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Phenethylamines

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https://www.readbyqxmd.com/read/29136874/a-rapid-detection-method-for-policy-sensitive-amines-real-time-supervision
#1
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
https://www.readbyqxmd.com/read/29128711/polysubstance-use-profiles-among-electronic-dance-music-party-attendees-in-new-york-city-and-their-relation-to-use-of-new-psychoactive-substances
#2
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...
November 4, 2017: Addictive Behaviors
https://www.readbyqxmd.com/read/29127940/deciphering-the-chemical-origin-of-the-semen-like-floral-scents-in-three-angiosperm-plants
#3
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
https://www.readbyqxmd.com/read/29117432/gas-chromatography-mass-spectrometry-gc-ms-for-identification-of-designer-stimulants-including-2c-amines-nbome-compounds-and-cathinones-in-urine
#4
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
https://www.readbyqxmd.com/read/29097307/effect-fingerprinting-of-new-psychoactive-substances-nps-what-can-we-learn-from-in-vitro-data
#5
REVIEW
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 (mCCP, TFMPP, BZP)...
October 30, 2017: Pharmacology & Therapeutics
https://www.readbyqxmd.com/read/29078252/analysis-of-new-psychoactive-substances-in-oral-fluids-by-means-of-microextraction-by-packed-sorbent-followed-by-uhplc-ms-ms
#6
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
https://www.readbyqxmd.com/read/29059613/capillary-electrophoresis-separation-of-phenethylamine-enantiomers-using-amino-acid-based-ionic-liquids
#7
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
https://www.readbyqxmd.com/read/28969043/isothiocyanates-suppress-the-invasion-and-metastasis-of-tumors-by-targeting-fak-mmp-9-activity
#8
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
https://www.readbyqxmd.com/read/28927604/preparation-of-a-novel-chitosan-based-biosorbent-cross-linked-with-phenethylamine-for-adsorption-of-aromatic-amino-acids
#9
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
https://www.readbyqxmd.com/read/28917801/development-of-a-quantitative-approach-in-blood-plasma-for-low-dosed-hallucinogens-and-opioids-using-lc-high-resolution-mass-spectrometry
#10
Achim T Caspar, Andreas B Kollas, Hans H Maurer, Markus R Meyer
The WHO annually reports an increasing abuse of new psychoactive substances (NPS), which are a heterogeneous group of synthetic drugs and are consumed as substitute for controlled drugs of abuse. In this work, we focused on highly potent derivatives such those of phenethylamine (2C), N-2-methoxybenzyl phenethylamine (NBOMes), lysergic acid diethylamide (LSD), and fentanyl. Severe to fatal intoxications were described due to their high potency. Therefore, they have to be taken at very low doses resulting in low blood concentration in the low ng/mL range, which is a challenge for reliable analytical detection and quantification...
January 1, 2018: Talanta
https://www.readbyqxmd.com/read/28890736/the-psychoactive-drug-25b-nbome-recapitulates-rhabdomyolysis-in-zebrafish-larvae
#11
Genri Kawahara, Hideyuki Maeda, Ruri Kikura-Hanajiri, Ken-Ichi Yoshida, Yukiko K Hayashi
N-Benzyl-substituted 2C class phenethylamines (NBOMes) are psychoactive designer drugs, with strong hallucinogenic and stimulant effects, even at low doses. The designer drug, 2-(4-bromo-2, 5-dimethoxyphenyl)-N-(2-methoxybenzyl) ethanamine (25B-NBOMe) is considered to be one of the most potent agonists of the serotonin-2A (5-HT2A) receptor. Recently, we reported the first lethal case of 25B-NBOMe intoxication with severe rhabdomyolysis, concluded by clinical, pathological and toxicological analyses. There are currently no good animal models that closely recapitulate serotonin receptor-dependent rhabdomyolysis...
