Quantification of morphine and its major metabolites M3G and M6G in antemortem and postmortem samples

Biomedical Chromatography

Volumn 28, Issue 9, 2014, Pages 1263-1270

  Oliveira, Ana ^a,b,c   Carvalho, Félix ^a   Pinho, Paula Guedes ^a   Remião, Fernando ^a   Medeiros, Rui ^a,b,c,d,e   Dinis Oliveira, Ricardo Jorge ^a,c,f  

^a UNIVERSITY OF PORTO   (Portugal)

^b PORTUGUESE ONCOLOGY INSTITUTE   (Portugal)

^c INSTITUTO DE INVESTIGAÇÃO E FORMAÇÃO AVANÇADA EM CIÊNCIAS E TECNOLOGIAS DA SAÚDE   (Portugal)

^d UNIVERSIDADE FERNANDO PESSOA   (Portugal)

^e LPCC   (Portugal)

^f University of Porto   (Portugal)

Author keywords

HPLC DAD electrochemical; Metabolism; Morphine; Morphine 3 glucuronide; Morphine 6 glucuronide

Indexed keywords

BIOMOLECULES; CHEMICAL DETECTION; CHROMATOGRAPHIC ANALYSIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METABOLISM; PHASE SEPARATION; POTASSIUM COMPOUNDS; SODIUM DODECYL SULFATE; SULFUR COMPOUNDS;

ELECTROCHEMICALS; GLUCURONIDES; HPLC-DAD-ELECTROCHEMICAL; HPLC/DAD; MORPHINE; MORPHINE-3-GLUCURONIDE; MORPHINE-6-GLUCURONIDE; OPIOIDS; POST-MORTEM SAMPLES; SIDE EFFECT;

METABOLITES;

ACETONITRILE; DODECYL SULFATE SODIUM; MORPHINE; MORPHINE 3 GLUCURONIDE; MORPHINE 6 GLUCURONIDE; POTASSIUM DIHYDROGEN PHOSPHATE; MORPHINE DERIVATIVE; MORPHINE-3-GLUCURONIDE; MORPHINE-6-GLUCURONIDE;

ANIMAL TISSUE; ARTICLE; AUTOPSY; BLOOD SAMPLING; BRAIN; CAVIA PORCELLUS; CONTROLLED STUDY; DRUG BLOOD LEVEL; DRUG BRAIN LEVEL; DRUG LIVER LEVEL; DRUG URINE LEVEL; ELECTROCHEMICAL DETECTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; KIDNEY; LIMIT OF DETECTION; LIVER; MEASUREMENT ACCURACY; NONHUMAN; SOLID PHASE EXTRACTION; TISSUE DISTRIBUTION; URINALYSIS; HUMAN; METABOLISM; POSTMORTEM CHANGE; PROCEDURES; REPRODUCIBILITY; STATISTICAL MODEL;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HUMANS; LIMIT OF DETECTION; LINEAR MODELS; MORPHINE; MORPHINE DERIVATIVES; POSTMORTEM CHANGES; REPRODUCIBILITY OF RESULTS; TISSUE DISTRIBUTION;

EID: 84905570766     PISSN: 02693879     EISSN: 10990801     Source Type: Journal    
DOI: 10.1002/bmc.3158     Document Type: Article

References (34)

