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Opium poppy

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https://www.readbyqxmd.com/read/29783146/gas-chromatographic-mass-spectrometric-characterization-of-thebaol-an-opium-constituent-and-its-structural-analogs
#1
Levan Megutnishvili, Nino Todua, Stephen Stein, Anzor Mikaia
A GC-MS method is described for the characterization of thebaol, a component of opium poppy. The method includes preliminary sample derivatization to TMS, TBDMS, TFA, PFP and HFB substituted products. Fragmentation of resulting derivatives is unique under electron ionization, and proceeds via consecutive loss of two radicals that violate the "even-electron rule". Peaks of [M-2CH3 ]+. and [M-C4 H9 -CH3 ]+. ions show maximum intensities in the spectra of trimethyl- and tert-butyldimethylsilyl-thebaols...
May 18, 2018: Journal of Pharmaceutical and Biomedical Analysis
https://www.readbyqxmd.com/read/29779229/codeinone-reductase-isoforms-with-differential-stability-efficiency-and-product-selectivity-in-opium-poppy
#2
Mehran Dastmalchi, Limei Chang, Miguel A Torres, Kenneth K S Ng, Peter J Facchini
Codeinone reductase (COR) catalyzes the reversible NADPH-dependent reduction of codeinone to codeine as the penultimate step of morphine biosynthesis in opium poppy (Papaver somniferum). COR also irreversibly reduces neopinone, which forms by spontaneous isomerization in aqueous solution from codeinone, to neopine. In a parallel pathway involving 3-O-desmethylated analogs, COR converts morphinone to morphine, and neomorphinone to neomorphine. Similar to neopine, neomorphine formation by COR is irreversible...
May 19, 2018: Plant Journal: for Cell and Molecular Biology
https://www.readbyqxmd.com/read/29723437/heterodimeric-o-methyltransferases-involved-in-the-biosynthesis-of-noscapine-in-opium-poppy
#3
Myung R Park, Xue Chen, Dean E Lang, Kenneth K S Ng, Peter J Facchini
Noscapine biosynthesis in opium poppy involves three characterized O-methyltransferases (OMTs) and a fourth responsible for the 4'-methoxyl on the phthalideisoquinoline scaffold. The first three enzymes are homodimers, whereas the latter is a heterodimer encoded by two linked genes (OMT2 and OMT3). Neither OMT2 nor OMT3 form stable homodimers, but yield a substrate-specific heterodimer when co-expressed in Escherichia coli. The only substrate, 4'-O-desmethyl-3-O-acetylpapaveroxine, is a seco-berbine pathway intermediate that undergoes ester hydrolysis subsequent to 4'-O-methylation leading to the formation of narcotine hemiacetal...
May 3, 2018: Plant Journal: for Cell and Molecular Biology
https://www.readbyqxmd.com/read/29610307/complete-biosynthesis-of-noscapine-and-halogenated-alkaloids-in-yeast
#4
Yanran Li, Sijin Li, Kate Thodey, Isis Trenchard, Aaron Cravens, Christina D Smolke
Microbial biosynthesis of plant natural products from simple building blocks is a promising approach toward scalable production and modification of high-value compounds. The pathway for biosynthesis of noscapine, a potential anticancer compound, from canadine was recently elucidated as a 10-gene cluster from opium poppy. Here we demonstrate the de novo production of noscapine in Saccharomyces cerevisiae , through the reconstruction of a biosynthetic pathway comprising over 30 enzymes from plants, bacteria, mammals, and yeast itself, including 7 plant endoplasmic reticulum (ER)-localized enzymes...
April 2, 2018: Proceedings of the National Academy of Sciences of the United States of America
https://www.readbyqxmd.com/read/29563567/the-effects-of-promoter-variations-of-the-n-methylcanadine-1-hydroxylase-cyp82y1-gene-on-the-noscapine-production-in-opium-poppy
#5
Davar Abedini, Sajad Rashidi Monfared, Alireza Abbasi
Noscapine is an antitumor alkaloid produced in opium poppy (Papaver somniferum) and some members of the Papaveraceae family. It has been primarily used for its antitussive effects; more recently, its anticancer properties were shown. Herein, we detected an SSR embedded in the promoter region of the CYP82Y1 gene, which was found to be the first committed-step enzyme in the noscapine biosynthesis pathway, using the MISA program. Some collected ecotypes of P. somniferum were investigated for understanding of SSRs role in the regulation of gene expression and metabolite content...
