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https://www.readbyqxmd.com/read/28444659/new-psychoactive-substances-nps-a-challenge-for-the-addiction-treatment-services
#1
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...
April 25, 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
#2
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...
April 24, 2017: Organic & Biomolecular Chemistry
https://www.readbyqxmd.com/read/28401525/new-world-tryptamine-hallucinogens-and-the-neuroscience-of-ayahuasca
#3
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
#4
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
#5
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
#6
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
#7
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
#8
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
#9
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...
March 13, 2017: Toxicology Letters
https://www.readbyqxmd.com/read/28290701/identification-of-pyridinium-with-three-indole-moieties-as-an-antimicrobial-agent
#10
Masahiro Okada, Tomotoshi Sugita, Chin Piow Wong, Toshiyuki Wakimoto, Ikuro Abe
A novel pyridinium with three indole moieties, tricepyridinium, was obtained from the culture of an Escherichia coli clone incorporating metagenomic libraries from the marine sponge Discodermia calyx. For the important structural elements of tricepyridinium to be investigated for antibacterial activity, tricepyridinium and its analogues were chemically synthesized. Tricepyridinium had antimicrobial activity, but not against E. coli, and cytotoxicity against P388 cells. Additional bioassays with its synthetic analogues revealed that the intriguing combination of the indole moieties, most likely derived from three tryptamines, as well as the pyridinium moiety were chiefly responsible for its potent biological activities...
March 14, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28208655/experimental-evidence-and-in-silico-identification-of-tryptophan-decarboxylase-in-citrus-genus
#11
Luigi De Masi, Domenico Castaldo, Domenico Pignone, Luigi Servillo, Angelo Facchiano
Plant tryptophan decarboxylase (TDC) converts tryptophan into tryptamine, precursor of indolealkylamine alkaloids. The recent finding of tryptamine metabolites in Citrus plants leads to hypothesize the existence of TDC activity in this genus. Here, we report for the first time that, in Citrus x limon seedlings, deuterium labeled tryptophan is decarboxylated into tryptamine, from which successively deuterated N,N,N-trimethyltryptamine is formed. These results give an evidence of the occurrence of the TDC activity and the successive methylation pathway of the tryptamine produced from the tryptophan decarboxylation...
February 11, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://www.readbyqxmd.com/read/28195396/development-of-a-validated-strategy-for-the-determination-of-tryptamine-in-human-cerebrospinal-fluid-in-the-presence-of-competitors-using-molecularly-imprinted-polymers
#12
Piotr Luliński, Magdalena Bamburowicz-Klimkowska, Mariusz Dana, Dorota Maciejewska
This study presents a validated strategy for the determination of tryptamine in the presence of its competitors, which involves the molecularly imprinted solid-phase extraction combined with high-performance liquid chromatography coupled with fluorimetric detection. Tryptamine-imprinted microscale sorbent was produced from 4-vinylbenzoic acid and ethylene glycol dimethacrylate in methanol by precipitation polymerization, and its imprinting factor was equal to 15.4 in static experiments or 18.6 in dynamic binding experiments...
April 2017: Journal of Separation Science
https://www.readbyqxmd.com/read/28171832/design-and-synthesis-of-novel-phenyl-1-4-beta-carboline-hybrid-molecules-as-potential-anticancer-agents
#13
S Samundeeswari, Bahubali Chougala, Megharaja Holiyachi, Lokesh Shastri, Manohar Kulkarni, Suneel Dodamani, Sunil Jalalpur, Shrinivas Joshi, Sheshagiri Dixit, Vinay Sunagar, Ravindra Hunnur
A series of beta-carbolines with other heterocycles linked by phenyl ring has been designed and synthesized. The key intermediates 3 and 5 were synthesized by condensing tryptamine and teraldehyde via Pictet- Spengler method. All the newly synthesized compounds were tested for their anticancer activity against sixty human cell lines at NCI. The five dose results of compounds 3 and 7a showed enhancement of anticancer activity (GI50 values range from 1.00 to 7.10 μM) against all the cell lines in comparison with some of earlier molecules...
March 10, 2017: European Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/28168149/roaming-mediated-ch2nh-elimination-from-the-ionization-of-aromatic-ethylamines
#14
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/28124911/desymmetrizing-hydroformylation-of-dihydromuconic-acid-diesters-application-to-the-synthesis-of-%C3%A2-vindeburnol
#15
Laura Salacz, Cyrille Charpentier, Jean Suffert, Nicolas Girard
The desymmetrizing hydroformylation of internal alkenes derived from dihydromuconic acid is described. The study of this reaction afforded easy access to polyfunction aldehydes. After the evaluation of the reactivity of the dimethyl ester derivative with various primary amines, this methodology was used to design a rapid synthesis of (±)-vindeburnol from tryptamine in only two steps.
