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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
Author(s) -
Neumeyer John L.,
AbdelMaksoud Hamdy M.,
Trainor Thomas M.,
Vouros Paul,
Davis Patrick J.
Publication year - 1986
Publication title -
biomedical and environmental mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0887-6134
DOI - 10.1002/bms.1200130504
Subject(s) - chemistry , mass spectrometry , demethylation , electron ionization , chromatography , gas chromatography , mass spectrum , aporphine , ether , gas chromatography–mass spectrometry , stereochemistry , organic chemistry , alkaloid , ion , biochemistry , gene expression , dna methylation , gene , ionization
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 the these isomeric aporphines were used to confirm their structures and were compared with the spectra of authentic synthetic samples.