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

doi:10.3762/bjoc.9.72

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

11 Citations (Scopus)

Abstract

γ-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.

Original language	English
Journal	Beilstein Journal of Organic Chemistry
Volume	9
Pages (from-to)	641-646
Number of pages	6
ISSN	2195-951X
DOIs	https://doi.org/10.3762/bjoc.9.72
Publication status	Published - 2 Apr 2013

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title = "Synthesis and stability study of a new major metabolite of gamma-hydroxybutyric acid",

abstract = "γ-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.",

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T1 - Synthesis and stability study of a new major metabolite of gamma-hydroxybutyric acid

AU - Petersen, Ida Nymann

AU - Kristensen, Jesper Langgaard

AU - Tortzen, Christian

AU - Breindahl, Torben

AU - Pedersen, Daniel Sejer

PY - 2013/4/2

Y1 - 2013/4/2

N2 - γ-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.

AB - γ-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.

U2 - 10.3762/bjoc.9.72

DO - 10.3762/bjoc.9.72

M3 - Journal article

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SN - 2195-951X

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EP - 646

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

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

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