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Phenethylamines

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https://www.readbyqxmd.com/read/28329723/analysis-of-synthetic-phenethylamine-street-drugs-using-direct-sample-analysis-coupled-to-accurate-mass-time-of-flight-mass-spectrometry
#1
Maura K McGonigal, Joshua A Wilhide, Philip B Smith, Noelle M Elliott, Frank L Dorman
Serious health complications and fatal overdoses have brought phenethylamine, otherwise known as 2C, drug abuse to the public's attention. These compounds are 2C-X series analogs of mescaline. The name "2C" results from the two carbons in the ethyl chain. The substituents on these emerging drugs are constantly changed in order to avoid listing as controlled substances. These synthetic drugs are marketed as having affects similar to LSD and MDMA and are typically consumed sublingually via blotter paper. Twenty-six commercially available standards were analyzed using a direct sample analysis technique coupled to accurate mass time of flight mass spectrometry...
March 8, 2017: Forensic Science International
https://www.readbyqxmd.com/read/28294505/metal-free-intermolecular-aminoarylation-of-alkynes
#2
Pauline T G Rabet, Scott Boyd, Michael F Greaney
A metal-free aminoarylation of internal alkynes is described, yielding tetrasubstituted enaminoates. The transformation proceeds in good to excellent yields through a tandem conjugate addition/Smiles rearrangement involving aryl and heteroaryl sulfonamides. Substrate scope is very broad under simple, user-friendly conditions, and the reaction can be used to easily access biologically active phenethylamine derivatives.
March 13, 2017: Angewandte Chemie
https://www.readbyqxmd.com/read/28199890/gc-ms-gc-ms-ms-and-gc-ir-differentiation-of-desoxy-cathinone-derivatives-cyclic-tertiary-amines-related-to-mdpv
#3
Younis Abiedalla, Jack DeRuiter, C Randall Clark
The desoxy phenethylamine analogues in this study represent a combination of alkyl side-chain and cyclic amines (azetidine, pyrrolidine, piperidine and azepane) to yield a set of molecules of identical elemental composition as well as major mass spectral fragment ions (base peaks) of identical elemental composition. These desoxy phenethylamine analogues of the aminoketone designer drug, 3,4-methylenedioxy-pyrrovalerone (MDPV) related to the natural product cathinone were prepared from piperonal (3,4-methylenedioxybenzaldehyde) via the intermediate precursor ketones...
March 24, 2017: Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences
https://www.readbyqxmd.com/read/28168149/roaming-mediated-ch2nh-elimination-from-the-ionization-of-aromatic-ethylamines
#4
Mengxing Zhang, Huijun Guo, Lidong Zhang
The ionization of aromatic ethylamines by photons or electrons leads to elimination of CH2NH fragments, supposedly deriving from the McLafferty rearrangement involving intramolecular γ-hydrogen transfer. Using tryptamine and phenethylamine as examples, the results reported here suggest that the McLafferty mechanism is inadequate for interpreting the observations of CH2NH elimination due to much higher calculated appearance energy than experimentally measured values. Furthermore, by considering the roaming-mediated effect, the calculated appearance energy for the elimination of CH2NH fragments is reduced and matches well with the experimental results and verifies the existence of roaming-mediated effect...
February 2017: ChemistryOpen
https://www.readbyqxmd.com/read/28140394/sticking-together-inter-species-aggregation-of-bacteria-isolated-from-iron-snow-is-controlled-by-chemical-signaling
#5
Jiro F Mori, Nico Ueberschaar, Shipeng Lu, Rebecca E Cooper, Georg Pohnert, Kirsten Küsel
Marine and lake snow is a continuous shower of mixed organic and inorganic aggregates falling from the upper water where primary production is substantial. These pelagic aggregates provide a niche for microbes that can exploit these physical structures and resources for growth, thus are local hot spots for microbial activity. However, processes underlying their formation remain unknown. Here, we investigated the role of chemical signaling between two co-occurring bacteria that each make up more than 10% of the community in iron-rich lakes aggregates (iron snow)...
January 31, 2017: ISME Journal
https://www.readbyqxmd.com/read/28139893/chemometrics-assisted-chromatographic-fingerprinting-an-illicit-methamphetamine-case-study
#6
Nafiseh Shekari, Maryam Vosough, Kourosh Tabar Heidar
The volatile chemical constituents in complex mixtures can be analyzed using gas chromatography with mass spectrometry. This analysis allows the tentative identification of diverse impurities of an illicit methamphetamine sample. The acquired two-dimensional data of liquid-liquid extraction was resolved by multivariate curve resolution alternating curve resolution to elucidate the embedded peaks effectively. This is the first report on the application of a curve resolution approach for chromatogram fingerprinting to identify particularly the embedded impurities of a drug of abuse...
