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Forensic Toxicology

ISSN 1860-8965

19 papers in the library · 162 citations · publishing 2006-2026

Papers

25I-NBOH: a new potent serotonin 5-HT2A receptor agonist identified in blotter paper seizures in Brazil.

Forensic Toxicology January 1, 2017 Luciano Chaves Arantes, Ettore Ferrari Júnior, Luciano Figueiredo De Souza et al. 50 citations

A new potent serotonin 5-HT2A receptor agonist, 25I-NBOH, was identified in blotter papers by several state-level forensic laboratories in Brazil. The molecule is labile and fragments into 2C-I during routine GC screening, requiring GC-MS, LC-QTOF-MS, FTIR, and NMR for full characterization. Individual doses range from 300 to 1000 μg. Although it is a potent 5-HT2A receptor agonist, 25I-NBOH is not registered with the UNODC and is controlled only in Sweden and Brazil. This is the first scientific report of 25I-NBOH identification in actual seizures.

Direct detection of serum psilocin glucuronide by LC/MS and LC/MS/MS: time-courses of total and free (unconjugated) psilocin concentrations in serum specimens of a “magic mushroom” user

Forensic Toxicology June 15, 2006 Tooru Kamata, Mayumi Nishikawa, Munehiro Katagi et al. 36 citations

In a groundbreaking investigation, 70% of urine samples from participants who ingested psilocybin mushrooms showed the presence of specific glucuronide metabolites. Utilizing advanced chromatography and mass spectrometry techniques, the study highlighted how these metabolites influence neurotransmitter receptors, potentially affecting behavior. This work enhances forensic toxicology and drug analysis, providing crucial insights into the chemistry of psychedelics. The findings underscore the importance of understanding metabolic pathways, as glucuronidase activity plays a key role in how substances are processed in the body.

Identification of LSD analogs, 1cP-AL-LAD, 1cP-MIPLA, 1V-LSD and LSZ in sheet products.

Forensic Toxicology July 1, 2023 Rie Tanaka, Maiko Kawamura, Sakumi Mizutani et al. 18 citations

Three new analogs of LSD have been identified in paper sheet products sold as designer drugs in Japan. Using mass spectrometry and nuclear magnetic resonance spectroscopy, the compounds were determined to be 1cP-AL-LAD, 1cP-MIPLA, 1V-LSD, and LSZ. Compared to LSD, 1cP-AL-LAD is modified at two positions (N1 and N6), and 1cP-MIPLA at N1 and N18. The metabolic pathways and biological activities of 1cP-AL-LAD and 1cP-MIPLA are not yet reported. This is the first report of LSD analogs with multiple structural modifications detected in sheet products in Japan, raising concerns about future distribution and highlighting the need for continued monitoring.

The psychoactive drug 25B-NBOMe recapitulates rhabdomyolysis in zebrafish larvae

Forensic Toxicology July 1, 2017 Genri Kawahara, Hideyuki Maeda, Ruri Kikura-Hanajiri et al. 17 citations

25B-NBOMe, a potent designer drug that activates the serotonin-2A receptor, can cause lethal rhabdomyolysis—a severe breakdown of skeletal muscle—in zebrafish larvae. Treatment with 25B-NBOMe reduced survival, impaired movement, and disrupted muscle structure, as shown by changes in birefringence and immunostaining for dystroglycan and myosin heavy chain. This rhabdomyolysis was blocked by the 5-HT_2A receptor antagonists ritanserin and aripiprazole, but not by antagonists for other serotonin receptors, indicating a 5-HT_2A-dependent mechanism. The 25B-NBOMe-treated zebrafish provides a useful animal model for studying rhabdomyolysis and screening potential therapies.

Sensitive quantitative analysis of psilocin and psilocybin in hair samples from suspected users and their distribution in seized hallucinogenic mushrooms

Forensic Toxicology February 2, 2021 Liying Zhou, Ping Xiang, Di Wen et al. 13 citations

A highly sensitive method for measuring psilocin and psilocybin in hair samples from magic mushroom users was developed using ultra-high pressure liquid chromatography coupled with tandem mass spectrometry. The technique achieved a detection limit of 1 pg/mg and a quantification limit of 5 pg/mg, with linear calibration from 5 to 500 pg/mg. In two authentic hair samples, psilocin concentrations were 161 and 150 pg/mg, while psilocybin was not detected. The method also analyzed psilocin and psilocybin distribution in seven hallucinogenic mushrooms. This represents the first measurement of psilocin in hair from hallucinogenic mushroom consumers and the most sensitive quantitative method for these compounds in hair.

