Method for the quantification of diamorphine and its metabolites in pediatric plasma samples by liquid chromatography-tandem mass spectrometry

Journal of Analytical Toxicology

Volumn 34, Issue 4, 2010, Pages 177-195

  Al Asmari, Ahmed ^a,b   Anderson, Robert A ^a   Kidd, Susan ^c   Thomson, Alison H ^d  

^a UNIVERSITY OF GLASGOW   (United Kingdom)

^b Poison Control and Forensic Chemistry Centre   (Saudi Arabia)

^c ROYAL HOSPITAL FOR SICK CHILDREN   (United Kingdom)

^d UNIVERSITY OF STRATHCLYDE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

DIAMORPHINE; DRUG METABOLITE; MORPHINE; MORPHINE 3 GLUCURONIDE; MORPHINE 6 ACETATE; MORPHINE 6 GLUCURONIDE; NORMORPHINE; NARCOTIC ANALGESIC AGENT;

ADOLESCENT; ARTICLE; CHILD; CLINICAL ARTICLE; CONTROLLED STUDY; DRUG BLOOD LEVEL; DRUG ELIMINATION; DRUG HALF LIFE; DRUG STABILITY; ELECTROSPRAY MASS SPECTROMETRY; FEMALE; HUMAN; HYDROLYSIS; LIQUID CHROMATOGRAPHY; MALE; PAIN; PRESCHOOL CHILD; SCHOOL CHILD; SOLID PHASE EXTRACTION; TANDEM MASS SPECTROMETRY; VALIDATION PROCESS; BLOOD; CALIBRATION; CHEMISTRY; COMPARATIVE STUDY; HALF LIFE TIME; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INTRANASAL DRUG ADMINISTRATION; INTRAVENOUS DRUG ADMINISTRATION; METABOLISM; METHODOLOGY; REPRODUCIBILITY; SOLID PHASE MICROEXTRACTION; STATISTICAL PARAMETERS; TIME; VALIDATION STUDY;

ADMINISTRATION, INTRANASAL; ADOLESCENT; ANALGESICS, OPIOID; CALIBRATION; CHILD; CHILD, PRESCHOOL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FEMALE; HALF-LIFE; HEROIN; HUMANS; INJECTIONS, INTRAVENOUS; LIMIT OF DETECTION; MALE; MICROCHEMISTRY; REPRODUCIBILITY OF RESULTS; SOLID PHASE MICROEXTRACTION; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TANDEM MASS SPECTROMETRY; TIME FACTORS;

EID: 77955479478     PISSN: 01464760     EISSN: 01464760     Source Type: Journal    
DOI: 10.1093/jat/34.4.177     Document Type: Article

References (75)

