Synthetic Aminoindanes: A Summary of Existing Knowledge

Pinterová, Nikola; Horsley, Rachel Rutter; Páleníček, Tomáš

doi:10.3389/fpsyt.2017.00236

Cited by 28 publications

(25 citation statements)

References 41 publications

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“…Aminoindane designer drugs ( Fig. 4) have become widely available when first-generation designer stimulants, including mephedrone, were finally placed under legal control (Pinterova et al 2017;Sainsbury et al 2011). Aminoindanes are conformationally restricted analogs of amphetamine that were originally investigated as bronchodilatory, analgesic, and anti-Parkinson agents, and subsequently as drugs with psychotherapeutic value (Pinterova et al 2017;Solomons and Sam 1973).…”

Section: Aminoindanesmentioning

confidence: 99%

“…4) have become widely available when first-generation designer stimulants, including mephedrone, were finally placed under legal control (Pinterova et al 2017;Sainsbury et al 2011). Aminoindanes are conformationally restricted analogs of amphetamine that were originally investigated as bronchodilatory, analgesic, and anti-Parkinson agents, and subsequently as drugs with psychotherapeutic value (Pinterova et al 2017;Solomons and Sam 1973). Some aminoindane designer drugs have been reported to be entactogens with lower serotonergic neurotoxicity relative to non-aminoindane entactogens (Johnson et al 1990;Nichols et al 1991).…”

Section: Aminoindanesmentioning

confidence: 99%

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Designer drugs: mechanism of action and adverse effects

2020

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Psychoactive substances with chemical structures or pharmacological profiles that are similar to traditional drugs of abuse continue to emerge on the recreational drug market. Internet vendors may at least temporarily sell these so-called designer drugs without adhering to legal statutes or facing legal consequences. Overall, the mechanism of action and adverse effects of designer drugs are similar to traditional drugs of abuse. Stimulants, such as amphetamines and cathinones, primarily interact with monoamine transporters and mostly induce sympathomimetic adverse effects. Agonism at l-opioid receptors and c-aminobutyric acid-A (GABA A) or GABA B receptors mediates the pharmacological effects of sedatives, which may induce cardiorespiratory depression. Dissociative designer drugs primarily act as N-methyl-D-aspartate receptor antagonists and pose similar health risks as the medically approved dissociative anesthetic ketamine. The cannabinoid type 1 (CB 1) receptor is thought to drive the psychoactive effects of synthetic cannabinoids, which are associated with a less desirable effect profile and more severe adverse effects compared with cannabis. Serotonergic 5-hydroxytryptamine-2A (5-HT 2A) receptors mediate alterations of perception and cognition that are induced by serotonergic psychedelics. Because of their novelty, designer drugs may remain undetected by routine drug screening, thus hampering evaluations of adverse effects. Intoxication reports suggest that several designer drugs are used concurrently, posing a high risk for severe adverse effects and even death.

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Section: Aminoindanesmentioning

confidence: 99%

Section: Aminoindanesmentioning

confidence: 99%

Designer drugs: mechanism of action and adverse effects

2020

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“…5-IAI causes 5-HT and DA release, but not NE release, although it acts as a potent NET inhibitor (Iversen et al 2013;Simmler et al 2014b). According to user reports, MDAI and 5-IAI cause euphoria and have entactogenic properties (Pinterova et al 2017). Interestingly, MMAI was shown to be selective for SERT over DAT and NET when inducing uptake inhibition and transporter-mediated release (Johnson et al 1991;Luethi et al 2017).…”

Section: Mdma-like Aminoindansmentioning

confidence: 99%

Pharmacology of MDMA- and Amphetamine-Like New Psychoactive Substances

Simmler

Liechti

2018

Handbook of Experimental Pharmacology

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New psychoactive substances (NPS) with amphetamine-, aminoindan-, and benzofuran basic chemical structures have recently emerged for recreational drug use. Detailed information about their psychotropic effects and health risks is often limited. At the same time, it emerged that the pharmacological profiles of these NPS resemble those of amphetamine or 3,4-methylenedioxymethamphetamine (MDMA). Amphetamine-like NPS induce psychostimulation and euphoria mediated predominantly by norepinephrine (NE) and dopamine (DA) transporter (NET and DAT) inhibition and transporter-mediated release of NE and DA, thus showing a more catecholamine-selective profile. MDMA-like NPS frequently induce well-being, empathy, and prosocial effects and have only moderate psychostimulant properties. These MDMA-like substances primarily act by inhibiting the serotonin (5-HT) transporter (SERT) and NET, also inducing 5-HT and NE release. Monoamine receptor interactions vary considerably among amphetamine- and MDMA-like NPS. Clinically, amphetamine- and MDMA-like NPS can induce sympathomimetic toxicity. The aim of this chapter is to review the state of knowledge regarding these substances with a focus on the description of the in vitro pharmacology of selected amphetamine- and MDMA-like NPS. In addition, it is aimed to provide links between pharmacological profiles and in vivo effects and toxicity, which leads to the conclusion that abuse liability for amphetamine-like NPS may be higher than for MDMA-like NPS, but that the risk for developing the life-threatening serotonin syndrome may be increased for MDMA-like NPS.

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“…Varying patterns of DA, NA and 5‐HT reuptake inhibition and release . Conformationally‐restricted phenylethylamine.…”

Section: Resultsmentioning

confidence: 99%

Chemoinformatic Consideration of Novel Psychoactive Substances: Compilation and Preliminary Analysis of a Categorised Dataset

Firman

Belfield

Jackson

et al. 2019

Molecular Informatics

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This paper is dedicated to Prof. Paola Gramatica on the occasion of her retirement.Abstract: Recent years have seen the emergence into circulation of a growing array of novel psychoactive substances (NPS). Knowledge of the pharmacological profiles and risk liability of these compounds is typically very scarce. Development of chemoinformatic tools enabling prediction of properties within uncharacterised analogues has potential be of particular use. In order to facilitate this, compilation of a chemical inventory comprising known NPS is a necessity. Sourcing a variety of published governmental and analytical reports, a dataset composed of 690 distinct acknowledged NPS, complete with defined chemical structures, has been constructed. This is supplemented by a complementary series of 155 established psychoactive drugs of abuse (EPDA). Classification was performed in accordance with their key molecular structural features, subjective effect profiles and pharmacological mechanisms of action. In excess of forty chemical groupings, spanning seven subjective effect categories and six broad mechanisms of pharmacological action, were identified. Co-occurrence of NPS and EPDA within specific classes was common, showcasing inherent scope both for chemical read-across and for the derivation of structural alerts.

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Synthetic Aminoindanes: A Summary of Existing Knowledge

Cited by 28 publications

References 41 publications

Designer drugs: mechanism of action and adverse effects

Designer drugs: mechanism of action and adverse effects

Pharmacology of MDMA- and Amphetamine-Like New Psychoactive Substances

Chemoinformatic Consideration of Novel Psychoactive Substances: Compilation and Preliminary Analysis of a Categorised Dataset

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