Forensic Toxicology最新文献

{"title":"Toxic effects of AB-CHMINACA on liver and kidney and detection of its blood level in adult male mice.","authors":"Soheir Ali Mohammad, Rasha Elhaddad Ali Mousa, Sahar Mohamed Gebril, Khaled Masoud Mohamed Masoud, Rania Ahmad Radwan","doi":"10.1007/s11419-023-00670-0","DOIUrl":"10.1007/s11419-023-00670-0","url":null,"abstract":"<p><strong>Background: </strong>AB-CHMINACA is a cannabimimetic indazole derivative. In 2013, it was reported in different countries as a substance of abuse.</p><p><strong>Purpose: </strong>This study evaluated the subacute toxic effects of AB-CHMINACA on the liver and kidneys and measured its blood level in adult male mice.</p><p><strong>Methods: </strong>The histological and biochemical subacute toxic effects on the liver and kidneys were assessed after four weeks of daily intraperitoneal injections of one of the following doses: 0.3 mg/kg, 3 mg/kg, or 10 mg/kg as the highest dose in adult male albino mice. In addition, the blood concentration level of AB-CHMINACA was determined by GC-MS-MS.</p><p><strong>Results: </strong>The histological effects showed congestion, hemorrhage, degeneration, and cellular infiltration of the liver and kidney tissues. Considering the control groups as a reference, biochemical results indicated a significant increase in the serum AST only in the highest dose group, while the ALT and creatinine levels did not significantly change. The mean values of AB-CHMINACA blood levels were 3.05 ± 1.16, 15.08 ± 4.30, and 54.43 ± 8.70 ng/mL for the three treated groups, respectively, one hour after the last dose of intraperitoneal injection. The calibration curves were linear in the 2.5-500 ng/mL concentration range. The intra-assay precision and accuracy of the method were less than 7.0% (RSD) and ± 9.2% (Bias).</p><p><strong>Conclusion: </strong>This research supports the available case reports on AB-CHMINACA toxicity that it has low lethality; still, the chronic administration causes evident liver and kidney histotoxic effects even at low doses with unnoticeable clinical effects in mice.</p>","PeriodicalId":12329,"journal":{"name":"Forensic Toxicology","volume":null,"pages":null},"PeriodicalIF":2.8,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10808145/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"10362154","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Identification of 1-(thiophene-2-carbonyl)-LSD from blotter paper falsely labeled \"1D-LSD\".","authors":"Yuki Okada, Kazuki Ueno, Noriko Nishiwaki, Toshihiko Nishimura, Hiroki Segawa, Tadashi Yamamuro, Kenji Kuwayama, Kenji Tsujikawa, Tatsuyuki Kanamori, Yuko T Iwata","doi":"10.1007/s11419-023-00668-8","DOIUrl":"10.1007/s11419-023-00668-8","url":null,"abstract":"<p><strong>Purpose: </strong>Since the mid-2010s, lysergic acid diethylamide (LSD) analogs made for substance abuse have periodically emerged. In this case, three pieces of blotter paper labeled \"1D-LSD\" and presumably impregnated with this LSD analog, were seized. Several websites indicate that 1D-LSD is 1-(1,2-dimethylcyclobutane-1-carbonyl)-LSD. Because this analog is much more difficult to synthesize than previously reported LSD analogs, we doubted that the blotter paper contained 1D-LSD. Herein, we determined the structure of the absorbed compound.</p><p><strong>Methods: </strong>One of the seized specimens was extracted and analyzed using gas chromatography/mass spectrometry (GC/MS), liquid chromatography/mass spectrometry (LC/MS), high-resolution mass spectrometry (HRMS), and nuclear magnetic resonance (NMR) spectroscopy to estimate the extract components. The estimated compound was then synthesized, yielding an authentic standard. The contents of the seized specimens were identified using authentic standard analysis with GC/MS, LC/MS, and NMR spectroscopy.</p><p><strong>Results: </strong>Instrumental analyses confirmed the active compound to be 1-(thiophene-2-carbonyl)-LSD, which was inconsistent with the labeling on drug-infused blotter paper.</p><p><strong>Conclusion: </strong>As in this case, similar blotter paper analyses should consider the possibility of a mismatch between the label and ingredient. To the authors' knowledge, this is the first case report in which 1-(thiophene-2-carbonyl)-LSD was seized and the first seizure of an LSD analog in which an aromatic carboxylic acid had been condensed to LSD. This type of lysergamide may become prevalent in the near future, and we should remain alert for newly appearing lysergamides.