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Tryptamines

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https://www.readbyqxmd.com/read/28721631/1-trichloromethyl-1-2-3-4-tetrahydro-beta-carboline-taclo-alters-cell-cycle-progression-in-human-neuroblastoma-cell-lines
#1
Rakesh Kumar Sharma, Eduardo Candelario-Jalil, Doris Feineis, Gerhard Bringmann, Bernd L Fiebich, Ravi Shankar Akundi
1-Trichloromethyl-1,2,3,4-tetrahydro-β-carboline, abbreviated as TaClo, is an endogenous neurotoxin capable of formation in the brain through the condensation of neuronal tryptamine with ingested exogenous toxins such as trichloroethylene or chloral hydrate. Due to its structural resemblance to 1-methyl-4-phenyl-1,2,5,6-tetrahydropyridine (MPTP), and similar ability to inhibit mitochondrial complex I, TaClo has been implicated in the etiology of Parkinson's disease. Previous studies have shown the cytotoxicity of TaClo in various cell culture models...
July 18, 2017: Neurotoxicity Research
https://www.readbyqxmd.com/read/28710517/urinary-profiling-of-tryptophan-and-its-related-metabolites-in-patients-with-metabolic-syndrome-by-liquid-chromatography-electrospray-ionization-mass-spectrometry
#2
Ji Sun Oh, Hong Seong Seo, Kyoung Heon Kim, Heesoo Pyo, Bong Chul Chung, Jeongae Lee
Tryptophan (Trp) is an essential amino acid that plays an important role in protein synthesis and is a precursor of various substances related to diverse biological functions. An imbalance in Trp metabolites is associated with inflammatory diseases. The accurate and precise measurement of these compounds in biological specimens would provide meaningful information for understanding the biochemical states of various metabolic syndrome-related diseases, such as hyperlipidemia, hypertension, diabetes, and obesity...
July 14, 2017: Analytical and Bioanalytical Chemistry
https://www.readbyqxmd.com/read/28708056/metarhizium-robertsii-produces-indole-3-acetic-acid-which-promotes-root-growth-in-arabidopsis-and-enhances-virulence-to-insects
#3
Xinggang Liao, Brian Lovett, Weiguo Fang, Raymond J St Leger
The plant root colonizing insect-pathogenic fungus Metarhizium robertsii has been shown to boost plant growth, but little is known about the responsible mechanisms. Here we show that M. robertsii promotes lateral root growth and root hair development of Arabidopsis seedlings in part through an auxin [indole-3-acetic acid (IAA)]-dependent mechanism. M. robertsii, or its auxin-containing culture filtrate promoted root proliferation, activated IAA-regulated gene expression and rescued the root hair defect of the IAA-deficient rhd6 Arabidopsis mutant...
July 15, 2017: Microbiology
https://www.readbyqxmd.com/read/28705171/formula-diet-driven-microbiota-shifts-tryptophan-metabolism-from-serotonin-to-tryptamine-in-neonatal-porcine-colon%C3%AF
#4
Manish Kumar Saraf, Brian D Piccolo, Anne K Bowlin, Kelly E Mercer, Tanya LeRoith, Sree V Chintapalli, Kartik Shankar, Thomas M Badger, Laxmi Yeruva
BACKGROUND: The gut microbiota of breast-fed and formula-fed infants differ significantly, as do the risks for allergies, gut dysfunction, and upper respiratory tract infections. The connections between breast milk, various formulas, and the profiles of gut bacteria to these childhood illnesses, as well as the mechanisms underlying the effects, are not well understood. METHODS: We investigated distal colon microbiota by 16S RNA amplicon sequencing, morphology by histomorphometry, immune response by cytokine expression, and tryptophan metabolism in a pig model in which piglets were sow-fed, or fed soy or dairy milk-based formula from postnatal day (PND) 2 to 21...
July 14, 2017: Microbiome
https://www.readbyqxmd.com/read/28677880/study-of-the-in-vitro-and-in-vivo-metabolism-of-the-tryptamine-5-meo-mipt-using-human-liver-microsomes-and-real-case-samples
#5
Katharina Elisabeth Grafinger, Marianne Hädener, Stefan König, Wolfgang Weinmann
The synthetic tryptamine 5-methoxy-N-methyl-N-isopropyltryptamine (5-MeO-MiPT) has recently been abused as a hallucinogenic drug in Germany and Switzerland. This study presents a case of 5-MeO-MiPT intoxication and the structural elucidation of metabolites in pooled human liver microsomes (pHLM), blood, and urine. Microsomal incubation experiments were performed using pHLM to detect and identify in vitro metabolites. In August 2016, the police encountered a naked man, agitated and with aggressive behavior on the street...
July 5, 2017: Drug Testing and Analysis
https://www.readbyqxmd.com/read/28649074/neurochemical-and-behavioral-effects-of-green-tea-camellia-sinensis-as-observed-in-animals-exposed-to-restraint-stress
#6
Huma Ikram, Beenish Mirza, Darakhshan Jabeen Haleem
Clinical studies on psychiatric patients suggest that life events stress precipitates depression. The possible involvement of 5-Hydroxy tryptamine (5-HT; Serotonin) in depression and other behavioral deficits is also suggested by clinical studies. As a natural stimulant, green tea (Camellia Sinensis) diminishes stress, worry and anxiety, allowing the brain to focus and concentrate better. Previously we have reported that beneficial effects of green tea might be associated with altered levels of 5-HT, which in turn may help in coping with stress...
