(641-36-1)

Safety Data

• WGK Germany: 3
• RTECS: CE1045000
• Hazardous Substances Data: 641-36-1(Hazardous Substances Data)

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

• 58-00-4 apomorphin 
• 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 

Relevant articles and documents

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.

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.

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.