Amitraz

Amitraz
IUPAC ime
 
N,N'-[(metilimino)dimetilidin]di-2,4-ksilidin
Identifikacija
CAS registarski broj 33089-61-1 DaY
PubChem[1][2] 36324
ChemSpider[3] 33405 DaY
UNII 33IAH5017S DaY
KEGG[4] D02380
ChEMBL[5] CHEMBL1365675 DaY
ATCvet code QP53AD01
Jmol-3D slike Slika 1
SMILES

N(=C/N(\C=N\c1ccc(cc1C)C)C)\c2ccc(cc2C)C

InChI

InChI=1S/C19H23N3/c1-14-6-8-18(16(3)10-14)20-12-22(5)13-21-19-9-7-15(2)11-17(19)4/h6-13H,1-5H3/b20-12+,21-13+ DaY
Kod: QXAITBQSYVNQDR-ZIOPAAQOSA-N DaY

InChI=1/C19H23N3/c1-14-6-8-18(16(3)10-14)20-12-22(5)13-21-19-9-7-15(2)11-17(19)4/h6-13H,1-5H3/b20-12+,21-13+
Kod: QXAITBQSYVNQDR-ZIOPAAQOBL

Svojstva
Molekulska formula C19H23N3
Molarna masa 293,41 g/mol
Tačka topljenja

86–87 °C

Rastvorljivost u vodi Insoluble
Napon pare 2,6 x 10-6 mm Hg.

 DaY (šta je ovo?)   (verifikuj)

Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje (25 °C, 100 kPa) materijala

Infobox references

Amitraz (BTS27419) je nesistemski akaricid i insekticid.[6] On je prvobitno sintetisan u kompaniji Boots Co. u Engleskoj 1969.[7] Amitraz deluje kao repelant insekata, insekticid i kao pesticidni pojačavač.[8] Amitraz je alfa-adrenergički agonist, ligand oktopaminskog receptora centralnog nervnog sistema i inhibitor monoaminske oksidaze i prostaglandinske sinteze.[9] On dovodi do prekomernog pobuđivanja i konsekventno paralize i smrti insekata. Amitraz je manje štetan za sisare, te je između ostalog poznat kao insekticid protiv infestacije pasa gnjidama ili krpeljima.[6]

Reference

  1. ↑ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519.  edit
  2. ↑ Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1. 
  3. ↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846.  edit
  4. ↑ Joanne Wixon, Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast 17 (1): 48–55. DOI:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H. 
  5. ↑ Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594.  edit
  6. ↑ 6,0 6,1 Corta, E., Bakkali, A., Berrueta, L. A., Gallo, B., & Vicente, F. (1999). Kinetics and mechanism of amitraz hydrolysis in aqueous media by HPLC and GC-MS. Talanta, 48(1), 189-199.
  7. ↑ Harrison, I. R., et al. (1973). 1,3,5-Triazapenta-1, 4-dienes: Chemical aspects of a new group of pesticides. Pestic. Sci. 4: 901.
  8. ↑ PubChem Substance. Amitraz – Substance Summary. retrieved from
  9. ↑ Bonsall, J. L., & Turnbull, G. J. (1983). Extrapolation from safety data to management of poisoning with reference to amitraz (a formamidine pesticide) and xylene. Human Toxicology