March 2017: Journal of Separation Science
https://www.readbyqxmd.com/read/28133938/characterisation-of-hallucinogenic-phenethylamines-using-high-resolution-mass-spectrometry-for-non-targeted-screening-purposes
#7
Daniel Pasin, Adam Cawley, Sergei Bidny, Shanlin Fu
Hallucinogenic phenethylamines such as 2,5-dimethoxyphenethylamines (2C-X) and their N-(2-methoxybenzyl) derivatives (25X-NBOMe) has seen an increase in novel analogues in recent years. These rapidly changing analogues make it difficult for laboratories to rely on traditional targeted screening methods to detect unknown new psychoactive substances (NPS). In this study, twelve 2C-X, six 2,5-dimethoxyamphetamines (DOX) and fourteen 25X-NBOMe derivatives, including two deuterated derivatives (2C-B-d6 and 25I-NBOMe-d9 ), were analysed using ultra-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry (UPLC-QTOF-MS)...
January 29, 2017: Drug Testing and Analysis
https://www.readbyqxmd.com/read/28130905/characterization-of-complexes-between-phenethylamine-enantiomers-and-%C3%AE-cyclodextrin-derivatives-by-capillary-electrophoresis-determination-of-binding-constants-and-complex-mobilities
#8
Joachim Wahl, Takayuki Furuishi, Etsuo Yonemochi, Lorenz Meinel, Ulrike Holzgrabe
To optimize chiral separation conditions and to improve the knowledge of enantioseparation, it is important to know the binding constants K between analytes and cyclodextrins and the electrophoretic mobilities of the temporarily formed analyte-cyclodextrin-complexes. K values for complexes between eight phenethylamine enantiomers, namely ephedrine, pseudoephedrine, methylephedrine and norephedrine, and four different β-cyclodextrin derivatives were determined by affinity capillary electrophoresis. The binding constants were calculated from the electrophoretic mobility values of the phenethylamine enantiomers at increasing concentrations of cyclodextrins in running buffer...
January 28, 2017: Electrophoresis
https://www.readbyqxmd.com/read/28130544/mistaking-2c-p-for-2c-b-what-a-difference-a-letter-makes
#9
Adrian Stoller, Patrick C Dolder, Michael Bodmer, Felix Hammann, Katharina M Rentsch, Aristomenis K Exadaktylos, Matthias E Liechti, Evangelia Liakoni
2,5-Dimethoxy-4(n)-propylphenethylamine (2C-P) is a synthetic phenethylamine derivative belonging to the large family of the so-called 2C drugs. These compounds can differ significantly in receptor affinity, potency and duration of action, and an important structural difference is the ligand in the 4 position of the phenyl ring, such as propyl in 2C-P or bromine in 2,5-dimethoxy-4-bromophenethylamine (2C-B). The 2C drugs are known for their hallucinogenic properties. We present a case of a 19-year-old male admitted to the emergency department with severe hallucinations, mydriasis, tachycardia, agitation and confusion following the use of a substance sold as 2C-B...
January 2017: Journal of Analytical Toxicology
https://www.readbyqxmd.com/read/28097528/pharmacology-and-toxicology-of-n-benzylphenethylamine-nbome-hallucinogens
#10
Adam L Halberstadt
Serotonergic hallucinogens induce profound changes in perception and cognition. The characteristic effects of hallucinogens are mediated by 5-HT2A receptor activation. One class of hallucinogens are 2,5-dimethoxy-substituted phenethylamines, such as the so-called 2C-X compounds 2,5-dimethoxy-4-bromophenethylamine (2C-B) and 2,5-dimethoxy-4-iodophenethylamine (2C-I). Addition of an N-benzyl group to phenethylamine hallucinogens produces a marked increase in 5-HT2A-binding affinity and hallucinogenic potency...
January 18, 2017: Current Topics in Behavioral Neurosciences
https://www.readbyqxmd.com/read/28088737/the-hemostatic-effect-study-of-cirsium-setosum-on-regulating-%C3%AE-1-ars-via-mediating-norepinephrine-synthesis-by-enzyme-catalysis
#11
Nianwei Chang, Yanmei Li, Mengge Zhou, Jie Gao, Yuanyuan Hou, Min Jiang, Gang Bai
BACKGROUND: Cirsium setosum (CS) is the aboveground part of Cephalanoplos segetum Kitam. Although it has been used as a hemostatic treatment for thousands of years and is still in use today, the mechanism of CS on regulating ARs is still not clear. PURPOSE: In this study, we aimed to clarify the mechanism of CS on regulating ARs. METHODS: We developed a simple method based on UPLC/Q-TOF MS combined adrenergic receptor dual-luciferase reporter assay systems for the rapid determination of active constituents in CS...
