GC-MS detection and characterization of thebaine as a urinary marker of opium use

Forensic Toxicology

Volumn 25, Issue 2, 2007, Pages 62-68

  El Haj, Babiker M ^a   Al Amri, Abdelkader M ^a   Ali, Heyam S ^b   Ahmed, Iqbal ^b  

^a Sharjah Police Forensic Sci Lab   (United Arab Emirates)

^b DUBAI PHARMACY COLLEGE   (United Arab Emirates)

Author keywords

GC MS; Opium use; Oral route; Thebaine; Trimethylsilyl derivatization; Urinary marker

Indexed keywords

CODEINE; METHADONE; OPIATE; THEBAINE; TRIMETHYLSILYL DERIVATIVE;

ARTICLE; CONTROLLED STUDY; DIAGNOSTIC ACCURACY; GAS CHROMATOGRAPHY; HEROIN DEPENDENCE; HUMAN; MAJOR CLINICAL STUDY; MASS SPECTROMETRY; MOLECULAR STABILITY; OPIATE ADDICTION; PRIORITY JOURNAL; URINALYSIS;

PAPAVER;

EID: 38049047038     PISSN: 18608965     EISSN: 18608973     Source Type: Journal    
DOI: 10.1007/s11419-007-0028-4     Document Type: Article

References (29)

1. Al-Amri AM, Smith RM, El-Haj BM, Juma'a MAH (2004) GC-MS detection and characterization of reticuline as opium use marker. Forensic Sci Int 142:61-69
2. Al-Amri AM, Smith RM, El-Haj BM (2005) The GC-MS detection and characterization of neopine resulting from opium use and codeine metabolism and its potential as an opiate-product-use marker. Anal Bioanal Chem 382:839-835
3. Al-Amri AM (2004) Marker compounds in urine for opiate product use. Doctoral thesis, Department of Chemistry, Loughborough University, UK
4. Yeh SY, Gorodetzky CW, McQuinn RL (1976) Urinary excretion of heroin and its metabolites in man. J Pharmacol Exp Ther 196:249-256
5. Brenneisen R, Hasler F, Wursch D (2002) Acetylcodeine as a urinary marker to differentiate the use of street heroin and pharmaceutical heroin. J Anal Toxicol 26:561-566
6. Sweetman SC (ed) (2002) Martindale the complete drug reference, 33rd edn. Pharmaceutical, London, p 1333
7. Bogusz MJ, Maier RD, Erkens M, Kohls U (2001) Detection of non-prescription heroin markers in urine with liquid chromatography-atmospheric pressure chemical ionization mass spectrometry. J Anal Toxicol 25:431-438
8. Mclachlan-Troup N, Taylor GW, Trathen BC (2001) Diamorphine treatment for opiate dependence: putative markers of contaminant heroin misuse. Addict Biol 6:223-231
9. El-Haj BM, Al-Amri AM, Ali HS (2007) GC-MS detection and tentative characterization of two noscapine metabolites and their potential as markers for opium and illicit heroin use. Forensic Toxicol 25:22-29 DOI 10.1007/s11419-007-0023-9
10. Tsunoda N, Yoshimura H (1979) Metabolic fate of noscapine, II. Isolation and identification of novel metabolites produced by C-C bond cleavage. Xenobiotica 9:181-187
11. Tsunoda N, Yoshimura H (1981) Metabolic fate of noscapine III: further studies on identification and determination of the metabolites. Xenobiotica 11:23-32
12. ElSohly HN, Stanford DF, Jones AB, ElSohly MA, Snyder H, Pedersen C (1988) Gas chromatography/mass spectrometric analysis of morphine and codeine in human urine of poppy seed eaters. J Forensic Sci 33:347-355
13. Cassella G, Wu AHB, Shaw BR, Hill DW (1997) The analysis of thebaine in urine for the detection of poppy seed consumption. J Anal Toxicol 21:376-383
14. Lewis RJ, Johnson RD, Hattrup RA (2005) Simultaneous analysis of thebaine, 6-MAM and six abused opiates in postmortem fluids and tissues using Zymark automated solidphase extraction and gas chromatography-mass spectrometry. J Chromatogr B 822:137-145
15. Meadway C, George S, Braithwaite R (1998) Opiate concentration following the ingestion of poppy seed products-evidence for 'the poppy seed defense'. Forensic Sci Int 96:29-38
16. Johnson RD, Lewis J, Hattrup RA (2005) Poppy seed consumption or opiate use: the determination of thebaine and opiates of abuse in postmortem fluids and tissues. DOT/FAA/AM-05/11, Office of Aerospace Medicine, Washington DC, 20591. www.cami.jccbi.gov/aam-400a/Abstracts/2005/FULL20%TEXT/0511.pdf. Cited 7 December 2006
17. Schiff PL Jr (2002) Opium and its alkaloids. Am J Pharm Educ 66:186-194
18. Chen W, Wu H, Bernard D, Metcalf MD, Deschamps JR, Flippen L, Mackerell AD Jr, Coop A (2003) Rearrangement of 5-trimethylsilylthebaine on treatment with L-selectride: an efficient synthesis of (+)-bractazonine. J Org Chem 68:1929-1932
19. Kushnir MM, Crockett DK, Nelson G, Urry FM (1999) Comparison of four derivatizing reagents for 6-acetylmorphine GC-MS analysis. J Anal Toxicol 23:262-269
20. Penton Z (2002) Derivatization of drugs prior to GC-MS analysis. Varian Product Information Bulletin, Application Note number MSP 2218, Palo Alto, CA
21. Yinon J (1995) Forensic applications of mass spectrometry. CRC, London, p 33
22. Regis Technologies (2000) GC derivatization. www.registech.com/gc/ gcderrev.pdf. Cited 21 December 2006
23. Little JL (1999) Artifacts in trimethylsilyl derivatization reactions and ways to avoid them. J Chromatogr A 844:1-22
24. Chen W, Parrish DA, Deschamps JR, Coop A (2005) Functionalization of the 6,14-bridge of the orvinols 1. Preparation of Diels-Alder reaction of 7-phenylsilylthebaine. Helv Chim Acta 88:822-829
25. Soine WH (1986) Clandestine drug synthesis. Med Res Rev 6:41-74
26. 6-monoacetyl morphine in urine samples by GC-MS as evidence for heroin use. J Anal Toxicol 9:2-7
27. Cone EJ, Welch P, Mitchell JM, Paul D (1991) 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
28. Westermeyer J (1987) Cultural patterns of drug and alcohol use: an analysis of host and agent in the cultural environment. UNODC Bull Narcotics 2:11-27
29. Wu F-F, Dobberstein RH (1977) Quantitative determination of thebaine in Papaver bracteatum by high-pressure liquid chromatography. J Chromatogr 140:65-70