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

Research output: Contribution to journal › Journal article › Research › peer-review

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Synthesis and stability study of a new major metabolite of gamma-hydroxybutyric acid. / Petersen, Ida Nymann; Kristensen, Jesper Langgaard; Tortzen, Christian; Breindahl, Torben; Pedersen, Daniel Sejer.

In: Beilstein Journal of Organic Chemistry, Vol. 9, 2013, p. 641-646.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Petersen, IN, Kristensen, JL, Tortzen, C, Breindahl, T & Pedersen, DS 2013, 'Synthesis and stability study of a new major metabolite of gamma-hydroxybutyric acid', Beilstein Journal of Organic Chemistry, vol. 9, pp. 641-646. https://doi.org/10.3762/bjoc.9.72

APA

Petersen, I. N., Kristensen, J. L., Tortzen, C., Breindahl, T., & Pedersen, D. S. (2013). Synthesis and stability study of a new major metabolite of gamma-hydroxybutyric acid. Beilstein Journal of Organic Chemistry, 9, 641-646. https://doi.org/10.3762/bjoc.9.72

Vancouver

Petersen IN, Kristensen JL, Tortzen C, Breindahl T, Pedersen DS. Synthesis and stability study of a new major metabolite of gamma-hydroxybutyric acid. Beilstein Journal of Organic Chemistry. 2013;9:641-646. https://doi.org/10.3762/bjoc.9.72

Author

Petersen, Ida Nymann ; Kristensen, Jesper Langgaard ; Tortzen, Christian ; Breindahl, Torben ; Pedersen, Daniel Sejer. / Synthesis and stability study of a new major metabolite of gamma-hydroxybutyric acid. In: Beilstein Journal of Organic Chemistry. 2013 ; Vol. 9. pp. 641-646.

Bibtex

@article{70c12342db47495494acfb64aaef910b,
title = "Synthesis and stability study of a new major metabolite of gamma-hydroxybutyric acid",
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.",
author = "Petersen, {Ida Nymann} and Kristensen, {Jesper Langgaard} and Christian Tortzen and Torben Breindahl and Pedersen, {Daniel Sejer}",
year = "2013",
doi = "10.3762/bjoc.9.72",
language = "English",
volume = "9",
pages = "641--646",
journal = "Beilstein Journal of Organic Chemistry",
issn = "2195-951X",
publisher = "Beilstein - Institut zur Foerderung der Chemischen Wissenschaften",

}

RIS

TY - JOUR

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

Y1 - 2013

N2 - ¿-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 - ¿-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

C2 - 23616808

VL - 9

SP - 641

EP - 646

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

SN - 2195-951X

ER -

ID: 45105629