First online: 08 July 2009Synthesis of thiourea derivatives of the alkaloid anabasine and crystal structure of N -(anabasino1-thiocarbonyl)furan-2-carboxamide
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A series of new N -acylsubstituted thioureas, the compositions and structures of which were determined by IR and PMR spectroscopy and mass spectrometry, were synthesized from the alkaloid anabasine. The crystal structure of one of the products, N -(anabasino-1-thiocarbonyl)furan-2-carboxamide, was confirmed by x-ray structure analysis. It was also shown that this compound exhibited moderate antibacterial activity.Key words
alkaloid anabasine thiourea derivatives isothiocyanates PMR spectroscopy x-ray structure analysis antibacterial activity
Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 183–185, March–April, 2009.
A series of novel nicotine and anabasine related conformationally restricted compounds including those with pi-bonds in the connecting tether were synthesized following the hitherto unprecedented phenylsulfanyl group assisted generation of pyridine o-quinodimethane intermediates and their trapping by an intramolecular Diels-Alder reaction. Pharmacological characterization of some of these analogues at activating alpha3beta4 nAChRs was investigated, and constrained anabasine analogues 35 and 43 as well as constrained nicotine analogue 42 were found to exhibit moderately potent nicotinic agonist activity. Of special note is the fact that the pyrrolidinic nitrogen in these compounds is bound to a carbomethoxy group and, therefore, is not free to be protonated unlike all the known analogues of nicotine and anabasine, specifically designed as nAChRs agonists/antagonists. The structure-activity relationship studies indicate that when pi-cation interaction is absent, the position of chlorine atom in the pyridine ring and steric bulk at the connecting tether between the pyridine and pyrrolidine ring of the constrained nicotinic ligands are important descriptors for their binding affinity at alpha4beta2 and alpha3beta4 nAChRs as well as the subtype selectivity issue. These findings are likely to improve our understanding of the structural requirements for selectivity, which, at present, is probably the most important goal in the field of nicotinic ligands.
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Writing a essay for class,need criteria on it.
Culture an Inescapable Thing
People are what their culture makes them. It brings people together or separate them, through heritage. As it is our interaction with the world; influenced through our childhood and heritage. Culture is the most influential element in society, it impacts the way a person views their surroundings, affecting their morals, values, and decisions.
Culture becomes our guidelines sometimes blinding us. A person acts the way they do, because they were raised that way. This is especial true in Robert Lake's letter "An Indian father's plea". In the letter he informs his son's teacher how his classmates are treating him due to him being cultural different. The classmates act in this way due to their culture, and the values they have inheritance from their ancestors. These values are racist and judgmental, for example "He ask why one young white girl at school who is his friend tells him, "I like you, Wind-Wolf, because you are a good Indian." This shows that his classmate's culture is infused with judgment of others based on the color of their skin. Similar Pico Iyer's essay "where worlds collide" shows another case where cultural views are clouding one's judgement. "Yes on proposition 187. Mexicans go home" (Iyer 51), shows a negative view of Mexicans, as proposition 187 issued in 1994 stated that no alien make receive public benefits. This shows how American people wanted to separate Mexicans from Americans, this issue resulted from cultural differences.
Culture stays with one's self throughout their life. People don't leave their comfort zone, as such they don't abandon their traditions and morals that were passed down to them. One stays true to one's culture, this is especial expressed in "everyday use" by Alice Walker. The story is about mother and her two daughters, Maggie and Dee. The idea of heritage is show through the quilts, as the central argument is over the cultural values of the quilts. "I can 'member grandma Dee without the quilts"(Walker 65). This quote shows that Maggie has no need for a physical manifest of her culture unlike Dee; she can remember with the values and lessons she was taught.
