Ampyrone

{{chembox

| Watchedfields = changed

| verifiedrevid = 443387760

| ImageFile_Ref = {{chemboximage|correct|??}}

| ImageFile = Ampyrone structure.png

| ImageClass = skin-invert-image

| ImageSize =

| PIN = 4-Amino-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one{{Cite web|last=PubChem|title=4-Aminoantipyrine|date=25 March 2005|url=https://pubchem.ncbi.nlm.nih.gov/compound/2151#section=IUPAC-Name|access-date=2022-05-09|website=PubChem|language=en}}

| OtherNames = solvapyrin A, aminoazophene, aminoantipyrene, aminoantipyrine, metapyrazone

|Section1={{Chembox Identifiers

| 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

| InChIKey = RLFWWDJHLFCNIJ-UHFFFAOYAT

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 1165011

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C11H13N3O/c1-8-10(12)11(15)14(13(8)2)9-6-4-3-5-7-9/h3-7H,12H2,1-2H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = RLFWWDJHLFCNIJ-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 83-07-8

| PubChem = 2151

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 2066

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 0M0B7474RA

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 59026

| SMILES = O=C2\C(=C(/N(N2c1ccccc1)C)C)N

}}

|Section2={{Chembox Properties

| C=11 | H=13 | N=3 | O=1

| MolarMass = 203.24 g/mol

| Appearance =

| Density = 1.207g/cm³

| MeltingPtC = 106 to 110

| MeltingPt_notes =

| BoilingPtC = 309

| BoilingPt_notes = @760mmHg

| Solubility = }}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPtC = 140.7

| AutoignitionPtC =

}}

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Ampyrone is a metabolite of aminopyrine with analgesic, anti-inflammatory, and antipyretic properties. While the parent drug, aminopyrine, has been discouraged due to the risk of agranulocytosis,{{Cite journal |last=Bailey |first=D. N. |date=1983 |title=The unusual occurrence of 4-aminoantipyrine (4-aminophenazone) in human biological fluids |url=https://pubmed.ncbi.nlm.nih.gov/6855207/ |journal=Journal of Analytical Toxicology |volume=7 |issue=2 |pages=76–78 |doi=10.1093/jat/7.2.76 |issn=0146-4760 |pmid=6855207}}{{Cite web |last=PubChem |title=Aminopyrine |url=https://pubchem.ncbi.nlm.nih.gov/compound/6009 |access-date=2024-08-26 |website=pubchem.ncbi.nlm.nih.gov |language=en}} ampyrone itself has significantly lower toxicity.{{Cite web |last=PubChem |title=4-Aminoantipyrine |url=https://pubchem.ncbi.nlm.nih.gov/compound/2151 |access-date=2024-08-26 |website=pubchem.ncbi.nlm.nih.gov |language=en}} It is used as a reagent for biochemical reactions producing peroxides or phenols.{{Cite web|date=25 March 2005|title=4-Aminoantipyrine|url=https://pubchem.ncbi.nlm.nih.gov/compound/2151#:~:text=A%20metabolite%20of%20AMINOPYRINE%20with,water|access-date=2022-05-09|website=pubchem.ncbi.nlm.nih.gov|language=en}} Ampyrone stimulates liver microsomes and is also used to measure extracellular water.