title: Transformation of codeine and codeine-6-glucuronide to opioid analogues by urine adulteration with pyridinium chlorochromate: potential issue for urine drug testing.
abstract: BACKGROUND
  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.
authors.affiliation: Centre for Forensic Science, School of Chemistry and Forensic Science, University of Technology, Sydney (UTS), PO Box 123 Broadway, NSW 2007, Australia.
authors.forename: Susan
authors.initials: S
authors.lastname: Luong
authors.forename: Alison T
authors.initials: AT
authors.lastname: Ung
authors.forename: John
authors.initials: J
authors.lastname: Kalman
authors.forename: Shanlin
authors.initials: S
authors.lastname: Fu
mesh_terms: D000328:Adult; D003061:Codeine / Q000031:analogs & derivatives / Q000737:chemistry / Q000652:urine; D004340:Drug Contamination / Q000517:prevention & control; D005260:Female; D006801:Humans; D008297:Male; D008875:Middle Aged; D011726:Pyridinium Compounds / Q000737:chemistry*; D015813:Substance Abuse Detection / Q000379:methods* / Q000592:standards*; D014867:Water
chemical_list: D011726:Pyridinium Compounds; D014867:Water; C111019:pyridinium chlorochromate; D003061:Codeine