Abstract
Detection of gamma-hydroxybutyric acid (GHB) became crucial in many clinical and forensic settings due to its increasing use for recreational purposes and drug-facilitated sexual assault. Its narrow window of detection of about 3–12 h in urine represents a major problem. Analogous to ethyl glucuronide, the recently identified GHB-glucuronide exhibits a longer window of detection than the parent drug. It appeared reasonable that a sulfonated metabolite of GHB (GHB-SUL) will also be formed. Due to the lack of an appropriate standard, GHB was incubated with a human liver cytosolic fraction to produce GHB-SUL. Following development of a liquid chromatography/tandem mass spectrometry (LC-MS/MS) assay to measure GHB and GHB-SUL, authentic urine samples (n = 5) were tested for GHB-SUL. These investigations revealed detectable signals of both GHB and GHB-SUL, strongly indicating that GHB is not only glucuronidated but also sulfonated. Given that sulfonated metabolites generally have longer half-life times than the corresponding free drugs, GHB-SUL may serve as a biomarker of GHB misuse along with its glucuronide.
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References
Andresen-Streichert H, Sprys N, Schmoldt A, Mueller A, Iwersen-Bergmann S (2010) Gamma-hydroxy butyrate in serum and urine: additional data supporting current cut-off recommendations. Forensic Sci Int 200:93–99
Carter LP, Pardi D, Gorsline J, Griffiths RR (2009) Illicit gamma-hydroxybutyrate (GHB) and pharmaceutical sodium oxybate (Xyrem®): differences in characteristics and misuse. Drug Alcohol Depend 104:1–10
Galloway GP, Frederick S, Staggers FE, Gonzales M, Stalcup S, Smith DE (1997) Gamma-hydroxybutyrate: an emerging drug of abuse that causes physical dependence. Addiction 92:89–96
Hall J, Moore C (2008) Drug facilitated sexual assault—a review. J Forensic Legal Med 15:291–297
Wood DM, Davies S, Puchnarewicz M, Johnston A, Dargan PI (2012) Acute toxicity associated with the recreational use of the ketamine derivative methoxetamine. Eur J Clin Pharmacol 68:853–856
Petersen IN, Tortzen C, Kristensen JL, Pedersen DS, Breindahl T (2013) Identification of a new metabolite of GHB: gamma-hydroxybutyric acid glucuronide. J Anal Toxicol 37:291–297
Dziadosz M (2015) γ-Hydroxybutyrate analysis in human serum with liquid chromatography-tandem mass spectrometry on the basis of M3 mass transition. J Chromatogr B 986–987:8–11
Dresen S, Kempf J, Weinmann W (2007) Prevalence of γ-hydroxybutyrate (GHB) in serum samples of amphetamine, methamphetamine and ecstasy impaired drivers. Forensic Sci Int 173:112–116
Ingels ASM, Wille SM, Samyn N, Lambert WE, Stove CP (2014) Screening and confirmation methods for GHB determination in biological fluids. Anal Bioanal Chem 406:3553–3577
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Stephanie Hanisch and Nicole Stachel contributed equally to this work.
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Hanisch, S., Stachel, N. & Skopp, G. A potential new metabolite of gamma-hydroxybutyrate: sulfonated gamma-hydroxybutyric acid. Int J Legal Med 130, 411–414 (2016). https://doi.org/10.1007/s00414-015-1235-x
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DOI: https://doi.org/10.1007/s00414-015-1235-x