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https://www.readbyqxmd.com/read/27799032/herbal-highs-review-on-psychoactive-effects-and-neuropharmacology
#1
Silvia Graziano, Laura Orsolini, Maria Concetta Rotolo, R Tittarelli, Fabrizio Schifano, Simona Pichini
BACKGROUND: A new trend among users of new psychoactive substances' the consumption of "herbal highs": plant parts containing psychoactive substances. Most of the substances extracted from herbs, in old centuries were at the centre of religious ceremonies of ancient civilizations. Currently, these herbal products are mainly sold by internet web sites and easily obtained since some of them have no legal restriction. OBJECTIVE: We reviewed psychoactive effects and neuropharmacology of the most used "herbal highs" with characterized active principles, with studies reporting mechanisms of action, pharmacological and subjective effects, eventual secondary effects including intoxications and/or fatalities Method: The PubMed database was searched using the following key...
October 31, 2016: Current Neuropharmacology
https://www.readbyqxmd.com/read/27759387/a-hexacyclic-iboga-derived-monoterpenoid-indole-with-a-contracted-tetrahydroazepine-c-ring-and-incorporation-of-an-isoxazolidine-moiety-a-seco-corynanthean-an-aspidosperma-aspidosperma-bisindole-with-anticancer-properties-and-the-absolute-configuration-of-the
#2
Choy-Eng Nge, Kae-Shin Sim, Siew-Huah Lim, Noel F Thomas, Yun-Yee Low, Toh-Seok Kam
Examination of the EtOH extract of the Malayan Tabernaemontana corymbosa resulted in the isolation of three new alkaloids, viz., cononuridine (1), an unusual hexacyclic, iboga-derived, monoterpenoid indole characterized by contraction of the tetrahydroazepine C-ring and incorporation of an additional isoxazolidine ring, taberisidine (2), a seco-corynanthean alkaloid, and conofolidine (3), an Aspidosperma-Aspidosperma bisindole that showed pronounced in vitro growth inhibitory activity against an array of human cancer cell lines, including KB, vincristine-resistant KB, PC-3, LNCaP, MCF7, MDA-MB-231, HT-29, and HCT 116 cells...
October 19, 2016: Journal of Natural Products
https://www.readbyqxmd.com/read/27734823/-ibogaine-structure-influence-on-human-body-clinical-relevance
#3
Zygmunt Zdrojewicz, Bartłomiej Kuszczak, Natalia Olszak
Ibogaine is a natural chemical compound, which belongs to the indole alkaloid family. It can be naturally found within the root bark of african plant Tabernanthe iboga. Ibogaine plays a significant role among tribal cultures. Ibogaine, in small amount, causes reduction of hunger, thirst and exhaustion. In bigger amount, however, it can cause intensive visions. Other effects include reduction or complete disappearance of absitnence symptoms visible in people addicted to the nicotine, alcohol, methamphetamine, cocaine or opioids, what has been scientifically proven after the tests on animals and small groups of people...
July 29, 2016: Polski Merkuriusz Lekarski: Organ Polskiego Towarzystwa Lekarskiego
https://www.readbyqxmd.com/read/27704811/vobasinyl-iboga-alkaloids-from-tabernaemontana-elegans-cell-cycle-arrest-and-apoptosis-inducing-activity-in-hct116-colon-cancer-cells
#4
Angela Paterna, Sofia E Gomes, Pedro M Borralho, Silva Mulhovo, Cecília M P Rodrigues, Maria-José U Ferreira
Phytochemical investigation of the roots of the African medicinal plant Tabernaemontana elegans led to the isolation of three new (1-3) and two known (4 and 5) bisindole alkaloids of the vobasinyl-iboga type. The structures of 1-3 were assigned by spectroscopic methods, mainly using 1D and 2D NMR experiments. All of the isolated compounds were evaluated for their cytotoxicity against HCT116 colon and HepG2 liver carcinoma cells by the MTS metabolism assay. Compounds 1-3 and 5 were found to be cytotoxic to HCT116 colon cancer cells, displaying IC50 values in the range 8...
October 5, 2016: Journal of Natural Products
https://www.readbyqxmd.com/read/27616029/-3-r-hydroxytabernaelegantine-c-a-bisindole-alkaloid-with-potent-apoptosis-inducing-activity-in-colon-hct116-sw620-and-liver-hepg2-cancer-cells
#5
Angela Paterna, Sofia E Gomes, Pedro M Borralho, Silva Mulhovo, Cecília M P Rodrigues, Maria-José U Ferreira
ETHNOPHARMACOLOGICAL RELEVANCE: Tabernaemontana elegans Stapf. (Apocynaceae) is a medicinal plant traditionally used in African countries to treat cancer. AIMS OF THE STUDY: To discover new apoptosis inducing lead compounds from T. elegans and provide scientific validation of the ethnopharmacological use of this plant. MATERIALS AND METHODS: Through fractionation, (3'R)-hydroxytaberanelegantine C (1), a vobasinyl-iboga bisindole alkaloid, was isolated from a cytotoxic alkaloid fraction of the methanol extract of T...
