Improved GC/MS analysis of opiates with use of oxime-TMS derivatives

Cremese, Michael; Wu, Aihua; Cassella, Gina; O'Connor, Edward F.; Rymut, Kathy; Hill, Dennis W.

doi:10.1016/s1353-1131(99)90225-0

Cited by 3 publications

(7 citation statements)

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“…These characteristics certainly have great potential to improve the resolving power of a selected chromatographic system. Improved resolutions of opioids by sequential derivatization have been reported by other researchers [3][4][5][6]. More comprehensive studies are currently underway in the Table 4 Relative intensity and cross-contribution data a of ions b with potential for designating the analyte and the adapted internal standard-phenylpropanolamine/ phenylpropanolamine-d 3 Fig.…”

Section: Chromatographic Characteristicsmentioning

confidence: 82%

“…Analytes possessing more than one reactive site allow for simultaneous or sequential application of multiple derivatization reagents. Merits of this approach have been demonstrated in a very limited number of studies [2][3][4][5][6], in which improved chromatographic performance characteristics were emphasized. In this current study, mass spectrometric characteristics of the singly and multiply derivatized amphetamines will be examined and compared, focusing on the ''cross-contributions'' to the intensity of the ion designated for the analyte by the internal standard, and vice versa.…”

Section: Introductionmentioning

confidence: 99%

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Mass spectrometric data characteristics of commonly abused amphetamines with sequential derivatization at two active sites

Wang

Chye

Liu

et al. 2006

Forensic Science International

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Section: Chromatographic Characteristicsmentioning

confidence: 82%

Section: Introductionmentioning

confidence: 99%

Mass spectrometric data characteristics of commonly abused amphetamines with sequential derivatization at two active sites

Wang

Chye

Liu

et al. 2006

Forensic Science International

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“…2, However, when forming TMS derivatives of ketone-containing opiates, such as hydrocodone, hydromorphone, and oxycodone, numerous derivatives for each compound can be formed due to keto-enol tautamerization. , 22 Tautamerization can be avoided by an initial pre-derivatization reaction with hydroxylamine. Hydroxylamine reacts with the ketone moiety of these opiates to form an oxime, which then forms a TMS derivative.…”

Section: Methods Validationmentioning

confidence: 99%

“…Hydroxylamine reacts with the ketone moiety of these opiates to form an oxime, which then forms a TMS derivative. 22,23 After evaluating numerous derivatizing agents, we chose to employ TMS and oxime-TMS derivatives due to the efficiency of the derivatizing reaction. We initially investigated the use of a % hydroxylamine solution for oxime formation, but this concentration did not produce consistent results across a broad opiate concentration range.…”

Section: Methods Validationmentioning

confidence: 99%

Poppy Seed Consumption or Opiate Use: The Determination of Thebaine and Opiates of Abuse in Postmortem Fluids and Tissues

Johnson¹,

Lewis²,

Hattrup³

2005

PsycEXTRA Dataset

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Opiates are some of the most widely prescribed drugs in America. Some opiate compounds are highly addictive and are often abused. Opiate abuse transcends all social, racial, and economic boundaries. Demonstrating the presence or absence of opiate compounds in postmortem fluids and/or tissues derived from fatal civil aviation accidents can have serious legal consequences and may help determine the cause of impairment and/or death. However, the consumption of poppy seed products can result in a positive opiate drug test. Therefore, the interpretation of positive opiate results must be viewed with caution. We have developed a simple method for the simultaneous determination of 8 opiate compounds from one extraction. These compounds are hydrocodone, dihydrocodeine, codeine, oxycodone, hydromorphone, 6monoacetylmorphine, morphine, and thebaine. The inclusion of thebaine is notable as it is an indicator of poppy seed consumption and may help explain morphine/codiene positives in cases where no opiate use was indicated. This method incorporates a Zymark RapidTrace™ automated solid-phase extraction system, gas chromatography/mass spectrometry, and trimethyl silane (TMS) and oxime-TMS derivitives. The limits of detection ranged from 0.78-12.5 ng/mL. The linear dynamic range for most analytes was 6.25-1600 ng/mL. The extraction efficiencies ranged from 70-103%. We applied this method to 8 separate aviation fatalities where opiate compounds had previously been detected. The specimens analyzed for the determination of these 8 opiate compounds were blood, urine, liver, kidney, and skeletal muscle. This method has proven to be simple, robust, and accurate for the simultaneous determination of 8 opiate compounds in postmortem fluids and tissues.

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“…Evaporate the solvent to dryness under a stream of nitrogen at 50°C. Reconstitute with ethyl acetate for GC-MS. [1][2][3][4][5][6][7][8][9]13 Hydroxylimino To the dried analyte (see the procedure described in the 'General step' entry), add 2 ml 0.1 M acetate buffer pH D 4.5 and 0.5 ml 10% NH 2 OH. Cap the tube, vortex, and incubate at 60°C with in a heating block for 1 h. Add 800 µl NaHCO 3 extraction for 10 min and add 3 ml methyl dichloride.…”

Section: Methoxyiminomentioning

confidence: 99%

GC‐MS analysis of multiply derivatized opioids in urine

2007

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Opiates such as hydrocodone, hydromorphone, oxycodone, noroxycodone, and oxymorphone reportedly may interfere with the analysis of morphine and codeine. The analysis of these compounds themselves also is an important issue. Thus, double derivatization approaches utilizing methoxyamine and hydroxylamine to first form oxime products with keto-opiates, followed by the derivatization with trimethylsilyl (TMS) or propionyl groups, have been developed for the simultaneous analysis of these compounds. However, these studies have not included all compounds of interest and resulted in inadequate chromatographic resolution or significant intensity cross-contribution between the ions designating the analyte and its deuterated internal standard for certain compounds. By exploring three-step derivatization approaches with the combination of various derivatization groups and orders, this study concluded that application of methoxyimino/propionyl/TMS groups, in the order listed, facilitated the simultaneous analysis of eight opiates (morphine, 6-acetylmorphine, hydromorphone, oxymorphone, codeine, hydrocodone, oxycodone and noroxycodone) in urine samples, achieving satisfactory limits of quantitation and detection. In addition, the adapted approach resulted in two usable products for morphine and codeine providing alternatives, should interferences render any of these products non-usable.

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Improved GC/MS analysis of opiates with use of oxime-TMS derivatives

Cited by 3 publications

References 0 publications

Mass spectrometric data characteristics of commonly abused amphetamines with sequential derivatization at two active sites

Mass spectrometric data characteristics of commonly abused amphetamines with sequential derivatization at two active sites

Poppy Seed Consumption or Opiate Use: The Determination of Thebaine and Opiates of Abuse in Postmortem Fluids and Tissues

GC‐MS analysis of multiply derivatized opioids in urine

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