N-methyl-8-azabicyclo[3.2.1]octanes best known for the ones found in PLANTS.

Simultaneous SPECT studies of pre- and postsynaptic dopamine binding sites in baboons. (1/281)

The central nervous system dopamine transporters (DATs) and dopamine D2/D3 receptors are implicated in a variety of neurological disorders. Both sites are also targets for drug treatment. With the successful development of [99mTc]TRODAT-1, single-isotope imaging studies using this ligand for DAT imaging can be complemented by additional use of 123I-labeled D2/D3 receptor ligand co-injected to assess both pre- and postsynaptic sites of the dopaminergic system simultaneously. METHODS: Twelve SPECT scans of the brain were obtained in two baboons after intravenous administration of 740 MBq (20 mCi) [99mTc]-TRODAT-1 (technetium, [2-[[2-[[[3-(4-chlorophenyl)-8-methyl-8-azabicyclo[3,2,1]oct-2-yl]methyl ](2-mercaptoethyl) amino]ethyl]-amino]ethanethiolato (3-)]- oxo-[1R-(exo-exo)]) and 185 MBq (5 mCi) [123I]iodobenzamide or [123I]iodobenzofuran. SPECT data were acquired by a triple-head gamma camera equipped with ultra-high-resolution fanbeam collimators (scan duration = 210 min). Two sets of SPECT data were obtained using energy windows of 15% centered on 140 keV for 99mTc and 10% asymmetric with a lower bound at 159 keV for 123I. After coregistration with MRI, region-of-interest analysis was performed using predefined templates from coregistered MRI. In blocking studies, baboons were pretreated with N-methyl-2beta-carbomethoxy-3beta-(4-fluorophenyl)tropane (CFT, 14 mg) or raclopride (14 mg) to block DAT or D2/D3 binding site, respectively. RESULTS: Image quality of dual-isotope studies was similar to that obtained from single-isotope studies. When one site was blocked with CFT or raclopride, the binding of the respective ligand to the other site was not affected. CONCLUSION: This is the first example that clearly demonstrates the feasibility of simultaneous imaging of both pre- and postsynaptic sites of the dopaminergic system in baboons with dual-isotope SPECT studies. With or without corrections for cross-contamination of 123I into the 99mTc window, striatum-to-cerebellum ratios (target-to-nontarget) of dual-isotope experiments did not differ significantly from single-isotope experiments. This method may be a valuable and cost-effective tool for gaining comprehensive information about the dopaminergic system in one SPECT imaging session.  (+info)

One-day protocol for imaging of the nigrostriatal dopaminergic pathway in Parkinson's disease by [123I]FPCIT SPECT. (2/281)

Parkinson's disease is characterized by degeneration of dopaminergic neurons, resulting in loss of dopamine transporters in the striatum. Recently, the tracer 1231-N-omega-fluoropropyl-2beta-carbomethoxy-3beta-(4-iodoph enyl)nortropane (FPCIT) was developed for imaging dopamine transporters with SPECT. The purpose of this study was to develop an [123I]FPCIT SPECT protocol for routine clinical studies. METHODS: We examined the time course of [123I]FPCIT binding to dopamine transporters in 10 healthy volunteers and 19 patients with Parkinson's disease. RESULTS: We found that the time of peak specific striatal [123I]FPCIT binding was highly varied among subjects, but specific binding peaked in all controls and patients within 3 h postinjection. Between 3 and 6 h, the ratio of specific-to-nonspecific striatal [123I]FPCIT binding was stable in both groups, although, as expected, it was significantly lower in patients. In the patients, [123I]FPCIT binding in the putamen was lower than in the caudate nucleus, and contralateral striatal binding was significantly lower than ipsilateral striatal binding. The subgroup of patients with hemi-Parkinson's disease showed loss of striatal dopamine transporters, even on the ipsilateral side. CONCLUSION: For routine clinical [123I]FPCIT SPECT studies, we recommend imaging at a single time point, between 3 and 6 h postinjection, and using a tissue ratio as the outcome measure. The [123I]FPCIT SPECT technique is sensitive enough to distinguish control subjects from patients with Parkinson's disease, even at an early stage of the disease.  (+info)

Pharmacological characterization of nicotine's interaction with cocaine and cocaine analogs. (3/281)

Cocaine and a number of 3beta-phenyltropane cocaine analogs were investigated for their potential to block various pharmacological effects of nicotine in animals. They blocked the antinociceptive effect of nicotine in the tail-flick test after systemic administration in a dose-dependent manner. Similarly, cocaine was also able to block nicotine-induced motor impairment in mice. Furthermore, cocaine blocked nicotine-induced seizures at a lower potency than for antinociception, but failed to block nicotine's effect on body temperature and drug discrimination. The antagonistic potencies of the 3beta-phenyltropane cocaine analogs were not correlated with their affinity for monoamines transporters. Additionally, bupropion, nomifensin, GBR 12909, and nisoxetine, but not methylphenidate and fluoxetine, blocked nicotine-induced antinociception; however, their antagonistic potencies were unrelated to their affinities for the transporters. Taken together, these results suggest that the mechanism of cocaine's antagonistic activity is not related to its binding and uptake of inhibition on monoamine neurotransporters. The failure of lidocaine and procaine to antagonize nicotine's effects in the tail-flick assay rules out local anesthetic effects. In addition, cocaine blocked differentially the response of nicotine in the oocyte receptor expression system for the alpha4beta2 and alpha3beta2 subtypes in a dose-dependent manner. Our results suggest that cocaine is a noncompetitive nicotinic antagonist with some selectivity for neuronal nicotinic receptor subtypes. Our studies also demonstrate that 3beta-phenyltropane analogs constitute a new class of nicotinic antagonists. Elucidation of the mechanism of action of this new class of antagonists may provide an explanation for the effectiveness of agents such as bupropion for the treatment of smoking cessation.  (+info)

Tetraethylammonium and 4-aminopyridine enhancement of 5-HT3 receptor-mediated contraction of guinea pig ileum in vitro. (4/281)

