| Solid-state esterification of codeine phosphate by the acid constituent of effervescent tablets. | |
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MedLine Citation:
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PMID: 3585724 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Codeine phosphate in a paracetamol:codeine effervescent tablet was found to react at room temperature and 37 degrees C with the citric acid constituent to form citrate esters of codeine. The esterification was confirmed in a solid-state reaction at elevated temperature. The structures of the three possible monosubstituted esters (1-3) were elucidated from spectroscopic data (nuclear magnetic resonance and mass spectrometry) and by selective hydrolysis of the dimethyl esters to give symmetrical and asymmetrical dimethyl citrates. In the degradation reaction, formation of the symmetrically substituted citrate ester of codeine, 1, was found to predominate. Tartaric acid, which can be used in effervescent tablet formulations, was also found to give an ester with codeine phosphate in a similar nonsolvolytic reaction. A liquid chromatographic method was developed for the separation of the citrate esters of codeine. |
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Authors:
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B Silver; E G Sundholm |
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Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: Journal of pharmaceutical sciences Volume: 76 ISSN: 0022-3549 ISO Abbreviation: J Pharm Sci Publication Date: 1987 Jan |
Date Detail:
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Created Date: 1987-07-01 Completed Date: 1987-07-01 Revised Date: 2008-11-21 |
Medline Journal Info:
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Nlm Unique ID: 2985195R Medline TA: J Pharm Sci Country: UNITED STATES |
Other Details:
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Languages: eng Pagination: 53-5 Citation Subset: IM |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Chemical Phenomena Chemistry Chromatography, High Pressure Liquid Citrates Citric Acid Codeine / analysis* Esters / chemical synthesis Magnetic Resonance Spectroscopy Mass Spectrometry Tablets Tartrates |
| Chemical | |
Reg. No./Substance:
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0/Citrates; 0/Esters; 0/Tablets; 0/Tartrates; 526-83-0/tartaric acid; 76-57-3/Codeine; 77-92-9/Citric Acid |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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