1. A.I. Al-Asmari and R.A. Anderson. Method for quantification of opioids and their metabolites in autopsy blood by liquid chromatography-tandem mass spectrometry. J. Anal. Toxicol. 31: 394- 408 (2007).
2. E.J. Rook, M.J. Hillebrand, H. Rosing, J. M. van Ree, and J.H. Beijnen. The quantitative analysis of heroin, methadone and their metabolites and the simultaneous detection of cocaine, acetylcodeine and their metabolites in human plasma by high-performance liquid chromatography coupled with tandem mass spectrometry. J. Chromatogr. B Analyt. Technol. Biomed. Life. Sci. 24: 213-221(2005).
3. E.J. Rook, A.D. Huitema, W. van den Brink, J.M. van Ree, and J.H. Beijnen. Population pharmacokinetics of heroin and its major metabolites. Clin. Pharmacokinet. 45: 401-417 (2006).
4. K.M. Rentsch, G.A. Kullak-Ublick, C. Reichel, P.J. Meier, and K. Fattinger. Arterial and venous pharmacokinetics of intravenous heroin in subjects who are addicted to narcotics. Clin. Pharmacol. Ther. 70: 237-246 (2001).
5. D.A. Barrett, D.P. Barker, N. Rutter, M. Pawula, and P.N. Shaw. Morphine, morphine-6-glucuronide and morphine-3-glucuronide pharmacokinetics in newborn infants receiving diamorphine infusions. Br. J. Clin. Pharmacol. 41: 531-537 (1996).
6. J.M. Kendall and V.S. Latter. Intranasal diamorphine as an alternative to intramuscular morphine: pharmacokinetic and pharmacodynamic aspects. Clin. Pharmacokinet. 42: 501-513 (2003).
7. E.J. Rook, A. Juitema, W. Brink, J. Ree, and J. Beijnen. Pharma-cokinetics and pharmacokinetic variability of heroin and its metabolites: review of the literature. Curr. Clin. Pharmacol. 1: 109-118 (2006).
8. F. Girardin, K.M. Rentsch, M.A. Schwab, M. Maggiorini, C. PauliMagnus, G.A. Kullak-Ublick, P.J. Meier, and K. Fattinger. Pharmacokinetics of high doses of intramuscular and oral heroin in narcotic addicts. Clin. Pharmacol. Ther. 74: 341-352 (2003).
9. S. Paterson, N. Lintzeris, T.B. Mitchell, R. Cordero, L. Nestor, and J. Strang. Validation of techniques to detect illicit heroin use in patients prescribed pharmaceutical heroin for the management of opioid dependence. Addiction 100: 1832-1839 (2005).
10. F.M. Fairlie, L. Marshall, J.J. Walker, and D. Elbourne. Intramuscular opioids for maternal pain relief in labour: a randomised controlled trial comparing pethidine with diamorphine. Br. J. Obstet. Gynaecol. 106: 1181-1187 (1999).
11. M. Teesson, J. Ross, S. Darke, M. Lynskey, R. Ali, A. Ritter, and R. Cooke. One year outcomes for heroin dependence: findings from the Australian Treatment Outcome Study (ATOS). Drug Alcohol Depend. 83: 174-180 (2006).
12. R.J. McInnes, E. Hillan, D. Clark, and H. Gilmour. Diamorphine for pain relief in labour: a randomised controlled trial comparing intramuscular injection and patient-controlled analgesia. Bjog. 111: 1081-1089 (2004).
13. A. Hallett, F. O'Higgins, V. Francis, and T.M. Cook. Patient-controlled intranasal diamorphine for postoperative pain: an acceptability study. Anaesthesia 55: 532-539 (2000).
14. J. Sawynok. The therapeutic use of heroin: a review of the pharmacological literature. Can. J. Physiol. Pharmacol. 64: 1-6 (1986).
15. D.A. Barrett, A.C. Elias-Jones, N. Rutter, P.N. Shaw, and S.S. Davis. Morphine kinetics after diamorphine infusion in premature neonates. Br. J. Clin. Pharmacol. 32: 31-37 (1991).
16. J.M. Kendall, B.C. Reeves, and V.S. Latter. Multicentre randomised controlled trial of nasal diamorphine for analgesia in children and teenagers with clinical fractures. Br. Med. J. 322: 261-265 (2001).
17. E.J. Cone, B.A. Holicky, T.M. Grant, W.D. Darwin, and B.A. Goldberger. Pharmacokinetics and pharmacodynamics of intranasal "snorted" heroin. J. Anal. Toxicol. 17: 327-337 (1993).
18. M.H. Hanna, S.J. Peat, M. Woodham, A. Knibb, and C. Fung. Analgesic efficacy and CSF pharmacokinetics of intrathecal morphine-6-glucuronide: comparison with morphine. Br. J. Anaesth. 64: 547-550 (1990).
19. K. Hewett, A.H. Dickenson, and H.J. McQuay. Lack of effect of morphine-3-glucuronide on the spinal antinociceptive actions of morphine in the rat: an electrophysiological study. Pain 53: 59- 63 (1993).
