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https://www.readbyqxmd.com/read/28537942/locomotor-and-discriminative-stimulus-effects-of-four-novel-hallucinogens-in-rodents
#1
Michael B Gatch, Sean B Dolan, Michael J Forster
There has been increasing use of novel synthetic hallucinogenic compounds, 2-(4-bromo-2,5-dimethoxyphenyl)-N-(2-methoxybenzyl)ethanamine hydrochloride (25B-NBOMe), 2-(4-chloro-2,5-dimethoxyphenyl)-N-(2-methoxybenzyl)ethanamine hydrochloride (25C-NBOMe), 2-(4-iodo-2,5-dimethoxyphenyl)-N-(2-methoxybenzyl)ethanamine hydrochloride (25I-NBOMe), and N,N-diallyl-5-methoxy tryptamine (5-MeO-DALT), which have been associated with severe toxicities. These four compounds were tested for discriminative stimulus effects similar to a prototypical hallucinogen (-)-2,5-dimethoxy-4-methylamphetamine (DOM) and the entactogen (±)-3,4-methylenedioxymethamphetamine (MDMA)...
May 19, 2017: Behavioural Pharmacology
https://www.readbyqxmd.com/read/28527056/pathogenesis-of-chronic-cluster-headache-and-bouts-role-of-tryptamine-arginine-metabolism-and-%C3%AE-1-agonists
#2
G D'Andrea, G Bussone, P Di Fiore, F Perini, A Gucciardi, A Bolner, M Aguggia, G Saracco, E Galloni, G Giordano, A Leon
The aim of this study was to explore the possible role of tryptamine in the pathogenesis of chronic cluster headache along with that of adrenaline and noradrenaline (α-agonists) together with arginine metabolism in the origin of cluster bouts. Plasma levels of tyramine, tryptamine, serotonin, 5-hydroxyindolacetic acid, noradrenalin, adrenalin and the markers of arginine metabolism such as arginine, homoarginine, citrulline, ADMA and NMMA, were measured in 23 chronic cluster headache patients (10 chronic cluster ab initio and 13 transformed from episodic cluster) and 28 control subjects...
May 2017: Neurological Sciences
https://www.readbyqxmd.com/read/28514972/the-effect-of-tetraneura-ulmi-l-galling-process-on-the-activity-of-amino-acid-decarboxylases-and-the-content-of-biogenic-amines-in-siberian-elm-tissues
#3
K Kmieć, C Sempruch, G Chrzanowski, P Czerniewicz
Tetraneura ulmi (L.), a member of Eriosomatinae subfamily, is one of the gall-forming aphids occurring on elms. Sap-sucking behaviour of founding mothers results in the formation of new plant organs. This study documents the changes in the content of plant biogenic amines (putrescine, cadaverine, spermidine, tryptamine, spermine and histamine) and key enzymes of their biosynthesis: lysine decarboxylase (LDC), tyrosine decarboxylase and ornithine decarboxylase (ODC) in galls and other parts of Siberian elm (Ulmus pumila L...
May 18, 2017: Bulletin of Entomological Research
https://www.readbyqxmd.com/read/28506496/twins-labeling-liquid-chromatography-mass-spectrometry-based-metabolomics-for-absolute-quantification-of-tryptophan-and-its-key-metabolites
#4
Huimin Guo, Yu Jiao, Xu Wang, Tao Lu, Zunjian Zhang, Fengguo Xu
Tryptophan metabolism plays a crucial role in mediating gastrointestinal function. Here, in order to absolutely quantify tryptophan and its metabolites, a liquid chromatography-mass spectrometry (LC-MS) based targeted metabolomics approach was developed using N-dimethyl-/N-diethyl-amino naphthalene-1-sulfonyl chloride (Dns/Dens-Cl) as twins labeling (TL) reagents. Dns-Cl is famous in amine and phenol derivations, and structure is similar with Dens-Cl. The introduction of easily protonated moiety of tertiary ammonium-containing part in the derivatives from Dns to tryptophan and its metabolites not only improved the LC separation but also enhanced their MS response...
May 5, 2017: Journal of Chromatography. A
https://www.readbyqxmd.com/read/28503967/cytotoxic-and-cytoprotective-effects-of-tryptamine-4-5-dione-on-neuronal-cells-a-double-edged-sword
#5
Naoko Suga, Akira Murakami, Yoshimasa Nakamura, Akari Ishisaka, Noritoshi Kitamoto, Mikiko Ito, Yoji Kato
Serotonin (5-hydroxytryptamine) is a putative substrate for myeloperoxidase, which may convert it into the reactive quinone tryptamine-4,5-dione (TD). In this study, we found that the viability of human SH-SY5Y neuroblastoma cells treated with 25 µM TD was increased to approximately 117%. On the other hand, the cell viability was significantly decreased by exposure to TD (150-200 μM), with an increase in intracellular reactive oxygen species (ROS). Interestingly, pretreatment of SH-SY5Y cells with 100 μM TD prevented cell death and suppressed intracellular ROS generation evoked by the addition of hydrogen peroxide (H2O2)...