1. Acworth IN. The application of HPLC with coulometric electrochemical array detection to the study of natural products and botanicals: from targeted analyses to metabolomics. Planta Medica 2011; 77: SL22.
2. Ary K and Rona K. LC determination of morphine and morphine glucuronides in human plasma by coulometric and UV detection. Journal of Pharmaceutical and Biomedical Analysis 2001; 26: 179-187.
3. Beike J, Köhler H, Brinkmann B and Blaschke G. Immunoaffinity extraction of morphine, morphine-3-glucuronide and morphine-6-glucuronide from blood of heroin victims for simultaneous high-performance liquid chromatographic determination. Journal of Chromatography B: Biomedical Sciences and Applications 1999; 726: 111-119.
4. Bosch ME, Sánchez AR, Rojas FS and Ojeda CB. Morphine and its metabolites: analytical methodologies for its determination. Journal of Pharmaceutical and Biomedical Analysis 2007; 43: 799-815.
5. Bourquin D, Lehmann T, Hammig R, Buhrer M and Brenneisen R. High-performance liquid chromatographic monitoring of intravenously administered diacetylmorphine and morphine and their metabolites in human plasma. Journal of Chromatography B: Biomedical Sciences and Applications 1997; 694: 233-238.
6. Carrupt PA, Testa B, Bechalany A, El Tayar N, Descas P and Perrissoud D. Morphine 6-glucuronide and morphine 3-glucuronide as molecular chameleons with unexpected lipophilicity. Journal of Medicinal Chemistry 1991; 34: 1272-1275.
7. Christrup LL. Morphine metabolites. Acta Anaesthesiologica Scandinavica 1997; 41: 116-122.
8. Costa I, Oliveira A, Guedes de Pinho P, Teixeira HM, Moreira R, Carvalho F and Dinis-Oliveira RJ. Postmortem redistribution of tramadol and o-desmethyltramadol. Journal of Analytical Toxicology 2013; 37: 670-675.
9. Dinis-Oliveira RJ, Carvalho F, Duarte JA, Remiao F, Marques A, Santos A and Magalhaes T. Collection of biological samples in forensic toxicology. Toxicology Mechanisms and Methods 2010; 20: 363-414.
10. Dinis-Oliveira RJ, Carvalho F, Moreira R, Duarte JA, Proenca JB, Santos A and Magalhaes T. Clinical and forensic signs related to opioids abuse. Current Drug Abuse Reviews 2012a; 5: 273-290.
11. Dinis-Oliveira RJ, Santos A and Magalhães T. 'Foam cone' exuding from the mouth and nostrils following heroin overdose. Toxicology Mechanisms and Methods 2012b; 22: 159-160.
12. Edwards SR and Smith MT. Simultaneous determination of morphine, oxycodone, morphine-3-glucuronide, and noroxycodone concentrations in rat serum by high performance liquid chromatography-electrospray ionization-tandem mass spectrometry. Journal of Chromatography, B: Analytical Technologies in the Biomedical and Life Sciences 2005; 814: 241-249.
13. EMA. Guidelines on Bioanalytical Method Validation. European Medicines Agency: London, 2011.
14. Fujita K, Ando Y, Yamamoto W, Miya T, Endo H, Sunakawa Y, Araki K, Kodama K, Nagashima F, Ichikawa W, Narabayashi M, Akiyama Y, Kawara K, Shiomi M, Ogata H, Iwasa H, Okazaki Y, Hirose T and Sasaki Y. Association of UGT2B7 and ABCB1 genotypes with morphine-induced adverse drug reactions in Japanese patients with cancer. Cancer Chemotherapy and Pharmacology 2010; 65: 251-258.
15. Gouveia CA, Oliveira A, Pinho S, Vasconcelos C, Carvalho F, Moreira RF and Dinis-Oliveira RJ. Simultaneous quantification of morphine and cocaine in hair samples from drug addicts by GC-EI/MS. Biomedical Chromatography 2012; 26: 1041-1047.
16. Holthe M, Klepstad P, Zahlsen K, Borchgrevink PC, Hagen L, Dale O, Kaasa S, Krokan HE and Skorpen F. Morphine glucuronide-to-morphine plasma ratios are unaffected by the UGT2B7 H268Y and UGT1A1*28 polymorphisms in cancer patients on chronic morphine therapy. European Journal of Clinical Pharmacology 2002; 58: 353-356.
17. Huwyler J, Rufer S, Küsters E and Drewe J. Rapid and highly automated determination of morphine and morphine glucuronides in plasma by on-line solid-phase extraction and column liquid chromatography. Journal of Chromatography. B, Biomedical Applications 1995; 674: 57-63.
