Sympathomimetic toxicity in a case of analytically confirmed recreational use of naphyrone (naphthylpyrovalerone)

Derungs, Adrian; Schietzel, Simeon; Meyer, Markus R.; Maurer, Hans H.; Krähenbühl, Stephan; Liechti, Matthias E.

doi:10.3109/15563650.2011.592838

Cited by 46 publications

(41 citation statements)

References 9 publications

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“…MDPV and naphyrone rather than 2-DPMP have been found in some samples of "ivory wave" [72]. Similar to MDPV [4] and naphyrone [73], 2-DPMP and D2PM are highly lipophilic. Compared with methylphenidate, 2-DPMP lacks polar groups that are typically targeted by metabolic enzymes, resulting in a longer half-life [74,75].…”

Section: Pipradrol Derivativesmentioning

confidence: 90%

Pharmacological profiles of aminoindanes, piperazines, and pipradrol derivatives

Simmler

Rickli

Schramm

et al. 2014

Biochemical Pharmacology

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108

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Aminoindanes, piperazines, and pipradrol derivatives are novel psychoactive substances found in "Ecstasy" tablets as replacements for 3,4-methylenedioxymethamphetamine (MDMA) or substances sold as "ivory wave." The pharmacology of these MDMA-and methylphenidate-like substances is poorly known. We characterized the pharmacology of the aminoindanes 5,6-methylenedioxy-2-aminoindane (MDAI), 5-iodoaminoindane (5-IAI), and 2-aminoindane (2-AI), the piperazines meta-chlorophenylpiperazine (m-CPP), trifluoromethylphenylpiperazine (TFMPP), and 1-benzylpiperazine (BZP), and the BZP, D2PM, and 2-DPMP lacked serotonergic activity and TAAR 1 binding, in contrast to the aminoindanes and phenylpiperazines. In summary, all of the substances were monoamine transporter inhibitors, but marked differences were found in their 3 DAT vs. SERT inhibition profiles, release properties, and receptor interactions. The pharmacological profiles of D2PM and 2-DPMP likely predict a high abuse liability.

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Section: Pipradrol Derivativesmentioning

confidence: 90%

Pharmacological profiles of aminoindanes, piperazines, and pipradrol derivatives

Simmler

Rickli

Schramm

et al. 2014

Biochemical Pharmacology

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108

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“…One feature of intoxication with pyrovalerone cathinones is their long duration of insomnia, which can last up to several days (Derungs et al, 2011;Eiden et al, 2013). The long duration of action could be linked to the high potency of the drugs and an increased risk of overdosing.…”

Section: Discussionmentioning

confidence: 99%

“…In fact, MDPV and α-PVP are considered highly addictive (Aarde et al, 2013;Baumann et al, 2013;Watterson et al, 2014). Additionally, intoxication with MDPV, naphyrone, and α-PVP is associated with pronounced agitation, prolonged insomnia, psychotic symptoms, tachycardia, and cardiac arrest (Derungs et al, 2011;Eiden et al, 2013; European Monitoring Center for Drugs and Drug Addiction, 2014b; Spiller et al, 2011).…”

Section: Discussionmentioning

confidence: 99%

“…The long duration of action could be linked to the high potency of the drugs and an increased risk of overdosing. Additionally, the pyrovalerones are all highly lipophilic substances with associated high brain penetration (Simmler et al, 2013) and a high volume of distribution, resulting in longer plasma and tissue half-lives (Derungs et al, 2011).…”

Section: Discussionmentioning

confidence: 99%

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Monoamine transporter and receptor interaction profiles of novel psychoactive substances: Para-halogenated amphetamines and pyrovalerone cathinones

Rickli

Hoener

Liechti

2015

European Neuropsychopharmacology

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169

188

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The pharmacology of novel psychoactive substances is mostly unknown. We evaluated the transporter and receptor interaction profiles of a series of para-(4)-substituted amphetamines and pyrovalerone cathinones. We tested the potency of these compounds to inhibit the norepinephrine (NE), dopamine (DA), and serotonin (5-HT) transporters (NET, DAT, and SERT, respectively) using human embryonic kidney 293 cells that express the respective human transporters. We also tested the substance-induced efflux of NE, DA, and 5-HT from monoamine-loaded cells, binding affinities to monoamine receptors, and 5-HT 2B receptor activation.Para- (4)

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“…Accordingly, NPS that mostly interact with the SERT can be expected to produce more empathogenic MDMAlike effects, in contrast to NPS that mostly interact with the NET and DAT and are thus expected to produce more stimulant-type effects and addiction similar to methamphetamine (Liechti, 2015;Simmler et al, 2013). Additionally, we noted that substances, such as MDMA, that primarily release endogenous monoamines via the transporter may have a shorter duration of action despite having a long plasma half-life (Hysek et al, 2012c) than substances that only inhibit a transporter (e.g., pyrovalerone cathinones; Derungs et al, 2011) or interact with postsynaptic receptors (e.g., hallucinogens; Dolder et al, 2015;Rickli et al, 2015c).…”

Section: Methods For Studying Transporter and Receptor Pharmacology Imentioning

confidence: 96%

Interactions of Cathinone NPS with Human Transporters and Receptors in Transfected Cells

Simmler

Liechti

2016

Current Topics in Behavioral Neurosciences

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Pharmacological assays carried out in transfected cells have been very useful for describing the mechanism of action of cathinone new psychoactive substances (NPS). These in vitro characterizations provide fast and reliable information on psychoactive substances soon after they emerge for recreational use. Well-investigated comparator compounds, such as methamphetamine, 3,4-methylenedioxymethamphetamine, cocaine, and lysergic acid diethylamide, should always be included in the characterization to enhance the translation of the in vitro data into clinically useful information. We classified cathinone NPS according to their pharmacology at monoamine transporters and receptors. Cathinone NPS are monoamine uptake inhibitors and most induce transportermediated monoamine efflux with weak to no activity at pre-or postsynaptic receptors. Cathinones with a nitrogen-containing pyrrolidine ring emerged as NPS that are extremely potent transporter inhibitors but not monoamine releasers. Cathinones exhibit clinically relevant differences in relative potencies at serotonin vs. dopamine transporters. Additionally, cathinone NPS have more dopaminergic vs. serotonergic properties compared with their non-β-keto amphetamine analogs, suggesting more stimulant and reinforcing properties. In conclusion, in vitro pharmacological assays in heterologous expression systems help to predict the psychoactive and toxicological effects of NPS.

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Sympathomimetic toxicity in a case of analytically confirmed recreational use of naphyrone (naphthylpyrovalerone)

Abstract: Based on the present case report and user web-reports, as well as on the chemical structure and pharmacological characteristics, naphyrone produces stimulant-like psychotropic effects and sympathomimetic toxicity.

Cited by 46 publications

References 9 publications

Pharmacological profiles of aminoindanes, piperazines, and pipradrol derivatives

Pharmacological profiles of aminoindanes, piperazines, and pipradrol derivatives

Monoamine transporter and receptor interaction profiles of novel psychoactive substances: Para-halogenated amphetamines and pyrovalerone cathinones

Interactions of Cathinone NPS with Human Transporters and Receptors in Transfected Cells

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