Literatura

  • Hollingworth, R. M. (1976). Chemistry, biological activity, and uses of formamidine pesticides. Environmental Health Perspectives, 14(April), 57-69.
  • Environmental Protection Agency. (1996). R.E.D. Facts – Amitraz. Prevention, Pesticides And Toxic Substances (7508W), November 1996 retrieved from http://www.epa.gov/oppsrrd1/REDs/factsheets/0234fact.pdf
  • Brown, P. M. (1977). Toxicological problems associated with the manufacture of triazapentadienes. Proceedings of the Royal Society of Medicine, 70(1), 41-43.
  • IPCS INCHEM. (1984). Pesticide residues in food – 1984. retrieved from http://www.inchem.org/documents/jmpr/jmpmono/v84pr03.htm
  • Peter R., de Bruin C., Odendaal D., Thompson P.N. The use of a pour-on and spray dip containing Amitraz to control ticks (Acari: Ixodidae) on cattle. J S Afr Vet Assoc, 2006, 77(2), 66-9
  • Tarallo V.D., Lia R.P., Sasanelli M., Cafarchia C., Otranto D. Efficacy of Amitraz plus Metaflumizone for the treatment of canine demodicosis associated with Malassezia pachydermatis. Parasit Vectors, 2009, 2(1)
  • Chou, C.-P. et al. (2004). Solid-Phase Extraction and GC-MSD Determination of Amitraz and Metabolites in Urine. Journal of Food and Drug Analysis. Vol. 12, No. 3, 2004, 212-216.
  • IPCS INCHEM. (2012). Amitraz. retrieved from http://www.inchem.org/documents/jmpr/jmpmono/v098pr02.htm
  • Terence Robert Roberts, T.R.R. (1999). Metabolic pathways of agrochemicals. Cambridge: The Royal Society of Chemistry, pp 729 – 733
  • Pierpoint, A. C. Et al (1997). Kinetics and Mechanism of Amitraz Hydrolysis. Journal of Agricultural and Food Chemitry. 45 (5), pp 1937–1939
  • Ellenhorn, M.J., S. Schonwald, G. Ordog, J. Wasserberger. Ellenhorn's Medical Toxicology: Diagnosis and Treatment of Human Poisoning. 2nd ed. Baltimore, MD: Williams and Wilkins, 1997., p. 1730
  • Agin, H., Calkavur, S., Uzun, H., & Bak, M. (2004). Amitraz poisoning: clinical and laboratory findings. Indian Pediatrics, 41(5), 482-486.
  • Chen-Izu, Y., Xiao, R. P., Izu, L. T., Cheng, H., Kuschel, M., Spurgeon, H., & Lakatta, E. G. (2000). G(i)-dependent localization of beta(2)-adrenergic receptor signaling to L-type Ca(2+) channels. Biophysical Journal, 79(5), 2547–2556
  • Hsu, W. H. and Lu, Z.-X. (1984). Amitraz' induced delay of gastrointestinal transit in mice: Mediated by α2 adrenergic receptors. Drug Development Research, Volume 4 (6), 655- 680.
  • Chen, A. C., He, H., & Davey, R. B. (2007). Mutations in a putative octopamine receptor gene in amitraz-resistant cattle ticks. Veterinary Parasitology, 148(3-4), 379-383.
  • Grohmann, L., Blenau, W., Erber, J., Ebert, P. R., Strünker, T., & Baumann, A. (2003). Molecular and functional characterization of an octopamine receptor from honeybee (Apis mellifera) brain. Journal of Neurochemistry, 86(3), 725-735.
  • Li, A. Y., Davey, R. B., Miller, R. J., & George, J. E. (2004). Detection and characterization of amitraz resistance in the southern cattle tick, Boophilus microplus (Acari: Ixodidae). Journal of Medical Entomology, 41(2), 193-200.
  • Tipton KF, Boyce S, O'Sullivan J, Davey GP, Healy J (August 2004). "Monoamine oxidases: certainties and uncertainties". Curr. Med. Chem. 11 (15): 1965–82
  • Yim, G. K., Holsapple, M. P., Pfister, W. R., & Hollingworth, R. M. (1978). Prostaglandin synthesis inhibited by formamidine pesticides. Life Sciences, 23(25), 2509–2515
  • Grossman M.R. Amitraz toxicosis associated with ingestion of an acaricide collar in a dog. J Am Vet Med Assoc, 1993, 203(1), 55-7
  • Gifte.de. (2007) Amitraz. retrieved from http://www.gifte.de/Chemikalien/amitraz.htm
  • USEPA Office of Pesticide Programs, Health Effects Division, Science Information Management Branch. (2006).Chemicals Evaluated for Carcinogenic Potential (April 2006)
  • Hayes W.J. et al. (1991). Handbook of Pesticide Toxicology. Volume 3 Classes of Pesticides. pg.1487
  • Lewis, R. J. (1996). Sax's Dangerous Properties of Industrial Materials. 9th edition, Volume 1-3, pg. 2227
  • Budavari, S. The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 85
  • Tomlin, C.D.S. The Pesticide Manual - World Compendium, 11 th ed., British Crop Protection Council, Surrey, England 1997, p. 39
  • Chemical Book. (2010). Amitraz. retrieved from http://www.chemicalbook.com/ChemicalProductProperty_EN_CB9680920.htm
  • Chemical Book. (2008). Amitraz Basic Information. Retrieved from http://www.chemicalbook.com/ProductChemicalPropertiesCB9680920_EN.htm
  • Thomas A. Unger, T.A.U. (1996). Pesticide synthesis handbook. New Jersey: Noyes Publications, pp. 836.
  • PubChem Substance. Amitraz – Substance Summary. retrieved from http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=13178
  • PubChem Substance. Amitraz – Substance Summary. Retrieved from http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=13178#x321

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