AIM: To study the effects of tetraethylammonium (TEA) and 4-aminopyridine (4-AP) on 5-HT3 receptor-mediated contractions of the isolated guinea pig ileum longitudinal muscle-myenteric plexus strip preparations (GPI). METHODS: GPI contractions were recorded with a chart recorder through isometric transducers. The effect of TEA and 4-AP on binding properties of 5-HT3 receptors was assessed using [3H]GR65630 binding assay in membrane preparation of rat entorhinal cortex. RESULTS: (1) Both TEA 0.5 mmol.L-1 and 4-AP 5 mumol.L-1 increased the spontaneous activity, and elicited contractions of GPI; atropine 10 mumol.L-1 or the selective 5-HT3 receptor antagonist MDL72222 100 mumol.L-1 prevented these effects. (2) Both TEA 0.05-0.5 mmol.L-1 and 4-AP 1-10 mumol.L-1 enhanced GPI contractions induced by the selective 5-HT3 receptor agonists 2-methyl-5-HT in concentration-dependent manners. (3) Both TEA 0.5 mmol.L-1 and 4-AP 5 mumol.L-1 attenuated the inhibitory effects of the selective 5-HT3 receptor antagonists tropisetron 0.1 mumol.L-1 and benesetron 1 mumol.L-1 on 5-HT3 receptor-mediated GPI contractions. (4) Neither TEA 0.1-0.5 mmol.L-1 nor 4-AP 5-10 mumol.L-1 affected GPI contractions evoked by the selective M-ACh receptor agonist carbachol 1 mumol.L-1. (5) TEA 0.5 mmol.L-1 and 4-AP 10 mumol.L-1 had no effect on the properties of binding of the selective 5-HT3 receptor radioligand [3H]GR65630 to 5-HT3 receptors. CONCLUSION: The enhancement by TEA and 4-AP of 5-HT3 receptor-mediated GPI contractile responses was due to blocking K+ channels in prejunctional myenteric neurons.  (+info)

Quantification and visualization of defects of the functional dopaminergic system using an automatic algorithm. (5/281)

In SPECT, the binding of radiotracers in brain areas is usually assessed by manual positioning of regions of interest (ROIs). The disadvantages of this method are that it is an observer-dependent procedure and that it may not be sensitive for assessing defects significantly smaller than the ROI. To circumvent these limitations, we developed a fully automatic three-dimensional technique that quantifies neuronal radiotracer binding on a voxel-by-voxel basis. METHODS: To build a model of normal 123I-labeled N-omega-fluoropropyl-2beta-carbomethoxy-3beta-(4-iodophenyl) nortropane (FPCIT) binding, 17 studies of healthy volunteers were registered to the same orientation. After registration, the specific-to-nonspecific binding ratio was calculated for each voxel of the striatal volumes of interest (VOIs). The mean and SD of that binding ratio were then calculated on a voxel-by-voxel basis. For the analysis of 10 healthy volunteer studies (control group) and 21 studies of drug-naive patients with Parkinson's disease, the registration and calculation of the specific-to-nonspecific [123I]FPCIT binding ratio were performed by the same method. Subsequently, a voxel of the striata was classified as a diminished [123I]FPCIT binding ratio if its value was lower than the mean -2 x SD. For each subject, the defect size, the relative number of voxels with a diminished binding ratio and the binding ratio of the whole striatal VOIs were calculated and compared with the binding ratio as assessed by the traditional ROI method. RESULTS: The results of the automatic method correlated significantly with the results of the traditional ROI method. Furthermore, for the ipsilateral side, the automatically calculated defect size had less overlap between the patient and the control group than the traditionally calculated binding ratio. CONCLUSION: The method presented quantifies [123I]FPCIT binding ratio automatically on a voxel-by-voxel basis, by comparison with a model of healthy volunteers. We have shown that it is appropriate to use the automatic method as a replacement for the traditional manual method, which enables us to study the localized dopaminergic degeneration process in Parkinson's disease more precisely and without any inter- or intraobserver variability.  (+info)

Effects of age on dopamine transporters in healthy humans. (6/281)

99mTc-TRODAT-1 is a new radiopharmaceutical that selectively binds the dopamine transporters. This study characterized the effects of aging on its regional cerebral distribution in healthy human volunteers. METHODS: The sample consisted of 27 men and 28 women with a mean age of 41.1 +/- 17.1 y (age range 18.7-73.8 y). Dynamic SPECT scans of the brain were obtained with a standardized acquisition and processing protocol on a triple-head camera. Mean counts per pixel were measured in multiple regions of interest within each basal ganglia. Regression analyses were used to relate the specific uptake values at 3-4 h after administration to age. Both linear and nonlinear models of aging were tested. RESULTS: The relative concentration of radioactivity in most subregions of the basal ganglia decreased significantly with age (all P values < 0.0001). Nonlinear models of aging fit the data significantly better than a straight line. The rate of decline was significantly faster in young adults than in older volunteers (P < 0.001). The break-point age at which the rate of change slowed down and became more stable was 36 y old for the whole striatum and ranged from 32 to 44 y old depending on subregion. CONCLUSION: The effects of aging on central nervous system dopamine transporters do not appear to be linear. Most effects seem to occur during young adulthood before people reach their 40s. The distribution then appears to remain relatively stable until late in life. The findings suggest that the adult life cycle is better characterized as a series of phases than as a continuum.  (+info)

UB-165: a novel nicotinic agonist with subtype selectivity implicates the alpha4beta2* subtype in the modulation of dopamine release from rat striatal synaptosomes. (7/281)

