title: The chemical interconversion of GHB and GBL: forensic issues and implications.
abstract: In this work, the interconversion of GHB and GBL in a variety of aqueous media was studied. The effects of solution pH and time were determined by spiking GHB or GBL into pure water and buffered aqueous solutions, and determining the GHB and GBL contents at various time intervals. The degree of GBL hydrolysis to GHB was determined for several commercial aqueous-based GBL products, and further studied as a function of time. The effects of temperature and time were also determined for five commercial beverages spiked with GHB or GBL. GHB and GBL contents were determined using high performance liquid chromatography (HPLC). GHB and/or GBL confirmations were made using gas chromatography-mass spectrometry (GC-MS) and/or infrared spectroscopy (IR). Solution pH, time, and storage temperature were determined to be important factors affecting the rate and extent of GBL hydrolysis to GHB. Under strongly alkaline conditions (pH 12.0), GBL was completely converted to GHB within minutes. In pure water, GBL reacted to form an equilibrium mixture comprising ca. 2:1 GBL:GHB over a period of months. This same equilibrium mixture was established from either GHB or GBL in strongly acidic solution (pH 2.0) within days. A substantial portion of GBL (ca. 1/3) was hydrolyzed to GHB in aqueous-based GBL products, and in spiked commercial beverages, after ambient storage for a period ranging from several weeks to several months. Heat increased and refrigeration decreased the rate of GBL hydrolysis relative to ambient conditions. These studies show that hydrolysis of GBL to GHB does occur in aqueous-based solutions, with samples and time frames that are relevant to forensic testing. Implications for forensic testing and recommendations are discussed.
authors.affiliation: U.S. Food and Drug Administration Forensic Chemistry, Cincinnati, OH 45237, USA.
authors.forename: L A
authors.initials: LA
authors.lastname: Ciolino
authors.forename: M Z
authors.initials: MZ
authors.lastname: Mesmer
authors.forename: R D
authors.initials: RD
authors.lastname: Satzger
authors.forename: A C
authors.initials: AC
authors.lastname: Machal
authors.forename: H A
authors.initials: HA
authors.lastname: McCauley
authors.forename: A S
authors.initials: AS
authors.lastname: Mohrhaus
mesh_terms: D015107:4-Butyrolactone / Q000032:analysis / Q000737:chemistry*; D001628:Beverages; D002851:Chromatography, High Pressure Liquid; D004355:Drug Stability; D008401:Gas Chromatography-Mass Spectrometry; D006801:Humans; D006863:Hydrogen-Ion Concentration; D006885:Hydroxybutyrates / Q000032:analysis / Q000737:chemistry*; D013287:Illicit Drugs / Q000032:analysis / Q000737:chemistry*; D012996:Solutions; D017550:Spectroscopy, Fourier Transform Infrared; D014481:United States; D014486:United States Food and Drug Administration; D014867:Water / Q000737:chemistry
chemical_list: D006885:Hydroxybutyrates; D013287:Illicit Drugs; D012996:Solutions; D014867:Water; C111420:4-hydroxybutyric acid; D015107:4-Butyrolactone