The effects of benzofury (5-APB) on the dopamine transporter and 5-HT2-dependent vasoconstriction in the rat

Dawson, Patrick; Opacka‐Juffry, Jolanta; Moffatt, James D.; Daniju, Yusuf; Dutta, Neelakshi; Ramsey, John; Davidson, Charles S.

doi:10.1016/j.pnpbp.2013.08.013

Cited by 52 publications

(43 citation statements)

References 42 publications

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“…1), "Fury X", and "Fury Extreme" (Chan et al, 2013;Jebadurai et al, 2013). These two compounds are (Dawson et al, 2014;Iversen et al, 2013, Rickli et al, 2015b. As 5-HT 2B receptors have been implicated in a substance-used heart valve fibrosis (Bhattacharyya et al, 2009), high agonist activity of 5-APB and 6-APB at these receptors suggests that their long term use could cause cardiotoxicity (Dawson et al, 2014;Iversen et al, 2013).…”

Section: Benzofuran Analogues Of Amphetamines: 5-apb and 6-apbmentioning

confidence: 99%

Next generation of novel psychoactive substances on the horizon – A complex problem to face

Zawilska

Andrzejczak

2015

Drug and Alcohol Dependence

166

123

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Section: Benzofuran Analogues Of Amphetamines: 5-apb and 6-apbmentioning

confidence: 99%

Next generation of novel psychoactive substances on the horizon – A complex problem to face

Zawilska

Andrzejczak

2015

Drug and Alcohol Dependence

166

123

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“…Furthermore, 5-APB showed high binding affinity on the 5-HT 2B receptor and was confirmed as potent full agonist. In addition, Dawson et al showed that 5-APB bound to the DA transporter blocking the reuptake and increased in higher concentrations the level of basal DA comparable to amphetamine and thus claimed to be a modest amphetamine-type stimulant (ATS) [3]. They also found 5-APB being an agonist at the 5-HT 2A and 5-HT 2B receptor.…”

mentioning

confidence: 99%

“…In the MS3 of 280.1542, fragment ions were observed at m/z 207.1017, resulting from the loss of N-methyl-acetamide (73 u), and at m/z 220.1333, resulting from cleavage of one acetyl group and a subsequent loss of water. The MS 2 spectrum of threefold acetylated 3-hydroxyethyl-4-hydroxy amphetamine (8; PM at m/z 322.1636) showed fragment ions at m/z 280.1543 resulting from loss of one acetyl group and fragment ion at m/z 262.1438 indicating the hydroxy group at the alkyl chain because of the loss of water (18.0105 u) from m/z 280.1543.…”

mentioning

confidence: 99%

Benzofuran analogues of amphetamine and methamphetamine: studies on the metabolism and toxicological analysis of 5-APB and 5-MAPB in urine and plasma using GC-MS and LC-(HR)-MSn techniques

et al. 2014

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5-APB (5-(2-aminopropyl)benzofuran) and its N-methyl derivative 5-MAPB (N-methyl-5-(2-aminopropyl)benzofuran) are analogues of amphetamine and methamphetamine, respectively, and belong to the so-called novel psychoactive substances (NPS). They were consumed as stimulants or entactogens with euphoric and empathogenic effects. Being controlled in some countries, both compounds should be covered by drug testing in clinical and forensic toxicology. Therefore, metabolism studies have been performed by working up rat urine samples after a high single dose of the corresponding NPS with solid-phase extraction without and after enzymatic conjugates cleavage. The phase I metabolites were separated and identified after acetylation by GC-MS and/or LC-HR-MS(n) and the phase II metabolites by LC-HR-MS(n). The main metabolite of 5-APB was 3-carboxymethyl-4-hydroxy amphetamine and the main metabolites of 5-MAPB were 5-APB (N-demethyl metabolite) and 3-carboxymethyl-4-hydroxy methamphetamine. The cytochrome P450 (CYP) isoenzymes involved in the 5-MAPB N-demethylation were CYP1A2, CYP2B6, CYP2C19, and CYP2D6, and according to the kinetic parameters, CYP2B6 was responsible for the main part of the total CYP-dependent clearance. An intake of a common users' dose of 5-APB or 5-MAPB could be confirmed in rat urine using the authors' GC-MS and the LC-MS(n) standard urine screening approaches with the corresponding parent drugs as major target. In authentic human urine samples after ingestion of unknown doses of 5-MAPB, both metabolites could also be detected besides the parent drug. The plasma concentrations determined in six clinical cases ranged from 5 to 124 μg/L for 5-MAPB and from 1 to 38 μg/L for its N-demethyl metabolite 5-APB.

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“…However, the compound may lead to severe cardiotoxicity because of its potent 5-HT 2B agonist property. Due to its structural similarity with MDA, the compound is sold as a controlled substance in the market [145].…”

Section: Triple Reuptake Inhibitors As Potential Next-generation Antimentioning

confidence: 99%

Triple Reuptake Inhibitors as Potential Next-Generation Antidepressants: A New Hope?

Santra

Dutta

2015

Future Med. Chem.

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The current therapy for depression is less than ideal with remission rates of only 25–35% and a slow onset of action with other associated side effects. The persistence of anhedonia originating from depressed dopaminergic activity is one of the most treatment-resistant symptoms of depression. Therefore, it has been hypothesized that triple reuptake inhibitors (TRIs) with potency to block dopamine reuptake in addition to serotonin and norepinephrine transporters should produce higher efficacy. The current review comprehensively describes the development of TRIs and discusses the importance of evaluation of in vivo transporter occupancy of TRIs, which should correlate with efficacy in humans.

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The effects of benzofury (5-APB) on the dopamine transporter and 5-HT2-dependent vasoconstriction in the rat

Cited by 52 publications

References 42 publications

Next generation of novel psychoactive substances on the horizon – A complex problem to face

Next generation of novel psychoactive substances on the horizon – A complex problem to face

Benzofuran analogues of amphetamine and methamphetamine: studies on the metabolism and toxicological analysis of 5-APB and 5-MAPB in urine and plasma using GC-MS and LC-(HR)-MSn techniques

Triple Reuptake Inhibitors as Potential Next-Generation Antidepressants: A New Hope?

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