R(-)-apocodeine hydrochloride

The Uses of R(-)-apocodeine hydrochloride

A metabolite of Apomorphine (A727500). Dopamine receptor agonist. Emetic.

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.]