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Bromethalin

Bromethalin is a neurotoxic rodenticide that damages the central nervous system.[1]

Bromethalin
Names
Preferred IUPAC name
N-Methyl-2,4-dinitro-N-(2,4,6-tribromophenyl)-6-(trifluoromethyl)aniline
Other names
2,4,6-Tribromo-N-[2,4-dinitro-6-(trifluoromethyl)phenyl]-N-methylaniline
Identifiers
  • 63333-35-7 Y
3D model (JSmol)
  • Interactive image
ChemSpider
  • 40463 Y
ECHA InfoCard 100.109.042
KEGG
  • C18697 N
  • 44465
UNII
  • GM59MTH1FS Y
  • DTXSID8032590
  • InChI=1S/C14H7Br3F3N3O4/c1-21(13-9(16)2-6(15)3-10(13)17)12-8(14(18,19)20)4-7(22(24)25)5-11(12)23(26)27/h2-5H,1H3 Y
    Key: USMZPYXTVKAYST-UHFFFAOYSA-N Y
  • InChI=1/C14H7Br3F3N3O4/c1-21(13-9(16)2-6(15)3-10(13)17)12-8(14(18,19)20)4-7(22(24)25)5-11(12)23(26)27/h2-5H,1H3
    Key: USMZPYXTVKAYST-UHFFFAOYAX
  • Brc2cc(Br)cc(Br)c2N(c1c([N+]([O-])=O)cc([N+]([O-])=O)cc1C(F)(F)F)C
Properties
C14H7Br3F3N3O4
Molar mass 577.93 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

History edit

Bromethalin was discovered in the early 1980s through an approach to find replacement rodenticides for first-generation anticoagulants, especially to be useful against rodents that had become resistant to Warfarin-type anticoagulant poisons. A structured study was undertaken to develop a substance that would be both poisonous to rodents, but also would be readily eaten by rodents. Bromethalin—N-methyl-2,4-dinitro-N (2,4,6-tribromophenyl)-6-(trifluoromethyl) benzeneamine— was the outcome of that study, as the specific formulation had both desired rodenticidal properties.[1]

Mechanism of action edit

Bromethalin works by being metabolised to n-desmethyl-bromethalin and uncoupling mitochondrial oxidative phosphorylation, which causes a decrease in adenosine triphosphate (ATP) synthesis. The decreased ATP inhibits the activity of the Na/K ATPase enzyme, thereby leading to a subsequent buildup of cerebral spinal fluid (CSF) and vacuolization of myelin. The excess CSF results in increased intracranial pressure, which in turn permanently damages neuronal axons. This damage to the central nervous system can cause paralysis, convulsions, and death.[1][2][full citation needed]

Risk of poisoning to humans and pets edit

Despite risk of severe symptoms and death, most unintentional pediatric exploratory exposures (licking or tasting a pellet) have not shown serious effects, and no deaths have been reported at this time in children, though toxicity is possible if significant amounts are ingested.[3] Due to need for active metabolite generation to produce toxicity, fatal toxicity may be delayed by hours to days.[4] All cases should be managed in consultation with a local poison control center. All intentional ingestions for self harm carry significant risk of death or severe neurologic effects and require monitoring in a hospital setting.[3]

In humans the most common initial effects of unintentional exposure are nausea, vomiting, abdominal pain, and diarrhea, though delayed seizures have been reported.[3] No antidote for bromethalin is known; care is symptomatic and supportive.

In pets, signs to watch for include severe muscle tremors, hyperexcitability, fits, extreme sensitivity to being touched (hyperesthesia) and seizures that appear to be caused by light or noise.[5] Owners of animals that have eaten bromethalin accidentally should seek immediate veterinary attention and be decontaminated. Contacting an animal poison control center can help ensure that timely and appropriate therapy is started.[citation needed]

References edit

  1. ^ a b c Dreikorn, Barry A.; O'Doherty, George O. P. (1984). "The Discovery and Development of Bromethalin, an Acute Rodenticide with a Unique Mode of Action". Pesticide Synthesis Through Rational Approaches. ACS Symposium Series. Vol. 255. pp. 45–63. doi:10.1021/bk-1984-0255.ch004. ISBN 0-8412-0852-2.
  2. ^ Bromethalin, Animal Disease Diagnostic Laboratory, Spring 1997 Newsletter
  3. ^ a b c Feldman, Ryan; Stanton, Matthew; Borys, Douglas; Kostic, Mark; Gummin, David (November 2019). "Medical outcomes of bromethalin rodenticide exposures reported to US poison centers after federal restriction of anticoagulants". Clinical Toxicology. 57 (11): 1109–1114. doi:10.1080/15563650.2019.1582776. ISSN 1556-9519. PMID 30892957.
  4. ^ Pasquale-Styles, Melissa A.; Sochaski, Mark A.; Dorman, David C.; Krell, Willane S.; Shah, Aashit K.; Schmidt, Carl J. (September 2006). "Fatal bromethalin poisoning". Journal of Forensic Sciences. 51 (5): 1154–1157. doi:10.1111/j.1556-4029.2006.00218.x. ISSN 0022-1198. PMID 17018099. S2CID 33324699.
  5. ^ Peterson, Michael E. (February 2013). "Bromethalin". Topics in Companion Animal Medicine. 28 (1): 21–23. doi:10.1053/j.tcam.2013.03.005. ISSN 1946-9837. PMID 23796484.