May 14, 2017: Free Radical Research
https://www.readbyqxmd.com/read/28485987/assessing-self-reported-use-of-new-psychoactive-substances-the-impact-of-gate-questions
#6
Joseph J Palamar, Patricia Acosta, Fermín Fernández Calderón, Scott Sherman, Charles M Cleland
BACKGROUND: New psychoactive substances (NPS) continue to emerge; however, few surveys of substance use ask about NPS use. Research is needed to determine how to most effectively query use of NPS and other uncommon drugs. OBJECTIVE: To determine whether prevalence of self-reported lifetime and past-year use differs depending on whether or not queries about NPS use are preceded by "gate questions." Gate questions utilize skip-logic, such that only a "yes" response to the use of specific drug class is followed by more extensive queries of drug use in that drug class...
May 9, 2017: American Journal of Drug and Alcohol Abuse
https://www.readbyqxmd.com/read/28466889/asymmetric-fluorinative-dearomatization-of-tryptamine-derivatives
#7
Xiao-Wei Liang, Chuan Liu, Wei Zhang, Shu-Li You
An asymmetric fluorinative dearomatization reaction of tryptamine derivatives was developed by using a chiral anion phase transfer catalyst (PTC) system, and the preliminary results of the reaction mechanistic study were achieved. This method is characterized by a simple operation, facile introduction of a fluorine atom in a highly enantioselective manner and construction of two contiguous quaternary stereogenic centers.
May 3, 2017: Chemical Communications: Chem Comm
https://www.readbyqxmd.com/read/28466676/daily-rhythm-in-plasma-n-acetyltryptamine
#8
Peter S Backlund, Henryk F Urbanski, Mark A Doll, David W Hein, Marjan Bozinoski, Christopher E Mason, Steven L Coon, David C Klein
Normal physiology undergoes 24-h changes in function that include daily rhythms in circulating hormones, most notably melatonin and cortical steroids. This study focused on N-acetyltryptamine, a little-studied melatonin receptor mixed agonist-antagonist and the likely evolutionary precursor of melatonin. The central issue addressed was whether N-acetyltryptamine is physiologically present in the circulation. N-acetyltryptamine was detected by LC-MS/MS in daytime plasma of 3 different mammals in subnanomolar levels (mean ± SEM: rat, 0...
May 1, 2017: Journal of Biological Rhythms
https://www.readbyqxmd.com/read/28466505/total-synthesis-of-%C3%A2-corymine
#9
Benxiang Zhang, Xiaoqing Wang, Chao Cheng, Deqian Sun, Chaozhong Li
The first total synthesis of hexacyclic indole alkaloids (±)-corymine is described. Starting from the readily available N-protected tryptamine, the title compound was achieved in 21 steps in 3.4% overall yield. Key steps of the synthesis include: a) the addition of a malonate to a 3-bromooxindole to afford 3,3-disubstituted oxindole, b) the formation of 12-membered cyclic enol ether via intramolecular O-propargylation, immediately followed by propargyl Claisen rearrangement to provide the α-allenyl ketone stereospecifically, c) the DMDO oxidation to install the hydroxyl group in highly stereoselective manner, and d) the SmI2-mediated reductive C-O bond cleavage to remove the α-keto carboxyl group...
May 3, 2017: Angewandte Chemie
https://www.readbyqxmd.com/read/28460972/bioactive-amines-in-passiflora-are-affected-by-species-and-fruit-development
#10
Larissa L Bomtempo, Ana Maria Costa, Herbert Lima, Nicki Engeseth, Maria Beatriz A Gloria
Bioactive amines were determined in selected passion fruit species and throughout fruit development. The same amines (spermine, spermidine, agmatine, putrescine and tryptamine) were found in four Passiflora species (2008-2010 growing seasons) at different concentrations: P. alata had higher polyamines (spermine+spermidine, 8.41mg/100g); P. setacea and P. nitida had higher putrescine (>7.0mg/100g); and P. setacea had higher agmatine contents (1.37mg/100g) compared to the others. The indolamine tryptamine was present at low concentrations in all species (~0...
