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Markus R Meyer
This summarizing and descriptive review article is an update on previously published reviews. It covers English-written and PubMed-listed review articles and original studies published between May 2016 and November 2017 on the toxicokinetics of new psychoactive substances (NPS). Compounds covered include stimulants and entactogens, synthetic cannabinoids, tryptamines, phenethylamine and phencyclidine-like drugs, benzodiazepines, and opioids. First, an overview and discussion is provided on selected review articles followed by an overview and discussion on selected original studies...
February 24, 2018: Handbook of Experimental Pharmacology
Gerard J Marek, Brian P Ramos
5-Hydroxytryptamine2A (5-HT2A ) receptors are enriched in layers I and Va of the rat prefrontal cortex and neocortex and their activation increases the frequency of glutamatergic excitatory post-synaptic potentials/currents (EPSP/Cs) onto layer V pyramidal cells. A number of other G-protein coupled receptors (GPCRs) are also enriched in cortical layers I and Va and either induce (α1 -adrenergic and orexin2 ) or suppress (metabotropic glutamate2 [mGlu2 ], adenosine A1 , μ-opioid) both 5-HT-induced EPSCs and head twitches or head shakes induced by the phenethylamine hallucinogen 2,5-dimethoxy-4-iodoamphetamine (DOI)...
2018: Frontiers in Pharmacology
Lucie Borovcová, Volodymyr Pauk, Karel Lemr
New psychoactive substances represent serious social and health problem as tens of new compounds are detected in Europe annually. They often show structural proximity or even isomerism which complicates their analysis. Two methods based on ultra high performance supercritical fluid chromatography and ultra high performance liquid chromatography with mass spectrometric detection were validated and compared. A simple dilute-filter-and-shoot protocol utilizing propan-2-ol or methanol for supercritical fluid or liquid chromatography, respectively, was proposed to detect and quantify 15 cathinones and phenethylamines in human urine...
February 20, 2018: Journal of Separation Science
Xinna Wang, Yawei Liang, Yaqi Wang, Mingqin Fan, Yanni Sun, Jianli Liu, Ning Zhang
We described a simple, rapid, selective and sensitive HPLC method coupled with fluorescence detection (HPLC-FLD) for simultaneous determination of ten kinds of biogenic amines (BAs: tryptamine, 2-phenethylamine, putrescine, cadaverine, histamine, 5-hydroxytryptamine, tyramine, spermidine, dopamine, spermine). BAs and I.S were derivated with dansyl chloride. A fluorescence detection (λex/λem = 340/510 nm) was used. A satisfactory result of method validation was obtained. The assay was shown to be linear over the range of 0...
February 15, 2018: Biomedical Chromatography: BMC
Jianping Zhao, Mei Wang, Bharathi Avula, Ikhlas A Khan
Phenethylamines (PEAs) are popular substances found in weight-loss and sports nutrition supplements. They are generally pharmacologically active and primarily affect the sympathetic nervous system. Many PEAs are synthetic chemicals and are on the prohibited list of the World Anti-Doping Agency. In this study, nuclear magnetic resonance (NMR) spectroscopy was applied to detect and identify the presence of PEAs in sports dietary supplements without the need for chromatographic separation or pre-knowledge on formulation...
January 26, 2018: Journal of Pharmaceutical and Biomedical Analysis
John M Bennett, Jonathan D Shapiro, Krystina N Choinski, Yingbin Mei, Sky M Aulita, Giovanny M Dominguez, Max M Majireck
Decomposition of N-tosyl-1,2,3-triazoles with rhodium(II) acetate dimer in the presence of alcohols forms synthetically versatile N-(2-alkoxyvinyl)sulfonamides, which react under a variety of conditions to afford useful N- and O-containing compounds. Acid-catalyzed addition of alcohols or thiols to N-(2-alkoxyvinyl)sulfonamide-containing phthalans provides access to ketals and thioketals, respectively. Selective reduction of the vinyl group in N-(2-alkoxyvinyl)sulfonamide-containing phthalans via hydrogenation yields the corresponding phthalan in good yield, whereas reduction with sodium bis(2-methoxyethoxy)aluminumhydride generates a ring-opened phenethylamine analogue...
January 3, 2018: Journal of Visualized Experiments: JoVE
E Papaseit, M Torrens, C Pérez-Mañá, R Muga, M Farré
MDMA, 3,4-methylenedioxymethamphetamine, is a synthetic phenethylamine derivative with structural and pharmacological similarities to both amphetamines and mescaline. MDMA produces characteristic amphetamine-like actions (euphoria, well-being), increases empathy, and induces pro-social effects that seem to motivate its recreational consumption and provide a basis for its potential therapeutic use. Areas covered: The aim of this review is to present the main interindividual determinants in MDMA pharmacodynamics...
