Opioid analgesics are the treatment of choice for chronic, severe pain. During the course of developing new derivatives of morphine and codeine, we observed an unanticipated S2' substitution reaction product during an attempted 3-O-demethylation of codeine using BBr. NMR spectroscopy and X-ray crystallographic data indicate that a significant product is -bromocodide, a useful intermediate for the production of C-6-demethoxythebaine derivatives. Herein we report the first, single-step synthesis of -bromocodide.
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J Pharm Sci Pharmacol
March 2014
Department of Pharmaceutical Sciences, University of Maryland School of Pharmacy, Baltimore, MD 21201, USA.
Opioid analgesics are the treatment of choice for chronic, severe pain. During the course of developing new derivatives of morphine and codeine, we observed an unanticipated S2' substitution reaction product during an attempted 3-O-demethylation of codeine using BBr. NMR spectroscopy and X-ray crystallographic data indicate that a significant product is -bromocodide, a useful intermediate for the production of C-6-demethoxythebaine derivatives.
View Article and Find Full Text PDFThe preparation of 6-spin-labeled codeine and morphine is described. Treatment of either 6-chlorocodide or 8-bromocodide with 4-amino-2,2,6,6-tetramethylpiperidino-1-oxyl free radical in dimethylformamide afforded 6-spin-labeled codeine. Similar treatment of 6-chloromorphide afforded 6-spin-labeled morphine.
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