A fatal blood concentration of 5-APB

Krpo, Maja; Luytkis, Hege Cathrine; Haneborg, An-Magritt; Høiseth, Gudrun

doi:10.1016/j.forsciint.2018.08.044

Cited by 11 publications

(6 citation statements)

References 12 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…LC-QTOF-MS, in the low energy range, was also used to distinguish the isomers 3- and 4-MeO-PCP based on the different relative ratios of the fragments 189 and 274 m/z ( De Jong et al, 2019 ). The ion ratio approach was also used by Krpo et al (2018) to differentiate between the positional isomers 5-APB and 6-APB by UHPLC-QTOF-MS and UHPLC-MS/MS analysis to solve a fatal case.…”

Section: Analytical Methods Applied In Toxicological Routine Analysismentioning

confidence: 99%

See 1 more Smart Citation

Fatal cases involving new psychoactive substances and trends in analytical techniques

et al. 2022

View full text Add to dashboard Cite

New psychoactive substances (NPS) are an emerging public health issue and deaths are commonly associated with polydrug abuse. Moreover, the number of new substances available is constantly increasing, causing intoxications in low doses, characteristics that impose to toxicology and forensic laboratories to keep routine methods up to date, with high detectability and constantly acquiring new analytical standards. Likewise, NPS metabolites and respective elimination pathways are usually unknown, making it difficult the detection and confirmation of the drug involved in the fatal case in an analytical routine. A literature search was performed on PubMed, Scopus and Web of Science databases for papers related to chromatographic analyses from fatal cases related to NPS use published from 2016 to 2021. A total of 96 papers were retrieved and reviewed in this study. Opioids, synthetic cathinones, phenethylamines/amphetamines and cannabinoids were the NPS classes most found in the fatal cases. In many cases, multiple compounds were detected in the biological samples, including prescription and other illegal drugs. Liquid chromatography-tandem mass spectrometry, an alternative to overcome the gas chromatography–mass spectrometry limitations for some compounds, was the analytical technique most used in the studies, and high resolution mass spectrometry was often applied to NPS metabolite investigation and structural characterization and identification of unknown compounds. Toxicological screening and quantitation methods need to be continuously updated to include new substances that are emerging on the drug market that can be fatal at very low doses.

show abstract

Section: Analytical Methods Applied In Toxicological Routine Analysismentioning

confidence: 99%

“…No other substance was detected in the screening and the cause of death was assumed as intoxication with 5-APB/6-APB. In a Norwegian fatal case involving 5-APB, blood analysis showed levels of 860 ng/ml, which was considered the cause of death ( Krpo et al, 2018 ).…”

Section: Fatal Cases Involving New Psychoactive Substance Intakementioning

confidence: 99%

Fatal cases involving new psychoactive substances and trends in analytical techniques

et al. 2022

View full text Add to dashboard Cite

show abstract

“…Anecdotal evidence from people who use such substances suggests that both 5-APB and 6-APB produce psychostimulant and entactogen-like effects similar those produced by 3,4methylenedioxymethamphetamine (MDMA) (Greene 2013;Nugteren-van Lonkhuyzen et al 2015). A number of intoxication cases with adverse effects, including fatalities, have been described where 5-APB and 6-APB were forensically confirmed (Adamowicz et al 2014;Chan et al 2013;Daveluy et al 2016;Elliott and Evans 2014;McIntyre et al 2015;Nugteren-van Lonkhuyzen et al 2015), and recent data indicate these compounds are still used (Krpo et al 2018). The Trans European Drug Information (TEDI) project, designed to carry out chemical analysis of drug samples submitted by recreational users as a harm reduction strategy, identified the appearance of 4-APB, 5-APB and 6-APB in samples and tablets circulating on the "ecstasy" market (Brunt et al 2017).…”

Section: Introductionmentioning

confidence: 99%

The psychoactive aminoalkylbenzofuran derivatives, 5-APB and 6-APB, mimic the effects of 3,4-methylenedioxyamphetamine (MDA) on monoamine transmission in male rats

