Synthesis and stability study of a new major metabolite of gamma-hydroxybutyric acid
Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt
¿-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.
Originalsprog | Engelsk |
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Tidsskrift | Beilstein Journal of Organic Chemistry |
Vol/bind | 9 |
Sider (fra-til) | 641-646 |
Antal sider | 6 |
ISSN | 2195-951X |
DOI | |
Status | Udgivet - 2013 |
ID: 45105629