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4'-Aminopropiophenone

4'-Aminopropiophenone (para-aminopropiophenone or PAPP) is a chemical compound. It is highly toxic, and can cause injury or death upon physical contact or inhalation of fumes.[1]

4'-Aminopropiophenone
Names
Preferred IUPAC name
1-(4-Aminophenyl)propan-1-one
Other names
1-(4-Aminophenyl)-1-propanone
para-Aminopropiophenone
PAPP
Identifiers
  • 70-69-9 Y
3D model (JSmol)
  • Interactive image
ChemSpider
  • 6034
ECHA InfoCard 100.000.675
  • 6270
UNII
  • 79GF917W6U Y
  • DTXSID7021738
  • InChI=1S/C9H11NO/c1-2-9(11)7-3-5-8(10)6-4-7/h3-6H,2,10H2,1H3
    Key: FSWXOANXOQPCFF-UHFFFAOYSA-N
  • InChI=1/C9H11NO/c1-2-9(11)7-3-5-8(10)6-4-7/h3-6H,2,10H2,1H3
    Key: FSWXOANXOQPCFF-UHFFFAOYAU
  • O=C(c1ccc(N)cc1)CC
Properties
C9H11NO
Molar mass 149.193 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

The toxicity of PAPP is derived from its action on circulating hemoglobin, rapidly converting it to methemoglobin (similar to nitrite poisoning). As methemoglobin is not capable of transporting oxygen like hemoglobin, elevated blood levels (methemoglobinemia) lead to hypoxia, coma, and death due to the inhibition of cellular respiration.[2]

PAPP was first assessed at the Denver Wildlife Research Centre for its potential as a predator control agent in the United States in the early 1980s yet was not developed into a practical technology.[3] From the 1990s scientists based at the then Victorian Institute of Animal Science (Australia) were the first to demonstrate that PAPP could be formulated as a rapid acting and humane means of feral cat and exotic red fox control.[4]

Improved animal welfare outcomes and the existence of an antidote to treat accidental poisoning was an attractive feature of the agent given that the humaneness of the most commonly used poison (sodium fluoroacetate or '1080') is equivocal and no antidote exists for treating accidental 1080 poisoning. Due to the short duration after consumption before death it is critical the antidote be administered as soon as possible. The only antidote treatment that has been shown to work reliably to date is by intravenous (IV) administration.[5]

Researchers also discovered that the delivery of PAPP in feral cat baits within a specialised capsule, which exploits the unique dentition and feeding strategies of feral cats, could greatly limit the exposure of non-target animals to PAPP even if they consume a bait.[6] This became a significant feature adopted in the development of a feral cat bait[7] that became known as 'Curiosity'

Initially collaborating with scientists in Victoria, New Zealand researchers independently developed PAPP formulations and baiting techniques for introduced predators.[8] Initial indications that PAPP was far more toxic to mammals than birds was an attractive feature of its use in New Zealand where it was formulated to control stoats, weasels, and feral cats and registered for use in New Zealand in 2011.[9] PAPP is being further investigated in Australia for use on feral cats, red foxes and wild dogs.[10] In New Zealand PAPP kills stoats at low bait concentrations that are not lethal to far more tolerant exotic possums and rats. In New Zealand it is approved for use in paste form or in fresh minced meat, so will only provide effective stoat control as part of intensive ground control. The potential for environmental contamination appears to be low since it does not leave residues in the environment. At this stage the risk of non-target impacts (by-kill) is thought to be acceptably low using paste formulations, although more recent assessments have shown that some birds are more susceptible to PAPP than previously anticipated.[11]