Presynaptic nicotinic acetylcholine receptors (nAChRs) on striatal synaptosomes stimulate dopamine release. Partial inhibition by the alpha3beta2-selective alpha-conotoxin-MII indicates heterogeneity of presynaptic nAChRs on dopamine terminals. We have used this alpha-conotoxin and UB-165, a novel hybrid of epibatidine and anatoxin-a, to address the hypothesis that the alpha-conotoxin-MII-insensitive subtype is composed of alpha4 and beta2 subunits. UB-165 shows intermediate potency, compared with the parent molecules, at alpha4beta2* and alpha3-containing binding sites, and resembles epibatidine in its high discrimination of these sites over alpha7-type and muscle binding sites. (+/-)-Epibatidine, (+/-)-anatoxin-a, and (+/-)-UB-165 stimulated [(3)H]-dopamine release from striatal synaptosomes with EC(50) values of 2.4, 134, and 88 nM, and relative efficacies of 1:0.4:0.2, respectively. alpha-Conotoxin-MII inhibited release evoked by these agonists by 48, 56, and 88%, respectively, suggesting that (+/-)-UB-165 is a very poor agonist at the alpha-conotoxin-MII-insensitive nAChR subtype. In assays of (86)Rb(+) efflux from thalamic synaptosomes, a model of an alpha4beta2* nAChR response, (+/-)-UB-165 was a very weak partial agonist; the low efficacy of (+/-)-UB-165 at alpha4beta2 nAChR was confirmed in Xenopus oocytes expressing various combinations of human nAChR subunits. In contrast, (+/-)-UB-165 and (+/-)-anatoxin-a were similarly efficacious and similarly sensitive to alpha-conotoxin-MII in increasing intracellular Ca(2+) in SH-SY5Y cells, a functional assay for native alpha3-containing nAChR. These data support the involvement of alpha4beta2* nAChR in the presynaptic modulation of striatal dopamine release and illustrate the utility of exploiting a novel partial agonist, together with a selective antagonist, to dissect the functional roles of nAChR subtypes in the brain.  (+info)

Binding of [99mTc]TRODAT-1 to dopamine transporters in patients with Parkinson's disease and in healthy volunteers. (8/281)

[99mTc]TRODAT-1 is a radiolabeled tropane that binds dopamine transporters. The primary goal of this study was to determine whether its regional cerebral distribution could differentiate between patients with Parkinson's disease and healthy human volunteers. METHODS: The sample consisted of 42 patients with Parkinson's disease, 23 age-matched controls, and 38 healthy adults younger than 40 y old. SPECT scans of the brain were acquired on a triple-head gamma camera 3-4 h after the intravenous injection of 740 MBq (20 mCi) [99mTc]TRODAT-1. Mean counts per pixel were measured manually in subregions of the basal ganglia and normalized to the mean background counts to give specific uptake values ([SUVs] approximately k3/k4). Patient and control groups were also compared with automated statistical parametric mapping techniques. Logistic discriminant analyses were performed to determine the optimum uptake values for differentiating patients from age-matched controls. RESULTS: Quantitative image analysis showed that the group mean SUVs in patients were less than the mean values in controls for all regions (all Ps < 0.000001). There was overlap in the caudate as well as in the anterior-most portion of the putamen, but not in the posterior putamen, even when the asymptomatic sides of 5 patients with clinically defined hemi-Parkinson's disease were factored in. CONCLUSION: The findings indicate that Parkinson's disease can be detected with [99mTc]TRODAT by simply inspecting the images for uptake in the posterior putamen. Appropriate asymmetries seem to be visible with quantification in patients with clinically defined hemi-Parkinson's disease, even though changes in the putamen contralateral to the clinically unaffected side in these patients appear to precede the development of symptoms.  (+info)

Tropane alkaloids are a class of naturally occurring compounds that contain a tropane ring in their chemical structure. This ring is composed of a seven-membered ring with two nitrogen atoms, one of which is part of a piperidine ring. Tropane alkaloids are found in various plants, particularly those in the Solanaceae family, which includes nightshade, belladonna, and datura. Some well-known tropane alkaloids include atropine, scopolamine, and cocaine. These compounds have diverse pharmacological activities, such as anticholinergic, local anesthetic, and central nervous system stimulant effects.

