Acute Toxicity Associated With the Recreational Use of the Novel Psychoactive Benzofuran N -methyl-5-(2 aminopropyl)benzofuran

Hofer, Katharina E.; Faber, Katrin; Müller, Daniel; Hauffe, Till; Wenger, Urs; Kupferschmidt, Hugo; Rauber-Lüthy, Christine

doi:10.1016/j.annemergmed.2016.03.042

Cited by 22 publications

(20 citation statements)

References 13 publications

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“…Using LC‐MS, GC‐MS and 1 H nuclear magnetic resonance, Stanczuk, Morris, Gardner and Kavanagh () were able to distinguish between four (2‐aminopropyl) benzofuran isomers. More recent works have also employed these analytical methods to assess and quantify new benzo fury compounds, in both biological and non‐biological samples (Hofer et al, ; Kim, Suh, Park, & In, ; Liu, Jia, Qian, Li, & Hua, ; Vallersnes et al, ; van der Gouwe, Brunt, van Laar, & van der Pol, ). Details of these case reports are displayed in Table .…”

Section: Chemistry and Chemical Analysismentioning

confidence: 99%

“…No systematic data regarding absorption of benzofurans is available, but it is well acknowledged that the most common route of administration is oral ingestion; inhalation is described as very painful (Barcelo et al, ; Hofer et al, ; Jebadurai et al, ). The information currently available pertaining to the body distribution of benzofurans following administration is sparse, but the analysis of data from a few case reports shed some light on this matter.…”

Section: Toxicokineticsmentioning

confidence: 99%

“…The drug was 46.4× more concentrated in urine, 1 hour 39 minutes after admission. By performing repeated measures of the drug concentration in the patient's serum and urine, the authors remarked that the toxicokinetics of this benzofuran presents similarities to MDMA due to the 6.5 h half‐life and first‐order elimination kinetics (Hofer et al, ).…”

Section: Toxicokineticsmentioning

confidence: 99%

“…The clinical features reported in the intoxication cases in which benzofurans were detected are similar to those described for MDMA and MDA (Jebadurai et al, ; Zawilska & Andrzejczak, ) and are displayed in Table . Among the undesired effects described are hypertension, tachycardia, hyperthermia, mydriasis, jaw clenching, reduced level of consciousness, psychosis, hallucinations, insomnia and seizures (Barcelo et al, ; Chan et al, ; Hofer et al, ; McIntyre et al, ; Welter‐Luedeke & Maurer, ). Of concern, 5‐APB and 6‐APB have been implicated in an elevated number of deaths in the UK, but in the majority of the reported fatal intoxications other entactogens and alcohol were also present (Nugteren‐van Lonkhuyzen, van Riel, Brunt, & Hondebrink, ).…”

Section: Clinical Toxicologymentioning

confidence: 99%

“…Benzofurans, also known by users as benzo fury or benzofury , are synthetic phenethylamines and constitute the third most prominent group of new psychoactive substances (NPS) that have been introduced to the market during the current decade (United Nations Office on Drug and Crime, ). As the popularity of these novel phenethylamine derivatives increased, the number of reported intoxications, including some deaths, have been also proportionally reported in the scientific literature (Adamowicz et al, ; Adamowicz, Zuba, & Byrska, ; Barcelo et al, ; Chan, Wood, Hudson, & Dargan, ; Clemente, Chiappini, Claridge, Goodair, & Loi, ; Helander, Beck, & Backberg, ; Hofer et al, ; Jebadurai, Schifano, & Deluca, ; Kamour et al, ; Krpo, Luytkis, Haneborg, & Hoiseth, ; McIntyre, Gary, Trochta, Stolberg, & Stabley, ; Seetohul & Pounder, ; Turcant et al, ; Vallersnes et al, ). However, their toxicological profiles are far from being fully elucidated and information on the mechanisms responsible for their detrimental effects is yet to be disclosed.…”

Section: Introductionmentioning

confidence: 99%

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Benzo fury: A new trend in the drug misuse scene

Bravo

Carmo

Carvalho

et al. 2019

J of Applied Toxicology

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Benzofurans, also known by users as benzo fury or benzofury, are synthetic phenethylamines and constitute the third most prominent group of new psychoactive substances (NPS). As the use of these substances has been spread as an alternative to the classic illicit psychostimulants, such as amphetamines, their legal status was reviewed, resulting in an utter prohibition of these NPS in many countries worldwide.Herein, the prevalence of abuse, chemistry, biological effects, metabolism, and the potential harms and risky behaviors associated with the abuse of benzofurans are reviewed. The congeners of this group are mainly consumed recreationally at electronic dance music parties, in polydrug abuse settings. Benzofurans preferentially act by disturbing the functioning of serotonergic circuits, which induces their entactogenic and stimulant effects and is the reason behind the considerable number of recent benzo fury-related deaths. The slight interaction of these drugs with the dopaminergic system justifies the rewarding effects of these drugs. To date, published evidence on the mechanisms of toxicity of benzo fury is very limited but a body of research is now beginning to emerge revealing an alarming public health threat regarding the abuse of these NPS.