March 21, 2018: Scientific Reports
https://www.readbyqxmd.com/read/29433083/inhibition-of-phospholipases-influences-the-metabolism-of-wound-induced-benzylisoquinoline-alkaloids-in-papaver-somniferum-l
#6
Veronika Jablonická, Jörg Ziegler, Zuzana Vatehová, Desana Lišková, Ingo Heilmann, Marek Obložinský, Mareike Heilmann
Benzylisoquinoline alkaloids (BIAs) are important secondary plant metabolites and include medicinally relevant drugs, such as morphine or codeine. As the de novo synthesis of BIA backbones is (still) unfeasible, to date the opium poppy plant Papaver somniferum L. represents the main source of BIAs. The formation of BIAs is induced in poppy plants by stress conditions, such as wounding or salt treatment; however, the details about regulatory processes controlling BIA formation in opium poppy are not well studied...
April 2018: Journal of Plant Physiology
https://www.readbyqxmd.com/read/29416103/development-of-a-method-to-extract-opium-poppy-papaver-somniferum-l-dna-from-heroin
#7
Michael A Marciano, Sini X Panicker, Garrett D Liddil, Danielle Lindgren, Kevin S Sweder
This study is the first to report the successful development of a method to extract opium poppy (Papaver somniferum L.) DNA from heroin samples. Determining of the source of an unknown heroin sample (forensic geosourcing) is vital to informing domestic and foreign policy related to counter-narcoterrorism. Current profiling methods focus on identifying process-related chemical impurities found in heroin samples. Changes to the geographically distinct processing methods may lead to difficulties in classifying and attributing heroin samples to a region/country...
February 7, 2018: Scientific Reports
https://www.readbyqxmd.com/read/29408320/crystal-structure-of-thebaine-6-o-demethylase-from-the-morphine-biosynthesis-pathway
#8
Anna Kluza, Ewa Niedzialkowska, Katarzyna Kurpiewska, Zuzanna Wojdyla, Matthew Quesne, Ewa Kot, Przemyslaw J Porebski, Tomasz Borowski
Thebaine 6-O-demethylase (T6ODM) from Papaver somniferum (opium poppy), which belongs to the non-heme 2-oxoglutarate/Fe(II)-dependent dioxygenases (ODD) family, is a key enzyme in the morphine biosynthesis pathway. Initially, T6ODM was characterized as an enzyme catalyzing O-demethylation of thebaine to neopinone and oripavine to morphinone. However, the substrate range of T6ODM was recently expanded to a number of various benzylisoquinoline alkaloids. Here, we present crystal structures of T6ODM in complexes with 2-oxoglutarate (T6ODM:2OG, PDB: 5O9W) and succinate (T6ODM:SIN, PDB: 5O7Y)...
February 14, 2018: Journal of Structural Biology
https://www.readbyqxmd.com/read/29220602/an-observational-study-of-treatment-seeking-users-of-natural-opiates-from-india
#9
Arpit Parmar, Vaibhav Patil, Siddharth Sarkar, Ravindra Rao
BACKGROUND: The type of opioid used influences the severity and complications experienced. Natural opiates (opium and poppy husk) use is a socio-culturally accepted phenomenon reported in India. However, studies on their profile, quality of life, and addiction severity are limited. OBJECTIVES: The objective of this cross-sectional, observational study was to assess the socio-demographic profile, clinical profile, addiction severity, and quality of life of treatment-seeking natural opiate users...
December 8, 2017: Substance Use & Misuse
https://www.readbyqxmd.com/read/29134077/investigation-of-the-acid-base-behaviour-of-the-opium-alkaloid-thebaine-in-lc-esi-ms-mobile-phase-by-nmr-spectroscopy
#10
Michelle G Carlin, John R Dean, Jonathan L Bookham, Justin J B Perry
As part of a research programme to establish an analytical method for the simultaneous detection of the five major opium alkaloids in poppy seeds by liquid chromatography-electrospray ionization-mass spectrometry (LC-ESI-MS) it was discovered that the inclusion of thebaine produced two peaks for the same compound. This was in contrast to the effective simultaneous detection, by LC-ESI-MS, of morphine, codeine, papaverine and noscapine. The presence of these two peaks for thebaine was investigated using nuclear magnetic resonance spectroscopy with deuterated solvents to emulate the mobile phase conditions experienced...
