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Journal articles on the topic 'Aminopropiophenone'

Author: Grafiati

Published: 4 June 2021

Last updated: 28 July 2025

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1

Marrs, T. C., R. H. Inns, J. E. Bright, and S. G. Wood. "The Formation of Methaemoglobin by 4-aminopropiophenone (PAPP) and 4-(N-hydroxy) aminopropiophenone." Human & Experimental Toxicology 10, no. 3 (1991): 183–88. http://dx.doi.org/10.1177/096032719101000306.

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Oral dosing of rats with the cyanide antidote 4-aminopropiophenone (PAPP), brought about peak methaemoglobin levels at 15-40 min, but peak levels were attained at 15-25 min after intravenous dosing. After both oral and intravenous administration at equimolar doses, 4-(N-hydroxy)aminopropiophenone (PHAPP), the putative methaemoglobin-producing metabolite of PAPP, produced higher peak levels of methaemoglobin than PAPP. Plasma from rats injected with PAPP was capable of forming methaemoglobin when added to naive rat erythrocytes. The identity of the metabolite responsible is discussed.

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2

Vera, William J., and Ajoy K. Banerjee. "First synthesis of 3-methoxy-4-aminopropiophenone." Journal of Chemical Research 36, no. 9 (2012): 543–44. http://dx.doi.org/10.3184/174751912x13418461206368.

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3

Fisher, P., and C. O'Connor. "Oral toxicity of p-aminopropiophenone to ferrets." Wildlife Research 34, no. 1 (2007): 19. http://dx.doi.org/10.1071/wr06125.

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Ferrets (Mustela furo) are pests in New Zealand and new methods are being sought for their control. The hydrochloride form of p-aminopropiophenone (PAPP) was highly toxic to ferrets when delivered by gavage, with LD50 and LD99 values of 15.52 and 20.80 mg kg–1, respectively. Signs of toxicosis progressed through pallor and cyanosis, impaired coordination, prostration with reduced responses to stimuli, with death in ~2 h. In a preliminary assessment of effective doses of PAPP in bait, 19 of 20 ferrets consumed chick carcasses containing ~46 mg PAPP within 40 min. Ferrets that ate chick baits al

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4

Bright, J. E., and T. C. Marrs. "Effect of p-aminopropiophenone (PAPP), a cyanide antidote, on cyanide given by intravenous infusion." Human Toxicology 6, no. 2 (1987): 133–37. http://dx.doi.org/10.1177/096032718700600205.

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1 Beagle bitches were infused with potassium cyanide solution after protection with p-aminopropiophenone (PAPP). 2 Methaemoglobin levels fell very rapidly after the start of the infusion. 3 Whole blood and plasma cyanide estimations revealed that most of the cyanide was sequestered inside the red cells. 4 Animals survived a supralethal dose of cyanide when protected with PAPP.

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5

Marrs, T. C., and J. E. Bright. "Kinetics of Methaemoglobin Production (1)." Human Toxicology 5, no. 5 (1986): 295–301. http://dx.doi.org/10.1177/096032718600500501.

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Methaemoglobin profiles have been studied by using ISIS, a simulation package, and NONLIN, a ion-linear least-squares analysis regression program. A simple kinetic model which satisfactorily describes methaemoglobin profiles after p-aminopropiophenone (PAPP) administration and 4-dimethylaminophenol (DMAP) administration has been developed. The two compounds differed nainly in their effective rates of elimination. The model less satisfactorily described methaemoglobin profiles after p-hydroxyaminopropiophenone (PHAPP) administration.

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6

Bright, J. E., and T. C. Marrs. "Kinetics of Methaemoglobin Production (2). Kinetics of the Cyanide Antidote p-Aminopropiophenone During Oral Administration." Human Toxicology 5, no. 5 (1986): 303–7. http://dx.doi.org/10.1177/096032718600500502.

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The kinetics of methaemoglobin production by orally administered p-aminopropiophenone (PAPP) was studied by using a kinetic model previously developed to describe methaemoglobinaemia consequent on intravenous injection of PAPP. Both ISIS, a simulation package, and NONLIN, a non-linear least-squares regression analysis program, were used to analyse the data. Some modification of the model was necessary to describe oral profiles and 40-50% of the administered PAPP appeared to be being metabolized at first pass to a non-active metabolite.