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Section: Chemistry and Chemical Analysismentioning

confidence: 99%

Section: Toxicokineticsmentioning

confidence: 99%

Section: Toxicokineticsmentioning

confidence: 99%

Section: Clinical Toxicologymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Benzo fury: A new trend in the drug misuse scene

Bravo

Carmo

Carvalho

et al. 2019

J of Applied Toxicology

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Preventive effects of fructose and N‐acetyl‐L‐cysteine against cytotoxicity induced by the psychoactive compounds N‐methyl‐5‐(2‐aminopropyl)benzofuran and 3,4‐methylenedioxy‐N‐methamphetamine in isolated rat hepatocytes

Nakagawa

Suzuki

Inomata

2017

J of Applied Toxicology

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Psychoactive compounds, N-methyl-5-(2-aminopropyl)benzofuran (5-MAPB) and 3,4-methylenedioxy-N-methamphetamine (MDMA), are known to be hepatotoxic in humans and/or experimental animals. As previous studies suggested that these compounds elicited cytotoxicity via mitochondrial dysfunction and/or oxidative stress in rat hepatocytes, the protective effects of fructose and N-acetyl-l-cysteine (NAC) on 5-MAPB- and MDMA-induced toxicity were studied in rat hepatocytes. These drugs caused not only concentration-dependent (0-4 mm) and time-dependent (0-3 hours) cell death accompanied by the depletion of cellular levels of adenosine triphosphate (ATP) and glutathione (reduced form; GSH) but also an increase in the oxidized form of GSH. The toxic effects of 5-MAPB were greater than those of MDMA. Pretreatment of hepatocytes with either fructose at a concentration of 10 mm or NAC at a concentration of 2.5 mm prevented 5-MAPB-/MDMA-induced cytotoxicity. In addition, the exposure of hepatocytes to 5-MAPB/MDMA caused the loss of mitochondrial membrane potential, although the preventive effect of fructose was weaker than that of NAC. These results suggest that: (1) 5-MAPB-/MDMA-induced cytotoxicity is linked to mitochondrial failure and depletion of cellular GSH; (2) insufficient cellular ATP levels derived from mitochondrial dysfunction were ameliorated, at least in part, by the addition of fructose; and (3) GSH loss via oxidative stress was prevented by NAC. Taken collectively, these results indicate that the onset of toxic effects caused by 5-MAPB/MDMA may be partially attributable to cellular energy stress as well as oxidative stress.

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Distinguishing of 2‐MAPB and 6‐MAPB: Solution of the problem

Шевырин

Shafran

2017

J Mass Spectrom

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Differentiation of new psychoactive substance (NPS), 6-(2-methylaminopropyl)benzofuran (6-MAPB), and its positional isomer, 2-(2-methylaminopropyl)benzofuran (2-MAPB), by means of gas chromatography/mass spectrometry (GC/MS) with quadrupole detection is ambiguous. Reliable distinguishing of the two isomers could be achieved by MS/MS spectra recorded after collision-induced dissociation (CID) of precursor ions. Both electron ionization (EI) and electrospray ionization (ESI) methods could be used for these purposes.

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Acute Toxicity Associated With the Recreational Use of the Novel Psychoactive Benzofuran N -methyl-5-(2 aminopropyl)benzofuran

Cited by 22 publications

References 13 publications

Benzo fury: A new trend in the drug misuse scene

Benzo fury: A new trend in the drug misuse scene

Preventive effects of fructose and N‐acetyl‐L‐cysteine against cytotoxicity induced by the psychoactive compounds N‐methyl‐5‐(2‐aminopropyl)benzofuran and 3,4‐methylenedioxy‐N‐methamphetamine in isolated rat hepatocytes

Distinguishing of 2‐MAPB and 6‐MAPB: Solution of the problem

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