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Novel Psychoactive Substances (Designer Drugs): Overview and Pharmacology of Modulators of Monoamine Signalling

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Novel Psychoactive Substances (Designer Drugs): Overview and Pharmacology of Modulators of Monoamine Signalling Review article: Medical intelligence | Published 14 January 2015, doi:10.4414/smw.2015.14043 Cite this as: Swiss Med Wkly. 2015;145:w14043 Novel psychoactive substances (designer drugs): overview and pharmacology of modulators of monoamine signalling Matthias E. Liechti Division of Clinical Pharmacology and Toxicology, Department of Biomedicine and Department of Clinical Research, University Hospital and University of Basel, Switzerland Summary piperidines, aminoindanes benzofurans, and tryptamines. Pharmacologically, these substances interact with various Novel psychoactive substances are newly used designer monoaminergic targets. Typically, stimulants inhibit the drugs (“internet drugs”, “research chemicals”, “legal transport of dopamine and noradrenaline (pipradrols, pyro- highs”) potentially posing similar health risks to classic valerone cathinones) or induce the release of these illicit substances. Chemically, many novel psychoactive monoamines (amphetamines and methamphetamine-like substances can be classified as phenethylamines, amphet- cathinones), entactogens predominantly enhance serotonin amines, synthetic cathinones, piperazines, pipradrols/ release (phenylpiperazines, aminoindanes, para-substituted amphetamines, and MDMA-like cathinones) similar to List of abbreviations MDMA (ecstasy), and hallucinogens (tryptamines, hallu- AMT alpha-methyltryptamine; cinogenic phenethylamines) are direct agonists at sero- 5-APB 5-(2-aminopropyl)benzofuran; tonergic 5-HT2A receptors. Synthetic cannabinoids are an- 6-APB 6-(2-aminopropyl)benzofuran; other group of novel substances which all act as agonists at BZP benzylpiperazine; the cannabinoid CB receptor similar to THC but are chem- CB cannabinoid; 1 2C-B 2,5-dimethoxy-4-bromophenethylamine; ically diverse. In particular, the relative serotonergic vs 2C-I 2,5-dimethoxy-4-iodophenethylamine; dopaminergic activity (determined by the dopamine/sero- m-CPP meta-chlorophenylpiperazine; tonin transporter inhibition ratio in vitro) can be helpful to DAT dopamine transporter; predict the desired psychotropic but also the toxic effects DMT dimethyltryptamine; of novel substances as well as their potential for addiction. DOB 2,5-dimethoxy-4-bromoamphetamine; Although the use of novel psychoactive substances mostly DOI 2,5-dimethoxy-4-iodoamphetamine; produces minor or moderate poisonings, serious complica- DOM 2,5-dimethoxy-4-methylamphetamine; 2-DPMP 2-diphenylmethylpiperidine; tions occur. Serotonergic drugs (entactogens and hallucino- D2PM diphenyl-2-pyrrolidinemethanol; gens) are associated with acute serotonin syndrome, hyper- EMCDDA European Monitoring Centre for Drugs and Drug thermia, seizures, and hyponatremia. Dopaminergic drugs Addiction; are highly addictive and acute toxicity includes prolonged Euro-DEN European Drug Emergency Network; stimulation, insomnia, agitation, and psychosis. Agitation, 3-FMC 3–fluoromethcathinone; anxiety, paranoia, hypertension, and rarely myocardial in- 4-HO-MET 4-hydroxy-N-methyl-N-ethyltryptamine; 5-IAI 5-iodoaminoindane; farction and renal failure are seen with synthetic cannabin- MDAI 5,6-methylenedioxy-2-aminoindane; oids. Treatment is supportive. MDMA 3,4-methylenedioxymethamphetamine; MDPV 3,4-methylenedioxypyrovalerone; Key words: novel psychoactive substances; designer 4-MEC 4-methylethylcathinone; drugs; amphetamines; research chemicals; pharmacology; 4-MTA 4-methylthioamphetamine; toxicology; serotonin; dopamine 25I-NBOMe 4-Iodo-2,5-dimethoxy-N- (2-methoxybenzyl)phenethylamine; NET noradrenaline (norepinephrine) transporter; Introduction PMA paramethoxyamphetamine; PMMA paramethoxymethamphetamine; The term “novel psychoactive substances” refers to newly- α-PVP α-pyrrolidinopentiophenone; misused narcotic or psychotropic drugs that may pose a SERT serotonin transporter; threat to public health comparable to classic previously TFMPP trifluoromethylphenylpiperazine; listed psychotropic substances. Typically, the novel sub- THC tetrahydrocannabinol stances or “designer drugs” are analogues or chemical de- Swiss Medical Weekly · PDF of the online version · www.smw.ch Page 1 of 12 Review article: Medical intelligence Swiss Med Wkly. 2015;145:w14043 rivatives of controlled substances designed to produce ef- oid CB1 receptor and have mostly hallucinogenic but also fects similar to the controlled substances they mimic. In some stimulant properties. Currently, the compounds are contrast to classic illicit drugs (“street drugs”), novel psy- classified based on their common pharmacological action choactive substances are typically sold through the Internet rather than similar chemical structures. (“internet