8-Azabicyclo[3.2.1]octane (tropane without the N-methyl group) is known as nortropane or nor-tropane. Phenyltropane Tropane ... Tropane is a nitrogenous bicyclic organic compound. It is mainly known for the other alkaloids derived from it, which include ... Tropane alkaloids occur in plants of the families Erythroxylaceae (including coca) and Solanaceae (including mandrake, henbane ... While carbons 1 and 5 are asymmetric carbons, tropane itself is optically inactive due to mirror symmetry. ...
... s are a class of bicyclic [3.2.1] alkaloids and secondary metabolites that contain a tropane ring in their ... Tropane alkaloids occur naturally in many members of the plant family Solanaceae. Certain tropane alkaloids such as cocaine and ... Particular tropane alkaloids such as these have pharmacological properties and can act as anticholinergics or stimulants. ... The biosynthesis of the tropane alkaloids have attracted intense interest because of their high physiological activity as well ...
3β-(p-Fluorobenzoyloxy)tropane, (8-Methyl-8-azabicyclo[3.2.1]oct-3-yl 4-fluorobenzoic acid ester, 4-fluorotropacocaine, 3- ... January 2012). "The syntheses and characterization 3β-(4-fluorobenzoyloxy)tropane (fluorotropacocaine) and its 3α isomer". Drug ... Pseudotropyl-4-fluorobenzoate, 3-pseudotropyl-4-fluorobenzoate, pFBT) is a tropane derivative drug which acts as a local ... Tropanes, Dopamine reuptake inhibitors, Stimulants, Local anesthetics, Fluoroarenes, Benzoate esters). ...
... (WF-31, PIT) is a cocaine analogue which acts as a serotonin-norepinephrine-dopamine ... Tropanes, Serotonin-norepinephrine-dopamine reuptake inhibitors, Stimulants, Ketones, All stub articles, Nervous system drug ...
2β-Propanoyl-3β-(4-tolyl)tropane also known as WF-11 or 2-PTT is a cocaine analogue 20 times more potent than cocaine at ... December 2000). "A cocaine analog, 2beta-propanoyl-3beta-(4-tolyl)-tropane (PTT), reduces tyrosine hydroxylase in the ... Tropanes, Stimulants, Norepinephrine-dopamine reuptake inhibitors, Ketones, All stub articles, Nervous system drug stubs). ...
... or WF-23 (Wake Forest-23, named after the university where it was first created) is a ... June 1998). "Long-acting blockade of biogenic amine transporters in rat brain by administration of the potent novel tropane ... Tropanes, Serotonin-norepinephrine-dopamine reuptake inhibitors, Stimulants, 2-Naphthyl compounds, Ketones). ... 2beta-propanoyl-3beta-(2-Naphthyl)-tropane". The Journal of Pharmacology and Experimental Therapeutics. 285 (3): 1246-1254. ...
... or WF-33 is a cocaine analogue. It, along with WF-23 the other "2-naphthyl" ... List of cocaine analogues "Biologically active tropane derivatives - US Patent 5763455". Archived from the original on 2013-04- ... Tropanes, Dopamine reuptake inhibitors, Stimulants, Naphthol ethers, Phenol ethers, All stub articles, Nervous system drug ...
Tropanes. Various types of tropanes have been isolated from different species of the genus. Derivatives of hydroxytropane and ... up to the dimeric and trimeric derivatives of tropanes, such as those found in Schizanthus grahamii (grahamine) or the tropanol ...
... - a tropane alkaloid - is a weakly alkaline compound, and can therefore combine with acidic compounds to form salts. ... The tropane ring system undergoes hydrolysis, SAM-dependent methylation, and reduction via NADPH for the formation of ... The major contribution of L-ornithine and L-arginine as a precursor to the tropane ring was confirmed by Edward Leete. ... Decarboxylation leads to tropane alkaloid formation. The reduction of tropinone is mediated by NADPH-dependent reductase ...
ISBN 978-0-85404-544-0. Humphrey, A. J.; O'Hagan, D. (2001). "Tropane alkaloid biosynthesis. A century old problem unresolved ... Tropinone and the alkaloids cocaine and atropine all share the same tropane core structure. Its corresponding conjugate acid at ...
The tropane ring system undergoes hydrolysis, SAM-dependent methylation, and reduction via NADPH for the formation of ... ISBN 978-0-470-74276-1. R. J. Robins; T. W. Abraham; A. J. Parr; J. Eagles; N. J. Walton (1997). "The Biosynthesis of Tropane ... In the biosynthesis of cocaine, however, only the (S)-enantiomer can cyclize to form the tropane ring system of cocaine. The ... The second phase incorporates a C4 unit with formation of the bicyclic tropane core. The biosynthesis begins with L-glutamine, ...
Tropane alkaloid biosynthesis. A century old problem unresolved. Nat. Prod. Rep. 18 (2001) 494-502 (doi:10.1039/b001713m) ( ...
1988). "A revision of the generally accepted hypothesis for the biosynthesis of the tropane moiety of cocaine". Journal of the ... Jirschitzka, Jan; Dolke, Franziska; d'Auria, John C. (2013). "Increasing the Pace of New Discoveries in Tropane Alkaloid ... Leete, Edward (1983). "Chemistry of the tropane alkaloids. 33. 2-Carbomethoxy-3-tropinone: An advanced intermediate in the ... Humphrey, Andrew J.; O'Hagan, David (2001). "Tropane alkaloid biosynthesis. A century old problem unresolved". Natural Product ...
"The Tropane Alkaloids" (PDF). Medicinal Chemistry and Drug Design. Archived from the original (PDF) on 2007-09-27. Retrieved ...
Tropanes: The term "tropane" comes from a genus in which they are found, Atropa (the belladonna genus). Atropa is named after ... Like the tropanes, it acts on cholinergic neurons, but with the opposite effect (it is an agonist as opposed to an antagonist ... The tropanes are the most well-known of the alkaloids found in the Solanaceae. The plants that contain these substances have ... Tropane alkaloids of the Solanaceae. En: HAWKES, LESTER and SHELDING (eds.). The biology and taxonomy of the Solanaceae. Linn. ...
It mostly contains tropane alkaloids. Scopolamine and atropine are major alkaloids of this tree. Other alkaloids include ...