March 2017: Biomedicine & Pharmacotherapy, Biomédecine & Pharmacothérapie
https://www.readbyqxmd.com/read/28088088/prevalence-of-new-psychoactive-substances-in-northeast-asia-from-2007-to-2015
#12
Junhui Lee, Songhee Yang, Yujin Kang, Eunyoung Han, Ling-Yi Feng, Jih-Heng Li, Heesun Chung
The proliferation of new psychoactive substances (NPS) has been a global trend in drug abuse and its regulation has been a worldwide concern. There is no doubt that it is necessary to share information related to these emerging substances between countries and continents for the effective regulation of NPS. With efforts for the efficient regulation of NPS, many studies and information have been published for the prevalence of NPS in the United States and other countries in Europe and Oceania. However, there is lack of information available for the prevalence of NPS in Asian and African countries...
October 20, 2016: Forensic Science International
https://www.readbyqxmd.com/read/28059498/rapid-screening-method-for-new-psychoactive-substances-of-forensic-interest-electrochemistry-and-analytical-determination-of-phenethylamines-derivatives-nbome-via-cyclic-and-differential-pulse-voltammetry
#13
Ana Flávia B Andrade, Samuel Kasahun Mamo, Jose Gonzalez-Rodriguez
The NBOMe derivatives are phenethylamines derived from the 2C class of hallucinogens. Only a few human pharmacologic studies have been conducted on these drugs, and several cases of intoxication and deaths have been reported. Presently, NBOMe are not a part of the routine drugs-of-abuse screening procedure for many police forces, and there are no rapid immunoassay screening tests that can detect the presence of those compounds. In this Article, the voltammetric behavior of 25B NBOMe and 25I NBOMe were investigated and their electroanalytical characteristics determined for the first time...
February 7, 2017: Analytical Chemistry
https://www.readbyqxmd.com/read/28057408/dithiocarbamates-effectively-inhibit-the-%C3%AE-carbonic-anhydrase-from-the-dandruff-producing-fungus-malassezia-globosa
#14
Daniela Vullo, Sonia Del Prete, Alessio Nocentini, Sameh M Osman, Zeid AlOthman, Clemente Capasso, Murat Bozdag, Fabrizio Carta, Paola Gratteri, Claudiu T Supuran
A series of dithiocarbamates (DTCs) was investigated for the inhibition of the β-class carbonic anhydrase (CAs, EC 4.2.1.1) from the fungal parasite Malassezia globosa, MgCA, a validated anti-dandruff drug target. These DTCs incorporate various scaffold, among which those of N,N-dimethylaminoethylenediamine, the aminoalcohols with 3-5 carbon atoms in their molecule, 3-amino-quinuclidine, piperidine, morpholine and piperazine derivatives, as well as phenethylamine and its 4-sulfamoylated derivative. Several DTCs resulted more effective in inhibiting MgCA compared to the standard sulfonamide drug acetazolamide (KI of 74μM), with KIs ranging between 383 and 6235nM...
February 1, 2017: Bioorganic & Medicinal Chemistry
https://www.readbyqxmd.com/read/28000107/analytical-validation-of-a-portable-mass-spectrometer-featuring-interchangeable-ambient-ionization-sources-for-high-throughput-forensic-evidence-screening
#15
Zachary E Lawton, Angelica Traub, William L Fatigante, Jose Mancias, Adam E O'Leary, Seth E Hall, Jamie R Wieland, Herbert Oberacher, Michael C Gizzi, Christopher C Mulligan
Forensic evidentiary backlogs are indicative of the growing need for cost-effective, high-throughput instrumental methods. One such emerging technology that shows high promise in meeting this demand while also allowing on-site forensic investigation is portable mass spectrometric (MS) instrumentation, particularly that which enables the coupling to ambient ionization techniques. While the benefits of rapid, on-site screening of contraband can be anticipated, the inherent legal implications of field-collected data necessitates that the analytical performance of technology employed be commensurate with accepted techniques...
