Aporphines 65: chemical, microbial synthesis and characterization by gas chromatography/mass spectrometry of (R)-(-)-10-hydroxy 11-methoxy-N-n-propylnoraporphine, a potential metabolite of N-n-propylnorapomorphine.
The title compound has been synthesized by a multistep sequence from (R)(-)-morphine, and compared with the product obtained by microbial O-demethylation of (R)- and (S)-10,11-dimethoxy-N-n-propylnoraporphine (N-n-propylnorapomorphine dimethyl ether). The comparison was based on an analysis of the trifluoroacetyl derivatives of the microbial products and the synthesized compounds using gas chromatography/mass spectrometry in the electron impact mode. Examination by gas chromatography/electron impact/mass spectrometry of the trifluoroacetyl derivatives of 11-hydroxy-10-methoxyaporphine (apocodeine, 3) and 10-methoxy-11-hydroxyaporphine (isoapocodeine, 5) has revealed their excellent chromatographic resolution, and the preferential loss of the methyl group as in 3 [M-15]+ or the trifluoroacetyl group from the 10-position of the aporphine ring as in 5 [M-97]+. Characteristic fragmentations of these isomeric aporphines were used to confirm their structures and were compared with the spectra of authentic synthetic samples.
D001058:Apomorphine / Q000031:analogs & derivatives* / Q000378:metabolism; D001060:Aporphines / Q000032:analysis* / Q000378:metabolism*; D001419:Bacteria / Q000378:metabolism; D001711:Biotransformation; D055598:Chemical Phenomena; D002621:Chemistry; D008401:Gas Chromatography-Mass Spectrometry
D001060:Aporphines; C009074:N-n-propylnorapomorphine; C009073:N-n-propylnorapocodeine; D001058:Apomorphine