Investigation of 4,5-epoxymorphinan degradation during analysis by HPLC

Quarry, M. A.; Sebastian, Dolores; Diana, Frank J.

doi:10.1016/s0731-7085(02)00166-8

Cited by 6 publications

(2 citation statements)

References 3 publications

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“…These authors noted the increased concentration of iron in the former and found measurable concentrations of extractable iron at low pH and elevated temperature (pH 3 and 80 °C.) A study with naloxone, nalbuphine, and oxymorphone similarly found higher amounts of their oxidation products after storage in amber glass vials versus clear vials, noting the presence of 0.3 ppm iron in solutions stored in amber glass vials at ambient temperature for 4 h, but undetectable levels with clear vials 53 . As we assayed the concentration of thiamine remaining in solution after storage by measuring thiochrome fluorescence, we cannot exclude the possibility of thiamine degradation by metal ion leachates from the glass containers and formation of non-fluorescent products.…”

Section: Resultsmentioning

confidence: 97%

Pre-analytical challenges from adsorptive losses associated with thiamine analysis

Edwards,

Randall,

Wolfe

et al. 2024

Sci Rep

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Thiamine (vitamin B1) is an essential vitamin serving in its diphosphate form as a cofactor for enzymes in the citric acid cycle and pentose-phosphate pathways. Its concentration reported in the pM and nM range in environmental and clinical analyses prompted our consideration of the components used in pre-analytical processing, including the selection of filters, filter apparatuses, and sample vials. The seemingly innocuous use of glass fiber filters, glass filter flasks, and glass vials, ubiquitous in laboratory analysis of clinical and environmental samples, led to marked thiamine losses. 19.3 nM thiamine was recovered from a 100 nM standard following storage in glass autosampler vials and only 1 nM of thiamine was obtained in the filtrate of a 100 nM thiamine stock passed through a borosilicate glass fiber filter. We further observed a significant shift towards phosphorylated derivatives of thiamine when an equimolar mixture of thiamine, thiamine monophosphate, and thiamine diphosphate was stored in glass (most notably non-silanized glass, where a reduction of 54% of the thiamine peak area was observed) versus polypropylene autosampler vials. The selective losses of thiamine could lead to errors in interpreting the distribution of phosphorylated species in samples. Further, some loss of phosphorylated thiamine derivatives selectively to amber glass vials was observed relative to other glass vials. Our results suggest the use of polymeric filters (including nylon and cellulose acetate) and storage container materials (including polycarbonate and polypropylene) for thiamine handling. Losses to cellulose nitrate and polyethersulfone filters were far less substantial than to glass fiber filters, but were still notable given the low concentrations expected in samples. Thiamine losses were negated when thiamine was stored diluted in trichloroacetic acid or as thiochrome formed in situ, both of which are common practices, but not ubiquitous, in thiamine sample preparation.

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Section: Resultsmentioning

confidence: 97%

Pre-analytical challenges from adsorptive losses associated with thiamine analysis

Edwards,

Randall,

Wolfe

et al. 2024

Sci Rep

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“…After separation and characterization, it was confirmed as impurity 13 . Nalbuphine, as reported by Frank Diana, has the structural characteristic of a phenolic group at the 3-position in 4,5-epoxymorphinans, which is sensitive to light, and could primarily degrade to 2,2′-dimer impurity 13 . To control and decrease the generation of 13 , the precautions should be taken to avoid the exposure of light in the step of recrystallization and the salt-formation process.…”

Section: Results and Discussionmentioning

confidence: 99%

One-Pot Process for Synthesis of Nalbuphine Hydrochloride and Impurity Control Strategy

Zhang

Chen

et al. 2020

Org. Process Res. Dev.

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An improved kilogram-scale process of synthesis of nalbuphine was developed by investigating the critical parameters. Ten process-related impurities were identified, of which the source and control strategy was elucidated. Moreover, tetramethylammonium triacetoxyborohydride (Me 4 NBH(OAc) 3 ) was developed to reduce the imine and ketone in one pot. As a result, 6-β-epimer was significantly controlled to only 0.08% in the crude nalbuphine. The improved process was robust at kilogram scale in 60.4% overall yield with 99.95% high-performance liquid chromatography (HPLC) purity.

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Late Stage Product Development

Jenke¹

2008

Compatibility of Pharmaceutical Products and Contact Materials

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Investigation of 4,5-epoxymorphinan degradation during analysis by HPLC

Cited by 6 publications

References 3 publications

Pre-analytical challenges from adsorptive losses associated with thiamine analysis

Pre-analytical challenges from adsorptive losses associated with thiamine analysis

One-Pot Process for Synthesis of Nalbuphine Hydrochloride and Impurity Control Strategy

Late Stage Product Development

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