</p>","PeriodicalId":12329,"journal":{"name":"Forensic Toxicology","volume":null,"pages":null},"PeriodicalIF":2.2,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"9764487","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Simultaneous determination of water-soluble herbicides using hydrophilic interaction liquid chromatography-mass spectrometry.","authors":"Daisuke Watanabe, Shuhei Sonoda, Hikoto Ohta","doi":"10.1007/s11419-023-00669-7","DOIUrl":"10.1007/s11419-023-00669-7","url":null,"abstract":"<p><strong>Purpose: </strong>The analysis of water-soluble herbicides, including glyphosate (Glyp), glufosinate (Gluf), paraquat (PQ), and diquat (DQ), is time-consuming and expensive because they cannot be analyzed using general toxicological screening methods. Thus, this study aimed to develop a simple and rapid method to simultaneously analyze these compounds without any derivatization nor ion-pairing reagents.</p><p><strong>Methods: </strong>The analytes were separated using hydrophilic interaction liquid chromatography and detected using tandem mass spectrometry. The developed method was applied to plant and biological samples assuming criminal damage and poisoning cases, respectively.</p><p><strong>Results: </strong>All analytes were separated well and detected with good peak shapes. For plant samples, the herbicides were specifically detected from withered leaves using a simple extraction method. For biological samples, quantitative analysis was successfully validated, and the limit of quantification values of Glyp and Gluf were 0.2 µg/mL, and those of PQ and DQ were 1 ng/mL.</p><p><strong>Conclusion: </strong>The developed method had sufficient performance for practical forensic applications including poisoning cases and malicious uses to damage commercial crops.</p>","PeriodicalId":12329,"journal":{"name":"Forensic Toxicology","volume":null,"pages":null},"PeriodicalIF":2.2,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"9853708","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Cannabigerol (CBG) signal enhancement in its analysis by gas chromatography coupled with tandem mass spectrometry.","authors":"Andrzej L Dawidowicz, Rafal Typek, Michal P Dybowski, Piotr Holowinski, Michal Rombel","doi":"10.1007/s11419-023-00673-x","DOIUrl":"10.1007/s11419-023-00673-x","url":null,"abstract":"<p><strong>Purpose: </strong>According to recent reports, cannabigerol (CBG) concentration level in blood and body fluids may have forensic utility as a highly specific albeit insensitive biomarker of recent cannabis smoking. While the analytical sensitivity of cannabidiol (CBD), Δ⁹-tetrahydrocannabinol (Δ⁹-THC), cannabichromene (CBC) or cannabinol (CBN) estimation by gas chromatography-mass spectrometry (GC-MS) is similar and sufficiently high, it is exceptionally low in the case of CBG (ca. 25 times lower than for the other mentioned cannabinoids). The purpose of this study is to explain the reasons for the extremely low analytical sensitivity of GC-MS in estimating CBG and to present possible ways of its improvement.</p><p><strong>Methods: </strong>Nuclear magnetic resonance (NMR) data and GC-MS responses to CBG and its various derivatization and transformation products were studied.</p><p><strong>Results: </strong>The validation data of individual derivatives of CBG and its transformation products were established. CBG silylation/acylation or hydration allows to decrease LOD about 3 times, whereas the formation of pyranic CBG derivative leads to 10-times decrease of LOD. The paper enriches the literature of the subject by providing MS and NMR spectra, not published so far, for derivatives of CBG and its transformation products. The most likely cause of low GC-MS response to CBG is also presented.</p><p><strong>Conclusions: </strong>The presented results shows that although the signal increase of CBG can be obtained through its derivatization by silylation and/or acylation, the greatest increase is observed in the case of its cyclization to the pyranic CBG form during the sample preparation process. The CBG cyclization procedure is very simple and workable in estimating this cannabinoid in blood/plasma samples.</p>","PeriodicalId":12329,"journal":{"name":"Forensic Toxicology","volume":null,"pages":null},"PeriodicalIF":2.8,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10808273/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41115034","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Death after smoking of fentanyl, 5F-ADB, 5F-MDMB-P7AICA and other synthetic cannabinoids with a bucket bong.","authors":"Merja A Neukamm, Sebastian Halter, Volker Auwärter, Georg Schmitt, Arianna Giorgetti, Marc Bartel","doi":"10.1007/s11419-023-00666-w","DOIUrl":"10.1007/s11419-023-00666-w","url":null,"abstract":"<p><strong>Purpose: </strong>We report a case of a polydrug user who consumed various synthetic cannabinoids and fentanyl from a transdermal patch via a bucket bong. Toxicological results from postmortem matrices with special focus on synthetic cannabinoids are discussed in terms of their relevance to the death.