Please use this identifier to cite or link to this item: doi:10.22028/D291-30905
Title: In vitro metabolic fate of nine LSD-based new psychoactive substances and their analytical detectability in different urinary screening procedures
Author(s): Wagmann, Lea
Richter, Lilian
Kehl, Tobias
Wack, Franziska
Pettersson Bergstrand, Madeleine
Brandt, Simon D.
Stratford, Simon
Maurer, Hans H.
Meyer, Markus R.
Language: English
Title: Analytical and Bioanalytical Chemistry
Volume: 411
Pages: 4751–4763
Publisher/Platform: Springer
Year of Publication: 2019
Free key words: Lysergamides
DDC notations: 500 Science
570 Life sciences, biology
Publikation type: Journal Article
Abstract: The market of new psychoactive substances (NPS) is characterized by a high turnover and thus provides several challenges for analytical toxicology. The analysis of urine samples often requires detailed knowledge about metabolism given that parent compounds either may be present only in small amounts or may not even be excreted. Hence, knowledge of the metabolism of NPS is a prerequisite for the development of reliable analytical methods. The main aim of this work was to elucidate for the first time the pooled human liver S9 fraction metabolism of the nine d-lysergic acid diethylamide (LSD) derivatives 1-acetyl-LSD (ALD-52), 1-propionyl-LSD (1P-LSD), 1-butyryl-LSD (1B-LSD), N6-ethyl-nor-LSD (ETH-LAD), 1-propionyl-N6-ethyl-nor-LSD (1P-ETH-LAD), N6-allyl-nor-LSD (AL-LAD), N-ethyl-N-cyclopropyl lysergamide (ECPLA), (2′S,4′S)-lysergic acid 2,4-dimethylazetidide (LSZ), and lysergic acid morpholide (LSM-775) by means of liquid chromatography coupled to high-resolution tandem mass spectrometry. Identification of the monooxygenase enzymes involved in the initial metabolic steps was performed using recombinant human enzymes and their contribution confirmed by inhibition experiments. Overall, N-dealkylation and hydroxylation, as well as combinations of these steps predominantly catalyzed by CYP1A2 and CYP3A4, were found. For ALD-52, 1P-LSD, and 1B-LSD, deacylation to LSD was observed. The obtained mass spectral data of all metabolites are essential for reliable analytical detection particularly in urinalysis and for differentiation of the LSD-like compounds as biotransformations also led to structurally identical metabolites. However, in urine of rats after the administration of expected recreational doses and using standard urine screening approaches, parent drugs or metabolites could not be detected.
DOI of the first publication: 10.1007/s00216-018-1558-9
Link to this record: urn:nbn:de:bsz:291--ds-309052
ISSN: 1618-2650
Date of registration: 22-May-2020
Faculty: M - Medizinische Fakultät
Department: M - Experimentelle und Klinische Pharmakologie und Toxikologie
Professorship: M - Prof. Dr. Markus Meyer
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