2017: Forensic Toxicology
https://www.readbyqxmd.com/read/28885973/hemorrhagic-stroke-in-a-young-healthy-male-following-use-of-pre-workout-supplement-animal-rage-xl
#12
Brandon F Harris, Coty Winn, Thomas B Ableman
So-called "pre-workout" supplements are substances marketed as natural dietary supplements with claims of helping athletes achieve more focused and intense workouts. The use of such products remains popular among American youth as a whole, but is especially high among active duty service members. Supplements are minimally regulated by the Food and Drug Administration (FDA), and unlike pharmaceuticals, supplements are often brought to market without any testing to show neither efficacy nor safety. Several case reports have documented serious adverse events and raise the question of whether supplement use was a causative factor...
September 2017: Military Medicine
https://www.readbyqxmd.com/read/28877397/meta-selective-c-h-borylation-of-benzylamine-phenethylamine-and-phenylpropylamine-derived-amides-enabled-by-a-single-anionic-ligand
#13
Holly J Davis, Georgi R Genov, Robert J Phipps
Selective functionalization at the meta position of arenes remains a significant challenge. In this work, we demonstrate that a single anionic bipyridine ligand bearing a remote sulfonate group enables selective iridium-catalyzed borylation of a range of common amine-containing aromatic molecules at the arene meta position. We propose that this selectivity is the result of a key hydrogen bonding interaction between the substrate and catalyst. The scope of this meta-selective borylation is demonstrated on amides derived from benzylamines, phenethylamines and phenylpropylamines; amine-containing building blocks of great utility in many applications...
October 16, 2017: Angewandte Chemie
https://www.readbyqxmd.com/read/28842491/conformational-state-interactions-provide-clues-to-the-pharmacochaperone-potential-of-serotonin-transporter-partial-substrates
#14
Shreyas Bhat, Peter S Hasenhuetl, Ameya Kasture, Ali El-Kasaby, Michael H Baumann, Bruce E Blough, Sonja Sucic, Walter Sandtner, Michael Freissmuth
Point mutations in SLC6 transporters cause misfolding, which can be remedied by pharmacochaperones. The serotonin transporter (SERT/SLC6A4) has a rich pharmacology including inhibitors, releasers (amphetamines, which promote the exchange mode), and more recently, discovered partial substrates. We hypothesized that partial substrates trapped the transporter in one or several states of the transport cycle. This conformational trapping may also be conducive to folding. We selected naphthylpropane-2-amines of the phenethylamine library (PAL) including the partial substrate PAL1045 and its congeners PAL287 and PAL1046...
October 6, 2017: Journal of Biological Chemistry
https://www.readbyqxmd.com/read/28830123/application-of-a-urine-and-hair-validated-lc-ms-ms-method-to-determine-the-effect-of-hair-color-on-the-incorporation-of-25b-nbome-25c-nbome-and-25i-nbome-into-hair-in-the-rat
#15
Lorna A Nisbet, Rafael Venson, Fiona M Wylie, Karen S Scott
NBOMes are a group of new psychoactive substances derived from phenethylamines. Recreational abuse is thought to have begun in 2010 and they are commonly associated with the "club drug" scene. They are administered in liquid form or as blotters due to their high potency. An LC-MS-MS method was validated using Scientific Working Group for Forensic Toxicology parameters for the detection of 25B-, 25C- and 4-iodo-2,5-dimethoxy-N-[(2-methoxyphenyl)methyl]-benzeneethanamine (25I-NBOMe) using 4-bromo-2,5-dimethoxy-N-[(2-methoxyphenyl)methyl]-benzeneethanamine (25B-NBOMe)-D3 as internal standard for urine and hair...