January 5, 2018: Expert Opinion on Drug Metabolism & Toxicology
Paul Calle, Nora Sundahl, Kristof Maudens, Sarah Mr Wille, Diederik Van Sassenbroeck, Koen De Graeve, Stefan Gogaert, Peter De Paepe, Dieter Devriese, Geert Arno, Peter Blanckaert
Introduction Medical problems are frequently encountered during electronic dance music (EDM) events. Problem There are uncertainties about the frequencies and severity of intoxications with different types of recreational drugs: ethanol, "classical" illicit party drugs, and new psychoactive substances (NPS). METHODS: Statistical data on the medical problems encountered during two editions of an indoor electronic dance event with around 30,000 attendants were retrieved from the Belgian Red Cross (Mechelen, Belgium) database...
December 29, 2017: Prehospital and Disaster Medicine
Margret Chinonso Ezeoke, Premanand Krishnan, Dawn Su-Yin Sim, Siew-Huah Lim, Yun-Yee Low, Kam-Weng Chong, Kuan-Hon Lim
From the leaves of Elaeocarpus tectorius (Lour.) Poir. four previously undescribed phenethylamine-containing alkaloids were isolated, namely, tectoricine, possessing an unprecedented isoquinuclidinone ring system incorporating a phenethylamine moiety, tectoraline, representing a rare alkamide incorporating two phenethylamine moieties, and tectoramidines A and B, representing the first naturally occurring trimeric and dimeric phenethylamine alkaloids incorporating an amidine function. The structures of these alkaloids were established by detailed spectroscopic analysis...
December 13, 2017: Phytochemistry
Alice Ameline, Audrey Farrugia, Jean-Sebastien Raul, Pascal Kintz
BACKGROUND: The abuse of new psychoactive substances or NPS has been dramatically increasing all around the world since the last half of the year 2000 and has become a serious public health problem. NPS are a challenge for the worldwide forensic community due to the difficulties to accurately document the cases. The N-benzylmethoxy (NBOMe) group is a new class of hallucinogenic designer drugs and has gained importance in recent years. 25I-NBOMe (2-(4-iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)- methyl]ethanamine) is an analog of the 2C series of psychedelic phenethylamine drugs that contain an N-methoxybenzyl substituent, which significantly affects their pharmacological activities...
2017: Current Pharmaceutical Biotechnology
Gilbert Mercieca, Sara Odoardi, Marisa Cassar, Sabina Strano Rossi
In the last few years an increasing number of new psychoactive substances (NPS), with different chemical structures (of which 37% are stimulants), have been released into the illicit drug market. Their detection and identification in biological samples is hence of great concern. The aim of this work was to develop a high-throughput and rapid method for the determination of different classes of stimulants (amphetamine-type stimulants, cathinones, phenethylamines and ketamine analogues) from blood and urine samples using GC-MS...
February 5, 2018: Journal of Pharmaceutical and Biomedical Analysis
Haixu Zhang, Jinian Shu, Bo Yang, Peng Zhang, Pengkun Ma
Many organic amines that comprise a benzene ring are policy-sensitive because of their toxicity and links to social harm. However, to date, detection of such compounds mainly relies on offline methods. This study proposes an online pptv (parts per trillion by volume) level of detection method for amines, using the recently-built vacuum ultraviolet photoionization mass spectrometer (VUV-PIMS) combined with a new doping technique. Thus, the dichloromethane doping-assisted photoionization mass spectra of aniline, benzylamine, phenethylamine, amphetamine, and their structural isomers were recorded...
February 1, 2018: Talanta
Fermín Fernández-Calderón, Charles M Cleland, Joseph J Palamar
BACKGROUND: Electronic Dance Music (EDM) party attendees are often polysubstance users and are at high risk for use of new psychoactive substances (NPS). We sought to identify patterns of use of common illegal drugs among EDM party attendees, sociodemographic correlates, and use of NPS as a function of patterns of use of more common drugs to inform prevention and harm reduction. METHOD: Using time-space-sampling, 1045 individuals aged 18-40 were surveyed entering EDM parties in New York City...
March 2018: Addictive Behaviors
Xiaoping Zhang, Konstantin Chingin, Dacai Zhong, Liping Luo, Vladimir Frankevich, Huanwen Chen
The chemical origin and biological role of distinct semen-like odor occasionally found in some flowers are very curious but remain scarcely studied. Here, we used direct ambient corona discharge ionization mass spectrometry (MS) to study the volatile chemical composition behind the semen-like odor emitted by the fresh flowers of Photinia serrulata, Castanopsis sclerophylla and Stemona japonica without any chemical pretreatment. Chemical identification was performed using high-resolution MS analysis in combination with tandem MS analysis and whenever possible was confirmed by the analysis of standard reference compounds...