November 2016: Food Research International
https://www.readbyqxmd.com/read/28459438/pericytes-impair-capillary-blood-flow-and-motor-function-after-chronic-spinal-cord-injury
#11
Yaqing Li, Ana M Lucas-Osma, Sophie Black, Mischa V Bandet, Marilee J Stephens, Romana Vavrek, Leo Sanelli, Keith K Fenrich, Antonio F Di Narzo, Stella Dracheva, Ian R Winship, Karim Fouad, David J Bennett
Blood vessels in the central nervous system (CNS) are controlled by neuronal activity. For example, widespread vessel constriction (vessel tone) is induced by brainstem neurons that release the monoamines serotonin and noradrenaline, and local vessel dilation is induced by glutamatergic neuron activity. Here we examined how vessel tone adapts to the loss of neuron-derived monoamines after spinal cord injury (SCI) in rats. We find that, months after the imposition of SCI, the spinal cord below the site of injury is in a chronic state of hypoxia owing to paradoxical excess activity of monoamine receptors (5-HT1) on pericytes, despite the absence of monoamines...
May 1, 2017: Nature Medicine
https://www.readbyqxmd.com/read/28444659/new-psychoactive-substances-nps-a-challenge-for-the-addiction-treatment-services
#12
Norbert Scherbaum, F Schifano, Udo Bonnet
Over the last few years, hundreds of new psychoactive substances (NPS) have been identified in Europe. Apart from some herbal compounds, NPS mainly include synthetic cannabinoids and a range of new synthetic stimulants (e. g., cathinones). Synthetic NPS are often developed whilst modifying the basic chemical (e. g., phenethylamine or tryptamine) structure. Although the pharmacology and toxicology of most NPS are hardly known, they are being offered, especially online, as "bath salts," as "incense mixtures," or under other misleading labels...
May 2017: Pharmacopsychiatry
https://www.readbyqxmd.com/read/28436530/solvent-free-uncatalyzed-asymmetric-ene-reactions-of-n-tert-butylsulfinyl-3-3-3-trifluoroacetaldimines-a-general-approach-to-enantiomerically-pure-%C3%AE-trifluoromethyl-tryptamines
#13
Giuseppe Mazzeo, Giovanna Longhi, Sergio Abbate, Martina Palomba, Luana Bagnoli, Francesca Marini, Claudio Santi, Jianlin Han, Vadim A Soloshonok, Emilio Di Crescenzo, Renzo Ruzziconi
A novel approach to regioselectively substituted and stereoselectively α-trifluoromethylated tryptamines is reported based on the ene reaction of Boc-protected 3-methyleneindolines with optically pure (R)- or (S)-tert-butanesulfinyltrifluoroacetaldimine. Boc- and sulfinylamido-protected α-trifluoromethyltryptamines are obtained in 60-70% yield and 85/15 dr by just heating equimolar amounts of the two reaction partners at 80-90 °C for 2-3 h without a solvent. The absolute configuration of the amino α-carbon has been assigned based on the vibrational circular dichroism (VCD) spectral analysis...
May 10, 2017: Organic & Biomolecular Chemistry
https://www.readbyqxmd.com/read/28401525/new-world-tryptamine-hallucinogens-and-the-neuroscience-of-ayahuasca
#14
Dennis McKenna, Jordi Riba
New World indigenous peoples are noted for their sophisticated use of psychedelic plants in shamanic and ethnomedical practices. The use of psychedelic plant preparations among New World tribes is far more prevalent than in the Old World. Yet, although these preparations are botanically diverse, almost all are chemically similar in that their active principles are tryptamine derivatives, either DMT or related constituents. Part 1 of this paper provides an ethnopharmacological overview of the major tryptamine-containing New World hallucinogens...
April 2, 2017: Current Topics in Behavioral Neurosciences
https://www.readbyqxmd.com/read/28401524/chemistry-and-structure-activity-relationships-of-psychedelics
#15
David E Nichols
This chapter will summarize structure-activity relationships (SAR) that are known for the classic serotonergic hallucinogens (aka psychedelics), focusing on the three chemical types: tryptamines, ergolines, and phenethylamines. In the brain, the serotonin 5-HT2A receptor plays a key role in regulation of cortical function and cognition, and also appears to be the principal target for hallucinogenic/psychedelic drugs such as LSD. It is one of the most extensively studied of the 14 known types of serotonin receptors...
