title: A potential new metabolite of gamma-hydroxybutyrate: sulfonated gamma-hydroxybutyric acid.
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.
authors.affiliation: Institute of Legal and Traffic Medicine, University Hospital, Voss-Str. 2, Heidelberg, 69115, Germany.
authors.forename: Stephanie
authors.initials: S
authors.lastname: Hanisch
authors.affiliation: Institute of Legal and Traffic Medicine, University Hospital, Voss-Str. 2, Heidelberg, 69115, Germany. nicole.stachel@med.uni-heidelberg.de.
authors.forename: Nicole
authors.initials: N
authors.lastname: Stachel
authors.affiliation: Institute of Legal and Traffic Medicine, University Hospital, Voss-Str. 2, Heidelberg, 69115, Germany. gisela_skopp@med.uni-heidelberg.de.
authors.forename: Gisela
authors.initials: G
authors.lastname: Skopp
mesh_terms: D000759:Adjuvants, Anesthesia / Q000737:chemistry* / Q000652:urine; D002853:Chromatography, Liquid; D006801:Humans; D006885:Hydroxybutyrates / Q000737:chemistry* / Q000652:urine; D013058:Mass Spectrometry; D012978:Sodium Oxybate / Q000737:chemistry* / Q000652:urine; D015813:Substance Abuse Detection; D013431:Sulfates / Q000737:chemistry* / Q000652:urine
chemical_list: D000759:Adjuvants, Anesthesia; D006885:Hydroxybutyrates; D013431:Sulfates; C111420:4-hydroxybutyric acid; D012978:Sodium Oxybate
keywords: Gamma-hydroxy butyrate; LC-MS/MS; Sulfate; Urine