... (Ukrainian: Борис Якович Тропанець, Russian: Борис Яковлевич Тропанец, lit. 'Boris Yakovlevich Tropanets'; 11 October 1964 - 22 May 2008) was a Moldovan professional football coach and a player of Ukrainian descent. He made his professional debut in the Soviet Top League in 1984 for FC Chornomorets Odesa. He played 4 games in the UEFA Intertoto Cup 1996 for FC KAMAZ-Chally Naberezhnye Chelny. A stadium was named in his honor in the village of Zorya, where played in local club FC Balkany Zorya. Boris Tropaneț at FootballFacts.ru (in Russian) Boris Tropaneț - K League stats at kleague.com (in Korean) v t e v t e (Articles with Russian-language sources (ru), Articles with short description, Short description matches Wikidata, Use dmy dates from October 2021, Articles containing Ukrainian-language text, Articles containing Russian-language text, Articles with Korean-language sources (ko), 1964 births, 2008 deaths, Ukrainian emigrants to ...
Prepn: Gadzikowska, M; Grynkiewicz, G (2002). "Tropane alkaloical and phytochemical analysis". Acta Poloniae Pharmaceutica. 59 ...
The genus is a valuable one, since its species are not only of considerable medicinal value, being rich in tropane alkaloids, ... Other tropanes present include apoatropine, aposcopolamine and 6-hydroxyatropine. Chinese équipe have recently studied ... for a tropane-containing plant, P. praealta has been recognised in India to have the belladonna-like property of causing ... Tropane-containing, Solanaceous plants (such as Datura and Hyoscyamus spp.) have a long history of use as entheogens in ...
Unsurprisingly for a tropane-rich Solanaceous plant, the effects produced by consumption of Latua pubiflora closely resemble ... Muñoz, O.; Casale, J. F. (2003). "Tropane Alkaloids from Latua pubiflora" (PDF). Zeitschrift für Naturforschung C. 58c (9-10): ... Latua pubiflora produces four Tropane alkaloids: scopolamine, hyoscyamine, apoatropine and 3α-cinnamoyloxitropane, giving it a ... due to tropane alkaloid content and is used by Chilean machi (shamans) of the Mapuche-Huilliche people in traditional medicine ...
Tropane-derivatives, their preparation and use. U.S. Patent 6,288,079 Larsen MH, Rosenbrock H, Sams-Dodd F, Mikkelsen JD ( ...
Tropane alkaloids are potentially highly toxic. A wide range of lipids and lipid-like compounds were also identified. " ... "Tropane Alkaloids", Drugs & Diseases, Medscape, retrieved 2015-04-08 Hanuš, Lumír O.; Řezanka, Tomáš; Spížek, Jaroslav & ... The main alkaloids were the tropane alkaloids scopolamine (hyoscine), apohyoscine and hyoscyamine; others detected included ...
Tropane alkaloids are potentially highly toxic. The roots of M. caulescens contain hyoscine and anisodamine, which are used ... Like all species of Mandragora, it contains tropane alkaloids, making it toxic. It is used in traditional Chinese medicine. ... Wagner, Richard A.; Keim, Samuel M. (2013), "Tropane Alkaloids", Drugs & Diseases, Medscape, retrieved 2015-04-08 (Articles ... tropane alkaloids in particular. The different parts of the plant contain different proportions and concentrations of alkaloids ...
I. Tropane-2 ,3 -diol derivatives. A reverse ester of cocaine". The Journal of Organic Chemistry. 37 (10): 1665-9. doi:10.1021/ ... Modification of the tropane n-substituent was found to mitigate the anticholinergic effects of benztropine analogues by ... This is due to when the eighth carbon tropane position is freely rotatable and unbound it preferably occupies the axial ... There are eight stereoisomers of cocaine (excluding mesomers and modifications to the internal portion of the tropane ring). ...
I. Tropane-2 ,3 -diol derivatives. A reverse ester of cocaine". The Journal of Organic Chemistry. 37 (10): 1665-9. doi:10.1021/ ... Cocaine reverse ester, (also known as Reverse ester cocaine or REC) is a tropane derivative drug which is a reverse ester of ... 3-(p-Fluorobenzoyloxy)tropane 4′-Fluorococaine Benzoylecgonine Methylecgonine cinnamate Salicylmethylecgonine Daum SJ, Martini ...
Srinivasan, Prashanth; Smolke, Christina D. (September 2020). "Biosynthesis of medicinal tropane alkaloids in yeast". Nature. ... Tropane alkaloids: Hyoscyamine and scopolamine GMO yeast: Baker's yeast Precursor chemicals derived from genetically modified ...
... is a prominent tropane alkaloid found in coca leaves. It is metabolite of cocaine, and may be used as a ... El Bazaoui A, Bellimam MA, Soulaymani A (March 2011). "Nine new tropane alkaloids from Datura stramonium L. identified by GC/MS ... El Bazaoui, Ahmed; Bellimam, My Ahmed; Soulaymani, Abdelmajid (2012). "Tropane Alkaloids of Datura innoxia from Morocco". ... Tropane alkaloids, All stub articles, Alkaloid stubs). ...
The tropane alkaloid brugine is found in the bark of this species. Bruguiera exaristata is a mangrove, forming mangrove swamps ... ISBN 978-1-316-79065-6. Srivastava, Vikas; Mehrotra, Shakti; Mishra, Sonal (2021). Tropane Alkaloids: Pathways, Potential and ...
Tropane-containing nightshades have played an integral role in Old World folklore and European witchcraft. Henbane is reputed ... Other, lesser known plant sources of scopolamine and related tropanes include Scopolia carniolica endemic to Europe, Latua ... ISBN 978-0-89815-169-5. Griffin WJ, Lin GD (March 2000). "Chemotaxonomy and geographical distribution of tropane alkaloids". ... some tropane alkaloids, such as those found in plants of the Datura genus, are exceptionally toxic and can cause death due to ...
Todd, Fred G.; Stermitz, Frank R.; Schultheis, Partricia; Knight, Anthony P.; Traub-Dargatz, Josie (May 1995). "Tropane ...
8-Azabicyclo[3.2.1]octane (tropane without the N-methyl group) is known as nortropane or nor-tropane. Phenyltropane Tropane ... Tropane is a nitrogenous bicyclic organic compound. It is mainly known for the other alkaloids derived from it, which include ... Tropane alkaloids occur in plants of the families Erythroxylaceae (including coca) and Solanaceae (including mandrake, henbane ... While carbons 1 and 5 are asymmetric carbons, tropane itself is optically inactive due to mirror symmetry. ...
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Although most tropane alkaloids cause an anticholinergic syndrome, a case report indicates that the tropane alkaloid-containing ... encoded search term (Tropane Alkaloid Poisoning) and Tropane Alkaloid Poisoning What to Read Next on Medscape ... Plants that contain tropane alkaloids include the following:. * Datura species (jimson weed, angels trumpet, thorn apple) [3, ... Tropane Alkaloid Poisoning. Updated: Jun 21, 2023 * Author: Richard A Wagner, MD, PhD, FACEP, FAAEM; Chief Editor: Asim Tarabar ...
