4'-Aminopropiophenone

Last updated
4'-Aminopropiophenone
4'-Aminopropiophenone.svg
Names
Preferred IUPAC name
1-(4-Aminophenyl)propan-1-one
Other names
1-(4-Aminophenyl)-1-propanone
para-Aminopropiophenone
PAPP
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.000.675 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • 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).

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]

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]

Related Research Articles

<span class="mw-page-title-main">Cyanide</span> Any molecule with a cyano group (–C≡N)

In chemistry, a cyanide is a chemical compound that contains a C≡N functional group. This group, known as the cyano group, consists of a carbon atom triple-bonded to a nitrogen atom.

<span class="mw-page-title-main">Feral pigeon</span> Domestic pigeons that returned to the wild

Feral pigeons, also called city doves, city pigeons, or street pigeons, are descendants of domestic pigeons that have returned to the wild. The domestic pigeon was originally bred from the wild rock dove, which naturally inhabits sea-cliffs and mountains. Rock, domestic, and feral pigeons are all the same species and will readily interbreed. Feral pigeons find the ledges of buildings to be a substitute for sea cliffs, have become adapted to urban life, and are abundant in towns and cities throughout much of the world.

<span class="mw-page-title-main">Molluscicide</span> Pesticide used to kill molluscs

Molluscicides – also known as snail baits, snail pellets, or slug pellets – are pesticides against molluscs, which are usually used in agriculture or gardening, in order to control gastropod pests specifically slugs and snails which damage crops or other valued plants by feeding on them.

<span class="mw-page-title-main">Feral cat</span> Unowned or untamed domestic cat in the outdoors

A feral cat or a stray cat is an unowned domestic cat that lives outdoors and avoids human contact: it does not allow itself to be handled or touched, and usually remains hidden from humans. Feral cats may breed over dozens of generations and become an aggressive local apex predator in urban, savannah and bushland environments. Some feral cats may become more comfortable with people who regularly feed them, but even with long-term attempts at socialization, they usually remain aloof and are most active after dusk. Of the 700 million cats in the world, 480 million of them are feral.

<span class="mw-page-title-main">Rodenticide</span> Chemical used to kill rodents

Rodenticides are chemicals made and sold for the purpose of killing rodents. While commonly referred to as "rat poison", rodenticides are also used to kill mice, squirrels, woodchucks, chipmunks, porcupines, nutria, beavers, and voles. Despite the crucial roles that rodents play in nature, there are times when they need to be controlled.

<span class="mw-page-title-main">Sodium fluoroacetate</span> Chemical compound

Sodium fluoroacetate, also known as compound 1080, is an organofluorine chemical compound with the formula FCH2CO2Na. This colourless salt has a taste similar to that of sodium chloride and is used as a rodenticide.

<span class="mw-page-title-main">Island restoration</span>

The ecological restoration of islands, or island restoration, is the application of the principles of ecological restoration to islands and island groups. Islands, due to their isolation, are home to many of the world's endemic species, as well as important breeding grounds for seabirds and some marine mammals. Their ecosystems are also very vulnerable to human disturbance and particularly to introduced species, due to their small size. Island groups such as New Zealand and Hawaii have undergone substantial extinctions and losses of habitat. Since the 1950s several organisations and government agencies around the world have worked to restore islands to their original states; New Zealand has used them to hold natural populations of species that would otherwise be unable to survive in the wild. The principal components of island restoration are the removal of introduced species and the reintroduction of native species.

<span class="mw-page-title-main">Western Shield</span> Nature conservation program

Western Shield, managed by Western Australia's Department of Parks and Wildlife, is a nature conservation program safeguarding Western Australia's animals and protecting them from extinction. The program was set up in 1996 and as of 2009 was the largest and most successful wildlife conservation program ever undertaken in Australia.

<span class="mw-page-title-main">Poison shyness</span>

Poison shyness, also called conditioned food aversion, is the avoidance of a toxic substance by an animal that has previously ingested that substance. Animals learn an association between stimulus characteristics, usually the taste or odor, of a toxic substance and the illness it produces; this allows them to detect and avoid the substance. Poison shyness occurs as an evolutionary adaptation in many animals, most prominently in generalists that feed on many different materials. It is often called bait shyness when it occurs during attempts at pest control of insects and animals. If the pest ingests the poison bait at sublethal doses, it typically detects and avoids the bait, rendering the bait ineffective.

<span class="mw-page-title-main">Brodifacoum</span> Chemical compound

Brodifacoum is a highly lethal 4-hydroxycoumarin vitamin K antagonist anticoagulant poison. In recent years, it has become one of the world's most widely used pesticides. It is typically used as a rodenticide, but is also used to control larger pests such as possums.