July 1, 2017: Journal of Analytical Toxicology
https://www.readbyqxmd.com/read/28813419/vaccine-driven-pharmacodynamic-dissection-and-mitigation-of-fenethylline-psychoactivity
#16
Cody J Wenthur, Bin Zhou, Kim D Janda
Fenethylline, also known by the trade name Captagon, is a synthetic psychoactive stimulant that has recently been linked to a substance-use disorder and 'pharmacoterrorism' in the Middle East. Although fenethylline shares a common phenethylamine core with other amphetamine-type stimulants, it also incorporates a covalently linked xanthine moiety into its parent structure. These independently active pharmacophores are liberated during metabolism, resulting in the release of a structurally diverse chemical mixture into the central nervous system...
August 24, 2017: Nature
https://www.readbyqxmd.com/read/28766952/inhibition-of-the-%C3%AE-carbonic-anhydrase-from-the-dandruff-producing-fungus-malassezia-globosa-with-monothiocarbamates
#17
Alessio Nocentini, Daniela Vullo, Sonia Del Prete, Sameh M Osman, Fatmah A S Alasmary, Zeid AlOthman, Clemente Capasso, Fabrizio Carta, Paola Gratteri, Claudiu T Supuran
A series of monothiocarbamates (MTCs) was investigated for the inhibition of the β-class carbonic anhydrase (CAs, EC 4.2.1.1) from the fungal parasite Malassezia globosa, MgCA. These MTCs incorporate various scaffolds, among which aliphatic amine with 1-4 carbons atom in their molecule, morpholine, piperazine, as well as phenethylamine and benzylamine derivatives. All the reported MTCs displayed a better efficacy in inhibiting MgCA compared to the clinically used sulphonamide drug acetazolamide (KI of 74 μM), with KIs spanning between 1...
December 2017: Journal of Enzyme Inhibition and Medicinal Chemistry
https://www.readbyqxmd.com/read/28762065/lc-high-resolution-ms-ms-for-identification-of-69-metabolites-of-the-new-psychoactive-substance-1-4-ethylphenyl-n-2-methoxyphenyl-methyl-propane-2-amine-4-ea-nbome-in-rat-urine-and-human-liver-s9-incubates-and-comparison-of-its-screening-power-with-further
#18
Achim T Caspar, Folker Westphal, Markus R Meyer, Hans H Maurer
4-EA-NBOMe (N-(2-methoxybenzyl)-4-ethylamphetamine, 1-(4-ethylphenyl-)-N-[(2-methoxyphenyl)methyl]propane-2-amine) is an amphetamine-derived new psychoactive substance (NPS) of the N-methoxybenzyl (NBOMe) group first seized by German custom authorities. In contrast to the phenethylamine NBOMes, studies on the pharmacological, toxicological, or metabolic properties are not yet published. The aims of the presented work were the use of LC-HR-MS/MS for identification of the phase I and II metabolites of 4-EA-NBOMe in rat urine and pooled human S9 fraction (pS9) incubations, to compare metabolite formation in both models, to identify involved monooxygenases, and to elucidate its detectability in standard urine screening approaches (SUSAs) using GC-MS, LC-MS(n), and LC-HR-MS/MS...
July 31, 2017: Analytical and Bioanalytical Chemistry
https://www.readbyqxmd.com/read/28747562/isothiocyanates-suppress-the-invasion-and-metastasis-of-tumors-by-targeting-fak-mmp-9-activity
#19
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...
July 12, 2017: Oncotarget
https://www.readbyqxmd.com/read/28720478/monoamine-receptor-interaction-profiles-of-4-thio-substituted-phenethylamines-2c-t-drugs
#20
Dino Luethi, Daniel Trachsel, Marius C Hoener, Matthias E Liechti
BACKGROUND: 4-Thio-substituted phenethylamines (2C-T drugs) are potent psychedelics with poorly defined pharmacological properties. Because of their psychedelic effects, 2C-T drugs are sometimes sold as new psychoactive substances (NPSs). The aim of the present study was to characterize the monoamine receptor and transporter interaction profiles of a series of 2C-T drugs. METHODS: We determined the binding affinities of 2C-T drugs at monoamine receptors and transporters in human cells that were transfected with the respective receptors or transporters...
July 15, 2017: Neuropharmacology
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