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7

Bright, J. E., A. C. Woodman, T. C. Marrs, and S. G. Wood. "Sex differences in the production of methaemoglobinaemia by 4-aminopropiophenone." Xenobiotica 17, no. 1 (1987): 79–83. http://dx.doi.org/10.3109/00498258709047177.

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8

Baskin, Steven I., and Robert F. Fricke. "The Pharmacology of p-Aminopropiophenone in the Detoxification of Cyanide." Cardiovascular Drug Reviews 10, no. 3 (1992): 358–75. http://dx.doi.org/10.1111/j.1527-3466.1992.tb00256.x.

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9

Fisher, Penny M., Cheryl E. O'Connor, and Elaine C. Murphy. "Acute oral toxicity of p‐aminopropiophenone to stoats (Mustela erminea)." New Zealand Journal of Zoology 32, no. 3 (2005): 163–69. http://dx.doi.org/10.1080/03014223.2005.9518409.

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10

KONTANI, Hitoshi, Akihiro MANO, Ryozo KOSHIURA, et al. "Central muscle relaxant activities of 2-methyl-3-aminopropiophenone derivatives." Folia Pharmacologica Japonica 89, no. 2 (1987): 91–101. http://dx.doi.org/10.1254/fpj.89.91.

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11

Wood, S. G., K. Fitzpatrick, J. E. Bright, R. H. Inns, and T. C. Marrs. "Studies of the Pharmacokinetics and Metabolism of 4-Aminopropiophenone (PAPP) in Rats, Dogs and Cynomolgus Monkeys." Human & Experimental Toxicology 10, no. 5 (1991): 365–74. http://dx.doi.org/10.1177/096032719101000511.

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The pharmacokinetics and metabolism of 4-aminopropiophenone (PAPP), a cyanide antidote, have been studied in rats, dogs and cynomolgus monkeys using 14C-PAPP. Radiolabelled material was rapidly excreted in all three species, mainly in urine. In rats, PAPP was metabolized by N-acetylation, while in dogs, ring and aliphatic hydroxylation occurred. In monkeys, both N-acetylation and oxidation took place. In the latter pathway, PAPP was oxidized to p-aminobenzoic acid which underwent amino acid-conjugation to p-aminohippuric acid. In rat blood in vitro, the PAPP metabolites, p-aminobenzoic, p-amin

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12

Marrs, T. C., and J. E. Bright. "Effect on Blood and Plasma Cyanide Levels and on Methaemoglobin Levels of Cyanide Administered with and without Previous Protection using PAPP." Human Toxicology 6, no. 2 (1987): 139–45. http://dx.doi.org/10.1177/096032718700600206.

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Hydrogen cyanide was administered intravenously at doses of 0.67 or 1.34 mg kg-1 to beagle pitches after protection with oral p-aminopropiophenone (0.5 mg kg-1). Hydrogen cyanide was also administered to unprotected bitches at the lower level (0.67 mg kg-1) only. PAPP protection caused sequestration of cyanide inside the red cells. In the case of the lower dose of cyanide this resulted in a lower plasma cyanide in protected than unprotected bitches. In the case of the higher dose it resulted in survival, despite 1.34 mg kg -1 being a known lethal dose. It is concluded that prior administration

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13

Marks, CA, F. Gigliotti, F. Busana, M. Johnston, and M. Lindeman. "Fox control using a para-aminopropiophenone formulation with the M-44 ejector." Animal Welfare 13, no. 4 (2004): 401–7. http://dx.doi.org/10.1017/s0962728600028657.

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AbstractThe M-44 ejector (‘ejector‘) has proven to be a highly target-specific means of delivering toxicants to the exotic European red fox (Vulpes vulpes) in south-eastern Australia. Para-aminopropiophenone (PAPP) is a potent methaemoglobin (MetHb) forming compound in canids. A formulation of PAPP, dimethylsulphoxide (DMS0) and condensed milk was investigated as a new toxicant formulation for delivery by the ejector. Dosage of eight foxes in the laboratory with a sequential dose demonstrated that the formulation caused a dose-dependent and rapid elevation of MetHb. A strong inverse correlatio

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14

Bauman, Richard Alexander, and John J. Widholm. "Operant leverpressing and wheelrunning were differentially reduced by PAPP (p-aminopropiophenone)-induced methemoglobinemia." Pharmacology Biochemistry and Behavior 87, no. 4 (2007): 444–52. http://dx.doi.org/10.1016/j.pbb.2007.05.021.