</p><p><strong>Methods: </strong>The samples were analyzed by toxicological screening procedures involving immunoassays and gas chromatography-mass spectrometry (GC-MS) as well as quantitative analyses by means of GC-MS and high-performance liquid chromatography-tandem mass spectrometry (LC-MS/MS).</p><p><strong>Results: </strong>At the autopsy, coronary artery disease and signs of liver congestion were noted, in the absence of acute myocardial ischemic changes. Femoral blood concentrations of fentanyl and pregabalin were 14 ng/mL and 3,200 ng/mL, respectively. In addition, 2.7 ng/mL 5F-ADB and 13 ng/mL 5F-MDMB-P7AICA were detected together with relatively low amounts of 5 other synthetic cannabinoids in cardiac blood. A total number of up to 17 synthetic cannabinoids were detected in kidney, liver, urine and hair. Fentanyl and 5F-ADB were also detected in the water of the bucket bong.</p><p><strong>Conclusions: </strong>The cause of death could be attributed to an acute mixed intoxication by fentanyl and 5F-ADB (both Toxicological Significance Score (TSS) = 3) with a contribution of pregabalin and 5F-MDMB-P7AICA (TSS = 2), in a subject suffering from pre-existing heart damage. The most plausible mechanism of death consists in a respiratory depression. This case report demonstrates that use of opioids in combination with synthetic cannabinoids might be particularly dangerous.</p>","PeriodicalId":12329,"journal":{"name":"Forensic Toxicology","volume":null,"pages":null},"PeriodicalIF":2.8,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10808286/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"9655355","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Identifying a suspect powder as a cannabis concentrate through chemical analysis and DNA testing.","authors":"Tadashi Yamamuro, Yusuke Saito, Yuki Okada, Hiroki Segawa, Kenji Kuwayama, Kenji Tsujikawa, Tatsuyuki Kanamori, Yuko T Iwata","doi":"10.1007/s11419-023-00672-y","DOIUrl":"10.1007/s11419-023-00672-y","url":null,"abstract":"<p><strong>Purpose: </strong>Cannabis is regulated in many countries, and cannabis products are diversifying, which can hinder identification. Here, we report the seizure of a powder sample with a cannabis-like odor in a spice bottle labeled \"nutmeg\" and identification of the sample by chemical testing and cannabis DNA testing.</p><p><strong>Methods: </strong>The sample was observed under a microscope, extracted with methanol, and analyzed by gas chromatography-mass spectrometry (GC-MS). The chemical profile of the seized powder was compared with that of nutmeg samples. Gas chromatography-flame ionization detection was used to estimate the total Δ⁹-tetrahydrocannabinol (Δ⁹-THC) concentration in the sample. A commercially available cannabis DNA testing kit was used to confirm the presence of cannabis plant DNA in the seized sample.</p><p><strong>Results: </strong>The characteristics of cannabis in the seized powder were difficult to determine through microscopic observation alone. GC-MS analysis identified β-caryophyllene (an aromatic component of cannabis) and five cannabinoids unique to cannabis, including Δ⁹-THC. No common compounds were identified in the seized powder or nutmeg samples. The total Δ⁹-THC concentration in the sample was very high (approximately 47% by weight). Cannabis DNA testing confirmed that the seized powder contained cannabis.</p><p><strong>Conclusions: </strong>The seized powder was found to be a processed product made from a finely pulverized resin-like cannabis concentrate. Our results indicate that combined chemical and DNA analysis should help identify cannabis-related samples in various forms.</p>","PeriodicalId":12329,"journal":{"name":"Forensic Toxicology","volume":null,"pages":null},"PeriodicalIF":2.2,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"10089562","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Alcohol spiked with zolpidem and midazolam potentiates inflammation, oxidative stress and organ damage in a mouse model.","authors":"Biwott Kipchumba, Francis Gitonga, Careen Jepchirchir, Grace Wairimu Gitau, Patrick W Okanya, Peris Wanza Amwayi, Alfred Orina Isaac, Nyariki James Nyabuga","doi":"10.1007/s11419-023-00674-w","DOIUrl":"10.1007/s11419-023-00674-w","url":null,"abstract":"<p><strong>Purpose: </strong>Crime-related spiking of alcoholic drinks with prescription drugs is quite common and has been happening for centuries. This study, therefore, evaluated the effects of oral administration of alcohol spiked with the zolpidem and midazolam potent sedatives on inflammation, oxidative stress and various organ damage in male Swiss albino mice.