20. R. Kaushik, B. Levine, and W.R. LaCourse. A brief review: HPLC methods to directly detect drug glucuronides in biological matrices (Part I). Anal. Chim. Acta 556: 255-266 (2006).
21. E.J. Cone, P. Welch, J.M. Mitchell, and B.D. Paul. Forensic drug testing for opiates: I. Detection of 6-acetylmorphine in urine as an indicator of recent heroin exposure; drug and assay considerations and detection times. J. Anal. Toxicol. 15: 1-7 (1991).
22. M. Von Euler, T. Villen, J.O. Svensson, and L. Stahle. Interpretation of the presence of 6-monoacetylmorphine in the absence of morphine-3-glucuronide in urine samples: evidence of heroin abuse. Ther. Drug Monit. 25: 645-648 (2003).
23. O.H. Drummer. Postmortem toxicology of drugs of abuse. Forensic Sci. Int. 142: 101-113 (2004).
24. L. Antonilli, F. Semeraro, C. Suriano, L. Signore, and P. Nencini. High levels of morphine-6-glucuronide in street heroin addicts. Psychopharmacol. 170: 200-204 (2003).
25. S. Pichini, I. Altieri, M. Pellegrini, P. Zuccaro, and R. Pacifici. The role of liquid chromatography-mass spectrometry in the determination of heroin and related opioids in biological fluids. Mass Spectrom. Rev. 18: 119-130 (1999).
26. D.E. Selley, C.C. Cao, T. Sexton, J.A. Schwegel, T.J. Martin, and S.R. Childers. mu Opioid receptor-mediated G-protein activation by heroin metabolites: evidence for greater efficacy of 6-monoacetylmorphine compared with morphine. Biochem. Pharmacol. 62: 447-455 (2001).
27. C.E. Inturrisi, M. Schultz, S. Shin, J.G. Umans, L. Angel, and E.J. Simon. Evidence from opiate binding studies that heroin acts through its metabolites. Life Sci. 33: 773-776 (1983).
28. G. Skopp, B. Ganssmann, E.J. Cone, and R. Aderjan. Plasma concentrations of heroin and morphine-related metabolites after intranasal and intramuscular administration. J. Anal. Toxicol. 21: 105-111 (1997).
29. J.K. Coller, L.L. Christrup, and A.A. Somogyi. Role of active metabolites in the use of opioids. Eur. J. Clin. Pharmacol. 65: 121-139 (2009).
30. R. Osborne, S. Joel, and M. Slevin. Morphine intoxication in renal failure; the role of morphine-6-glucuronide. Br. Med. J. 293: 1101 (1986).
31. M.L. Smith, E.T. Shimomura, J. Summers, B.D. Paul, A.J. Jenkins, W.D. Darwin, and E.J. Cone. Urinary excretion profiles for total morphine, free morphine, and 6-acetylmorphine following smoked and intravenous heroin. J. Anal. Toxicol. 25: 504-514 (2001).
32. S. Kidd, S. Brennan, R. Stephen, R. Minns, and T. Beattie. Comparison of morphine concentration-time profiles following intravenous and intranasal diamorphine in children. Arch. Dis. Child. 94: 974-978 (2009)
33. J.A. Wilson, J.M. Kendall, and P. Cornelius. Intranasal diamorphine for paediatric analgesia: assessment of safety and efficacy. J. Accid. Emerg. Med. 14: 70-72 (1997).
34. M. Ward, G. Minto, and J.M. Alexander-Williams. A comparison of patient-controlled analgesia administered by the intravenous or intranasal route during the early postoperative period. Anaesthesia 57: 48-52 (2002).
35. Clinical effectiveness committee, British Association for Emergency Medicine. Guideline for the Management of Pain in Children (2004). http://www.emergencymed.org.uk/BAEM/CEC/assets/cec_pain_in_children.pdf (accessed June 2008).
36. B.K. Matuszewski, M.L. Constanzer, and C.M. Chavez-Eng. Strategies for the assessment of matrix effect in quantitative bioanalytical methods based on HPLC-MS/MS. Anal. Chem. 75: 3019- 3030 (2003).
37. SOFT/AAFS. Forensic Toxicology Laboratory Guidelines. 2006 version. http://www.softtox.org/docs/Guidelines%202006%202020Final.pdf.
38. UNODC. Validation of Analytical Methodology and Calibration of Equipment used for Testing of Illicit Drugs in Seized Materials and Biological Specimens; 2009.
39. A.C. Moffat, M.D. Ossleton, B. Widdop, and L.Y. Galichet. Clarke's Analysis of Drugs and Poisons: Methadology and Analytical Techniques, Validation of New Method. Pharmaceutical Press, London, U.K., 2004.