October 2017: Royal Society Open Science
https://www.readbyqxmd.com/read/29037712/straightforward-analytical-method-to-determine-opium-alkaloids-in-poppy-seeds-and-bakery-products
#11
Patricia López, Diana P K H Pereboom-de Fauw, Patrick P J Mulder, Martien Spanjer, Joyce de Stoppelaar, Hans G J Mol, Monique de Nijs
A straightforward method to determine the content of six opium alkaloids (morphine, codeine, thebaine, noscapine, papaverine and narceine) in poppy seeds and bakery products was developed and validated down to a limit of quantification (LOQ) of 0.1mg/kg. The method was based on extraction with acetonitrile/water/formic acid, ten-fold dilution and analysis by LC-MS/MS using a pH 10 carbonate buffer. The method was applied for the analysis of 41 samples collected in 2015 in the Netherlands and Germany. All samples contained morphine ranging from 0...
March 1, 2018: Food Chemistry
https://www.readbyqxmd.com/read/28973785/quantification-of-morphine-codeine-and-thebaine-in-home-brewed-poppy-seed-tea-by-lc-ms-ms
#12
Deborah Powers, Stephen Erickson, Madeleine J Swortwood
Recently, medical examiners reported two cases of a 21-year-old male and 24-year-old male with high amounts of morphine in their blood at autopsy. It was suspected that the decedents ingested lethal amounts of morphine from home-brewed poppy seed tea. No studies to date have investigated opium alkaloid content extracted from poppy seeds by home-brewing methods. Various poppy seed products were purchased from online sources and extracted with four home-brewing methods representative of recipes found on drug user forums...
October 3, 2017: Journal of Forensic Sciences
https://www.readbyqxmd.com/read/28936080/maintainence-treatment-of-opioid-dependence-with-tramadol
#13
Siddharth Sarkar, Mohit Varshney, Vaibhav Patil, Rakesh Lal
BACKGROUND: Although tramadol has been used in the management of acute withdrawal in patients with opioid dependence, its use for maintenance treatment as a harm reduction approach has not been assessed systematically. This case series describes patients with opioid dependence who were treated with tramadol for long-term maintenance. METHODS: Patients with opioid dependence who received treatment at the National Drug Dependence Treatment Centre of All India Institute of Medical Sciences, New Delhi, were included in the study...
August 2017: Journal of Neurosciences in Rural Practice
https://www.readbyqxmd.com/read/28729873/ageratum-enation-virus-infection-induces-programmed-cell-death-and-alters-metabolite-biosynthesis-in-papaver-somniferum
#14
Ashish Srivastava, Lalit Agrawal, Rashmi Raj, Meraj Jaidi, Shri K Raj, Swati Gupta, Ritu Dixit, Poonam C Singh, Tusha Tripathi, Om P Sidhu, Brahma N Singh, Sudhir Shukla, Puneet S Chauhan, Susheel Kumar
A previously unknown disease which causes severe vein thickening and inward leaf curl was observed in a number of opium poppy (Papaver somniferum L.) plants. The sequence analysis of full-length viral genome and associated betasatellite reveals the occurrence of Ageratum enation virus (AEV) and Ageratum leaf curl betasatellite (ALCB), respectively. Co-infiltration of cloned agroinfectious DNAs of AEV and ALCB induces the leaf curl and vein thickening symptoms as were observed naturally. Infectivity assay confirmed this complex as the cause of disease and also satisfied the Koch's postulates...
2017: Frontiers in Plant Science
https://www.readbyqxmd.com/read/28681463/confirmation-of-recent-heroin-abuse-accepting-the-challenge
#15
REVIEW
Alexandra Maas, Burkhard Madea, Cornelius Hess
Confirmation or exclusion of recent heroin consumption is still one of the major challenges for forensic and clinical toxicologists. A great variety of biomarkers is available for heroin abuse confirmation, including various opium alkaloids (e.g. morphine, codeine), street heroin impurities (e.g. 6-acetylcodeine (6-AC), noscapine, papaverine) as well as associated metabolites (e.g. 6-monoacetylmorphine (6-MAM), morphine glucuronides). Though, the presence of most of these biomarkers cannot solely be attributed to a previous heroin administration but can, among other things, also be due to consumption of poppy seed products ('poppy seed defense'), opium preparations or specific medications, respectively...