March 26, 2017: Current Topics in Behavioral Neurosciences
https://www.readbyqxmd.com/read/28353056/pharmacokinetics-of-escalating-doses-of-oral-psilocybin-in-healthy-adults
#16
Randall T Brown, Christopher R Nicholas, Nicholas V Cozzi, Michele C Gassman, Karen M Cooper, Daniel Muller, Chantelle D Thomas, Scott J Hetzel, Kelsey M Henriquez, Alexandra S Ribaudo, Paul R Hutson
INTRODUCTION: Psilocybin is a psychedelic tryptamine that has shown promise in recent clinical trials for the treatment of depression and substance use disorders. This open-label study of the pharmacokinetics of psilocybin was performed to describe the pharmacokinetics and safety profile of psilocybin in sequential, escalating oral doses of 0.3, 0.45, and 0.6 mg/kg in 12 healthy adults. METHODS: Eligible healthy adults received 6-8 h of preparatory counseling in anticipation of the first dose of psilocybin...
March 28, 2017: Clinical Pharmacokinetics
https://www.readbyqxmd.com/read/28342193/metabolism-of-the-tryptamine-derived-new-psychoactive-substances-5-meo-2-me-dalt-5-meo-2-me-alcht-and-5-meo-2-me-dipt-and-their-detectability-in-urine-studied-by-gc-ms-lc-ms-n-and-lc-hr-ms-ms
#17
Achim T Caspar, Jonas B Gaab, Julian A Michely, Simon D Brandt, Markus R Meyer, Hans H Maurer
Many N,N-dialkylated tryptamines show psychoactive properties and were encountered as new psychoactive substances. The aims of the presented work were to study the phase I and II metabolism and the detectability in standard urine screening approaches (SUSA) of 5-methoxy-2-methyl-N,N-diallyltryptamine (5-MeO-2-Me-DALT), 5-methoxy-2-methyl-N-allyl-N-cyclohexyltryptamine (5-MeO-2-Me-ALCHT), and 5-methoxy-2-methyl-N,N-diisopropyltryptamine (5-MeO-2-Me-DIPT) using GC-MS, LC-MS(n) , and LC-HR-MS/MS. For metabolism studies, urine was collected over a 24-h period after administration of the compounds to male Wistar rats at 20 mg/kg body weight (BW)...
March 24, 2017: Drug Testing and Analysis
https://www.readbyqxmd.com/read/28342109/sensitivity-to-enterocins-of-biogenic-amine-producing-faecal-enterococci-from-ostriches-and-pheasants
#18
Andrea Lauková, Anna Kandričáková, Leona Buňková, Pavel Pleva, Jana Ščerbová
Enterococci are widespread bacteria forming the third largest genus among lactic acid bacteria. Some possess probiotic properties or they can produce beneficial proteinaceous antimicrobial substances called enterocins. On the other hand, some enterococci produce biogenic amines (BAs), so this study is focused on the sensitivity to enterocins of biogenic amine-producing faecal enterococci from ostriches and pheasants. Altogether, 60 enterococci isolated from faeces of ostriches and pheasants were tested for production of BAs...
March 24, 2017: Probiotics and Antimicrobial Proteins
https://www.readbyqxmd.com/read/28317753/bioactive-amines-and-phenolic-compounds-in-cocoa-beans-are-affected-by-fermentation
#19
Brenda de Nazaré do Carmo Brito, Renan Campos Chisté, Rosinelson da Silva Pena, Maria Beatriz Abreu Gloria, Alessandra Santos Lopes
Cocoa is the target of increased scientific research as it is one of the richest source of bioactive compounds. The formation of bioactive amines and their changes in cocoa beans during seven days of traditional fermentation was investigated for the first time. In addition, total phenolic compounds, anthocyanins contents and the scavenging capacity against ABTS radical were determined to monitor the fermentation process. Only two biogenic amines (tryptamine and tyramine) and two polyamines (spermidine and spermine) were detected in cocoa beans during fermentation...
August 1, 2017: Food Chemistry
https://www.readbyqxmd.com/read/28302559/in-vitro-monoamine-oxidase-inhibition-potential-of-alpha-methyltryptamine-analog-new-psychoactive-substances-for-assessing-possible-toxic-risks
#20
Lea Wagmann, Simon D Brandt, Pierce V Kavanagh, Hans H Maurer, Markus R Meyer
Tryptamines have emerged as new psychoactive substances (NPS), which are distributed and consumed recreationally without preclinical studies or safety tests. Within the alpha-methylated tryptamines, some of the psychoactive effects of the prototypical alpha-methyltryptamine (AMT) have been described decades ago and a contributing factor of its acute toxicity appears to involve the inhibition of monoamine oxidase (MAO). However, detailed information about analogs is scarce. Therefore, thirteen AMT analogs were investigated for their potential to inhibit MAO...
April 15, 2017: Toxicology Letters
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