Updated Recall of Some Batches of Organic Millet Pops due to the Possible Presence of Tropane Alkalo. Friday, 23 April 2021 ... Current: Updated Recall of Some Batches of Organic Millet Pops due to the Possible Presence of Tropane Alkalo ... Independent Irish Health Foods is recalling some batches of Organic Millet Pops due to the possible presence of tropane ... due to the possible presence of tropane alkaloids. These toxins which are naturally occurring in some plants can contaminate ...
The biosynthesis of tropane and tobacco alkaloids has been extensively studied since the 1950s. Their importance is due to two ... The Biosynthesis of Tropane and Tobacco Alkaloids in Datura and Nicotiana Transformed Root Cultures ... Watson, Alan Boyd (1991) The Biosynthesis of Tropane and Tobacco Alkaloids in Datura and Nicotiana Transformed Root Cultures. ... A critical review of the biosynthesis of the tropane and tobacco alkaloids is presented in conjunction with a simplified ...
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Tropane alkaloids. Tropane alkaloids (TAs) are secondary metabolites which naturally occur in plants of several families ...
Tropanes* Substances * Radiopharmaceuticals * Tropanes * 2-carbomethoxy-8-(3-fluoropropyl)-3-(4-iodophenyl)tropane ...
Cleavage of benzyl linker is achieved using acid chlorides in the presence of potassium iodide to give substituted tropane ... Cleavage of benzyl linker is achieved using acid chlorides in the presence of potassium iodide to give substituted tropane ... Solid-phase synthesis of functionalized tropane derivatives via 1,3-dipolar cycloaddition. Tetrahedron Letters, 2001, 42 (22), ... Solid-phase synthesis of functionalized tropane derivatives via 1,3-dipolar cycloaddition. ...
Food aid incident was largest known outbreak from tropane alkaloids. By Joe Whitworth on May 6, 2022. ... It was the largest documented outbreak caused by food contamination with tropane alkaloids, according…. Continue Reading Food ...
Tropane alkaloids. Fodor G, Dharanipragada R. Fodor G, et al. Nat Prod Rep. 1988 Feb;5(1):67-72. doi: 10.1039/np9880500067. Nat ... Tropane alkaloids. Fodor G, Dharanipragada R. Fodor G, et al. Nat Prod Rep. 1986 Apr;3(2):181-4. doi: 10.1039/np9860300181. Nat ... Tropane alkaloids. Fodor G, Dharanipragada R. Fodor G, et al. Nat Prod Rep. 1985 Jun;2(3):221-5. doi: 10.1039/np9850200221. Nat ... Tropane alkaloids. Fodor G, Dharanipragada R. Fodor G, et al. Nat Prod Rep. 1984 Jun;1(3):231-4. doi: 10.1039/np9840100231. Nat ...
Tropane alkaloids (TA) including anisodamine, anisodine, hyoscyamine and scopolamine are a group of important anticholinergic ... Kai, G., Yang, S., Luo, X. et al. Co-expression of AaPMT and AaTRI effectively enhances the yields of tropane alkaloids in ... Schematic biosynthetic pathway of tropane alkaloid in A. acutangulus. From the picture, we know that anisodine comes from the ... Co-expression of AaPMT and AaTRI effectively enhances the yields of tropane alkaloids in Anisodus acutangulus hairy roots. * ...
Further evaluation of the reinforcing effects of the novel cocaine analog 2β-propanoyl-3β-(4-tolyl)-tropane (PTT) in rhesus ... tropane (PTT) in rhesus monkeys. Together they form a unique fingerprint. ...
... tropane (17), 6,7-dehydro-3-apotropoyloxytropane (18), 3-(3-methoxytropoyloxy)tropane (23), and aponorscopolamine (25) are ... The alkaloids 5-(2-oxopropyl)-hygrine (8) and phygrine (20) are new for this species and 3-(hydroxyacetoxy)tropane (9), 6,7- ... Gas-Liquid Chromatography-Mass Spectrometry Investigation of Tropane Alkaloids in Hyoscyamus albus L. from Morocco. ...
Tropane (Cocaine) Class. Stimulant. 84. 3.6. Isotonitazene. Opioid Class (Non-Fentanyl, Non-Opiates). Opioid. 57. 2.5. ...
Tropane alkaloids Note: This list may not include all poisonous ingredients.. Where Found. ...
Novel Tropane-Based Irreversible Ligands for the Dopamine Transporter. Journal of Medicinal Chemistry 2001, 44 (25) , 4453-4461 ... Novel Conformationally Constrained Tropane Analogues by 6-endo-trig Radical Cyclization and Stille Coupling − Switch of ... Synthesis and Monoamine Transporter Binding Properties of 3β-(3,4-Disubstituted phenyl)tropane-2β-carboxylic Acid Methyl ... Irreversible binding of a novel phenylisothiocyanate tropane analog to monoamine transporters in rat brain. Biochemical ...
The present paper reports results of the effect of Potato virus X (PVX) on the contents of total phenols and alkaloids in leaves of Datura stramonium. A significant decrease in the contents of phenols and alkaloids was observed in leaves inoculated with PVX (X-I). However, there was an increase in the percentage of phenols in leaves rubbed with phosphate buffer (C1-I) and in leaves from the nodes immediately above, possibly induced by mechanical injury. Gas chromatography/mass spectroscopy revealed amounts of scopolamine in samples submitted to all treatments, except X-I, in which the amount of this alkaloid was low. High amounts of an unidentified compound (molecular ion m/z 302 and a prominent peak at m/z 129) were noted in extracts from leaves X-I, C1-I and leaves from the nodes immediately above the leaves inoculated with PVX. It is suggested that the synthesis and accumulation of the unidentified compound is a result of stress from mechanical injury and virus inoculation.. Potexvirus; ...
An example of this is the occurrence of pyrrolizidine or tropane alkaloids in (herbal) teas or spices. ...
Hemscheidt, T., (2000). Tropane and Related Alkaloids, Biosynthesis. Springer, pp. 175-206.. Henning, C. P. (2013). Compuestos ... Keywords: quinoline alkaloids, tropane alkaloids, Solanaceae, pharmaceutical application, natural alkaloids. References. Alves ... Grzegorz, G., Gadzikowska, M., (2008). Tropane alkaloids as medicinally useful natural. products and their synthetic ...
Tropane, piperidine and pyridine alkaloid biosynthesis. ec01100 Metabolic pathways. ec01110 Biosynthesis of secondary ...
All parts of the plant contain tropane alkaloids[254]. The leaves contain on average 0.4% active alkaloids, whilst the root ...
Tropane, piperidine and pyridine alkaloid biosynthesis. Orthology. K13610 13-hydroxylupinine O-tigloyltransferase [EC:2.3.1.93] ...
... tropane alkaloids in potatoes, tomatoes, and peppers; opiates in lettuce; prussic acid in stone fruits etc.).". Science again. ... tropane alkaloids in potatoes, tomatoes, and peppers; opiates in lettuce; prussic acid in stone fruits etc.). ...