References edit

  1. ^ Propiophenone, 4'-amino- at cameochemicals.noaa.gov.
  2. ^ Elaine C. Murphy; Charles T. Eason; Steve Hix; Duncan B. Macmorran (2007). (PDF). In G. W. Witmer; W. C. Pitt; K. A. Fagerstone (eds.). Managing Vertebrate Invasive Species: Proceedings of an International Symposium. Fort Collins, CO: USDA/APHIS Wildlife Services, National Wildlife Research Center. Archived from the original (PDF) on 2008-09-23.
  3. ^ Savarie, Peter J.; Pan, Huo Ping; Hayes, David J.; Roberts, Jerry D.; Dasch, Gary J.; Felton, Robert; Schafer, Edward W. Jr. (1983-12-01). "Comparative acute oral toxicity of para-aminopropiophenone (PAPP) in mammals and birds". Bulletin of Environmental Contamination and Toxicology. 30 (1): 122–126. doi:10.1007/BF01610109. ISSN 0007-4861. PMID 6831067. S2CID 26981555.
  4. ^ "Marks, C.A., Gigliotti, F., Busana, F., Johnston, M., Lindeman, M.(2004) Fox control using a para-aminopropiophenone formulation with the M-44 ejector. Animal Welfare v. 13, no. 4". agris.fao.org. Retrieved 2015-10-13.
  5. ^ "News".
  6. ^ Marks, C.A., Johnston, M.J., Fisher, P.M., Pontin, K. & Shaw, M.J. (2006) Differential particle size ingestion: promoting target-specific baiting of feral cats. Journal of Wildlife Management, 70, 1119-1124.
  7. ^ Johnston, M.J.; Shaw, M.J.; Robley, A.; Schedvin, N.K. (2007-01-01). "Bait uptake by feral cats on French Island, Victoria". Australian Mammalogy. 29 (1): 77–83. doi:10.1071/AM07009.
  8. ^ Dilks, P; Shapiro, L.; Greene, T.; Kavermann, MJ; Eason, CT; Murphy, EC (2011). "Field evaluation of para-aminopropiophenone (PAPP) for controlling stoats (Mustela erminea) in New Zealand". New Zealand Journal of Zoology. 38 (2): 143. doi:10.1080/03014223.2010.537668.
  9. ^ Shapiro, L.; Eason, C.T.; Murphy, E.; Dilks, P.; Hix, S.; Ogilvie, S.C.; MacMorran, D. (2010). "Para-aminopropiophenone (PAPP) research, development, registration, and application for humane predator control in New Zealand". In R.M. Timm; K.A. Fagerstone (eds.). Proc. 24th Vertebrate Pest Conference. pp. 108–114.
  10. ^ Denny, Elizabeth; Dickman, Christopher (2010). (PDF). p. 40. Archived from the original (PDF) on 2013-10-01. Retrieved 2012-10-11.
  11. ^ Eason, C.T., Miller, A., MacMorran, D.B. & Murphy, E.C. (2014) Toxicology and ecotoxicology of para-aminopropiophenone (PAPP)–a new predator control tool for stoats and feral cats in New Zealand. New Zealand Journal of Ecology, 38, 177-188.

