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Tryptamines

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https://www.readbyqxmd.com/read/28623006/a-longevity-study-with-enhancer-substances-selegiline-bpap-detected-an-unknown-tumor-manifestation-suppressing-regulation-in-rat-brain
#1
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...
June 13, 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
#2
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
#3
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
#4
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
#5
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
#6
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 30, 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
#7
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
#8
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
#9
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
#10
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
#11
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
#12
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
#13
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
#14
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
https://www.readbyqxmd.com/read/28460972/bioactive-amines-in-passiflora-are-affected-by-species-and-fruit-development
#15
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
#16
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...
June 2017: Nature Medicine
https://www.readbyqxmd.com/read/28444659/new-psychoactive-substances-nps-a-challenge-for-the-addiction-treatment-services
#17
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
#18
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
#19
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
#20
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
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