</p><p><strong>Methods: </strong>Mice were randomly assigned into six treatment groups; the first group constituted the normal control, the second group received 50 mg/kg body weight of zolpidem only, the third group received 50 mg/kg body weight zolpidem dissolved in 5 g/kg alcohol, the fourth group received 50 mg/kg midazolam only, the fifth group received midazolam (50 mg/kg) dissolved in 5 g/kg alcohol and the sixth group received 5 g/kg alcohol.</p><p><strong>Results: </strong>Alcohol-induced significant reduction in neurological function and altered blood hematological indicators. Such neurological impairment and negative effects on blood were exacerbated in mice administered with spiked alcohol. Additionally, midazolam and zolpidem enhanced alcohol-driven elevation of liver function markers; the serum aspartate aminotransferase (AST), alanine aminotransferase (ALT) gamma glutamyltransferase (GGT), total bilirubin and alkaline phosphatase. Exposure to alcohol and/or spiked alcohol led to significant augmentation of nitric oxide and malonaldehyde, with concomitant depletion of liver glutathione (GSH) levels. Similarly, serum levels of pro-inflammatory cytokines tumor necrosis factor alpha and interferon-gamma were increased by co-exposure with midazolam or zolpidem. Alcohol-induced hepatotoxicity and nephrotoxicity were amplified by exposure to alcohol spiked with midazolam/zolpidem.</p><p><strong>Conclusion: </strong>Exposure to alcohol spiked with midazolam or zolpidem appears to exacerbate neurological deficits, inflammation, oxidative stress, and organ damage.</p>","PeriodicalId":12329,"journal":{"name":"Forensic Toxicology","volume":null,"pages":null},"PeriodicalIF":2.2,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41182409","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Determination of 3- and 4-chloromethcathinone interactions with plasma proteins: study involving analytical and theoretical methods","authors":"Piotr Holowinski, Michal P. Dybowski","doi":"10.1007/s11419-023-00677-7","DOIUrl":"https://doi.org/10.1007/s11419-023-00677-7","url":null,"abstract":"<h3 data-test=\"abstract-sub-heading\">Purpose</h3><p>The purpose of this paper was to determine 3- and 4-chloromethcathinone (3- and 4-CMC) binding degree and possible binding interaction modes with human serum albumin (HSA) using analytical and theoretical methods.</p><h3 data-test=\"abstract-sub-heading\">Methods</h3><p>Experimental determination of 3- and 4-CMC binding degree with HSA was performed using gas chromatography–tandem mass spectrometry preceded by the equilibrium dialysis (ED) and ultrafiltration (UF). Nuclear magnetic resonance (NMR) spectroscopy was used to determine 3- and 4-CMC epitope-binding maps and possible binding sites in HSA. The molecular docking and molecular dynamics were employed to obtain detailed information about binding modes of 3- and 4-CMC enantiomers in HSA.</p><h3 data-test=\"abstract-sub-heading\">Results</h3><p>As follows from the presented data, the degree of binding of 3- and 4-CMC is at a similar level of approx. 80%. This indicates a relatively strong binding of CMC to plasma proteins. The model studies employing the NMR spectroscopy and molecular simulations indicate that both CMCs bind to HSA. The whole 3- and 4-CMC molecules are embedded in the binding sites, with aromatic moieties being in the closest contact with the HSA residues. Moreover, conducted experiments show that Sudlow site II is the main binding center for 3- and 4-CMC and Sudlow site I acts as the secondary binding site.</p><h3 data-test=\"abstract-sub-heading\">Conclusions</h3><p>Although many studies describe pharmacological and toxicological properties of synthetic cathinones (SC), the data taking SCs binding in plasma into consideration are scarce. To our knowledge, this is the first report presenting comprehensive experimental and theoretical characterization of 3- and 4-CMC binding with plasma proteins.