September 8, 2016: Journal of Ethnopharmacology
https://www.readbyqxmd.com/read/27426011/ibogaine-for-treating-drug-dependence-what-is-a-safe-dose
#6
REVIEW
L J Schep, R J Slaughter, S Galea, D Newcombe
The indole alkaloid ibogaine, present in the root bark of the West African rain forest shrub Tabernanthe iboga, has been adopted in the West as a treatment for drug dependence. Treatment of patients requires large doses of the alkaloid to cause hallucinations, an alleged integral part of the patient's treatment regime. However, case reports and case series continue to describe evidences of ataxia, gastrointestinal distress, ventricular arrhythmias and sudden and unexplained deaths of patients undergoing treatment for drug dependence...
September 1, 2016: Drug and Alcohol Dependence
https://www.readbyqxmd.com/read/27342343/death-related-to-consumption-of-rauvolfia-sp-powder-mislabeled-as-tabernanthe-iboga
#7
Thomas Gicquel, Chloé Hugbart, Françoise Le Devehat, Sylvie Lepage, Alain Baert, Renaud Bouvet, Isabelle Morel
Powdered roots of iboga (Tabernanthe iboga) contain ibogaine, an alkaloid that has been used to treat addictions. We report the case of a 30-year-old woman who died after ingesting a powder labeled as Tabernanthe iboga she had bought online. Analysis of the powder revealed the absence of ibogaine but the presence of toxic alkaloids (ajmaline, yohimbine and reserpine) found in Rauvolfia sp. plant species. An original and specific LC-MS/MS method developed to quantify ajmaline, yohimbine and reserpine showed respective concentrations of 109...
September 2016: Forensic Science International
https://www.readbyqxmd.com/read/27192438/remission-of-severe-opioid-use-disorder-with-ibogaine-a-case-report
#8
Laurie Cloutier-Gill, Evan Wood, Trevor Millar, Caroline Ferris, M Eugenia Socias
BACKGROUND: Opioid use disorders (OUD) translate into major health, social, and economic consequences. Opioid agonist medications, which generally require long-term administration, are the mainstay pharmacological treatment of OUD. However, a large proportion of individuals with OUD either refuse or fail to respond to these therapies. Ibogaine, a naturally occurring substance found in the Tabernanthe iboga plant, has shown potential to bring about transformative or spiritual experiences that have reportedly been associated with long-term abstinece...
July 2016: Journal of Psychoactive Drugs
https://www.readbyqxmd.com/read/27180314/effects-of-low-dose-ibogaine-on-subjective-mood-state-and-psychological-performance
#9
Bridget Forsyth, Liana Machado, Tim Jowett, Hannah Jakobi, Kira Garbe, Helen Winter, Paul Glue
ETHNOPHARMACOLOGICAL RELEVANCE: Root bark from Tabernanthe iboga has been used traditionally in West Africa as a psychoactive substance in religious rituals. In smaller doses it is reported anecdotally to have stimulant properties. AIM OF THE STUDY: To evaluate the influence of a single 20mg ibogaine dose on psychological variables reflecting subjective mood state and a range of cognitive functions. MATERIALS AND METHODS: 21 healthy male volunteers received single 20mg doses of ibogaine after 6 days pretreatment with double-blind paroxetine or placebo...
August 2, 2016: Journal of Ethnopharmacology
https://www.readbyqxmd.com/read/27160167/bioinspired-collective-syntheses-of-iboga-type-indole-alkaloids
#10
Gaoyuan Zhao, Xingang Xie, Haiyu Sun, Ziyun Yuan, Zhuliang Zhong, Shouchu Tang, Xuegong She
We present the application of a bioinspired collective synthesis strategy in the total syntheses of seven iboga-type indole alkaloids: (±)-tabertinggine, (±)-ibogamine, (±)-ibogaine, (±)-ibogaine hydroxyindolenine, (±)-3-oxoibogaine hydroxyindolenine, (±)-iboluteine, and (±)-ervaoffines D. In particular, tabertinggine and its congeners serve as iboga precursors for the subsequent biomimetic transformations into other iboga-type alkaloids.