Culture doesn't influence a person's decisions, and confuses them, the best example of this would be Dee in "Everyday use". She couldn't stand her culture as she was embarrassed by it, to the point that she once wrote to her mother "that no matter, where you live I will come see, but I won't bring my friends" (Walker 60). She left in order to find a better "culture", one that was completely different from her mother's and Maggie's. In my opinion the idea that Dee was not confused about her culture is untrue. Dee changes her name to better suite her African heritage, later she comes home with a false sense of heritage. She asks for the quilts so she can hang them in a museum like exhibit style, this suggests that she feels reverence for them but that to her they are essentially foreign, impersonal objects. She doesn't understand the true value of them as they were made from old clothes used by her ancestors meant for everyday use. She has created a false cultural identity as she doesn't understand her true heritage is the one of her Mother and not her African heritage.
One way or other cultural will somehow influence a, throughout their life, it might cloud their judgment. Culture often makes people biased on a certain topic, sometimes turning into pure racism as with Mexicans in "where worlds collide". A person stays true to the ideas and values that is their culture as with Maggie, who unlike Dee didn't try to create a false heritage. Culture is an inescapable thing that will always be the basics for all decisions that a person will ever make.
Sallio, R. Lebrun, S. Gigant, N. Gillaizeau, I. and Deniau, E. (2014), Asymmetric Synthesis of 2-Heteroaryl Cyclic Amines: Total Synthesis of (–)-Anabasine. Eur. J. Org. Chem. 2014: 4381–4388. doi: 10.1002/ejoc.201402202Author Information
Université Lille Nord de France, ENSCL, E.A. 4478 Chimie Moléculaire et Formulation, Cité Scientifique, 59652 Villeneuve d'Ascq Cedex, France, http://www.univ-lille1.fr
Institut de Chimie Organique et Analytique, UMR 7311 CNRS, Université d'Orléans, Rue de Chartres, 45067 Orléans Cedex 2, France, http://www.univ-orleans.fr
Email: Isabelle Gillaizeau (email@example.com), Eric Deniau (Eric.Deniau@univ-lille1.fr)
* Isabelle Gillaizeau, Institut de Chimie Organique et Analytique, UMR 7311 CNRS, Université d'Orléans, Rue de Chartres, 45067 Orléans Cedex 2, France===
Eric Deniau, Université Lille Nord de France, ENSCL, E.A. 4478 Chimie Moléculaire et Formulation, Cité Scientifique, 59652 Villeneuve d'Ascq Cedex, France===
880 Am J Clin Pathol 2006;126:880-887 880 DOI: 10.1309/LQ8U3UL956ET324X © American Society for Clinical Pathology Clinical Chemistry / DETECTION OF TOBACCO ALKALOIDS IN URINE
The AAPS Journal 2005; 7 (3) Article 75 (http://www.aapsj.org). E752 Themed Issue: Drug Addiction - From Basic Research to Therapies Guest Editors - Rao Rapaka and Wolfgang Sadée A General Procedure for the Enantioselective Synthesis of the Minor Tobacco Alkaloids Nornicotine, Anabasine. and.
Polarimetry data should be reported in the form shown in Table 7.1. 7.2 ISOLATION OF ANABASINE ANDAMMODENDRINE ENANTIOMERS 7.2.1 SYNTHESIS AND SEPARATION OF ANABASINE AND AMMODEN DRI N E- BASED DIASTEREOMERS Anahasine (0.55% yield) and ammodendrine (0.47% yield) were extracted and isolated from N. glauca.
Anabasine and Anatabine as Biomarkers for Tobacco Use during Nicotine Replacement Therapy 1 Peyton Jacob, III, 2 Dorothy Hatsukami, Herbert Severson, Sharon Hall, Lisa Yu, and
When the tobacco sample was spiked with known amounts of each alkaloid, nicotine and nornicotine were recovered with yields better than 95 j„ and anatabine and anabasine were recovered at approximatel y a 90 % yield.
Anabasine is not expected to be present in pharmaceutical grade nicotine. A urine specimen that contains equal to or greater than 3 ng/mL anabasine is not consistent with nicotine replacement therapy but rather, indicates tobacco use has occured (active smoking).
the subject is either actively using a tobacco product or is on high-dose nicotine patch therapy. The presence of anabasine and nornicotine indicates a subject on patch therapy who is actively using a tobacco
All samples containing impurity peaks with spectral library matches to cotinine, anabasine. myosmine, and β-nicotyrine were than analyzed on a Varian 320 Triple Quad GC-MS in either single reaction monitoring mode (SRM) or multiple reaction monitoring mode (MRM).
