The Analysis of Thebaine in Urine for the Detection of Poppy Seed Consumption

Abstract

The consumption of poppy seeds in various foods may lead to a positive opiate result in urine subjected to testing for drugs of abuse. As a natural constituent of poppy seeds, thebaine was investigated as a possible marker for poppy seed consumption. Poppy seeds were examined for opiate content by gas chromatography-ion trap mass spectrometry (GC-MS) after extraction with methanol. Urine samples spiked with thebaine and urine from subjects given 11 g of poppy seeds were tested for the presence of thebaine, codeine, and morphine. Street heroin, one morphine and one codeine tablet, and urine from individuals who had used heroin were also examined for thebaine. Urine specimens were screened by enzyme immunoassay (EMIT) and confirmed for thebaine by GC-MS using a solid-phase extraction method. The GC-MS assay showed a linear response over a range of 1-100 ng/mL and a limit of detection of 0.5 ng/mL. Thebaine was detectable in the urine of poppy seed eaters in concentrations ranging from 2 to 81 ng/mL. Because thebaine was absent in powdered drugs and the urine of true opiate drug users, thebaine is proposed as a direct marker for poppy seed use.

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

“…Cassella et al [13] reported positive results, while ElSohly et al [12] reported negative ones. Also at variance were reports on the amenability of thebaine to trimethylsilyl (TMS) derivatization.…”

“…Thebaine (Fig. 1), a constituent of both opium and poppy seeds, had been suggested as a urinary marker to differentiate between heroin use and the use of poppy seed-containing foods [12][13][14][15][16], which are common in North America and western European countries. Because thebaine is present at much higher concentrations in opium (0.1-2.5% w/w) [17] than in the poppy seeds (0.00003-0.0014% w/w) [12], it should be targeted as a marker of opium use.…”

“…Also at variance were reports on the amenability of thebaine to trimethylsilyl (TMS) derivatization. While Cassella et al [13] reported that 1 3 this alkaloid did not form a TMS derivative with bis(trimethylsilyl)trifl uoroacetamide (BSTFA) due to lack of functional hydrogen sites, Chen et al [18] reported the formation of a TMS derivative at position 5 ( Fig. 1), when the alkaloid was reacted with trimethylchlorosilane (TMCS) in the presence of tetramethylethylenediamine.…”

GC-MS detection and tentative characterization of two noscapine metabolites in human urine and their potential as markers for opium and illicit heroin use

“…These include reticuline [11], neopine [12], and thebaine for opium, and 6-monoacetylmorphine (6-MAM) [14] and acetylcodeine [15] for heroin. Thebaine has been recommended as a marker of poppy seed ingestion in differentiation from heroin use [16], and because it is present in a much higher content in opium than in poppy seeds, it can be also used as a marker of opium ingestion. In differentiation between opium use and illicit heroin use, when the latter cannot be confi rmed through the detection of 6-MAM and/or acetylcodeine because of their very narrow windows of detection [14,15], a marker inclusion/exclusion approach is recommended.…”

Development of chromatographic methods for thebaine detection and quantification along with some of related alkaloid derivatives

“…There are also other methods described in the literature, such as oxidative colorimetric analysis [22], determination of opiates by circular dichroism [23], colorimetric determination [24], TLC analysis of opiate alkaloids and drugs [25,26], ELISA (enzyme-linked immunosorbent assay) analysis of thebaine [27], FTIR spectroscopy of opiates and chemometric analysis [28], differential pulse polarography [29] and even a voltammetric analysis of thebaine [30]. (6) and noscapine (7) T a b l e 2 [31], gas chromatography-ion trap mass spectrometry (GC-MS) analysis [32], liquid chromatographicatmospheric pressure chemical ionization mass spectrometric analysis [33] or HPLC analysis [34,35], GC-MS analysis [36][37][38][39]. Alkaloids are also being analyzed in environmental studies to trace the pollution of the environment [40].…”