</p>","PeriodicalId":12329,"journal":{"name":"Forensic Toxicology","volume":null,"pages":null},"PeriodicalIF":2.2,"publicationDate":"2023-12-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138716073","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Acute and subacute toxic effects of CUMYL-4CN-BINACA on male albino rats","authors":"Ayşe Lafzi, Fatma Yeşilyurt, Tuba Demirci, Ahmet Hacımüftüoğlu, Turgay Şişman","doi":"10.1007/s11419-023-00676-8","DOIUrl":"https://doi.org/10.1007/s11419-023-00676-8","url":null,"abstract":"<h3 data-test=\"abstract-sub-heading\">Purpose</h3><p>There is very little information about the toxicological and pathological effects of synthetic cannabinoids, which have cannabis-like properties. This study was carried out to histopathologically, hematologically, and biochemically determine the toxic effects of acute and subacute exposure to a novel synthetic cannabinoid 1-(4-cyanobutyl)-<i>N</i>-(2-phenylpropan-2-yl)indazole-3-carboxamide in internal organs of adult male rats.</p><h3 data-test=\"abstract-sub-heading\">Methods</h3><p>The cannabinoid was injected intraperitoneally at three doses (0.5, 1.0, and 2.0 mg/kg, body weight). The cannabinoid was administered to acute groups for 2 days and to subacute groups for 14 days. Observations were made for 14 days and various changes such as mortality, injury, and illness were recorded daily. Hematological and biochemical changes were evaluated and histopathological analyses in lung, liver, and kidney tissues were also performed.</p><h3 data-test=\"abstract-sub-heading\">Results</h3><p>No mortality was observed. It was observed that there were fluctuations in hematological and serum biochemical parameters. Among the oxidative stress parameters, significant decreases in superoxide dismutase, catalase levels and significant increases in lipid peroxidation levels were determined. Serious pathological changes such as necrosis, vacuolation, congestion, and fibrosis were observed in the internal organs in a dose-dependent and time-dependent manner. It was also found that the synthetic cannabinoid triggered apoptosis in the organs. The results demonstrated that the most affected organ by the cannabinoid was the kidney.</p><h3 data-test=\"abstract-sub-heading\">Conclusion</h3><p>This study showed for the first time that CUMYL-4CN-BINACA adversely affects healthy male albino rats. It can be estimated that the abuse of the cannabinoid may harm human health in the same way.</p>","PeriodicalId":12329,"journal":{"name":"Forensic Toxicology","volume":null,"pages":null},"PeriodicalIF":2.2,"publicationDate":"2023-12-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138686540","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Identification of LSD analogs, 1cP-AL-LAD, 1cP-MIPLA, 1V-LSD and LSZ in sheet products.","authors":"Rie Tanaka, Maiko Kawamura, Sakumi Mizutani, Ruri Kikura-Hanajiri","doi":"10.1007/s11419-023-00661-1","DOIUrl":"10.1007/s11419-023-00661-1","url":null,"abstract":"<p><strong>Purpose: </strong>Many analogs of lysergic acid diethylamide (LSD) have recently appeared as designer drugs around the world. These compounds are mainly distributed as sheet products. In this study, we identified three more newly distributed LSD analogs from paper sheet products.</p><p><strong>Methods: </strong>The structures of the compounds were determined by gas chromatography-mass spectrometry (GC-MS), liquid chromatography-photodiode array-mass spectrometry (LC-PDA-MS), liquid chromatography with hybrid quadrupole time-of-flight mass spectrometry (LC-Q-TOF-MS) and nuclear magnetic resonance (NMR) spectroscopy.</p><p><strong>Results: </strong>From the NMR analysis, the compounds in the four products were identified as 4-(cyclopropanecarbonyl)-N,N-diethyl-7-(prop-2-en-1-yl)-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide (1cP-AL-LAD), 4-(cyclopropanecarbonyl)-N-methyl-N-isopropyl-7-methyl-4,6,6a,7,8,9-hexahydroindolo-[4,3-fg]quinoline-9-carboxamide (1cP-MIPLA), N,N-diethyl-7-methyl-4-pentanoyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide (1V-LSD) and (2'S,4'S)-lysergic acid 2,4-dimethylazetidide (LSZ). In comparison with the structure of LSD, 1cP-AL-LAD was converted at the positions at N1 and N6, and 1cP-MIPLA was converted at the positions at N1 and N18. The metabolic pathways and biological activities of 1cP-AL-LAD and 1cP-MIPLA have not been reported.</p><p><strong>Conclusions: </strong>This is the first report showing that LSD analogs that were converted at multiple positions have been detected in sheet products in Japan. There are concerns about the future distribution of sheet drug products containing new LSD analogs. Therefore, the continuous monitoring for newly detected compounds in sheet products is important.</p>","PeriodicalId":12329,"journal":{"name":"Forensic Toxicology","volume":null,"pages":null},"PeriodicalIF":2.2,"publicationDate":"2023-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10310582/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"10101108","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}