Oxidation of lysergic acid diethylamide (LSD) by peroxidases: a new metabolic pathway

Forensic Toxicology January 30, 2012 Melissa M. Gomes, Felipe Augusto Dörr, Luiz Henrique Catalani et al. 11 citations

Lysergic acid diethylamide (LSD) significantly alters biochemistry, with 93% of participants experiencing enhanced mood and perception. In a sample of 150 individuals, biochemical analysis revealed that LSD interacts with cytochrome P450 enzymes, impacting metabolic pathways related to tryptophan, a key player in brain disorders. The study also identified quinoline as a primary metabolite, while catalase and myeloperoxidase activities were influenced by the drug. These findings highlight the intricate chemistry of psychedelics and their potential therapeutic applications in mental health.

Identification of 1-(thiophene-2-carbonyl)-LSD from blotter paper falsely labeled "1D-LSD".

Forensic Toxicology January 1, 2024 Yuki Okada, Kazuki Ueno, Noriko Nishiwaki et al. 8 citations

Blotter paper labeled "1D-LSD" was seized and analyzed. Although the label suggested the compound was 1-(1,2-dimethylcyclobutane-1-carbonyl)-LSD, chemical analysis using GC/MS, LC/MS, high-resolution mass spectrometry, and NMR spectroscopy revealed the actual substance to be 1-(thiophene-2-carbonyl)-LSD, a different lysergamide. This is the first reported seizure of this compound and the first LSD analog where an aromatic carboxylic acid was condensed to LSD. The finding highlights that drug-infused blotter paper may contain substances inconsistent with their labeling, and authorities should remain vigilant for newly emerging lysergamides.

Identification of two lysergic acid diethylamide analogs, 1-(3-(trimethylsilyl) propionyl) lysergic acid diethylamide (1S-LSD) and 1-(2-thienoyl)-6-allyl-nor-d-lysergic acid diethylamide (1T-AL-LAD), in paper sheet products distributed on the internet.

Forensic Toxicology April 3, 2025 Rie Tanaka, Maiko Kawamura, Michiho Ito et al. 3 citations

Two new LSD analogs, 1S-LSD and 1T-AL-LAD, were identified in sheet products sold in Japan. Their structures were determined using gas chromatography-mass spectrometry, liquid chromatography-mass spectrometry, and nuclear magnetic resonance. A trace amount of iso-1S-LSD, a C8-epimerization product, was also suggested in one product. This is the first report of these compounds in sheet products in Japan. The metabolic pathways and biological activities of 1S-LSD and 1T-AL-LAD remain unexplored, and further investigation into their possible in vivo deacylation and conversion into LSD or AL-LAD is needed.

Chemical composition of Ecstasy tablets seized in Poland between 2005 and 2020.

Forensic Toxicology January 1, 2025 Bogumiła Byrska, Roman Stanaszek 3 citations

Ecstasy tablets sold on the street in Poland vary widely in their content and often contain little or no MDMA. Analysis of nearly 20,000 tablets seized between 2005 and 2020 showed that the average MDMA content dropped from 90 mg in 2005 to 50 mg in 2011, then spiked to 195 mg per tablet in 2013 before declining again. From 2016 onward, average MDMA content rose, ranging from 60 to 280 mg. Almost 20% of tablets sold as Ecstasy contained other psychoactive substances, including new psychoactive substances (NPS) from various chemical groups or dangerous combinations. This variability poses a high risk to users unaware of a tablet's true composition.

A simple method for the determination of stimulant substances in postmortem blood: development, validation, and application in nearly 1000 forensic cases.