July 6, 2017: Drug Testing and Analysis
https://www.readbyqxmd.com/read/28641826/the-chemical-history-of-morphine-an-8000-year-journey-from-resin-to-de-novo-synthesis
#16
Karolina Brook, Jessica Bennett, Sukumar P Desai
Evidence of human use of opium dates back as far as the sixth millennium BCE. Ancient societies through the Renaissance period created a variety of opium products, proliferating its common use and subsequent addiction. Because the active moiety was not known at this time, the potency of these opium concoctions could neither be predicted nor controlled. The first step in identifying opium's active ingredient, morphine, was its chemical isolation in the early 1800s by Wilhelm Sertürner. The subsequent elucidation of morphine's chemical formula and Sir Robert Robinson's derivation of morphine's structural formula, which won him the 1947 Nobel Prize in Chemistry, round out 150 years of the incremental advances in our chemical understanding of morphine...
April 2017: Journal of Anesthesia History
https://www.readbyqxmd.com/read/28630559/drug-policy-and-indigenous-peoples
#17
Julian Burger, Mary Kapron
This paper identifies the principal concerns of indigenous peoples with regard to current international treaties on certain psychoactive substances and policies to control and eradicate their production, trafficking, and sale. Indigenous peoples have a specific interest in the issue since their traditional lands have become integrated over time into the large-scale production of coca, opium poppy, and cannabis crops, in response to high demand from the American and European markets, among others. As a consequence, indigenous peoples are persecuted because of their traditional use of these and other plant-based narcotics and hallucinogens...
June 2017: Health and Human Rights
https://www.readbyqxmd.com/read/28609429/reciprocal-evolution-of-opiate-science-from-medical-and-cultural-perspectives
#18
George B Stefano, Nastazja Pilonis, Radek Ptacek, Richard M Kream
Over the course of human history, it has been common to use plants for medicinal purposes, such as for providing relief from particular maladies and self-medication. Opium represents one longstanding remedy that has been used to address a range of medical conditions, alleviating discomfort often in ways that have proven pleasurable. Opium is a combination of compounds obtained from the mature fruit of opium poppy, papaver somniferum. Morphine and its biosynthetic precursors thebaine and codeine constitute the main bioactive opiate alkaloids contained in opium...
June 13, 2017: Medical Science Monitor: International Medical Journal of Experimental and Clinical Research
https://www.readbyqxmd.com/read/28455458/an-interesting-case-of-opium-tea-toxicity
#19
Chitsa Seyani, Peregrine Green, Lisa Daniel, Amanda Pegden
We present an unusual cause of respiratory arrest resulting from sole ingestion of home-brewed opium tea. A 64-year-old woman was found unresponsive and in respiratory arrest by a first responder. There were no obvious signs of regular recreational drug use. On presentation to the local district general hospital, the patient was in extremis, with severe physiological and biochemical derangements. A naloxone infusion was commenced and she later made a good recovery. It was subsequently discovered that she had brewed opium tea from opium buds she had picked from a nearby commercial poppy farm, a practice she had learnt while in Afghanistan...
April 28, 2017: BMJ Case Reports
https://www.readbyqxmd.com/read/28208284/detection-of-papaverine-for-the-possible-identification-of-illicit-opium-cultivation
#20
Rustin Y Mirsafavi, Kristine Lai, Neal D Kline, Augustus W Fountain, Carl D Meinhart, Martin Moskovits
Papaverine is a non-narcotic alkaloid found endemically and uniquely in the latex of the opium poppy. It is normally refined out of the opioids that the latex is typically collected for, hence its presence in a sample is strong prima facie evidence that the carrier from whom the sample was collected is implicated in the mass cultivation of poppies or the collection and handling of their latex. We describe an analysis technique combining surface-enhanced Raman spectroscopy (SERS) with microfluidics for detecting papaverine at low concentrations and show that its SERS spectrum has unique spectroscopic features that allows its detection at low concentrations among typical opioids...
February 7, 2017: Analytical Chemistry
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