40. F. Bressolle, M. Bromet-Petit, and M. Audran. Validation of liquid chromatographic and gas chromatographic methods. Applications to pharmacokinetics. J. Chromatogr. B. Biomed. Appl. 686: 3-10 (1996).
41. F.T. Peters. Stability of analytes in biosamples-an important issue in clinical and forensic toxicology? Anal. Bioanal. Chem. 388: 1505-1519 (2007).
42. B.A. Goldberger, W.D. Darwin, T.M. Grant, A.C. Allen, Y.H. Caplan, and E.J. Cone. Measurement of heroin and its metabolites by isotope-dilution electron-impact mass spectrometry. Clin. Chem. 39: 670-675 (1993).
43. B.A. Goldberger, Y.H. Caplan, T. Maguire, and E.J. Cone. Testing human hair for drugs of abuse. III. Identification of heroin and 6-acetylmorphine as indicators of heroin use. J. Anal. Toxicol. 15: 226-231 (1991).
44. W.L. Wang, W.D. Darwin, and E.J. Cone. Simultaneous assay of cocaine, heroin and metabolites in hair, plasma, saliva and urine by gas chromatographymass spectrometry. J. Chromatogr. B Biomed. Appl. 660: 279-290 (1994).
45. J.G. Guillot, M. Lefebvre, and J.P. Weber. Determination of heroin, 6-acetylmorphine, and morphine in biological fluids using their propionyl derivatives with ion trap GC-MS. J. Anal. Toxicol. 21: 127-133 (1997).
46. P.P. Rop, F. Grimaldi, J. Burle, M.N. De Saint Leger, and A. Viala. Determination of 6-monoacetylmorphine and morphine in plasma, whole blood and urine using high-performance liquid chromatography with electrochemical detection. J. Chromatogr. B. Biomed. Appl. 661: 245-253 (1994).
47. M.E. Capella-Peiro, D. Bose, M. Gil-Agusti, J. Esteve-Romero, and S. Carda-Broch. Direct injection determination of benzoylecgonine, heroin, 6-monoacetylmorphine and morphine in serum by MLC. J. Chromatogr. A 1073: 277-283 (2005).
48. D. Bourquin, T. Lehmann, R. Hammig, M. Buhrer, and R. Brenneisen. High-performance liquid chromatographic monitoring of intravenously administered diacetylmorphine and morphine and their metabolites in human plasma. J. Chromatogr. B Biomed. Sci. Appl. 694: 233-238 (1997).
49. R. Dams, C.M. Murphy, W.E. Lambert, and M.A. Huestis. Urine drug testing for opioids, cocaine, and metabolites by direct injection liquid chromatography/tandem mass spectrometry. Rapid Commun. Mass Spectrom. 17: 1665-1670 (2003).
50. P. Zuccaro, R. Ricciarello, S. Pichini, R. Pacifici, I. Altieri, M. Pellegrini, and G. D'Ascenzo. Simultaneous determination of heroin 6-monoacetylmorphine, morphine, and its glucuronides by liquid chromatography-atmospheric pressure ionspray-mass spectrometry. J. Anal. Toxicol. 21: 268-277 (1997).
51. P. Kintz, R. Brenneisen, P. Bundeli, and P. Mangin. Sweat testing for heroin and metabolites in a heroin maintenance program. Clin. Chem. 43: 736-739 (1997).
52. J. Smeraglia, S.F. Baldrey, and D. Watson. Matrix effects and selectivity issues in LC-MS-MS. Chromatographia 55: 95-99 (2002).
53. Z. Yan, N. Maher, R. Torres, C. Cotto, B. Hastings, M. Dasgupta, R. Hyman, N. Huebert, and G.W. Caldwell. Isobaric metabolite interferences and the requirement for close examination of raw data in addition to stringent chromatographic separations in liquid chromatography/tandem mass spectrometric analysis of drugs in biological matrix. Rapid Commun. Mass Spectrom. 22: 2021- 2028 (2008).
54. P. Marquet. Systematic toxicological analysis with LC-MS. In Applications of LC-MS in Toxicology, A. Polettini, Ed. Pharmaceutical Press, London, U.K., 2006, pp 111-130.
55. M. Vogeser and C. Seger. A decade of HPLC-MS/MS in the routine clinical laboratory-goals for further developments. Clin. Biochem. 41(9): 649-662 (2008).
56. R. Karinen, J.M. Andersen, A. Ripel, I. Hasvold, A.B. Hopen, J. Morland, and A.S. Christophersen. Determination of heroin and its main metabolites in small sample volumes of whole blood and brain tissue by reversed-phase liquid chromatography- tandem mass spectrometry. J. Anal. Toxicol. 33: 345-350 (2009).
57. M. Gergov, P. Nokua, E. Vuori, and I. Ojanpera. Simultaneous screening and quantification of 25 opioid drugs in post-mortem blood and urine by liquid chromatography-tandem mass spectrometry. Forensic Sci. Int. 186: 36-43 (2009).