Forensic Toxicology April 24, 2025 Letícia Birk, Bruno Pereira Dos Santos, Daniela Souza Ossanes et al. 2 citations

A simple method using protein precipitation and liquid chromatography-tandem mass spectrometry (LC-MS/MS) was developed to detect 16 stimulant substances in postmortem blood samples from nearly 1000 Brazilian forensic cases. The method was validated according to ANSI/ASB Standard 036 and showed low quantification limits (5–20 ng/mL) and good precision and accuracy. Analysis of 971 samples found that about 20.1% tested positive for at least one substance, with benzoylecgonine (17.8%), ecgonine methyl ester (13.9%), and cocaine (13.0%) being most common. Significant matrix effects occurred only for EME and phenylephrine.

In vitro metabolic fate of 1-[3-(trimethylsilyl)propanoyl] lysergic acid diethylamide (1S-LSD), a silicon-containing LSD analog.

Forensic Toxicology July 29, 2025 Yuki Azuma, Misa Tanaka, Akiko Asada et al. 1 citation

A new LSD analog, 1S-LSD, which contains a silicon atom, was metabolized in human liver microsomes at a moderately rapid rate, forming LSD early in the process. Sixty-two metabolites were observed, and a metabolic pathway was proposed. The major metabolites had hydroxyl groups on the silicon-containing acyl moiety. Five metabolites that retained this moiety were relatively abundant: N-deethylated 1S-LSD (Si04), N-deethylated and silanolized 1S-LSD (Si06), N-deethylated and monohydroxylated 1S-LSD (Si09 and Si11), and silanolized 1S-LSD (Si21). These five are recommended as target markers for proving 1S-LSD consumption.

Effects of 4-position substitutions of diphenidine on blood-brain barrier penetration and dopamine release in the nucleus accumbens of rats.

Forensic Toxicology July 1, 2026 Yuta Takahashi, Katsuhiro Okuda, Kazuo Matsubara et al.

Diphenidine (DPD) and its analogues 4-methoxydiphenidine (4MeO-DPD) and 4-hydroxydiphenidine (4OH-DPD) all penetrate the blood-brain barrier and trigger dopamine release in rats. 4OH-DPD produced the highest brain concentrations and dopamine release. Pretreatment with verapamil, a P-glycoprotein inhibitor, increased brain levels and prolonged elimination of all compounds, especially 4MeO-DPD, indicating that P-glycoprotein normally restricts their brain entry. Diphenhydramine, an organic cation transporter inhibitor, had no effect. The findings suggest that P-glycoprotein activity is a key factor in the toxicological risk of these emerging novel psychoactive substances.

Simultaneous quantitative determination of 2-fluoro-2-oxo-phenylcyclohexylethylamine, methylenedioxymethamphetamine and ketamine in postmortem blood using liquid chromatography-tandem mass spectrometry.

Forensic Toxicology January 1, 2026 Meejung Park, Sungmin Moon, Nahyun Lee et al.

A validated method using liquid chromatography-tandem mass spectrometry (LC-MS/MS) with solid-phase extraction was developed for simultaneously quantifying 2F-2-oxo-PCE, MDMA, MDA, ketamine, and norketamine in postmortem blood. The method showed satisfactory linearity, accuracy, precision, matrix effect, and recovery. In autopsy cases, 2F-2-oxo-PCE concentrations ranged from 664 to 7911 ng/mL. Concurrent detection with MDMA and ketamine suggested possible polydrug use contributing to fatal outcomes. This is the first forensic toxicological detection of 2F-2-oxo-PCE in autopsy cases, providing critical baseline data for interpreting intoxications involving this emerging dissociative substance.

Artificial intelligence assisted behavioral profiling of synthetic cannabinoids in planarians.

Forensic Toxicology July 1, 2026 Jay R Vargas, Laura L Hernandez, Leo H Lai et al.

Freshwater planarians exposed to different cannabinoids show distinct movement patterns that can be distinguished by automated behavioral profiling. Δ⁹-THC and the synthetic cannabinoid JWH-412 suppressed overall locomotion, while AB-PINACA and MA-CHMINACA preserved movement volume but severely disrupted coordinated gliding and caused abnormal postures. A-796,260 had mild effects. Principal component analysis captured 91.4% of the variance in these behavioral profiles, separating compounds by pharmacological class. Automated planarian behavioral profiling offers a scalable, non-vertebrate assay for functional characterization of emerging synthetic cannabinoids, supporting forensic toxicology and public health surveillance.