May 20, 2016: Organic Letters
https://www.readbyqxmd.com/read/27126304/functional-neurotoxicity-evaluation-of-noribogaine-using-video-eeg-in-cynomolgus-monkeys
#11
Simon Authier, Michael V Accardi, Dominique Paquette, Mylène Pouliot, Joseph Arezzo, R John Stubbs, Ronald J Gerson, Lawrence T Friedhoff, Holger Weis
INTRODUCTION: Continuous video-electroencephalographic (EEG) monitoring remains the gold standard for seizure liability assessments in preclinical drug safety assessments. EEG monitored by telemetry was used to assess the behavioral and EEG effects of noribogaine hydrochloride (noribogaine) in cynomolgus monkeys. Noribogaine is an iboga alkaloid being studied for the treatment of opioid dependence. METHODS: Six cynomolgus monkeys (3 per gender) were instrumented with EEG telemetry transmitters...
September 2016: Journal of Pharmacological and Toxicological Methods
https://www.readbyqxmd.com/read/27077800/ibogan-aspidosperman-vincamine-and-bisindole-alkaloids-from-a-malayan-tabernaemontana-corymbosa-iboga-alkaloids-with-c-20%C3%AE-substitution
#12
Choy-Eng Nge, Kam-Weng Chong, Noel F Thomas, Siew-Huah Lim, Yun-Yee Low, Toh-Seok Kam
Ten new indole alkaloids (1-10) comprising five ibogan, two aspidosperman, one vincamine, and two bisindole alkaloids, in addition to 32 known alkaloids, were isolated from the stem-bark extract of a Malayan Tabernaemontana corymbosa. The structures of these alkaloids were determined based on analysis of the NMR and MS data and, in five instances (1, 3, 5, 6, 8), confirmed by X-ray diffraction analysis. Two of the iboga alkaloids, conodusines B (2) and C (3), and the iboga-containing bisindole tabernamidine B (10) are notable for the presence of an α-substituted acetyl group at C-20 of the iboga carbon skeleton...
May 27, 2016: Journal of Natural Products
https://www.readbyqxmd.com/read/26918761/vobatensines-a-f-cytotoxic-iboga-vobasine-bisindoles-from-tabernaemontana-corymbosa
#13
Dawn Su-Yin Sim, Wuen-Yew Teoh, Kae-Shin Sim, Siew-Huah Lim, Noel F Thomas, Yun-Yee Low, Toh-Seok Kam
Six new bisindole alkaloids of the iboga-vobasine type, vobatensines A-F (1-6), in addition to four known bisindoles (8-11), were isolated from a stem bark extract of a Malayan Tabernaemontana corymbosa. The structures of these alkaloids were determined based on analysis of the spectroscopic data and in the case of vobatensines A (1), B (2), and 16'-decarbomethoxyvoacamine (8) also confirmed by partial syntheses. Nine of these alkaloids (1-5, 8-11) showed pronounced in vitro growth inhibitory activity against human KB, PC-3, LNCaP, HCT 116, HT-29, MCF7, MDA-MB-231, and A549 cancer cells...
April 22, 2016: Journal of Natural Products
https://www.readbyqxmd.com/read/26827885/monoterpenoid-bisindole-alkaloids
#14
REVIEW
Mariko Kitajima, Hiromitsu Takayama
This chapter covers the literature on bisindole alkaloids consisting of monoterpenoid indoles, published up to June 2015. Bisindole alkaloids isolated from plants belonging to the families Apocynaceae and Loganiaceae, including Iboga-vobasine type, Aspidosperma-Aspidosperma type, eburnan-Aspidosperma type, Strychnos-Strychnos type, macroline-macroline type, and so on, are described. Some recent syntheses of monoterpenoid bisindole alkaloids are outlined as well.
2016: Alkaloids. Chemistry and Biology
https://www.readbyqxmd.com/read/26807959/how-toxic-is-ibogaine
#15
REVIEW
Ruud P W Litjens, Tibor M Brunt
CONTEXT: Ibogaine is a psychoactive indole alkaloid found in the African rainforest shrub Tabernanthe Iboga. It is unlicensed but used in the treatment of drug and alcohol addiction. However, reports of ibogaine's toxicity are cause for concern. OBJECTIVES: To review ibogaine's pharmacokinetics and pharmacodynamics, mechanisms of action and reported toxicity. METHODS: A search of the literature available on PubMed was done, using the keywords "ibogaine" and "noribogaine"...