March 2017: Pakistan Journal of Pharmaceutical Sciences
https://www.readbyqxmd.com/read/28623006/a-longevity-study-with-enhancer-substances-selegiline-bpap-detected-an-unknown-tumor-manifestation-suppressing-regulation-in-rat-brain
#7
J Knoll, K Baghy, S Eckhardt, P Ferdinandy, M Garami, L G Harsing, P Hauser, Z Mervai, T Pocza, Z Schaff, D Schuler, I Miklya
AIMS: First proof to show that (-)-deprenyl/selegiline (DEP), the first selective inhibitor of MAO-B, later identified as the first β-phenylethylamine (PEA)-derived synthetic catecholaminergic activity enhancer (CAE) substance and (2R)-1-(1-benzofuran-2-yl)-N-propylpentane-2-amine (BPAP), the tryptamine-derived presently known most potent, selective, synthetic enhancer substance, are specific markers of unknown enhancer-sensitive brain regulations. MAIN METHODS: Longevity study disclosing the operation of tumor-manifestation-suppressing (TMS) regulation in rat brain...
August 1, 2017: Life Sciences
https://www.readbyqxmd.com/read/28602505/proposal-of-5-methoxy-n-methyl-n-isopropyltryptamine-consumption-biomarkers-through-identification-of-in-vivo-metabolites-from-mice
#8
D Fabregat-Safont, M Barneo-Muñoz, F Martinez-Garcia, J V Sancho, F Hernández, M Ibáñez
New psychoactive substances (NPS) are a new breed of synthetically produced substances designed to mimic the effects of traditional illegal drugs. Synthetic cannabinoids and synthetic cathinones are the two most common groups, which try to mimic the effects of the natural compounds (9)Δ-tetrahydrocannabinol and cathinone, respectively. Similarly, synthetic tryptamines are designer compounds which are based on the compounds psilocin, N,N-dimethyltryptamine and 5-methoxy-N,N-dimethyltryptamine found in some mushrooms...
June 5, 2017: Journal of Chromatography. A
https://www.readbyqxmd.com/read/28569652/something-new-about-something-old-a-10-year-follow-up-on-classical-and-new-psychoactive-tryptamines-and-results-of-analysis
#9
Álvaro José Palma-Conesa, Mireia Ventura, Liliana Galindo, Francina Fonseca, Marc Grifell, Pol Quintana, Iván Fornís, Cristina Gil, Magí Farré, Marta Torrens
New psychoactive tryptamines may be a public health risk since they intend to mimic the hallucinogenic effects of regulated psychoactive drugs. Few studies describe uses and clinical effects of unregulated new psychoactive tryptamines. This study aims (1) to explore the presence of tryptamines classified as NPS among the substances delivered for analysis to a harm-reduction organization; (2) to describe the substances found in the samples after analysis; and (3) to compare analytical results of regulated vs...
June 1, 2017: Journal of Psychoactive Drugs
https://www.readbyqxmd.com/read/28554311/the-role-of-sigma-1-receptor-an-intracellular-chaperone-in-neurodegenerative-diseases
#10
Botond Penke, Lívia Fülöp, Mária Szűcs, Ede Frecska
Widespread protein aggregation occurs in the living system under stress or during aging, owing to disturbance of endoplasmic reticulum (ER) proteostasis. Many neurodegenerative diseases may have a common mechanism: the failure of protein homeostasis. Perturbation of ER results in unfolded protein response (UPR). Prolonged chronical UPR may activate apoptotic pathways and cause cell death. ER is associated to mitochondria by the mitochondria-associated ER-membrane, MAM. The sigma-1 receptor (Sig-1R), a well-known ER-chaperone localizes in the MAM...
May 28, 2017: Current Neuropharmacology
https://www.readbyqxmd.com/read/28540034/ayahuasca-dimethyltryptamine-and-psychosis-a-systematic-review-of-human-studies
#11
REVIEW
Rafael G Dos Santos, José Carlos Bouso, Jaime E C Hallak
Ayahuasca is a hallucinogen brew traditionally used for ritual and therapeutic purposes in Northwestern Amazon. It is rich in the tryptamine hallucinogens dimethyltryptamine (DMT), which acts as a serotonin 5-HT2A agonist. This mechanism of action is similar to other compounds such as lysergic acid diethylamide (LSD) and psilocybin. The controlled use of LSD and psilocybin in experimental settings is associated with a low incidence of psychotic episodes, and population studies corroborate these findings. Both the controlled use of DMT in experimental settings and the use of ayahuasca in experimental and ritual settings are not usually associated with psychotic episodes, but little is known regarding ayahuasca or DMT use outside these controlled contexts...
April 2017: Therapeutic Advances in Psychopharmacology
https://www.readbyqxmd.com/read/28537942/locomotor-and-discriminative-stimulus-effects-of-four-novel-hallucinogens-in-rodents
#12
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)...
August 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
#13
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
#14
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
#15
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
#16
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
#17
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...
September 2017: American Journal of Drug and Alcohol Abuse
https://www.readbyqxmd.com/read/28466889/asymmetric-fluorinative-dearomatization-of-tryptamine-derivatives
#18
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
#19
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...
June 2017: Journal of Biological Rhythms
https://www.readbyqxmd.com/read/28466505/total-synthesis-of-%C3%A2-corymine
#20
Benxiang Zhang, Xiaoqing Wang, Chao Cheng, Deqian Sun, Chaozhong Li
The first total synthesis of the hexacyclic indole alkaloid (±)-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 a 12-membered cyclic enol ether by intramolecular O-propargylation, immediately followed by propargyl Claisen rearrangement to provide the α-allenyl ketone stereospecifically, c) DMDO oxidation to install a hydroxy group in a 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
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