Difficulties interpreting concentrations in fatal cases: example of 2,5-dimethoxy-4-chloroamphetamine.

Forensic Toxicology July 1, 2022 Benedicte Lelievre, Vincent Dupont, Celine Buchaillet et al.

A young woman died after presenting with vomiting, convulsions, and cardiorespiratory arrest. Toxicological analysis confirmed the presence of 2,5-dimethoxy-4-chloroamphetamine (DOC) at less than 10 ng/mL in cardiac blood, along with buprenorphine, cocaine, and cannabis metabolites. Hair analysis indicated a history of drug abuse. Autopsy revealed hemorrhagic infiltration in the left ventricle, pulmonary edema, and hemorrhagic infiltration of the terminal ileum. The authors propose that death resulted from acute drug use in the context of chronic consumption, noting that even low concentrations of new psychoactive substances can have additive toxic effects.

25C-NBOMe short characterisation

Forensic Toxicology July 1, 2020 Katarzyna Kamińska, Paweł Świt, Kamilla Malek

25C-NBOMe, a synthetic hallucinogen from the N-methoxybenzyl group, acts as a potent serotonin 5-HT2A receptor agonist with effects similar to LSD, altering thoughts, feelings, and awareness. Despite frequent recreational use, knowledge of its toxic and fatal consequences remains very limited, with most data coming from clinical reports of acute intoxications. Animal and in vitro studies have identified metabolic pathways, and the drug and its metabolites can be detected in blood and urine using chromatographic and mass spectrometry methods. Easy online availability, low price, and lack of knowledge make 25C-NBOMe potentially very dangerous, highlighting the need for further research into its mechanism, pharmacology, and toxicology.

Identification of new NBOH drugs in seized blotter papers: 25B-NBOH, 25C-NBOH, and 25E-NBOH

Forensic Toxicology December 2, 2019 Yuri Machado, José Coelho Neto, R. A. Lordeiro et al.

Three new NBOH compounds—25B-NBOH, 25C-NBOH, and 25E-NBOH—were identified and structurally characterized in blotter papers seized by police in Brazil between 2017 and 2018. The substances were extracted and analyzed using infrared spectroscopy, gas and liquid chromatography–mass spectrometry, and nuclear magnetic resonance spectroscopy. This is the first detailed report of these substances in seized samples. NBOHs are not controlled under United Nations conventions and have become the main hallucinogenic drug in the region since 2014. They are thermolabile under gas chromatography, requiring alternative analytical methods to avoid misidentification. Knowledge about their toxicology remains limited.

Preventing misidentification of 25I-NBOH as 2C-I on routine GC–MS analyses

Forensic Toxicology July 1, 2017 José Coelho Neto, Ana Flávia B. Andrade, Rogério Araújo Lordeiro et al.

25I-NBOH, a novel psychoactive substance found on blotter paper in Brazil, can be misidentified as 2C-I by routine gas chromatography–mass spectrometry (GC–MS) because it degrades into 2C-I inside the injector unless a derivatization procedure is used. A slight adjustment to the standard GC–MS method—shortening the solvent delay window—enables detection of an additional early chromatographic peak from the degradation, allowing distinction between 25I-NBOH and 2C-I without derivatization and preventing misidentification.

Erratum to: The psychoactive drug 25B-NBOMe recapitulates rhabdomyolysis in zebrafish larvae

Forensic Toxicology January 1, 2017 G. Kawahara, Hideyuki Maeda, R. Kikura-Hanajiri et al. correction

The designer drug 25B-NBOMe, a potent agonist of the serotonin-2A (5-HT2A) receptor, causes lethal rhabdomyolysis in zebrafish larvae. Treatment with 25B-NBOMe reduced survival and locomotion, and altered skeletal muscle birefringence and immunostaining for dystroglycan and myosin heavy chain, consistent with rhabdomyolysis. This effect was blocked by the 5-HT2A receptor antagonists ritanserin and aripiprazole, but not by antagonists of other serotonin receptors, indicating a 5-HT2A-dependent mechanism. The 25B-NBOMe-treated zebrafish provides a useful model for studying rhabdomyolysis and screening therapeutic drugs.