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Transformation of codeine and codeine-6-glucuronide to opioid analogues by urine adulteration with pyridinium chlorochromate: potential issue for urine drug testing

Journal Article


Abstract


  • RATIONALE

    Pyridinium chlorochromate (PCC) is the active ingredient of 'Urine Luck', a commercially available in vitro adulterating agent used to conceal the presence of drugs in a urine specimen. The exposure of codeine and its major glucuronide metabolite codeine-6-glucuronide (C6G) to PCC was investigated to determine whether PCC is an effective masking agent for these opiate compounds.

    METHODS

    Following the addition of PCC to both spiked and authentic codeine and C6G-positive urine specimens, the samples were monitored using liquid chromatography/mass spectrometry (LC/MS). Stable reaction products were identified and characterized using high-resolution MS analysis and, where possible, nuclear magnetic resonance (NMR) analysis.

    RESULTS

    It was determined that PCC effectively oxidizes codeine and C6G, thus altering the original codeine-to-C6G ratio in the urine specimen. Four reaction products were identified for codeine: codeinone, 14-hydroxycodeinone, 6-O-methylcodeine and 8-hydroxy-7,8-dihydrocodeinone. Similarly, three reaction products were identified for C6G: codeinone, codeine and a lactone of C6G (tentative assignment).

    CONCLUSIONS

    Besides addressing the complications added to interpretation, more investigation is warranted to further determine their potential for use as markers for monitoring the presence of codeine and C6G in urine specimens adulterated with PCC.

UOW Authors


  •   Luong, Susan (external author)
  •   Ung, Alison T. (external author)
  •   Kalman, John (external author)
  •   Fu, Shanlin (external author)

Publication Date


  • 2014

Citation


  • Luong, S., Ung, A. T., Kalman, J. & Fu, S. (2014). Transformation of codeine and codeine-6-glucuronide to opioid analogues by urine adulteration with pyridinium chlorochromate: potential issue for urine drug testing. Rapid Communications in Mass Spectrometry, 28 (14), 1609-1620.

Scopus Eid


  • 2-s2.0-84901911716

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/3416

Has Global Citation Frequency


Number Of Pages


  • 11

Start Page


  • 1609

End Page


  • 1620

Volume


  • 28

Issue


  • 14

Place Of Publication


  • United Kingdom

Abstract


  • RATIONALE

    Pyridinium chlorochromate (PCC) is the active ingredient of 'Urine Luck', a commercially available in vitro adulterating agent used to conceal the presence of drugs in a urine specimen. The exposure of codeine and its major glucuronide metabolite codeine-6-glucuronide (C6G) to PCC was investigated to determine whether PCC is an effective masking agent for these opiate compounds.

    METHODS

    Following the addition of PCC to both spiked and authentic codeine and C6G-positive urine specimens, the samples were monitored using liquid chromatography/mass spectrometry (LC/MS). Stable reaction products were identified and characterized using high-resolution MS analysis and, where possible, nuclear magnetic resonance (NMR) analysis.

    RESULTS

    It was determined that PCC effectively oxidizes codeine and C6G, thus altering the original codeine-to-C6G ratio in the urine specimen. Four reaction products were identified for codeine: codeinone, 14-hydroxycodeinone, 6-O-methylcodeine and 8-hydroxy-7,8-dihydrocodeinone. Similarly, three reaction products were identified for C6G: codeinone, codeine and a lactone of C6G (tentative assignment).

    CONCLUSIONS

    Besides addressing the complications added to interpretation, more investigation is warranted to further determine their potential for use as markers for monitoring the presence of codeine and C6G in urine specimens adulterated with PCC.

UOW Authors


  •   Luong, Susan (external author)
  •   Ung, Alison T. (external author)
  •   Kalman, John (external author)
  •   Fu, Shanlin (external author)

Publication Date


  • 2014

Citation


  • Luong, S., Ung, A. T., Kalman, J. & Fu, S. (2014). Transformation of codeine and codeine-6-glucuronide to opioid analogues by urine adulteration with pyridinium chlorochromate: potential issue for urine drug testing. Rapid Communications in Mass Spectrometry, 28 (14), 1609-1620.

Scopus Eid


  • 2-s2.0-84901911716

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/3416

Has Global Citation Frequency


Number Of Pages


  • 11

Start Page


  • 1609

End Page


  • 1620

Volume


  • 28

Issue


  • 14

Place Of Publication


  • United Kingdom