Ampyrone

Last updated
Ampyrone
Ampyrone structure.png
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 InfoCard 100.001.321 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
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 Yes check.svgY
    Key: RLFWWDJHLFCNIJ-UHFFFAOYSA-N Yes check.svgY
  • 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 mass 203.24 g/mol
Density 1.207g/cm3
Melting point 106 to 110 °C (223 to 230 °F; 379 to 383 K)
Boiling point 309 °C (588 °F; 582 K) @760mmHg
Hazards
Flash point 140.7 °C (285.3 °F; 413.8 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Ampyrone is a metabolite of aminopyrine with analgesic, anti-inflammatory, and antipyretic properties. [2] While the parent drug, aminopyrine, has been discouraged due to the risk of agranulocytosis, [3] [4] ampyrone itself has significantly lower toxicity. [5] It is used as a reagent for biochemical reactions producing peroxides or phenols. [2] Ampyrone stimulates liver microsomes and is also used to measure extracellular 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

  1. ↑ PubChem (25 March 2005). "4-Aminoantipyrine". PubChem. Retrieved 2022-05-09.
  2. 1 2 3 4 "4-Aminoantipyrine". pubchem.ncbi.nlm.nih.gov. 25 March 2005. Retrieved 2022-05-09.
  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. Retrieved 2024-08-26.
  5. ↑ PubChem. "4-Aminoantipyrine". pubchem.ncbi.nlm.nih.gov. Retrieved 2024-08-26.
  6. ↑ "Researchers turn mouse scalp transparent to image brain development". news.stanford.edu. 2025-08-27. Retrieved 2025-08-28.
  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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