<span class="mw-page-title-main">M44 (cyanide device)</span>

The M44 cyanide device is used to kill coyotes, feral dogs, and foxes. It is made from four parts: a capsule holder wrapped with cloth or other soft material, a small plastic capsule containing 0.88 grams of sodium cyanide, a spring-powered ejector, and a 5-7 inch stake. To install the trap, the stake is first driven down into the ground, and then the capsule is put in the holder, screwed onto the cocked ejector, and secured to the stake. The wrapped capsule holder is smeared with scented bait to attract coyotes and make them bite and pull on it. When the trap is triggered, the spring propels a dose of sodium cyanide into the animal's mouth, and the sodium cyanide combines with water in the mouth to produce poisonous cyanide gas. In addition to the cyanide, the capsule contains a brightly-colored particle marker.

<span class="mw-page-title-main">1080 usage in New Zealand</span>

1080, the brand name given to the synthetic form of sodium fluoroacetate, is used in New Zealand in efforts to control populations of possums, rats, stoat and rabbits, which are invasive species in the New Zealand environment. Although the Parliamentary Commissioner for the Environment deemed the use of 1080 in New Zealand "effective and safe" in a 2011 re-evaluation and the substance is widely considered to be the most effective tool currently available for controlling possums over large areas, it remains a contentious issue, with the majority of the debate occurring between conservationists and livestock farmers on one side and hunters and animal-rights activists on the other.

<span class="mw-page-title-main">Stoat in New Zealand</span> Introduced ecological threat

The stoat was introduced into New Zealand to control introduced rabbits and hares, but is now a major threat to the native bird population. The natural range of the stoat is limited to parts of the Northern Hemisphere. Immediately before human settlement, New Zealand did not have any land-based mammals apart from bats, but Polynesian and European settlers introduced a wide variety of animals. Rarely, in Southland, the fur of stoats has been reported to turn white, being the fur known as ermine, which adorns royal robes.

<span class="mw-page-title-main">Introduced mammals on seabird breeding islands</span>

Seabirds include some of the most threatened taxa anywhere in the world. For example, of extant albatross species, 82% are listed as threatened, endangered, or critically endangered by the International Union for Conservation of Nature. The two leading threats to seabirds are accidental bycatch by commercial fishing operations and introduced mammals on their breeding islands. Mammals are typically brought to remote islands by humans either accidentally as stowaways on ships, or deliberately for hunting, ranching, or biological control of previously introduced species. Introduced mammals have a multitude of negative effects on seabirds including direct and indirect effects. Direct effects include predation and disruption of breeding activities, and indirect effects include habitat transformation due to overgrazing and major shifts in nutrient cycling due to a halting of nutrient subsidies from seabird excrement. There are other invasive species on islands that wreak havoc on native bird populations, but mammals are by far the most commonly introduced species to islands and the most detrimental to breeding seabirds. Despite efforts to remove introduced mammals from these remote islands, invasive mammals are still present on roughly 80% of islands worldwide.

<span class="mw-page-title-main">Cats in New Zealand</span> Overview of the role and status of cats in New Zealand

Cats are a popular pet in New Zealand. Cat ownership is occasionally raised as a controversial conservation issue due to the predation of endangered species, such as birds and lizards, by feral cats.

<span class="mw-page-title-main">Victoria Forest Park</span>

Victoria Forest Park, is situated on the West Coast of the South Island of New Zealand. At 2,069 square kilometres (799 sq mi) it is New Zealand's largest forest park. The park is administered by the Department of Conservation (DOC).

<span class="mw-page-title-main">Cat predation on wildlife</span> Interspecies animal behavior

Cat predation on wildlife is the result of the natural instincts and behavior of both feral and owned house cats to hunt small prey, including wildlife. Some people view this as a desirable phenomenon, such as in the case of barn cats and other cats kept for the intended purpose of pest control; but scientific evidence does not support the popular use of cats to control urban rat populations, and ecologists oppose their use for this purpose because of the disproportionate harm they do to beneficial native wildlife. As an invasive species and superpredator, they do considerable ecological damage.

Predator Free 2050 is a plan put forth by the New Zealand government with the goal of eradicating all of its mammalian introduced predators by 2050.

Heirisson Prong is a community managed reserve established for the conservation of threatened mammals at Shark Bay in Western Australia. The reserve is at the point of a long narrow peninsula of the same name that juts into Shark Bay from the south.

In biology, overabundant species refers to an excessive number of individuals and occurs when the normal population density has been exceeded. Increase in animal populations is influenced by a variety of factors, some of which include habitat destruction or augmentation by human activity, the introduction of invasive species and the reintroduction of threatened species to protected reserves.

References

  1. Propiophenone, 4'-amino- at cameochemicals.noaa.gov.
  2. 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.
  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). 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.
  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.