February 8, 2017: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/28109297/effects-of-phenolic-constituents-of-daylily-flowers-on-corticosterone-and-glutamate-treated-pc12-cells
#16
Huan Tian, Fei-Fei Yang, Chun-Yu Liu, Xin-Min Liu, Rui-Le Pan, Qi Chang, Ze-Sheng Zhang, Yong-Hong Liao
BACKGROUND: Daylily flowers, the flower and bud parts of Hemerocallis citrina or H. fulva, are well known as Wang-You-Cao in Chinese, meaning forget-one's sadness plant. However, the major types of active constituents responsible for the neurological effects remain unclear. This study was to examine the protective effects of hydroalcoholic extract and fractions and to identify the active fractions. METHODS: The extract of daylily flowers was separated with AB-8 resin into different fractions containing non-phenolic compounds, phenolic acid derivatives and flavonoids as determined using UPLC-DAD chromatograms...
January 21, 2017: BMC Complementary and Alternative Medicine
https://www.readbyqxmd.com/read/28105971/determination-of-tryptamines-and-%C3%AE-carbolines-in-ayahuasca-beverage-consumed-during-brazilian-religious-ceremonies
#17
Mônica Cardoso Santos, Sandro Navickiene, Alain Gaujac
Ayahuasca is a potent hallucinogenicbeverage prepared from <em>Banisteriopsis caapi</em>in combination with other psychoactive plants.<em>N</em>,<em>N</em>-dimethyltryptamine, tryptamine, harmine,harmaline, harmalol, and tetrahydroharmine werequantified in ayahuasca samples using a simpleand low-cost method based on SPE and LC with UVdiode-array detection. The experimental variablesthat affect the SPE method, such as type of solidphase and nature of solvent, were optimized...
January 19, 2017: Journal of AOAC International
https://www.readbyqxmd.com/read/28081155/evaluation-of-bufadienolides-as-the-main-antitumor-components-in-cinobufacin-injection-for-liver-and-gastric-cancer-therapy
#18
Xiaolu Wei, Nan Si, Yuefei Zhang, Haiyu Zhao, Jian Yang, Hongjie Wang, Lianmei Wang, Linyu Han, Baolin Bian
BACKGROUND: Cinobufacin injection, also known as huachansu, is a preparation form of Cinobufacini made from Cinobufacin extract liquid. Despite that Cinobufacin injection is shown to shrink liver and gastric tumors, improving patient survival and life quality, the effective components in Cinobufacin remain elusive. In this study, we aim to screen antitumor components from Cinobufacin injection to elucidate the most effective antitumor components for treatment of liver and gastric cancers...
2017: PloS One
https://www.readbyqxmd.com/read/28017762/structure-activity-relationship-studies-on-a-trp-dendrimer-with-dual-activities-against-hiv-and-enterovirus-a71-modifications-on-the-amino-acid
#19
Belén Martínez-Gualda, Liang Sun, Eva Rivero-Buceta, Aida Flores, Ernesto Quesada, Jan Balzarini, Sam Noppen, Sandra Liekens, Dominique Schols, Johan Neyts, Pieter Leyssen, Carmen Mirabelli, María-José Camarasa, Ana San-Félix
We have recently described a new class of dendrimers with tryptophan (Trp) on the surface that show dual antiviral activities against HIV and EV71 enterovirus. The prototype compound of this family is a pentaerythritol derivative with 12 Trps on the periphery. Here we complete the structure-activity relationship studies of this family to identify key features that might be significant for the antiviral activity. With this aim, novel dendrimers containing different amino acids (aromatic and non-aromatic), tryptamine (a "decarboxylated" analogue of Trp) and N-methyl Trp on the periphery have been prepared...
December 23, 2016: Antiviral Research
https://www.readbyqxmd.com/read/28008798/risk-assessment-of-dietary-exposure-to-tryptamine-for-the-austrian-population
#20
Nadja Wüst, Elke Rauscher-Gabernig, Johann Steinwider, Friedrich Bauer, Peter Paulsen
Tryptamine acts as a neuromodulator and vasoactive agent in the human body. Dose-response data on dietary tryptamine are scarce and neither a toxicological threshold value nor tolerable levels in foods have been established so far. This paper reviews dose-response characteristics and toxicological effects of tryptamine as well as tryptamine contents in food, estimates dietary exposure of Austrian consumers, and calculates risk-based maximum tolerable limits for food categories. A dose without effect of 8 mg kg(-1) body weight day(-1) was derived from literature data...
March 2017: Food Additives & Contaminants. Part A, Chemistry, Analysis, Control, Exposure & Risk Assessment
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