bromethalin, neurotoxic, rodenticide, that, damages, central, nervous, system, namespreferred, iupac, name, methyl, dinitro, tribromophenyl, trifluoromethyl, anilineother, names, tribromo, dinitro, trifluoromethyl, phenyl, methylanilineidentifierscas, number, . Bromethalin is a neurotoxic rodenticide that damages the central nervous system 1 Bromethalin NamesPreferred IUPAC name N Methyl 2 4 dinitro N 2 4 6 tribromophenyl 6 trifluoromethyl anilineOther names 2 4 6 Tribromo N 2 4 dinitro 6 trifluoromethyl phenyl N methylanilineIdentifiersCAS Number 63333 35 7 Y3D model JSmol Interactive imageChemSpider 40463 YECHA InfoCard 100 109 042KEGG C18697 NPubChem CID 44465UNII GM59MTH1FS YCompTox Dashboard EPA DTXSID8032590InChI InChI 1S C14H7Br3F3N3O4 c1 21 13 9 16 2 6 15 3 10 13 17 12 8 14 18 19 20 4 7 22 24 25 5 11 12 23 26 27 h2 5H 1H3 YKey USMZPYXTVKAYST UHFFFAOYSA N YInChI 1 C14H7Br3F3N3O4 c1 21 13 9 16 2 6 15 3 10 13 17 12 8 14 18 19 20 4 7 22 24 25 5 11 12 23 26 27 h2 5H 1H3Key USMZPYXTVKAYST UHFFFAOYAXSMILES Brc2cc Br cc Br c2N c1c N O O cc N O O cc1C F F F CPropertiesChemical formula C14H7Br3F3N3O4Molar mass 577 93 g molExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 History 2 Mechanism of action 3 Risk of poisoning to humans and pets 4 ReferencesHistory editBromethalin was discovered in the early 1980s through an approach to find replacement rodenticides for first generation anticoagulants especially to be useful against rodents that had become resistant to Warfarin type anticoagulant poisons A structured study was undertaken to develop a substance that would be both poisonous to rodents but also would be readily eaten by rodents Bromethalin N methyl 2 4 dinitro N 2 4 6 tribromophenyl 6 trifluoromethyl benzeneamine was the outcome of that study as the specific formulation had both desired rodenticidal properties 1 Mechanism of action editBromethalin works by being metabolised to n desmethyl bromethalin and uncoupling mitochondrial oxidative phosphorylation which causes a decrease in adenosine triphosphate ATP synthesis The decreased ATP inhibits the activity of the Na K ATPase enzyme thereby leading to a subsequent buildup of cerebral spinal fluid CSF and vacuolization of myelin The excess CSF results in increased intracranial pressure which in turn permanently damages neuronal axons This damage to the central nervous system can cause paralysis convulsions and death 1 2 full citation needed Risk of poisoning to humans and pets editDespite risk of severe symptoms and death most unintentional pediatric exploratory exposures licking or tasting a pellet have not shown serious effects and no deaths have been reported at this time in children though toxicity is possible if significant amounts are ingested 3 Due to need for active metabolite generation to produce toxicity fatal toxicity may be delayed by hours to days 4 All cases should be managed in consultation with a local poison control center All intentional ingestions for self harm carry significant risk of death or severe neurologic effects and require monitoring in a hospital setting 3 In humans the most common initial effects of unintentional exposure are nausea vomiting abdominal pain and diarrhea though delayed seizures have been reported 3 No antidote for bromethalin is known care is symptomatic and supportive In pets signs to watch for include severe muscle tremors hyperexcitability fits extreme sensitivity to being touched hyperesthesia and seizures that appear to be caused by light or noise 5 Owners of animals that have eaten bromethalin accidentally should seek immediate veterinary attention and be decontaminated Contacting an animal poison control center can help ensure that timely and appropriate therapy is started citation needed References edit a b c Dreikorn Barry A O Doherty George O P 1984 The Discovery and Development of Bromethalin an Acute Rodenticide with a Unique Mode of Action Pesticide Synthesis Through Rational Approaches ACS Symposium Series Vol 255 pp 45 63 doi 10 1021 bk 1984 0255 ch004 ISBN 0 8412 0852 2 Bromethalin Animal Disease Diagnostic Laboratory Spring 1997 Newsletter a b c Feldman Ryan Stanton Matthew Borys Douglas Kostic Mark Gummin David November 2019 Medical outcomes of bromethalin rodenticide exposures reported to US poison centers after federal restriction of anticoagulants Clinical Toxicology 57 11 1109 1114 doi 10 1080 15563650 2019 1582776 ISSN 1556 9519 PMID 30892957 Pasquale Styles Melissa A Sochaski Mark A Dorman David C Krell Willane S Shah Aashit K Schmidt Carl J September 2006 Fatal bromethalin poisoning Journal of Forensic Sciences 51 5 1154 1157 doi 10 1111 j 1556 4029 2006 00218 x ISSN 0022 1198 PMID 17018099 S2CID 33324699 Peterson Michael E February 2013 Bromethalin Topics in Companion Animal Medicine 28 1 21 23 doi 10 1053 j tcam 2013 03 005 ISSN 1946 9837 PMID 23796484 Retrieved from https en wikipedia org w index php title Bromethalin amp oldid 1194225865, wikipedia, wiki, book, books, library,

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