Objective: To assess the accuracy and clinical usefulness of [123I]β-CIT (2β-carbomethoxy-3β-(4-iodophenyl)tropane) SPECT in ... 123I]β-CIT (2β-carbomethoxy-3β-(4-iodophenyl)tropane) is a cocaine derivative radioligand which binds to dopamine transporters ...
Tropane-containing nightshades have played an integral role in Old World folklore and European witchcraft.[18][49][43] Henbane ... The toxic berry of Atropa belladonna which contains the tropane deliriants scopolamine, atropine, and hyoscyamine.. Contents. ... Other, lesser known plant sources of scopolamine and related tropanes include Scopolia carniolica endemic to Europe, Latua ... Griffin WJ, Lin GD (March 2000). "Chemotaxonomy and geographical distribution of tropane alkaloids". Phytochemistry. 53 (6): ...
... tropane alkaloids in potatoes, tomatoes, and peppers; opiates in lettuce; prussic acid in stone fruits etc.).". Science again. ... tropane alkaloids in potatoes, tomatoes, and peppers; opiates in lettuce; prussic acid in stone fruits etc.). ...
arvensis contained tropane alkaloids (Molyneux et al., 1993; Todd et al., 1995) and phenolic compounds (Hegab and Ghareib, 2010 ...
  • The tropane alkaloids atropine, scopolamine, and hyoscyamine are highly anticholinergic compounds found in a number of plants. (medscape.com)
  • A subgroup of the alkaloids is the alkaloid amines, which include three major pharmacologic groups: the hallucinogenic alkaloid amines, the stimulant alkaloid amines, and the tropane alkaloids (also called the belladonna alkaloids or bicyclic alkaloids). (medscape.com)
  • Chinese herbal medicines containing tropane alkaloids have been used to treat asthma, chronic bronchitis, pain, and flu symptoms. (medscape.com)
  • Many cultures worldwide add plants with tropane alkaloids (particularly Datura species) to alcoholic beverages to increase intoxication. (medscape.com)
  • The cereal was found to have been contaminated with tropane alkaloids from seeds of Datura stramonium that had invaded grain fields. (medscape.com)
  • Although most tropane alkaloids cause an anticholinergic syndrome, a case report indicates that the tropane alkaloid-containing medicinal herb Erycibe henri Prain ("Ting Kung Teng") contains a tropane alkaloid that may cause a cholinergic syndrome, as well as kidney, liver, and erythrocyte toxicity. (medscape.com)
  • [ 14 ] This is considered atypical for the tropane alkaloids, which are predominantly strongly anticholinergic. (medscape.com)
  • Toxicity from plants containing tropane alkaloids manifests as classic anticholinergic poisoning. (medscape.com)
  • Symptoms usually occur 30-60 minutes after ingestion and may continue for 24-48 hours because tropane alkaloids delay gastric emptying and absorption. (medscape.com)
  • Category 2 Food Alert for Information: Independent Irish Health Foods is recalling some batches of Organic Millet Pops due to the possible presence of tropane alkaloids. (fsai.ie)
  • The biosynthesis of tropane and tobacco alkaloids has been extensively studied since the 1950's. (gla.ac.uk)
  • The introduction of this thesis contains descriptions of tropane alkaloid structure and occurrence, tobacco alkaloid structure and occurrence, pharmacology of tropane alkaloids, pharmacology of tobacco alkaloids and finally, the aims of the project. (gla.ac.uk)
  • A critical review of the biosynthesis of the tropane and tobacco alkaloids is presented in conjunction with a simplified description of the production and manipulation of transformed root cultures. (gla.ac.uk)
  • Tropane alkaloids (TAs) are secondary metabolites which naturally occur in plants of several families including Brassicaceae, Solanaceae (e.g. mandrake, henbane, deadly nightshade, Jimson weed) and Erythroxylaceae (including coca). (fsai.ie)
  • Tropane alkaloids (TA) including anisodamine, anisodine, hyoscyamine and scopolamine are a group of important anticholinergic drugs with rapidly increasing market demand, so it is significant to improve TA production by biotechnological approaches. (biomedcentral.com)
  • The alkaloids 5-(2-oxopropyl)-hygrine (8) and phygrine (20) are new for this species and 3-(hydroxyacetoxy)tropane (9), 6,7-dehydro-3-phenylacetoxytropane (15), 3-(2'-phenylpropionyloxy) tropane (17), 6,7-dehydro-3-apotropoyloxytropane (18), 3-(3'-methoxytropoyloxy)tropane (23), and aponorscopolamine (25) are described for the first time for the genus Hyoscyamus. (degruyter.com)
  • An example of this is the occurrence of pyrrolizidine or tropane alkaloids in (herbal) teas or spices. (bund.de)
  • All parts of the plant contain tropane alkaloids[254]. (pfaf.org)
  • the manufacturer is immediately recalling Amaizin tortilla chips due to containing tropane alkaloids. (planetorganic.com)
  • This unfortunately resulted in the presence of tropane alkaloids in the chips. (planetorganic.com)
  • Chemical & Engineering News - Tropane alkaloids, a broad class of natural products from plants, have been used as medicines for more than a century. (ttu.edu)
  • Cocaine is extracted from coca leaves whose major chemical constituents are a complex mixture of tropane alkaloids, mainly cocaine and other ecgonine esters. (who.int)
  • Nearly 20% of plant species accumulate alkaloids, which mainly include terpenoid indole alkaloids, tropane alkaloids and purine alkaloids 3 . (scialert.net)
  • In addition the selectivity of the enzymes involved in tropane and tobacco alkaloid biosynthesis was studied. (gla.ac.uk)
  • Plant tropane alkaloid biosynthesis evolved independently in the Solanaceae and Erythroxylaceae. (mpg.de)
  • The reaction is investigated in the field of piperidine, piperazine, and tropane derivatives. (heterocycles.jp)
  • The toxic berry of Atropa belladonna which contains the tropane deliriants scopolamine , atropine , and hyoscyamine . (wikipedia.org)
  • I had began reading all about the datura and nightshade families and had become increasingly interested in tropane-containing plants. (erowid.org)
  • 123 I]β-CIT (2β-carbomethoxy-3β-(4-iodophenyl)tropane) is a cocaine derivative radioligand which binds to dopamine transporters with substantial striatal specificity at 24 hours postinjection. (bmj.com)