December 20, 2016: Journal of the American Society for Mass Spectrometry
https://www.readbyqxmd.com/read/27993913/direct-stamp-of-technology-or-origin-on-the-genotypic-and-phenotypic-variation-of-indigenous-saccharomyces-cerevisiae-population-in-a-natural-model-of-boiled-grape-juice-fermentation-into-traditional-msalais-wine-in-china
#16
Li-Xia Zhu, Guan-Qiong Wang, Ju-Lan Xue, Dong-Qi Gou, Chang-Qing Duan
Saccharomyces cerevisiae strains worldwide show genetic and phenotypic diversity and their population substructures are greatly affected by their technological application or geographical origins. Msalais is a traditional wine obtained via a unique method of spontaneous fermentation of local boiled grape juice in Southern Xinjiang. We analyzed 436 indigenous S. cerevisiae strains associated with Msalais fermentation. These strains were highly diverse with respect to the inter-delta region and 24 phenotypic traits, with apparent differentiation according to strain origins and technologies used to produce Msalais...
December 18, 2016: FEMS Yeast Research
https://www.readbyqxmd.com/read/27951637/ligand-enabled-meta-selective-c-h-arylation-of-nosyl-protected-phenethylamines-benzylamines-and-2-aryl-anilines
#17
Qiuping Ding, Shengqing Ye, Guolin Cheng, Peng Wang, Marcus E Farmer, Jin-Quan Yu
A Pd-catalyzed, meta-selective C-H arylation of nosyl-protected phenethylamines and benzylamines is disclosed using a combination of norbornene and pyridine-based ligands. Subjecting nosyl protected 2-aryl anilines to this protocol led to meta-C-H arylation at the remote aryl ring. A diverse range of aryl iodides are tolerated in this reaction, along with select heteroaryl iodides. Select aryl bromides bearing ortho-coordinating groups can also be utilized as effective coupling partners in this reaction. The use of pyridine ligands has allowed the palladium loading to be reduced to 2...
December 23, 2016: Journal of the American Chemical Society
https://www.readbyqxmd.com/read/27939599/i-like-the-old-stuff-better-than-the-new-stuff-subjective-experiences-of-new-psychoactive-substances
#18
Allison Matthews, Rachel Sutherland, Amy Peacock, Joe Van Buskirk, Elizabeth Whittaker, Lucinda Burns, Raimondo Bruno
BACKGROUND: Over the past decade, monitoring systems have identified the rapid emergence of new psychoactive substances (NPS). While the use of many NPS is minimal and transitory, little is known about which products have potential for capturing the attention of significant proportions of the drug consuming market. The aim of this study was to explore self-reported experiences of three commonly used NPS classes within the Australian context (synthetic cathinones, hallucinogenic phenethylamines and hallucinogenic tryptamines) relative to traditional illicit drug counterparts...
December 8, 2016: International Journal on Drug Policy
https://www.readbyqxmd.com/read/27888011/antiproliferative-and-ultrastructural-effects-of-phenethylamine-derivatives-on-promastigotes-and-amastigotes-of-leishmania-leishmania-infantum-chagasi
#19
Paula Ferreira Brasil, Júlia Araújo de Freitas, Anna Léa Silva Barreto, Camila Marques Adade, Leandro Figueira Reis de Sá, Pamella Constantino-Teles, Fabiano Travanca Toledo, Bruno A de Sousa, Augusto Cesar Gonçalves, Maria Teresa Villela Romanos, João V Comasseto, Alcindo A Dos Santos, Ana Claudia Tessis, Thais Souto-Padrón, Rosangela Maria A Soares, Antonio Ferreira-Pereira
Leishmania (Leishmania) infantum chagasi is one of the agents that cause visceral leishmaniasis. This disease occurs more frequently in third world countries, such as Brazil. The treatment is arduous, and is dependent on just a few drugs like the antimonial derivatives and amphotericin B. Moreover, these drugs are not only expensive, but they can also cause severe side effects and require long-term treatment. Therefore, it is very important to find new compounds that are effective against leishmaniasis. In the present work we evaluated a new group of synthetic amides against the promastigote and amastigote forms of L...
April 2017: Parasitology International
https://www.readbyqxmd.com/read/27874182/synthesis-and-analysis-of-glucuronic-acid-conjugated-metabolites-of-4-bromo-2-5-dimethoxyphenethylamine
#20
Tatsuyuki Kanamori, Tadashi Yamamuro, Kenji Kuwayama, Kenji Tsujikawa, Yuko T Iwata, Hiroyuki Inoue
In the study reported here, two glucuronic acid-conjugated metabolites of 4-bromo-2,5-dimethoxyphenethylamine (2C-B)-a ring-substituted psychoactive phenethylamine-were chemically synthesized for the first time and a method for analyzing them in urine was developed. β-D-Glucuronide of 4-bromo-2,5-dimethoxyphenylethylalcohol was successfully synthesized using methyl 2,3,4-tri-Ο-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucuronate as a glucuronyl donor and boron trifluoride diethylether complex as a Lewis acid catalyst...
November 22, 2016: Journal of Forensic Sciences
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