2016: Clinical Toxicology
https://www.readbyqxmd.com/read/26231157/coronaridine-an-iboga-type-alkaloid-from-tabernaemontana-divaricata-inhibits-the-wnt-signaling-pathway-by-decreasing-%C3%AE-catenin-mrna-expression
#16
Kensuke Ohishi, Kazufumi Toume, Midori A Arai, Samir K Sadhu, Firoj Ahmed, Masami Ishibashi
Four alkaloids, voacangine (1), isovoacangine (2), coronaridine (3), and coronaridine hydroxyindolenine (4), were isolated from the MeOH extract of Tabernaemontana divaricata aerial parts by activity-guided fractionation for Wnt signal inhibitory activity. Compounds 1-4 exhibited TCF/β-catenin inhibitory activities with IC50 values of 11.5, 6.0, 5.8, and 7.3 μM, respectively. Of these, coronaridine (3) decreased β-catenin levels in SW480 colon cancer cells, while this decrease in β-catenin was not suppressed by a co-treatment with 3 and MG132, a proteasome inhibitor...
September 15, 2015: Bioorganic & Medicinal Chemistry Letters
https://www.readbyqxmd.com/read/25919190/ibogan-tacaman-and-cytotoxic-bisindole-alkaloids-from-tabernaemontana-cononusine-an-iboga-alkaloid-with-unusual-incorporation-of-a-pyrrolidone-moiety
#17
Kuan-Hon Lim, Vijay J Raja, Tracey D Bradshaw, Siew-Huah Lim, Yun-Yee Low, Toh-Seok Kam
Six new indole alkaloids, viz., cononusine (1, a rare example of an iboga-pyrrolidone conjugate), ervaluteine (2), vincamajicine (3), tacamonidine (4), 6-oxoibogaine (5), and N(4)-chloromethylnorfluorocurarine chloride (6), and two new vobasinyl-iboga bisindole alkaloids, ervatensines A (7) and B (8), in addition to other known alkaloids, were isolated from the stem-bark extract of the Malayan Tabernaemontana corymbosa. The structures of these alkaloids were established on the basis of NMR and MS analyses and, in one instance (7), confirmed by X-ray diffraction analysis...
May 22, 2015: Journal of Natural Products
https://www.readbyqxmd.com/read/25660330/ex-vivo-effects-of-ibogaine-on-the-activity-of-antioxidative-enzymes-in-human-erythrocytes
#18
Aleksandra Nikolić-Kokić, Zorana Oreščanin-Dušić, Ivan Spasojević, Marija Slavić, Ana Mijušković, Roman Paškulin, Čedo Miljević, Mihajlo B Spasić, Duško P Blagojević
ETHNOPHARMACOLOGICAL RELEVANCE: Ibogaine is a naturally occurring alkaloid with psychotropic and metabotropic effects, derived from the bark of the root of the West African Tabernanthe iboga plant. The tribes of Kongo basin have been using iboga as a stimulant, for medicinal purposes, and in rite of passage ceremonies, for centuries. Besides, it has been found that this drug has anti-addictive effects. AIM OF THE STUDY: Previous studies have demonstrated that ibogaine changed the quantity of ATP and energy related enzymes as well as the activity of antioxidant enzymes in cells thus altering redox equilibrium in a time manner...
April 22, 2015: Journal of Ethnopharmacology
https://www.readbyqxmd.com/read/25636206/herg-blockade-by-iboga-alkaloids
#19
Kenneth Alper, Rong Bai, Nian Liu, Steven J Fowler, Xi-Ping Huang, Silvia G Priori, Yanfei Ruan
The iboga alkaloids are a class of naturally occurring and synthetic compounds, some of which modify drug self-administration and withdrawal in humans and preclinical models. Ibogaine, the prototypic iboga alkaloid that is utilized clinically to treat addictions, has been associated with QT prolongation, torsades de pointes and fatalities. hERG blockade as IKr was measured using the whole-cell patch clamp technique in HEK 293 cells. This yielded the following IC50 values: ibogaine manufactured by semisynthesis via voacangine (4...
January 2016: Cardiovascular Toxicology
https://www.readbyqxmd.com/read/25633249/constructing-iboga-alkaloids-via-c-h-bond-functionalization-examination-of-the-direct-and-catalytic-union-of-heteroarenes-and-isoquinuclidine-alkenes
#20
Andrew C Kruegel, Souvik Rakshit, Xiaoguang Li, Dalibor Sames
The iboga alkaloids have attracted considerable attention in both the scientific community and popular media due to their reported ability to reverse or markedly diminish cravings for, and self-administration of, the major drugs of abuse. We have developed three new intramolecular C-H functionalization procedures leading to the core seven-membered ring of the iboga skeleton, a cyclization that proved to be highly challenging. The electrophilic palladium salt Pd(CH3CN)4(BF4)2 was effective for the cyclization of diverse N-(2-arylethyl)isoquinuclidines with yields of 10-35%...
February 20, 2015: Journal of Organic Chemistry
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