Typical quantities of the minor alkaloids in the smoke of one cigarette are: nornicotine (27 to 88 pg), cotinine (9 to 50 pg), anabasine (3 to 12 pgl, anatabine (4 to 14 pg). myosmine (9 pg), and 2,3' dipyridyl (7 to 27 pg).
Simultaneous and sensitive measurement of anabasine. nicotine and nicotine metabolites in human urine by liquid chromatography tandem mass spectrometry.
Additional Names: 2-(3-pyridyl)piperidine; neonicotine
Molecular Formula: C 10 H 14 N 2
Molecular Weight: 162.23
Percent Composition: C 74.04%, H 8.70%, N 17.27%
Literature References: In Anabasis aphylla L. Chenopodiaceae: Orechoff, Menschikoff, Ber.64, 266 (1931); in Nicotiana glauca Graham, Solanaceae: Smith, J. Am. Chem. Soc.57, 959 (1935); Pyriki, Oehler, Pharmazie9, 685 (1954). Synthesis: Späth, Ber.70B, 70 (1937). Extracted on a large scale in Russia. Industrial extraction processes: Sadykov, Timbekov, J. Appl. Chem. USSR29, 148 (1956). Abs config: Lukes et al.,Collect. Czech. Chem. Commun.27, 751 (1962).
Properties: Liquid, bp 270-272°; bp 14 145-147°; bp 2 105°. Freezes at 9°. d 420 1.0455. n D20 1.5430. [ a ] D20 -83.1°. Sol in water and in most organic solvents.
Boiling point: bp 270-272°; bp 14 145-147°; bp 2 105°
Optical Rotation: [ a ] D20 -83.1°
Index of refraction:n D20 1.5430
Density: d 420 1.0455
Derivative Type: Hydrochloride
Properties: [ a ] D +16.5° (c = 10 in water).
Optical Rotation: [ a ] D +16.5° (c = 10 in water)
CAUTION:Acute and subacute toxicity: increased salivation, vertigo, confusion, disturbed vision and hearing, photophobia, cold extremities, nausea, vomiting, diarrhea, syncope, clonic spasms.
What does Anabasine mean as a name of something?
Anabasine is a pyridine and piperidine alkaloid found in the Tree Tobacco plant, a close relative of the common tobacco plant. It is a structural isomer of, and chemically similar to, nicotine. Its principal industrial use is as an insecticide.Printed dictionaries and other books with definitions for Anabasine
Click on a title to look inside that book (if available):Applications of Plant Metabolic Engineering (2007)
by Robert Verpoorte, A.W. Alfermann, T.S. Johnson
Anabasine is a minor alkaloid accompanying nicotine in N. tabacum. Nicotine production, strictly correlated rate wise with growth, and occurs in the root tips, while anabasine production seems to occur primarily in matured root tissues.Organic Chemistry (2016)
by Cram101 Textbook Reviews
Anabasine. Anabasine is a pyridine and piperidine alkaloid found in the Tree Tobacco plant, a close relative of the common tobacco plant (Nicotiana tabacum).Neuropathology of Drug Addictions and Substance Misuse Volume 1 (2016)
Foundations of Understanding, Tobacco, Alcohol, Cannabinoids and Opioids by Victor R. Preedy
Anabasine is a putative partial agonist of α4β2 nAChRs (Stolerman & Jarvis, 1995) and, when administered prior to nicotine self-administration sessions, has been shown to reduce nicotine self-administration in rats (Caine et al. 2014; Hall et.The ASAM Essentials of Addiction Medicine (2015)
by Abigail Herron, Timothy K. Brennan
Anabasine is a tobacco alkaloid that is not a metabolic product of nicotine, which is present in the urine of tobacco users but not in the urine of patients using NRT, and can distinguish abstinent tobacco users who are using NRT from those.e-Study Guide for Amino Group Chemistry: From Synthesis to the Life Sciences, textbook by Alfredo Ricci (Editor) (2012)
Chemistry, Organic chemistry by Cram101 Textbook Reviews
Anabasine. Anabasine is a pyridine alkaloid found in the Tree Tobacco.Plant Metabolism and Biotechnology (2010)
by Hiroshi Ashihara, Alan Crozier, Atsushi Komamine