18. Klepstad P, Kaasa S and Borchgrevink PC. Start of oral morphine to cancer patients: effective serum morphine concentrations and contribution from morphine-6-glucuronide to the analgesia produced by morphine. European Journal of Clinical Pharmacology 2000; 55: 713-719.
19. Klepstad P, Dale O, Skorpen F, Borchgrevink PC and Kaasa S. Genetic variability and clinical efficacy of morphine. Acta Anaesthesiologica Scandinavica 2005; 49: 902-908.
20. Kudo K, Ishida T, Nishida N, Yoshioka N, Inoue H, Tsuji A and Ikeda N. Simple and sensitive determination of free and total morphine in human liver and kidney using gas chromatography-mass spectrometry. Journal of Chromatography, B: Analytical Technologies in the Biomedical and Life Sciences 2006; 830: 359-363.
21. Kuo CK, Hanioka N, Hoshikawa Y, Oguri K and Yoshimura H. Species difference of site-selective glucuronidation of morphine. Journal of Pharmacobio-dynamics 1991; 14: 187-193.
22. Meng QC, Soleded Cepeda M, Kramer T, Zou H, Matoka DJ and Farrar J. High-performance liquid chromatographic determination of morphine and its 3- and 6-glucuronide metabolites by two-step solid-phase extraction. Journal of Chromatography B: Biomedical Sciences and Applications 2000; 742: 115-123.
23. Musshoff F, Trafkowski J, Kuepper U and Madea B. An automated and fully validated LC-MS/MS procedure for the simultaneous determination of 11 opioids used in palliative care, with 5 of their metabolites. Journal of Mass Spectrometry 2006; 41: 633-640.
24. Osborne R, Thompson P, Joel S, Trew D, Patel N and Slevin M. The analgesic activity of morphine-6-glucuronide. British Journal of Clinical Pharmacology 1992; 34: 130-138.
25. Pinho S, Oliveira A, Costa I, Gouveia CA, Carvalho F, Moreira RF and Dinis-Oliveira RJ. Simultaneous quantification of tramadol and O-desmethyltramadol in hair samples by gas chromatography-electron impact/mass spectrometry. Biomedical Chromatography 2013; 27: 1003-1011.
26. Ross JR, Rutter D, Welsh K, Joel SP, Goller K, Wells AU, Du Bois R and Riley J. Clinical response to morphine in cancer patients and genetic variation in candidate genes. Pharmacogenomics Journal 2005; 5: 324-336.
27. Samuelsson H, Hedner T, Venn R and Michalkiewicz A. CSF and plasma concentrations of morphine and morphine glucuronides in cancer patients receiving epidural morphine. Pain 1993; 52: 179-185.
28. Santos V, Lopez KJ, Santos LM, Yonamine M, Carmona MJ and Santos SR. Determining plasma morphine levels using GC-MS after solid phase extraction to monitor drug levels in the postoperative period. Clinics (São Paulo, Brazil) 2008; 63: 307-314.
29. Sawyer MB, Innocenti F, Das S, Cheng C, Ramirez J, Pantle-Fisher FH, Wright C, Badner J, Pei D, Boyett JM, Cook E, Jr and Ratain MJ. A pharmacogenetic study of uridine diphosphate-glucuronosyltransferase 2B7 in patients receiving morphine. Clinical Pharmacology and Therapeutics 2003; 73: 566-574.
30. Smith MT, Wright AWE, Williams BE, Stuart G and Cramond T. Cerebrospinal fluid and plasma concentrations of morphine, morphine-3-glucuronide, and morphine-6-glucuronide in patients before and after initiation of intracerebroventricular morphine for cancer pain management. Anesthesia and Analgesia 1999; 88: 109-116.
31. Staub C, Jeanmonod R and Fryc O. Morphine in postmortem blood: its importance for the diagnosis of deaths associated with opiate addiction. International Journal of Legal Medicine 1990; 104: 39-42.
32. Stone AN, Mackenzie PI, Galetin A, Houston JB and Miners JO. Isoform selectivity and kinetics of morphine 3- and 6-glucuronidation by human udp-glucuronosyltransferases: evidence for atypical glucuronidation kinetics by UGT2B7. Drug Metabolism and Disposition 2003; 31: 1086-1089.
33. Takata Y, Muto G. Flow coulometric detector for liquid chromatography. Analytical Chemistry 1973; 45: 1864-1868.
34. WHO. Cancer Pain Relief, 2nd edn. World Health Organisation: Geneva, 1996.