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15

Gagliardi, L., G. Cavazzutti, D. de Orsi, T. Rotunno, and D. Tonelli. "HPLC Determination of Aminopropiophenone as an Impurity in Phenylpropanolamine Bulk Drug and Pharmaceutical Formulations." Analytical Letters 26, no. 5 (1993): 937–45. http://dx.doi.org/10.1080/00032719308019876.

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16

Dilks, P., L. Shapiro, T. Greene, MJ Kavermann, CT Eason, and EC Murphy. "Field evaluation of para-aminopropiophenone (PAPP) for controlling stoats (Mustela erminea) in New Zealand." New Zealand Journal of Zoology 38, no. 2 (2011): 143–50. http://dx.doi.org/10.1080/03014223.2010.537668.

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17

Rennison, David, Daniel Conole, Malcolm D. Tingle, Junpeng Yang, Charles T. Eason, and Margaret A. Brimble. "Synthesis and methemoglobinemia-inducing properties of analogues of para-aminopropiophenone designed as humane rodenticides." Bioorganic & Medicinal Chemistry Letters 23, no. 24 (2013): 6629–35. http://dx.doi.org/10.1016/j.bmcl.2013.10.046.

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18

Blickenstaff, Robert T., Shailaja Reddy, and Robert Witt. "Potential radioprotective agents—V. Melatonin analogs. Oral activity of p-Aminopropiophenone and its ethylene ketal." Bioorganic & Medicinal Chemistry 2, no. 10 (1994): 1057–60. http://dx.doi.org/10.1016/s0968-0896(00)82055-6.

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19

Sorokin, V. I., O. S. Orlova, L. A. Semenova, E. A. Simonov та S. A. Savchuk. "Sample Preparation and the Detection of α-Aminopropiophenone and Amphetamine in Narcotic Drugs Using IR Spectroscopy". Journal of Analytical Chemistry 59, № 11 (2004): 1050–56. http://dx.doi.org/10.1023/b:janc.0000047007.05684.57.

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20

Olson, C. T., R. G. Menton, J. A. Blank, and D. W. Hobson. "An Automated Method for the Analysis of Methemoglobin." International Journal of Toxicology 16, no. 2 (1997): 165–73. http://dx.doi.org/10.1080/109158197227251.

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Production of methemoglobin (met Hb) is effective in treating or preventing cyanide intoxication due to the affinity of cyanide for met Hb. This paper describes an automated method for measuring met Hb in mouse blood utilizing the Roche COB AS FARA centrifugal analyzer and a modified Evelyn–Malloy procedure. Blood samples were spiked with various quantities of potassium ferricyanide to produce met Hb, and automated and manual analyses of these samples were compared. Following validation of the COB AS method, two known met Hb inducers, sodium nitrite and p-aminopropiophenone (PAPP), and two sul

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21

Davis, Franklin A., та Jing Chai. "α-Amino cyclic dithioketal mediated asymmetric synthesis of (S)-(-)-α-(N-p-toluenesulfonyl)aminopropiophenone (N-tosyl cathinone)". Arkivoc 2008, № 2 (2008): 190–203. http://dx.doi.org/10.3998/ark.5550190.0009.221.

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22

Marks, Clive A., Katherine Trought, Samantha Brown, Jane Arrow, and Brian Hopkins. "Sensitivity of High Conservation Value Birds to Para-Aminopropiophenone (PAPP) Determined by Sub-Lethal Dose–Response Assay." Animals 13, no. 3 (2023): 433. http://dx.doi.org/10.3390/ani13030433.

