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Severe 25E-NBOH intoxication associated with MDPHP intake: a case report, metabolism study, and literature review

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Abstract

N-Benzylphenethylamine derivatives are 5-HT2A receptor agonists with hallucinogenic properties, including NBOMe (N-(2-methoxybenzyl)-2-(3,4,5-trimethoxyphenyl)ethan-1-amine) and NBOH (2-(((2,5-dimethoxyphenethyl)amino)methyl)phenol). We reported here the case of a 23-year-old man who presented a serotoninergic syndrome and a loss of consciousness following the consumption of a powder labelled as 25I-NBOH. Toxicological analyses of biological samples were carried out using a liquid chromatography high-resolution mass spectrometry. Two new psychoactive substances were identified and confirmed with certified reference materials: 25E-NBOH (2-(((4-ethyl-2,5-dimethoxyphenethyl)amino)methyl)phenol) and MDPHP (1-(benzo[d][1,3]dioxol-5-yl)-2-(pyrrolidin-1-yl)hexan-1-one). Pharmaceuticals administered to the patient during his medical care were found in plasma and urine. 25E-NBOH and MDPHP concentrations were respectively at 2.3 ng/mL and 3.4 ng/mL in plasma, and 25.7 ng/mL and 30.5 ng/mL in urine. 25I-NBOH (2-(((4-iodo-2,5-dimethoxyphenethyl)amino)methyl)phenol) was specifically searched in both samples and was not detected. These results are discussed along with a literature review on human cases of exposure to N-benzylphenethylamine derivatives. Using molecular networking approach, we propose the first 25E-NBOH metabolism study using authentic biological samples (plasma and urine). We described seven metabolites (M1 to M7), including two phase I (m/z 330.172; m/z 288.160) and five phase II metabolites (m/z 464.191, m/z 478.207, m/z 492.223, m/z 508.218; m/z 396.156). The M6 (m/z 492.223) was the most intense ion detected in plasma and urine and could be proposed as a relevant 25E-NBOH consumption marker. Overall, we described an original case of 25E-NBOH poisoning and identified metabolites that could potentially be used as consumption markers to detect 25E-NBOH intoxications with a higher confidence level and probably a longer detection window.

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Author information

Authors and Affiliations

  1. INSERM, INRAE, CHU Rennes, Institut NuMeCan (Nutrition, Metabolism and Cancer), PREVITOX Network, F-35033, Rennes, France

    Romain Pelletier, Thomas Gicquel, Isabelle Morel & Brendan Le Daré

  2. Rennes University Hospital, Clinical and Forensic Toxicology Laboratory, F-35033, Rennes, France

    Romain Pelletier, Thomas Gicquel & Isabelle Morel

  3. AP-HM, DepaICMrtment of Intensive Care, Réanimation des Urgences, Medicine Intensive & Reanimation, Timone University Hospital, Marseille, France

    Julien Carvelli

  4. Bataillon des Marins Pompiers, Groupement Santé, Service Médical d’Urgence, 9 Boulevard de Strasbourg, 13233, Marseille Cedex 20, France

    Pierre Balaz

  5. Aix Marseille Univ, APHM, INSERM, INMED UMR 901, La Timone University Hospital, Legal Medicine Department, 13005, Marseille, France

    Anne-Laure Pelissier-Alicot

  6. LAT LUMTOX Laboratory, Lyon, France

    Charline Bottinelli

  7. Laboratory of Pharmacokinetics and Toxicology, La Timone University Hospital, 264 rue Saint Pierre, 13385, Marseille Cedex 5, France

    Caroline Solas & Nicolas Fabresse

  8. Rennes University Hospital, Pharmacy department, F-35033, Rennes, France

    Brendan Le Daré

  9. Aix Marseille University, INSERM, IRD, SESSTIM, Economic and Social Sciences of Health and Medical Information Processing, Marseille, France

    Nicolas Fabresse

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  1. Romain Pelletier
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Contributions

Conceptualization: NF, RP, TG, CB; methodology: NF, RP, TG, CB; formal analysis and investigation: all authors; writing — original draft preparation: NF, RP, TG, BLD; writing — review and editing: all authors; supervision: NF, TG.

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Correspondence to Romain Pelletier.

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Ethical approval was waived in view of the retrospective nature of the study, and all the procedures being performed were part of the routine care.

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Pelletier, R., Gicquel, T., Carvelli, J. et al. Severe 25E-NBOH intoxication associated with MDPHP intake: a case report, metabolism study, and literature review. Int J Legal Med 138, 815–822 (2024). https://doi.org/10.1007/s00414-023-03151-6

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