Synthesis and stability study of a new major metabolite of gamma-hydroxybutyric acid

Ida Nymann Petersen, Jesper Langgaard Kristensen, Christian Tortzen, Torben Breindahl, Daniel Sejer Pedersen

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12 Citationer (Scopus)

Abstract

¿-Hydroxybutanoic acid (GHB) is used as a date-rape drug, which renders the victims unconscious and defenceless. Intoxications are very difficult to detect for forensic scientists due to rapid metabolism to endogenous levels of GHB. We recently discovered a new major metabolite, 2, of GHB (1) that could potentially extend the analytical detection window for GHB intoxications. Herein we disclose synthetic procedures based on a Koenigs–Knorr glucuronidation approach that provides GHB glucuronide 2 and a deuterium-labelled analogue d4-2 of high purity suitable for analytical chemistry. In addition, we have assessed the stability of GHB glucuronide 2 by mimicking the natural pH range for urine, which is of importance in the development of new analytical methods. Using NMR we show that GHB glucuronide 2 is highly stable towards aqueous hydrolysis within the pH range normally observed for urine even at elevated temperature.
OriginalsprogEngelsk
TidsskriftBeilstein Journal of Organic Chemistry
Vol/bind9
Sider (fra-til)641-646
Antal sider6
ISSN2195-951X
DOI
StatusUdgivet - 2013

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