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Para-aminopropiophenone (PAPP) is a methaemoglobin (MetHb) forming compound used for the lethal control of invasive carnivores and mustelids. By measuring the dose-dependent inhibition of O2 transport arising from the oxidation of haemoglobin (HbFe2+) to MetHb (HbFe3+), we determined the sensitivity of nine bird species to PAPP. A methaemoglobinaemia absorbance index (MAI) was validated in five common bird species to determine thresholds associated with a 99% probability of survival (ST99) and a 50% probability of mortality (LT50). Dose–response trials in high conservation value birds sought M

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23

Fisher, P., C. E. O'Connor, and G. Morriss. "ORAL TOXICITY OF p-AMINOPROPIOPHENONE TO BRUSHTAIL POSSUMS (TRICHOSURUS VULPECULA), DAMA WALLABIES (MACROPUS EUGENII), AND MALLARDS (ANAS PLATYRHYNCHOS)." Journal of Wildlife Diseases 44, no. 3 (2008): 655–63. http://dx.doi.org/10.7589/0090-3558-44.3.655.

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24

Marks, Clive A., Lee Allen, and Heli Lindeberg. "Non-Lethal Dose-Response Models Replace Lethal Bioassays for Predicting the Hazard of Para-Aminopropiophenone to Australian Wildlife." Animals 13, no. 3 (2023): 472. http://dx.doi.org/10.3390/ani13030472.

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Para-aminopropiophenone (PAPP) is a potent methaemoglobin (MetHb) forming agent used for the lethal control of exotic carnivores and mustelids. To assess the sensitivity of Australian wildlife to PAPP we developed an in vivo assay that did not use death as an endpoint. Sub-lethal dose-response data were modelled to predict PAPP doses required to achieve an endpoint set at 80% MetHb (MetHb80). The comparative sensitivity of non-target mammals referenced to this endpoint was found to be highly variable, with southern brown bandicoots (Isoodon obesulus) the most sensitive species (MetHb80 = 6.3 m

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25

Allen, Benjamin L. "Para-aminopropiophenone (PAPP) in canid pest ejectors (CPEs) kills wild dogs and European red foxes quickly and humanely." Environmental Science and Pollution Research 26, no. 14 (2019): 14494–501. http://dx.doi.org/10.1007/s11356-019-04818-7.

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26

Gentle, Matthew, James Speed, Benjamin L. Allen, Stacy Harris, Hellen Haapakoski, and Kerry Bell. "The longevity of para-aminopropiophenone (PAPP) wild dog baits and the implications for effective and safe baiting campaigns." Environmental Science and Pollution Research 24, no. 13 (2017): 12338–46. http://dx.doi.org/10.1007/s11356-017-8668-3.

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27

Matsubara, Kouki, Keita Ueno, Yuji Koga та Kenji Hara. "Nickel−NHC-Catalyzed α-Arylation of Acyclic Ketones and Amination of Haloarenes and Unexpected PreferentialN-Arylation of 4-Aminopropiophenone". Journal of Organic Chemistry 72, № 14 (2007): 5069–76. http://dx.doi.org/10.1021/jo070313d.

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28

Coleman, Michael D., and Madeleine J. Kuhns. "Bioactivation of the cyanide antidote 4-aminopropiophenone (4-PAPP) by human and rat hepatic microsomal enzymes: effect of inhibitors." Environmental Toxicology and Pharmacology 7, no. 1 (1999): 75–80. http://dx.doi.org/10.1016/s1382-6689(98)00052-0.

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29

Johnston, Michael, Dave Algar, Michael O'Donoghue, Jim Morris, Tony Buckmaster, and Julie Quinn. "Efficacy and welfare assessment of an encapsulated para-aminopropiophenone (PAPP) formulation as a bait-delivered toxicant for feral cats (Felis catus)." Wildlife Research 47, no. 8 (2020): 686. http://dx.doi.org/10.1071/wr19171.

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Abstract ContextFeral cats are invasive predators of small and medium-sized fauna throughout Australia. The only broad-scale population-management technique for feral cats currently available in Australia is poison baiting. As poison baits for feral cats must be surface-laid, this can lead to the unintended exposure of non-target species consuming the baits. Encapsulation of a toxin within a robust, controlled-release pellet implanted within the meat lure (the combination of which is termed the Curiosity® bait) substantially reduces the potential risk to non-target species. Para-aminopropiophe

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30

Menton, R. G., F. M. Reid, C. T. Olson, et al. "Comparative Efficacy of three Methemoglobin Formers in Delaying Effects of Infused Sodium Cyanide." International Journal of Toxicology 16, no. 2 (1997): 151–64. http://dx.doi.org/10.1080/109158197227242.