anabasine is a major alkaloid. Figure 7.1 Alkaloids in Nicotiana species. 7.2. Pathways. and. Enzymes. In tobacco, nicotine and related.Advances in Plant Biotechnology (2012)
by D.D.Y. Ryu, Shintaro Furusaki
anabasine is a major alkaloid, we transformed N. tabacum cv. SamSum, cv. SR1 and cv. Pirat with the double 35S-ldc expression cassette pLX154.3. Among 35 kanamycin-resistant root cultures 6 lines contained distinctly increased levels.Insects and Hygiene (2013)
The biology and control of insect pests of medical and domestic importance by James Ronald Busvine
Anabasine is a similar alkaloid, from the plant Anabasis aphylla which grows wild over large parts of Asia; and this is used to some extent in the U .S.S.R. A mixture of alkaloids known as the veratrine group is obtained from the rhizomes of.Principles of Addiction Medicine (2012)
The Essentials by Christopher A. Cavacuiti
Anabasine is a tobacco alkaloid that is nota metabolic product of nicotine. Anabasine is.Insect Pathology V1 (2012)
An Advanced Treatise by Edward Steinhaus
Anabasine is a closely related alkaloid which facilitates and blocks synaptic transmission; experiments on crayfish have shown that it is less active than nicotine and may protect the ganglion against nicotine subsequently applied (' Viersma.Toxic Plants and Other Natural Toxicants (1998)
by Tam Garland, A. Catherine Barr
Anabasine is a known teratogen, and it is possible that the double bond derivative anabaseine would be more toxic and perhaps more potent as a teratogen (Panter et al. 1994). Alkaloids in L. formosus and L. arbustus are thought to have a.Medical Herbalism (2003)
The Science and Practice of Herbal Medicine by David Hoffmann, FNIMH, AHG
Anabasine is a tobacco alkaloid in which a pyridine ring is linked to a piperidine rather than a pyrrolidine nucleus. 6 Nicotine is a ganglion (nicotinic) cholinergic- receptor agonist with complex pharmacological actions, including effects.Phytochemical Dictionary (1998)
A Handbook of Bioactive Compounds from Plants, Second Edition by Herbert Baxter, J.B. Harborne, Gerald P. Moss
Anabasine is a tobacco alkaloid where a pyridine ring is linked to.
P M Gocze, I Szabo, D A FreemanAbstract
To reveal the well known effect of smoking on the incidence of early abortion, the possible effects of cigarette alkaloids on progesterone and estradiol synthesis were investigated. A suspected cause for early spontaneous abortion is corpus luteum insufficiency. The present experiments evaluate the effects of cigarette smoke alkaloids on progesterone and estradiol biosynthesis. Human granulosa cells were obtained from patients undergoing in vitro fertilization and embryo transfer treatment because of infertility. Incubation of the granulosa cells with cotinine, anabasine, with the combination of nicotine, cotinine and anabasine, or with an aqueous extract of cigarette smoke resulted in inhibition of progesterone synthesis. The alkaloids and smoke extract decreased the DNA content of the culture dish. These latter findings suggested a cytotoxic effect of the alkaloids. Both cotinine and anabasine slightly stimulated the synthesis of normalized estradiol. However, nicotine, combination of all three alkaloids, and cigarette smoke extract had no significant influence on estradiol production. Taken together, these data would suggest that cigarette alkaloids inhibit cellular progesterone synthesis both by inhibiting progesterone synthesis and by causing less specific toxic effects to the cell. In contrast, cigarette smoke alkaloids slightly stimulated or had no effect on estradiol production. These concomitant actions of cigarette alkaloids partly explain the higher incidence of early abortion in pregnant women who smoke.Related Materials