et al. 2020

View full text Add to dashboard Cite

RationaleThe non-medical use of new psychoactive substances (NPS) is a worldwide public health concern. The so-called "benzofury" compounds, 5-(2aminopropyl)benzofuran (5-APB) and 6-(2-aminopropyl)benzofuran (6-APB), are NPS with stimulant-like properties in human users. These substances are known to interact with monoamine transporters and 5-HT receptors in transfected cells, but less is known about their effects in animal models. Methods Here, we used in vitro monoamine transporter assays in rat brain synaptosomes to characterize the effects of 5-APB and 6-APB, together with their Nmethyl derivatives 5-MAPB and 6-MAPB, in comparison to 3,4methylenedioxyamphetamine (MDA) and 3,4-methylenedioxymethamphetamine (MDMA). In vivo neurochemical and behavioral effects of 5-APB (0.3 and 1.0 mg/kg, i.v.) and 6-APB (0.3 and 1.0 mg/kg, i.v.) were assessed in comparison to MDA (1.0 and 3.0 mg/kg, i.v.) using microdialysis sampling in the nucleus accumbens of conscious male rats. Results All four benzofuran derivatives were substrate-type releasers at dopamine transporters (DAT), norepinephrine transporters (NET) and serotonin transporters (SERT) with nanomolar potencies, similar to the profile of effects produced by MDA and MDMA. However, the benzofurans were at least 3-fold more potent than MDA and MDMA at evoking transporter-mediated release. Like MDA, both benzofurans induced dose-related elevations in extracellular dopamine and serotonin in the brain, but benzofurans were more potent than MDA. The benzofuran derivatives also induced profound behavioral activation characterized by forward locomotion which lasted for at least 2 h post-injection. Conclusions Overall, benzofurans are more potent than MDA in vitro and in vivo, producing sustained stimulant-like effects in rats. These data suggest that benzofuran-type compounds may have abuse liability, and could pose risks for adverse effects, especially if used in conjunction with abused drugs or medications which enhance monoamine transmission in the brain.

show abstract

“…In addition, 5‐APB produces partial substitution in rats trained to discriminate methamphetamine, cocaine, and the serotonergic hallucinogen 2,5‐dimethoxy‐4‐methylamphetamine (DOM). According to various case reports, abuse of 5‐APB or 6‐APB, either alone or in combination with other drugs, can result in severe toxicity and fatalities 11,27–32 …”

Section: Introductionmentioning

confidence: 99%

Syntheses and analytical characterizations of novel (2‐aminopropyl)benzo[b]thiophene (APBT) based stimulants

Brandt

Carlino

Kavanagh

et al. 2020

Drug Testing and Analysis

View full text Add to dashboard Cite

Two groups of amphetamine‐like drugs with psychostimulant properties that were first developed during the course of scientific studies and later emerged as new psychoactive substances (NPS) are based on the (2‐aminopropyl)indole (API) and (2‐aminopropyl)benzofuran (APB) structural scaffolds. However, sulfur‐based analogs with a benzo[b]thiophene structure (resulting in (2‐aminopropyl)benzo[b]thiophene (APBT) derivatives) have received little attention. In the present investigation, all six racemic APBT positional isomers were synthesized in an effort to understand their structure–activity relationships relative to API‐ and APB‐based drugs. One lesson learned from the NPS phenomenon is that one cannot exclude the appearance of such substances on the market. Therefore, an in‐depth analytical characterization was performed, including various single‐ and tandem mass spectrometry (MS) and ionization platforms coupled to gas chromatography (GC) and liquid chromatography (LC), nuclear magnetic resonance spectroscopy (NMR), and solid phase and GC condensed phase infrared spectroscopy (GC‐sIR). Various derivatizations have also been explored; it was found that all six APBT isomers could be differentiated during GC analysis after derivatization with heptafluorobutyric anhydride and ethyl chloroformate (or heptafluorobutyric anhydride and acetic anhydride) under non‐routine conditions. Discriminating analytical features can also be derived from NMR, GC‐EI/CI‐ single‐ and tandem mass spectrometry, LC (pentafluorophenyl stationary phase), and various infrared spectroscopy approaches (including GC‐sIR). Availability of detailed analytical data obtained from these novel APBT‐type stimulants may be useful to researchers and scientists in cases where forensic and clinical investigations are warranted.

show abstract

A fatal blood concentration of 5-APB

Cited by 11 publications

References 12 publications

Fatal cases involving new psychoactive substances and trends in analytical techniques

Fatal cases involving new psychoactive substances and trends in analytical techniques

The psychoactive aminoalkylbenzofuran derivatives, 5-APB and 6-APB, mimic the effects of 3,4-methylenedioxyamphetamine (MDA) on monoamine transmission in male rats

Syntheses and analytical characterizations of novel (2‐aminopropyl)benzo[b]thiophene (APBT) based stimulants

Contact Info

Product

Resources

About