drugs”). The substances are misbranded as “re- The substances exhibit a rather broad spectrum of dopam- search chemicals”, “bath salts”, “plant food”, and labelled inergic, noradrenergic, or serotonergic pharmacological ef- as “not for human consumption”. The substances are typ- fects even within their chemical family [7–9, 16]. Accord- ically chemically slightly different from already scheduled ingly, the psychotropic and clinical toxicological effects are drugs to circumvent regulations and are therefore also also quite diverse and vary considerable from drug to drug. termed “legal highs”. The fully synthetic drugs are mostly produced in China and South East Asia and sold world- Synthetic cannabinoids wide by numerous Internet retail vendors often as less ex- pensive replacements of classic stimulants or narcotics [1]. Herbal mixtures (“spices”) have emerged as legal altern- In the last years we have seen an unprecedented growth in atives to cannabis [17]. It was initially assumed that the the number of new psychoactive substances on the illicit psychotropic effects were derived from the plants them- drug market. In the European Union (EU), 41 novel psy- selves. However, synthetic compounds added to the herbal choactive substances were identified for the first time in blends and with action at the CB1 receptor were found 2010, 49 in 2011, 73 in 2012, 81 in 2013, and 37 by April to be responsible for the psychopharmacological activity 2014 within the European Early Warning System [2]. By [18]. “Spice” drugs have become popular alternatives to 2014, more than 300 novel substances have been detec- marijuana among teenagers and constitute an exceptionally ted since 2005. Currently, more than one new substance large class of novel psychoactive substances [2]. Synthetic is identified in one of the EU countries every week. The cannabinoids vary considerably in chemical structure while European Monitoring Centre for Drugs and Drug Addic- they uniformly act as agonists at the CB1 receptor [17]. tion (EMCDDA) collects information on these substances Many of the substance names (abbreviations) typically start from various national sources including police, customs, with the initials of the chemists (JWH or AM) followed forensic laboratory networks, health care systems, event or- by numbers. Most synthetic cannabinoids produce overall ganisers, drug checks, and Internet test purchase samples. similar effects and toxicity to tetrahydrocannabinol (THC) Internet snapshots are also an important method to describe [6, 17]. However, synthetic cannabinoids are thought to be trends in new substances available for online sale [3]. The associated with more severe psychosis and agitation and EMCDDA also regularly publishes reports on the risk as- more sympathomimetic effects because they are more po- sessments of novel psychoactive substances (ht- tent full receptor agonists and also lack cannabidiol, which tp://www.emcdda.europa.eu/activities/action-on-new- is contained in natural THC-containing products and has drugs). Furthermore, the European Drug Emergency Net- anxiolytic and antipsychotic properties. In fact, agitation, work (Euro-DEN) collects health emergency data from aggression, paranoid thinking and anxiety are common hospitals to look at trends in the acute harms associated symptoms after consumptions of synthetic cannabinoids with the use of novel psychoactive drugs [4]. The [19, 20]. However, more recently a second generation of University Hospital of Basel participates in the Euro-DEN synthetic cannabinoids has emerged both in the US and in and we characterised several intoxications with novel drugs Europe and lead to epidemics associated with more severe [5, 6] and in particular their pharmacological properties toxicity including collapses, seizures, and cardiac toxicity [7–9]. Data on the clinical characteristics of intoxications [11]. Cases with acute kidney injury have also been de- with novel psychoactive substances are also typically col- scribed [21]. The effect of the synthetic cannabinoids is lected and reported by poison centres [10–13]. typically short-lasting compared with amphetamine-type In this review I will describe the in vitro pharmacodynam- substances [5, 20]. Short-time monitoring and supportive ics of novel psychoactive substances acting on monoamine care is sufficient to treat most cases with intoxications. signalling and how it relates to the clinical effects of these Synthetic cannabinoids are not detected by drug screening compounds. Several excellent publications have more tests for THC, and highly specialised mass spectrometry comprehensively reviewed the pharmacology and toxico- techniques and time are required to document the presence logy of novel psychoactive substances [14, 15]. of these novel compounds in biological samples [6, 22]. Classification of novel psychoactive Phenethylamines and amphetamines substances
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