Neumeyer J L, Abdel-Maksoud H M, Trainor T M, Vouros P, Davis P J
Biomed Environ Mass Spectrom. 1986 May;13(5):223-9. doi: 10.1002/bms.1200130504.
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.
标题化合物是由（R）（-）-吗啡经多步反应合成的，并与通过微生物对（R）-和（S）-10,11-二甲氧基-N-正丙基去甲阿朴啡（N-正丙基去甲阿朴吗啡二甲醚）进行O-去甲基化得到的产物进行了比较。该比较基于使用电子轰击模式的气相色谱/质谱法对微生物产物和合成化合物的三氟乙酰衍生物进行的分析。通过气相色谱/电子轰击/质谱法对11-羟基-10-甲氧基阿朴啡（阿朴可待因，3）和10-甲氧基-11-羟基阿朴啡（异阿朴可待因，5）的三氟乙酰衍生物进行检测，结果表明它们具有出色的色谱分辨率，并且如3 [M-15]+那样优先失去甲基，或者如5 [M-97]+那样从阿朴啡环的10位优先失去三氟乙酰基。这些异构阿朴啡的特征性裂解用于确认其结构，并与真实合成样品的光谱进行了比较。