November 8, 2017: Phytochemistry
Hemamalini Ketha, Milad Webb, Larry Clayton, Sean Li
Phenethylamine derivatives are being increasingly exploited for recreational use as "designer" stimulants designed to mimic psychostimulant properties of amphetamine or other illicit substances like 3,4-methylenedioxymethamphetamine (MDMA [ecstasy]). Clandestine operations meticulously design phenethylamines so the user can bypass legal action when detected, as many of these are yet to be regulated by government authorities. Substituted phenethylamines or 2C amines, N-methoxybenzyl derivatives of the corresponding 2C amines commonly known as NBOMe compounds, and cathinones are among the most commonly abused phenethylamines...
November 8, 2017: Current Protocols in Toxicology
Laura Hondebrink, Anne Zwartsen, Remco H S Westerink
The use of new psychoactive substances (NPS) is increasing and currently >600 NPS have been reported. However, limited information on neuropharmacological and toxicological effects of NPS is available, hampering risk characterization. We reviewed the literature on the in vitro neuronal modes of action to obtain effect fingerprints of different classes of illicit drugs and NPS. The most frequently reported NPS were selected for review: cathinones (MDPV, α-PVP, mephedrone, 4-MEC, pentedrone, methylone), cannabinoids (JWH-018), (hallucinogenic) phenethylamines (4-fluoroamphetamine, benzofurans (5-APB, 6-APB), 2C-B, NBOMes (25B-NBOMe, 25C-NBOMe, 25I-NBOMe)), arylcyclohexylamines (methoxetamine) and piperazine derivatives (mCPP, TFMPP, BZP)...
February 2018: Pharmacology & Therapeutics
Rachele Rocchi, Maria Chiara Simeoni, Camilla Montesano, Gabriele Vannutelli, Roberta Curini, Manuel Sergi, Dario Compagnone
In recent years, new drugs, commonly known as new psychoactive substances (NPS), appeared on the market, which include, among others, synthetic cannabinoids, cathinones, and tryptamine analogs of psilocin. The aim of this work was to develop and validate a new method for simultaneous screening and quantification of 31 NPS in oral fluid by ultra-high-performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS). The chosen target analytes represented different chemical and toxicological NPS classes, such as synthetic cathinones, piperazines, phenethylamines, synthetic cannabinoids, and their metabolites...
October 27, 2017: Drug Testing and Analysis
Joachim Wahl, Ulrike Holzgrabe
In recent years increasing interest was drawn towards ionic liquids in analytical separation science, such as capillary electrophoresis. Ionic liquids combining tetrabutylammonium cations with chiral amino acid based anions were prepared and investigated as capillary electrophoresis background electrolyte additives for the enantioseparation of ephedrine, pseudoephedrine, and methylephedrine isomers. For the optimization of buffer pH and ionic liquid concentration a design of experiments approach was performed...
October 17, 2017: Journal of Pharmaceutical and Biomedical Analysis
Yun-Jeong Jeong, Hyun-Ji Cho, Fung-Lung Chung, Xiantao Wang, Hyang-Sook Hoe, Kwan-Kyu Park, Cheorl-Ho Kim, Hyeun-Wook Chang, Sang-Rae Lee, Young-Chae Chang
Isothiocyanates, which are present as glucosinolate precursors in cruciferous vegetables, have strong activity against various cancers. Here, we compared the anti-metastatic effects of isothiocyanates (benzyl isothiocyanate (BITC), phenethyl isothiocyanate (PEITC), and sulforaphane (SFN)) by examining how they regulate MMP-9 expression. Isothiocyanates, particularly PEITC, suppressed 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced MMP-9 activity and invasion in various cancer cell lines. By contrast, N-methyl phenethylamine, a PEITC analog without an isothiocyanate functional group, had no effect...
September 8, 2017: Oncotarget
Wen Jiang, Yang Yang, Renyou Tao, Xiaoqin Jiang, Xiaohua Zhou, Zhiming Zhou
Rice protein was successively hydrolyzed by rice protein hydrolysis special enzyme, chymotrypsin and carboxypeptidases A. Then a novel chitosan-based biosorbent cross-linked with phenethylamine (PMCCR) was synthesized and firstly used for adsorption of aromatic amino acids (AAA) from rice protein enzymatic hydrolysates (RPEH). The characterizations of PMCCR indicated that phenethylamine was successfully cross-linked with chitosan, and the particle size of PMCCR was 500-1000μm with pore diameter of 50-100μm...
November 15, 2017: Carbohydrate Polymers
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