  • I explained to her the plant I had picked and boiled into a tea contained several psychoactive tropanes and was poisonous. (erowid.org)
  • Tropane is a nitrogenous bicyclic organic compound. (wikipedia.org)
  • Synthesis, Fluorine-18 Radiolabeling, and Biological Evaluation of N-((E)-4-Fluorobut-2-en-1-yl)-2β-carbomethoxy-3β-(4′-halophenyl)nortropanes: Candidate Radioligands for In Vivo Imaging of the Brain Dopamine Transporter with Positron Emission Tomography. (acs.org)
  • The present study sought to determine whether doses of methamphetamine in the range of those used recreationally by humans produce brain dopamine (DA) neurotoxicity in baboons and to ascertain whether positron emission tomography (PET) imaging with the DA transporter (DAT) ligand [ 11 C]WIN-35,428 ([ 11 C]2β-carbomethoxy-3β-(4-fluorophenyl)-tropane) could be used to detect methamphetamine-induced DAT loss in living primates. (jneurosci.org)
  • The effects of MDMA use on cortical 5-HT neurons was studied by means of single-photon emission computed tomography with iodine 123 labeled 2-carbomethoxy-3-(4-iodophenyl) tropane ([123I]-CIT) by quantification of brain 5-HT transporter densities. (erowid.org)
  • Phenyltropane Tropane alkaloid Tropine Merck Index, 11th Edition, 9689. (wikipedia.org)
  • Furthermore, all the differential metabolite were mapped to KEGG pathway, revealing significant differences in linoleic acid metabolism, tyrosine metabolism,glutathione metabolism, pentose phosphate pathway, tropane, piperidine and pyridine alkaloid biosynthesis, phenylpropanol metabolism and glycosylphosphatidylinositol(GPI)-anchor biosynthesis over time. (researchsquare.com)
  • Nguyen TK, Jamali A, Lanoue A, Gontier E, Dauwe R. Unravelling the architecture and dynamics of tropane alkaloid biosynthesis pathways using metabolite correlation networks. (medscape.com)
  • Tropane Alkaloids: Chemistry, Pharmacology, Biosynthesis and Production. (ac.rs)
  • Typical tropane alkaloids are atropine, hyoscyamine, scopolamine and cocaine. (abc.net.au)
  • Their active principles are mainly hyossyamine and scopolamine, which are tropane alkaloids. (erowid.org)
  • Atropine Hyoscine (scopolamine) Hyoscyamine Tropane alkaloids Note: This list may not include all poisonous ingredients. (nih.gov)
  • Rich in the tropane alkaloids scopolamine and hyoscyamine, belladonna (which means beautiful woman) was used by women to dilate their pupils, to make them appear more alluring. (medicinehunter.com)
  • Are tropane alkaloids present in organic foods? (ac.rs)
  • According to Samorini, tropane alkaloids present in L. serriola can be also found in plants of the nightshade family, such as the legendary mandrake, long reputed for its magic and aphrodisiac powers. (abc.net.au)
  • Nov. 21, 2022 Tropane alkaloids (TAs) are heterocyclic nitrogenous metabolites found across seven orders of angiosperms, including Malpighiales (Erythroxylaceae) and Solanales (Solanaceae). (sciencedaily.com)
  • Worldwide Occurrence and Investigations of Contamination of Herbal Medicines by Tropane Alkaloids. (ac.rs)
  • Further to last Friday's recall of the Chinese medicinal herb Rhizoma Atractylodis (batch number 06010108) from customers of a Yuen Long Chinese medicine practitioner (CMP), Kong Chi-wing, because of contamination by tropane alkaloids, the Department of Health (DH) today (May 16) also advised patrons of another CMP in Mong Kok, Chik King-sing, to check whether they have been prescribed Rhizoma Atractylodis as well. (gov.hk)
  • Complex investigations involving international food safety experts indicate that the probable cause of the sickness was contamination of Super Cereal by tropane alkaloids during harvesting or production. (wfp.org)
  • 11 Malison R, Price L, Berman R. Reduced brain serotonin transporter availability in major depression as measured by [I 123 ]2 β-carbomethoxy-3 β-(4-iodophenyl)-tropane and single photon emission computed tomography. (thieme-connect.com)
  • Analysis of alkaloids (indole alkaloids, isoquinoline alkaloids, tropane alkaloids). (ac.rs)
  • The chemical reactions and pathways involving tropane alkaloids, compounds containing the 8-methyl-8-azabicyclo(3.2.1)octane ring system. (mcw.edu)
  • Also known as deadly nightshade, belladonna contains tropane alkaloids that can induce hallucinations, delirium, and even death. (edgarallanpoets.com)
  • 8-Azabicyclo[3.2.1]octane (tropane without the N-methyl group) is known as nortropane or nor-tropane. (wikipedia.org)
  • Ipratropium bromide is partially metabolized to ester hydrolysis products, tropic acid, and tropane. (nih.gov)
  • Tropane is a nitrogenous bicyclic organic compound. (wikipedia.org)
  • While carbons 1 and 5 are asymmetric carbons, tropane itself is optically inactive due to mirror symmetry. (wikipedia.org)
  • This study investigates whether there is a change in 123iodine-2ß- carbomethoxy-3ß-(4-iodophenyl) tropane ([123I]ß-CIT) uptake after short-term treatment with levodopa compared to either dopamine agonist or placebo. (drugpatentwatch.com)
  • Meanwhile, chemical analysis by the Government Laboratory on another batch of Rhizoma Atractylodis kept by KLH found no tropane alkaloids. (gov.hk)
  • The obtained results show the seriousness of the tropane alkaloids problem in maize as well as the need for monitoring and further research. (ac.rs)
  • Mandragora (all from the same Solananeae family) contain a well-defined group of tropane alkaloids. (medprep.info)
  • Determination of tropane alkaloids in cereals, tea and herbal infusions: Exploiting proficiency testing data as a basis to derive interlaboratory performance characteristics of an improved LC-MS/MS method. (ac.rs)
  • Tropane alkaloids are considered to be serious health hazard for humans and that their maximum residue levels in food and feed are still not established. (ac.rs)
  • Occurrence and Determination of Tropane Alkaloids in Food and Feed. (ac.rs)
  • This review on " The role of the Tropane skeleton in new drug research " was presented as a lecture by Dr. Laszlo Gyermek in Hungarian, on the occasion of his election as Foreign Member of the Hungarian Academy of Medical Sciences (Division V - Medical Sciences), on September 21, 2005. (inhn.org)
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