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A prophylactic treatment is needed to circumvent constraints of the current therapy for cyanide (CN-) intoxication: intravenous administration of sodium nitrite and sodium thiosulfate. Experiments were conducted to compare the anticyanide effects of three candidate pretreatment methemoglobin (MHb)-forming compounds in an anesthetized animal model. The experiment was conducted in 5 periods, with each of 9 animals receiving the vehicle control in period 1, 0.2 mg/kg p-aminopropiophenone (PA PP) in period 2, and 2.5 mg/kg WR242511 in period 3. Four of the animals received the vehicle control in p

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31

Marks, Clive A., Katherine Trought, Samantha Brown, Jane Arrow та Brian Hopkins. "Monitoring methaemoglobinaemia in birds using 5 μL of whole blood". PLOS ONE 18, № 3 (2023): e0282820. http://dx.doi.org/10.1371/journal.pone.0282820.

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Methaemoglobin (MetHb) forming compounds such as para-aminopropiophenone (PAPP) and sodium nitrite (NaNO2) have recently been adopted for the lethal control of a range of invasive carnivores and mustelids. Determining the relative hazard of these compounds to non-target bird species is an important component of ecological risks evaluation. Problematically, some potential non-target bird species may be as small as 10 g in body mass, thus placing limitations on blood volumes that can be routinely sampled. Accordingly, we developed methods to quantify markers of increasing methaemoglobinaemia at

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32

Mallick, Stephen, Matthew Pauza, Charles Eason, Nick Mooney, Robbie Gaffney, and Stephen Harris. "Assessment of non-target risks from sodium fluoroacetate (1080), para-aminopropiophenone (PAPP) and sodium cyanide (NaCN) for fox-incursion response in Tasmania." Wildlife Research 43, no. 2 (2016): 140. http://dx.doi.org/10.1071/wr15040.

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Context Access to effective toxicants and delivery systems that target red foxes (Vulpes vulpes) are likely to be required as part of a management strategy in the event of future red fox incursions into Tasmania. Potential toxicants include sodium fluoroacetate (1080), para-aminopropiophenone (PAPP) and sodium cyanide (NaCN). Aims To assess the risk of three toxicants (1080, PAPP and NaCN) to non-target native Tasmanian mammals and birds and domestic dogs and cats. Methods We identified native Tasmanian mammal and bird species that may potentially consume fox baits, by reviewing the ecological

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33

Southwell, D., V. Boero, O. Mewett, S. McCowen, and B. Hennecke. "Understanding the drivers and barriers to participation in wild canid management in Australia: Implications for the adoption of a new toxin, para-aminopropiophenone." International Journal of Pest Management 59, no. 1 (2013): 35–46. http://dx.doi.org/10.1080/09670874.2012.744493.

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34

Meek, Paul D., Stuart C. Brown, Jason Wishart, et al. "Efficacy of lethal-trap devices to improve the welfare of trapped wild dogs." Wildlife Research 46, no. 1 (2019): 89. http://dx.doi.org/10.1071/wr18129.

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Context Wildlife and pest managers and stakeholders should constantly aim to improve animal-welfare outcomes when foot-hold trapping pest animals. To minimise stress and trauma to trapped animals, traps should be checked at least once every 24h, normally as soon after sunrise as possible. If distance, time, environmental or geographical constraints prevent this, toxins such as strychnine can be fitted to trap jaws to induce euthanasia. However, strychnine is considered to have undesirable animal-welfare outcomes because animals are conscious while clinical signs of intoxication are present. A

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35

Foley, Kevin F., and Nicholas V. Cozzi. "Novel aminopropiophenones as potential antidepressants." Drug Development Research 60, no. 4 (2003): 252–60. http://dx.doi.org/10.1002/ddr.10297.

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36

Ermert, J., K. Hamacher та H. H. Coenen. "N.C.A.18F-labelled norephedrine derivatives via α-aminopropiophenones". Journal of Labelled Compounds and Radiopharmaceuticals 43, № 14 (2000): 1345–63. http://dx.doi.org/10.1002/1099-1344(200012)43:14<1345::aid-jlcr424>3.0.co;2-n.