58. K. Taylor and S. Elliott. A validated hybrid quadrupole linear iontrap LC-MS method for the analysis of morphine and morphine glucuronides applied to opiate deaths. Forensic Sci. Int. 187: 34- 41 (2009).
59. B.D. Paul, J.M. Holler, T.P. Lyons, and M.R. Past. Stable isotopes as valid components for identification of drugs in biological specimens. J. Anal. Toxicol. 31: 447-452 (2007).
60. R.A. de Zeeuw and J.P. Franke. 'General unknown' analysis. In Handbook of Analytical Separations, Vol. 2, Ch. 16, J.B. Maciej, Ed. Elsevier Science B.V., Atlanta, GA, 2000, pp 567-599.
61. C. Baumann, M.A. Cintora, M. Eichler, E. Lifante, M. Cooke, A. Przyborowska, and J.M. Halket. A library of atmospheric pressure ionization daughter ion mass spectra based on wideband excitation in an ion trap mass spectrometer. Rapid Comm. Mass Spectrom. 14: 349-356 (2000).
62. E. Gustavsson, M. Andersson, N. Stephanson, and O. Beck. Validation of direct injection electrospray LC-MS/MS for confirmation of opiates in urine drug testing. J. Mass Spectrom. 42: 881- 889 (2007).
63. J.M. Halket, D. Waterman, A.M. Przyborowska, R.K. Patel, P.D. Fraser, and P.M. Bramley. Chemical derivatization and mass spectral libraries in metabolic profiling by GC/MS and LC/MS/MS. J. Exp. Bot. 56: 219-243 (2005).
64. S.Gao, Z.P. Zhang, and H.T. Karnes. Sensitivity enhancementinliquid chromatography/atmospheric pressure ionization mass spectrometry using derivatization and mobile phase additives. J. Chromatogr.BAnalyt. Technol. Biomed. Life Sci. 825: 98-110 (2005).
65. F.T. Peters, O.H. Drummer, and F. Musshoff. Validation of new methods. Forensic Sci. Int. 165: 216-224 (2007).
66. A.I. Al-Asmari, R.A. Anderson, and G.A. Cooper. Oxycodone-related fatalities in the west of Scotland. J. Anal. Toxicol. 33: 423- 432 (2009).
67. A.I. Al-Asmari and R.A. Anderson. Comparison of nonhydrolysis and hydrolysis methods for the determination of buprenorphine metabolites in urine by liquid chromatography-tandem mass spectrometry. J. Anal. Toxicol. 39: 744-753 (2008).
68. A.J. Jenkins, R.M. Keenan, J.E. Henningfield, and E.J. Cone. Pharmacokinetics and pharmacodynamics of smoked heroin. J. Anal. Toxicol. 18: 317-330 (1994).
69. A.J. Jenkins, J.M. Oyler, and E.J. Cone. Comparison of heroin and cocaine concentrations in saliva with concentrations in blood and plasma. J. Anal. Toxicol. 19: 359-374 (1995).
70. L. Bachs, G. Hoiseth, S. Skurtveit, and J. Morland. Heroin-using drivers: importance of morphine and morphine-6-glucuronide on late clinical impairment. Eur. J. Clin. Pharmacol. 62: 905-912 (2006).
71. C.E. Inturrisi, M.B. Max, K.M. Foley, M. Schultz, S.U. Shin, and R.W. Houde. The pharmacokinetics of heroin in patients with chronic pain. N. Engl. J. Med. 310: 1213-1217 (1984).
72. T.B. Mitchell, N. Lintzeris, A. Bond, and J. Strang. Feasibility and acceptability of an intranasal diamorphine spray as an alternative to injectable diamorphine for maintenance treatment. Eur. Addict. Res. 12: 91-95 (2006).
73. E. Gyr, R. Brenneisen, D. Bourquin, T. Lehmann, D. Vonlanthen, and I. Hug. Pharmacodynamics and pharmacokinetics of intravenously, orally and rectally administered diacetylmorphine in opioid dependents, a two-patient pilot study within a heroin-assisted treatment program. Int. J. Clin. Pharmacol. Ther. 38: 486- 491 (2000).
74. M.G. Klous, A.D. Huitema, E.J. Rook, M.J. Hillebrand, V.M. Hendriks, W. Van den Brink, J.H. Beijnen, and J.M. Van Ree. Pharmacokinetic comparison of two methods of heroin smoking: 'chasing the dragon' versus the use of a heating device. Eur. Neuropsychopharmacol.15: 263-269 (2005).
75. E.J. Rook, J.M. van Ree, W. van den Brink, M.J. Hillebrand, A.D. Huitema, V.M. Hendriks, and J.H. Beijnen. Pharmacokinetics and pharmacodynamics of high doses of pharmaceutically prepared heroin, by intravenous or by inhalation route in opioid-dependent patients. Basic Clin. Pharmacol. Toxicol. 98: 86-96 (2006).