Combined in vitro and in silico approaches to the assessment of stimulant properties of novel psychoactive substances – The case of the benzofuran 5-MAPB

Sahai, Michelle A.; Davidson, Charles S.; Khelashvili, George; Barrese, Vincenzo; Dutta, Neelakshi; Weinstein, Harel; Opacka‐Juffry, Jolanta

doi:10.1016/j.pnpbp.2016.11.004

Cited by 18 publications

(55 citation statements)

References 41 publications

(62 reference statements)

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“…Benzofurans such as 5‐APB (5‐(2‐aminopropyl)benzofuran), 5‐APDB (5‐(2‐aminopropyl)‐2,3‐dihydrobenzofuran), 6‐APB (6‐(2‐aminopropyl)benzofuran), 6‐APDB (5‐(2‐aminopropyl)‐2,3‐dihydrobenzofuran), 4‐APB (4‐(2‐aminopropyl)benzofuran), 7‐APB (7‐(2‐aminopropyl)benzofuran), 5‐EAPB (5‐(2‐ethylaminopropyl)benzofuran) and 5‐MAPDB (1‐(2,3‐dihydrobenzofuran‐5‐yl)‐ N ‐methylpropan‐2‐amine) are all structurally similar to MDMA . Similar to MDMA, they were found to activate the 5‐HT 2B receptor (Dawson et al ., 2014), which induces heart valve fibrosis and inhibit dopamine transporters (DAT) …”

Section: Predictive Validity Of Nps Tests In Animal Tissuesupporting

confidence: 77%

“…modelling the effects of the drugs at receptors or transporters of interest. We have done this for some ketamine‐like NPS including diphenidine, methoxphenidine, MDMA, and some similar NPS including 5‐APB and 5‐MAPB . We also suggest that future studies focus more on measures of toxicity (e.g.…”

Section: Discussionmentioning

confidence: 99%

“…Some researchers have gone a step further, using in silico studies to predict addictive liability of NPS. The benzofurans 5‐APB and 5‐MAPB were predicted to bind to DAT in a similar way to MDMA, while ketamine‐like NPS diphenidine and methoxphenidine were predicted to bind differently at DAT …”

Section: Predictive Validity Of Nps Tests In Animal Tissuementioning

confidence: 99%

“…126 which induces heart valve fibrosis 124,135,136 and inhibit dopamine transporters (DAT). 84,99 MDPV (3,4-methylanedioxypyrovalerone) is a cathinone derivative with a nitrogen atom in the pyrrolidine ring and a 3,4-methylenedioxy group on the phenyl ring similar to MDMA. 137 in vitro and in vivo rodent models showed that MDPV blocks the dopamine and norepinephrine transporters in a similar way to the pyrovalerone analogues.…”

Section: Predictive Validity Of Nps Tests In Animal Tissuementioning

confidence: 99%

“…The benzofurans 5-APB and 5-MAPB were predicted to bind to DAT in a similar way to MDMA, 84 This decision was based on a report by the EMCDDA. 142 In this report there is evidence from preclinical studies in the 1970s and 80s that BZP had addictive liability and had similar properties to amphetamine or MDMA.…”

Section: Predictive Validity Of Nps Tests In Animal Tissuementioning

confidence: 99%

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How preclinical studies have influenced novel psychoactive substance legislation in the UK and Europe

Santos-Toscano

Guirguis

Davidson

2020

Brit J Clinical Pharma

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Novel psychoactive substances (NPS) are new drugs of abuse. Over the last 10 years 50–100 new NPS have been detected for the first time each year. This has led to numerous deaths and challenges to healthcare providers and law‐makers worldwide. We review preclinical studies of NPS and discuss how these studies have influenced legislative decisions. We focus on the UK legal system but include experiences from Europe. We reviewed manuscripts from 2008–2019 and have summarised the in vitro and in vivo data on NPS, highlighting how these studies define pharmacological mechanisms and how they might predict harm in humans. We found that only a small percentage of NPS have been examined in preclinical studies. Most preclinical studies of NPS focus on basic pharmacological mechanisms (46% of studies reviewed) and/or addictive liability (32%) rather than toxicity and harm (24%). Very few preclinical studies into NPS include data from chronic dosing schedules (9%) or female rodents (4%). We conclude that preclinical studies can predict harm to humans, but most of the predictions are based on basic pharmacology rather than demonstrated toxicity. Some of these studies have been used to make changes to the law in the UK and Europe and perhaps, because of the paucity of toxicology data, most NPS have been placed in the highly dangerous schedule 1 or Class A category in the UK. We suggest that in silico studies and high throughput toxicology screens might be the most economical way forward to rapidly screen the health harms of NPS.

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Section: Predictive Validity Of Nps Tests In Animal Tissuesupporting

confidence: 77%

Section: Discussionmentioning

confidence: 99%

Section: Predictive Validity Of Nps Tests In Animal Tissuementioning

confidence: 99%

Section: Predictive Validity Of Nps Tests In Animal Tissuementioning

confidence: 99%

Section: Predictive Validity Of Nps Tests In Animal Tissuementioning

confidence: 99%

See 3 more Smart Citations

How preclinical studies have influenced novel psychoactive substance legislation in the UK and Europe

Santos-Toscano

Guirguis

Davidson

2020

Brit J Clinical Pharma

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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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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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Combined in vitro and in silico approaches to the assessment of stimulant properties of novel psychoactive substances – The case of the benzofuran 5-MAPB

Cited by 18 publications

References 41 publications

How preclinical studies have influenced novel psychoactive substance legislation in the UK and Europe

How preclinical studies have influenced novel psychoactive substance legislation in the UK and Europe

Benzo fury: A new trend in the drug misuse scene

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

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