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37

MARKANTONIS, S. L., A. KYROUDIS, and A. H. BECKETT. "Evaluation of the percutaneous absorption and metabolism of some aminopropiophenones." Journal of Pharmacy and Pharmacology 38, no. 7 (1986): 515–19. http://dx.doi.org/10.1111/j.2042-7158.1986.tb04626.x.

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38

Pokrajac, M., B. Miljković, and B. Bisailović. "Mass spectrometric investigation of 2-aminopropiophenones and some of their metabolites." Rapid Communications in Mass Spectrometry 5, no. 2 (1991): 59–61. http://dx.doi.org/10.1002/rcm.1290050202.

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39

Shiozawa, A., K. Narita, G. Izumi, S. Kurashige, K. Sakitama, and M. Ishikawa. "Synthesis and activity of 2-methyl-3-aminopropiophenones as centrally acting muscle relaxants." European Journal of Medicinal Chemistry 30, no. 1 (1995): 85–94. http://dx.doi.org/10.1016/0223-5234(96)88213-4.

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40

SHIOZAWA, A., K. NARITA, G. IZUMI, S. KURASHIGE, K. SAKITAMA, and M. ISHIKAWA. "ChemInform Abstract: Synthesis and Activity of 2-Methyl-3-aminopropiophenones as Centrally Acting Muscle Relaxants." ChemInform 26, no. 28 (2010): no. http://dx.doi.org/10.1002/chin.199528114.

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41

Eason, Charles, Elaine Murphy, and Duncan MacMorran. "Para-aminopropiophenone and its Registration and Use as a Vertebrate Pesticide in New Zealand." Proceedings of the Vertebrate Pest Conference 26 (2014). http://dx.doi.org/10.5070/v426110576.

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42

Shapiro, Lee, Charles ,. T. Eason, Elaine Murphy, et al. "Para-aminopropiophenone (PAPP) Research, Development, Registration, and Application for Humane Predator Control in New Zealand." Proceedings of the Vertebrate Pest Conference 24 (2010). http://dx.doi.org/10.5070/v424110473.

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43

de Burgh, Natalie, Al Glen, Kellie Mayo, and Mark Mitchell. "Using para-aminopropiophenone (PAPP) as a tool to control feral cats in Hawke’s Bay, New Zealand." New Zealand Journal of Ecology, January 1, 2021. http://dx.doi.org/10.20417/nzjecol.45.10.

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44

Llewellyn, R., J. Cotela, C. Lauinger, et al. "Para‐aminopropiophenone toxicity in domestic dogs: a description of non‐target toxicosis in Victoria, Australia: 13 dogs (2016–2023)." Australian Veterinary Journal, January 11, 2025. https://doi.org/10.1111/avj.13405.

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BackgroundPAPP is widely used in Australia as a potent vertebrate bait, with potential for off‐target ingestion and poisoning in domestic dogs. Whilst toxicosis and resulting methaemoglobinaemia is anecdotally known to occur, this is the first description in the literature. This study reports thirteen clinical cases of suspected Para‐aminopropiophenone (PAPP) toxicity in dogs, with the aim of describing clinical presentation and current management of toxicosis in this species.Case reportThree veterinary clinics in Victoria provided records of dogs where PAPP toxicity was the likely diagnosis (

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45

Matsubara, Kouki, Keita Ueno, Yuji Koga та Kenji Hara. "Nickel—NHC-Catalyzed α-Arylation of Acyclic Ketones and Amination of Haloarenes and Unexpected Preferential N-Arylation of 4-Aminopropiophenone." ChemInform 38, № 48 (2007). http://dx.doi.org/10.1002/chin.200748063.

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46

OCCELLI, E., L. FONTANELLA, A. DIENA, and P. SCHIATTI. "ChemInform Abstract: SYNTHESIS AND PHARMACOLOGICAL ACTIVITY OF 3-AMINOPROPIOPHENONES AND 3-(AMINOMETHYL)CAMPHORS." Chemischer Informationsdienst 16, no. 30 (1985). http://dx.doi.org/10.1002/chin.198530258.

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