External links edit

  • Feral cat bait uptake in eastern Australia

aminopropiophenone, para, aminopropiophenone, papp, chemical, compound, highly, toxic, cause, injury, death, upon, physical, contact, inhalation, fumes, names, preferred, iupac, name, aminophenyl, propan, other, names, aminophenyl, propanonepara, aminopropioph. 4 Aminopropiophenone para aminopropiophenone or PAPP is a chemical compound It is highly toxic and can cause injury or death upon physical contact or inhalation of fumes 1 4 Aminopropiophenone Names Preferred IUPAC name 1 4 Aminophenyl propan 1 one Other names 1 4 Aminophenyl 1 propanonepara AminopropiophenonePAPP Identifiers CAS Number 70 69 9 Y 3D model JSmol Interactive image ChemSpider 6034 ECHA InfoCard 100 000 675 PubChem CID 6270 UNII 79GF917W6U Y CompTox Dashboard EPA DTXSID7021738 InChI InChI 1S C9H11NO c1 2 9 11 7 3 5 8 10 6 4 7 h3 6H 2 10H2 1H3Key FSWXOANXOQPCFF UHFFFAOYSA NInChI 1 C9H11NO c1 2 9 11 7 3 5 8 10 6 4 7 h3 6H 2 10H2 1H3Key FSWXOANXOQPCFF UHFFFAOYAU SMILES O C c1ccc N cc1 CC Properties Chemical formula C 9H 11N O Molar mass 149 193 g mol 1 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references The toxicity of PAPP is derived from its action on circulating hemoglobin rapidly converting it to methemoglobin similar to nitrite poisoning As methemoglobin is not capable of transporting oxygen like hemoglobin elevated blood levels methemoglobinemia lead to hypoxia coma and death due to the inhibition of cellular respiration 2 PAPP was first assessed at the Denver Wildlife Research Centre for its potential as a predator control agent in the United States in the early 1980s yet was not developed into a practical technology 3 From the 1990s scientists based at the then Victorian Institute of Animal Science Australia were the first to demonstrate that PAPP could be formulated as a rapid acting and humane means of feral cat and exotic red fox control 4 Improved animal welfare outcomes and the existence of an antidote to treat accidental poisoning was an attractive feature of the agent given that the humaneness of the most commonly used poison sodium fluoroacetate or 1080 is equivocal and no antidote exists for treating accidental 1080 poisoning Due to the short duration after consumption before death it is critical the antidote be administered as soon as possible The only antidote treatment that has been shown to work reliably to date is by intravenous IV administration 5 Researchers also discovered that the delivery of PAPP in feral cat baits within a specialised capsule which exploits the unique dentition and feeding strategies of feral cats could greatly limit the exposure of non target animals to PAPP even if they consume a bait 6 This became a significant feature adopted in the development of a feral cat bait 7 that became known as Curiosity Initially collaborating with scientists in Victoria New Zealand researchers independently developed PAPP formulations and baiting techniques for introduced predators 8 Initial indications that PAPP was far more toxic to mammals than birds was an attractive feature of its use in New Zealand where it was formulated to control stoats weasels and feral cats and registered for use in New Zealand in 2011 9 PAPP is being further investigated in Australia for use on feral cats red foxes and wild dogs 10 In New Zealand PAPP kills stoats at low bait concentrations that are not lethal to far more tolerant exotic possums and rats In New Zealand it is approved for use in paste form or in fresh minced meat so will only provide effective stoat control as part of intensive ground control The potential for environmental contamination appears to be low since it does not leave residues in the environment At this stage the risk of non target impacts by kill is thought to be acceptably low using paste formulations although more recent assessments have shown that some birds are more susceptible to PAPP than previously anticipated 11 References edit Propiophenone 4 amino at cameochemicals noaa gov Elaine C Murphy Charles T Eason Steve Hix Duncan B Macmorran 2007 Developing a New Toxin for Potential Control of Feral Cats Stoats and Wild Dogs in New Zealand PDF In G W Witmer W C Pitt K A Fagerstone eds Managing Vertebrate Invasive Species Proceedings of an International Symposium Fort Collins CO USDA APHIS Wildlife Services National Wildlife Research Center Archived from the original PDF on 2008 09 23 Savarie Peter J Pan Huo Ping Hayes David J Roberts Jerry D Dasch Gary J Felton Robert Schafer Edward W Jr 1983 12 01 Comparative acute oral toxicity of para aminopropiophenone PAPP in mammals and birds Bulletin of Environmental Contamination and Toxicology 30 1 122 126 doi 10 1007 BF01610109 ISSN 0007 4861 PMID 6831067 S2CID 26981555 Marks C A Gigliotti F Busana F Johnston M Lindeman M 2004 Fox control using a para aminopropiophenone formulation with the M 44 ejector Animal Welfare v 13 no 4 agris fao org Retrieved 2015 10 13 News Marks C A Johnston M J Fisher P M Pontin K amp Shaw M J 2006 Differential particle size ingestion promoting target specific baiting of feral cats Journal of Wildlife Management 70 1119 1124 Johnston M J Shaw M J Robley A Schedvin N K 2007 01 01 Bait uptake by feral cats on French Island Victoria Australian Mammalogy 29 1 77 83 doi 10 1071 AM07009 Dilks P Shapiro L Greene T Kavermann MJ Eason CT Murphy EC 2011 Field evaluation of para aminopropiophenone PAPP for controlling stoats Mustela erminea in New Zealand New Zealand Journal of Zoology 38 2 143 doi 10 1080 03014223 2010 537668 Shapiro L Eason C T Murphy E Dilks P Hix S Ogilvie S C MacMorran D 2010 Para aminopropiophenone PAPP research development registration and application for humane predator control in New Zealand In R M Timm K A Fagerstone eds Proc 24th Vertebrate Pest Conference pp 108 114 Denny Elizabeth Dickman Christopher 2010 Review of cat ecology and management strategies in Australia PDF p 40 Archived from the original PDF on 2013 10 01 Retrieved 2012 10 11 Eason C T Miller A MacMorran D B amp Murphy E C 2014 Toxicology and ecotoxicology of para aminopropiophenone PAPP a new predator control tool for stoats and feral cats in New Zealand New Zealand Journal of Ecology 38 177 188 External links editFeral cat bait uptake in eastern Australia Retrieved from https en wikipedia org w index php title 4 27 Aminopropiophenone amp oldid 1166766100, wikipedia, wiki, book, books, library,

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