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Solid-State Esterification of Codeine Phosphate by the Acid Constituent of Effervescent Tablets
- Source :
- Journal of Pharmaceutical Sciences. 76:53-55
- Publication Year :
- 1987
- Publisher :
- Elsevier BV, 1987.
-
Abstract
- 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.
- Subjects :
- Magnetic Resonance Spectroscopy
Chromatography
Chemical Phenomena
Codeine
Pharmaceutical Science
Esters
Codeine Phosphate
Mass spectrometry
Citric Acid
Mass Spectrometry
Dosage form
Chemistry
chemistry.chemical_compound
Hydrolysis
chemistry
Tartaric acid
medicine
Effervescent tablet
Citrates
Citric acid
Tartrates
Chromatography, High Pressure Liquid
Tablets
medicine.drug
Subjects
Details
- ISSN :
- 00223549
- Volume :
- 76
- Database :
- OpenAIRE
- Journal :
- Journal of Pharmaceutical Sciences
- Accession number :
- edsair.doi.dedup.....630a30cf745a82a4c4810270dc154aa8