Simultaneous identification and quantitation of codeine, morphine, hydrocodone, and hydromorphone in urine as trimethylsilyl and oxime derivatives by gas chromatography–mass spectrometry

Broussard, Larry A.; Presley, Lance; Pittman, T.S.; Clouette, Randy; Wimbish, Gary H.

doi:10.1093/clinchem/43.6.1029

Cited by 50 publications

(14 citation statements)

References 8 publications

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“…Sample Extraction. Quantitative analysis of oxycodone was based upon a previously described method (Broussard et al, 1997;Wolf and Poklis, 2010). This method is routinely performed in our laboratory for the analysis of opiates in blood and tissue samples.…”

Section: Methodsmentioning

confidence: 99%

Ethanol Reversal of Tolerance to the Antinociceptive Effects of Oxycodone and Hydrocodone

Jacob

Poklis

Akbarali

et al. 2017

J Pharmacol Exp Ther

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This study compared the development of tolerance to two orally bioavailable prescription opioids, oxycodone and hydrocodone, to that of morphine, and the reversal of this tolerance by ethanol. Oxycodone (s.c.) was significantly more potent in the mouse tail-withdrawal assay than either morphine or hydrocodone. Oxycodone was also significantly more potent in this assay than hydrocodone when administered orally. Tolerance was seen following chronic subcutaneous administration of each of the three drugs and by the chronic administration of oral oxycodone, but not following the chronic oral administration of hydrocodone. Ethanol (1 g/kg i.p.) significantly reversed the tolerance to the subcutaneous administration of each of the three opioids that developed when given 30 minutes prior to challenge doses. It took twice as much ethanol, when given orally, to reverse the tolerance to oxycodone. We investigated whether the observed tolerance to oxycodone and its reversal by ethanol were due to biodispositional changes or reflected a true neuronal tolerance. As expected, a relationship between brain oxycodone concentrations and activity in the tail-immersion test existed following administration of acute oral oxycodone. Following chronic treatment, brain oxycodone concentrations were significantly lower than acute concentrations. Oral ethanol (2 g/kg) reversed the tolerance to chronic oxycodone, but did not alter brain concentrations of either acute or chronic oxycodone. These studies show that there is a metabolic component of tolerance to oxycodone; however, the reversal of that tolerance by ethanol is not due to an alteration of the biodisposition of oxycodone, but rather is neuronal in nature.

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Section: Methodsmentioning

confidence: 99%

Ethanol Reversal of Tolerance to the Antinociceptive Effects of Oxycodone and Hydrocodone

Jacob

Poklis

Akbarali

et al. 2017

J Pharmacol Exp Ther

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“…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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Simultaneous identification and quantitation of codeine, morphine, hydrocodone, and hydromorphone in urine as trimethylsilyl and oxime derivatives by gas chromatography–mass spectrometry

Cited by 50 publications

References 8 publications

Ethanol Reversal of Tolerance to the Antinociceptive Effects of Oxycodone and Hydrocodone

Ethanol Reversal of Tolerance to the Antinociceptive Effects of Oxycodone and Hydrocodone

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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