A One-Step Synthesis of -Bromocodide from Codeine.

J Pharm Sci Pharmacol

Department of Pharmaceutical Sciences, University of Maryland School of Pharmacy, Baltimore, MD 21201, USA.

Published: March 2014

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.

Download full-text PDF

Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8474124PMC

Publication Analysis

Top Keywords

synthesis -bromocodide
8
one-step synthesis
4
-bromocodide codeine
4
codeine opioid
4
opioid analgesics
4
analgesics treatment
4
treatment choice
4
choice chronic
4
chronic severe
4
severe pain
4

Similar Publications

A One-Step Synthesis of -Bromocodide from Codeine.

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 PDF

The 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.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!