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Reactivity of Gamma-Hydroxybutyric Acid (GHB) and Gamm-Butyrolactone (GBL) in Alcohol Solutions

NCJ Number
207705
Journal
Journal of Forensic Sciences Volume: 49 Issue: 6 Dated: November 2004 Pages: 1220-1229
Author(s)
Sinead A. Hennessy B.Sc.; Siobhan M. Moane Ph.D.; Sean D. McDermott Ph.D.
Date Published
November 2004
Length
10 pages
Annotation
This study examined the stability of GBL (gamma-butyrolactone) and GHB (gamma-hydroxybutyric acid) in alcoholic media.
Abstract
There have been reports that GHB, a dose-dependent sedative that can produce unconsciousness, has been used, often in combination with alcohol, to render women more vulnerable to sexual assault. Another related compound that has been similarly abused is GBL, which converts into GHB both in-vivo and in aqueous solution. Since the possession of GHB is illegal and GBL is not, GBL is often substituted for GHB. A description of the materials and methods used to study the stability of GHB and GBL in alcoholic beverages addresses the reagents and standards, sample preparation, HPLC (high performance liquid chromatography) conditions, phosphate buffer preparation, GC (gas chromatography) conditions, MS (mass spectrometry) conditions, spiked beverages, wine samples, tea/coffee, and quantitative calculations. The study found that under acidic conditions, the GBL reacted with ethanol or methanol to produce the corresponding ethyl and methyl esters of GHB. Ester formation was dependent on the type of alcohol, the alcohol content of the solution, and the pH of the solution. Under the same conditions, GHB did not directly yield the corresponding ester when merely in the presence of an alcohol; however, the ester was formed when the conditions were present for the conversion of GHB to GBL followed by subsequent reaction with alcohol. In alcoholic beverage samples spiked with GBL, the expected conversion to GHB occurred, and the formation of the ethyl ester of GHB was also observed in some samples. Wine samples were analyzed for the presence of the ethyl ester of GHB, and the effect of adding GHB/GBL to hot beverages was also examined. 4 tables, 12 figures, and 38 references