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Ampyrone

From Wikipedia, the free encyclopedia
Ampyrone
Names
Preferred IUPAC name
4-Amino-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one[1]
Other names
solvapyrin A, aminoazophene, aminoantipyrene, aminoantipyrine, metapyrazone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.001.321Edit this at Wikidata
UNII
  • InChI=1S/C11H13N3O/c1-8-10(12)11(15)14(13(8)2)9-6-4-3-5-7-9/h3-7H,12H2,1-2H3 checkY
    Key: RLFWWDJHLFCNIJ-UHFFFAOYSA-N checkY
  • InChI=1/C11H13N3O/c1-8-10(12)11(15)14(13(8)2)9-6-4-3-5-7-9/h3-7H,12H2,1-2H3
    Key: RLFWWDJHLFCNIJ-UHFFFAOYAT
  • O=C2\C(=C(/N(N2c1ccccc1)C)C)N
Properties
C11H13N3O1[2]
Molar mass203.24 g/mol
Density1.207g/cm3
Melting point106 to 110 °C (223 to 230 °F; 379 to 383 K)
Boiling point309 °C (588 °F; 582 K) @760mmHg
Hazards
Flash point140.7 °C (285.3 °F; 413.8 K)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

Ampyrone is ametabolite ofaminopyrine withanalgesic,anti-inflammatory, andantipyretic properties.[2] While the parentdrug, aminopyrine, has been discouraged due to the risk ofagranulocytosis,[3][4] ampyrone itself has significantly lower toxicity.[5] It is used as areagent forbiochemical reactions producingperoxides orphenols.[2] Ampyrone stimulateslivermicrosomes and is also used to measureextracellular water.[2]

By applying an ampyrone solution, scientists can make skin temporarily transparent (to red light); and e.g. see directly into the brain (of living young mice, when the skull is very thin, thus transparent, the solution doesn't have such an effect on it): "This opens a literal window to peek into the brain's development .. Not only can we image the structures of these neurons, but we can also image the neural activity over time in an animal model. In the future, this approach could enable us to look at how these circuits form during the development of an animal."[6][7]

References

[edit]
  1. ^PubChem (25 March 2005)."4-Aminoantipyrine".PubChem. Retrieved2022-05-09.
  2. ^abcd"4-Aminoantipyrine".pubchem.ncbi.nlm.nih.gov. 25 March 2005. Retrieved2022-05-09.
  3. ^Bailey, D. N. (1983). "The unusual occurrence of 4-aminoantipyrine (4-aminophenazone) in human biological fluids".Journal of Analytical Toxicology.7 (2):76–78.doi:10.1093/jat/7.2.76.ISSN 0146-4760.PMID 6855207.
  4. ^PubChem."Aminopyrine".pubchem.ncbi.nlm.nih.gov. Retrieved2024-08-26.
  5. ^PubChem."4-Aminoantipyrine".pubchem.ncbi.nlm.nih.gov. Retrieved2024-08-26.
  6. ^"Researchers turn mouse scalp transparent to image brain development".news.stanford.edu. 2025-08-27. Retrieved2025-08-28.
  7. ^Keck, Carl H. C.; Schmidt, Elizabeth L.; Roth, Richard H.; Floyd, Brendan M.; Tsai, Andy P.; Garcia, Hassler B.; Cui, Miao; Chen, Xiaoyu; Wang, Chonghe; Park, Andrew; Zhao, Su; Liao, Pinyu A.; Casey, Kerriann M.; Reineking, Wencke; Cai, Sa (2025-08-26)."Color-neutral and reversible tissue transparency enables longitudinal deep-tissue imaging in live mice".Proceedings of the National Academy of Sciences.122 (35) e2504264122.doi:10.1073/pnas.2504264122.
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