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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2018-05-20 20:19:33 UTC
HMDB IDHMDB0015493
Secondary Accession Numbers
  • HMDB15493
Metabolite Identification
Common NameAminophenazone
DescriptionAminophenazone is only found in individuals that have used or taken this drug. It is a pyrazolone with analgesic, anti-inflammatory, and antipyretic properties but has risk of agranulocytosis. A breath test with 13C-labeled aminopyrine has been used as a non-invasive measure of cytochrome P-450 metabolic activity in liver function tests. [PubChem]Aminophenazone is metabolized very slowly by normal newborn babies. In older infants, a higher amount of exhaled 13-CO2 is observed.
Structure
Thumb
Synonyms
ValueSource
(dimethylamino)PhenazoneChEBI
1,5-Dimethyl-4-dimethylamino-2-phenyl-3-pyrazoloneChEBI
1-Phenyl-2,3-dimethyl-4-(dimethylamino)-5-pyrazoloneChEBI
1-Phenyl-2,3-dimethyl-4-dimethylaminopyrazol-5-oneChEBI
2,3-Dimethyl-4-dimethylamino-1-phenyl-5-pyrazoloneChEBI
3-keto-1,5-Dimethyl-4-dimethylamino-2-phenyl-2,3-dihydropyrazoleChEBI
4-(dimethylamino)-1,2-dihydro-1,5-Dimethyl-2-phenyl-3H-pyrazol-3-oneChEBI
4-(dimethylamino)-1,5-Dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-oneChEBI
4-(dimethylamino)AntipyrineChEBI
4-dimethylamino-1-Phenyl-2,3-dimethylpyrazoloneChEBI
4-dimethylamino-2,3-Dimethyl-1-phenyl-3-pyrazolin-5-oneChEBI
4-dimethylamino-2,3-Dimethyl-1-phenyl-5-pyrazoloneChEBI
4-DimethylaminoantipyrineChEBI
4-DimethylaminophenazoneChEBI
AminofenazonaChEBI
AminofenazoneChEBI
AminophenazonChEBI
AminophenazonumChEBI
AminopyrineChEBI
DimethylaminoantipyrineChEBI
DimethylaminoazopheneChEBI
DimethylaminophenazonChEBI
DimethylaminophenazoneChEBI
DimethylaminophenyldimethylpyrazoloneChEBI
DipyrineChEBI
AmidophenMeSH
AmidophenazonMeSH
Aminophenazone berlin-chemie brandMeSH
Berlin-chemie brand OF aminophenazoneMeSH
Dimethyl-N-aminoantipyrineMeSH
Berlin chemie brand OF aminophenazoneMeSH
Dimethyl N aminoantipyrineMeSH
EufibronMeSH
AmidazophenMeSH
AmidopyrineMeSH
Chemical FormulaC13H17N3O
Average Molecular Weight231.2936
Monoisotopic Molecular Weight231.137162181
IUPAC Name4-(dimethylamino)-1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one
Traditional Nameaminophenazone
CAS Registry Number58-15-1
SMILES
CN(C)C1=C(C)N(C)N(C1=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C13H17N3O/c1-10-12(14(2)3)13(17)16(15(10)4)11-8-6-5-7-9-11/h5-9H,1-4H3
InChI KeyRMMXTBMQSGEXHJ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpyrazoles. These are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassPyrazoles
Direct ParentPhenylpyrazoles
Alternative Parents
Substituents
  • Phenylpyrazole
  • Tertiary aliphatic/aromatic amine
  • Dialkylarylamine
  • Monocyclic benzene moiety
  • Pyrazolinone
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous amide
  • Lactam
  • Tertiary amine
  • Azacycle
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point134.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility22.5 g/LNot Available
LogP1.00HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility22.5 g/LALOGPS
logP0.94ALOGPS
logP1.15ChemAxon
logS-1ALOGPS
pKa (Strongest Basic)3.47ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.79 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity70.11 m³·mol⁻¹ChemAxon
Polarizability25.87 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-053s-9250000000-c3308b81b44067a47f7eView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9100000000-40e7051a3536ae680d1aView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-053s-9250000000-c3308b81b44067a47f7eView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9100000000-40e7051a3536ae680d1aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0159-4970000000-8cb60fc41366bf1c7f80View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03dr-1900000000-49de43a88698c1df262bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0190000000-d7bfbe39ac8d423c5cfdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03e9-4940000000-243b2713c256a2ab8b6cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03dj-9700000000-3ef4e69c38623bfd699fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-06r2-9300000000-762e3df6382a5e2052a3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0592-9100000000-b9c175ecf48888c0267aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4j-9100000000-9fa64e7904c1473d9d32View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0290000000-27bac0f1542859b73671View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03e9-4940000000-a4c3f3e347d595ad803eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03dj-9700000000-ac217c24c44682808465View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-06xt-9300000000-f8259f5a45014efc58eeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-052b-9100000000-307762c9c387df2fcbf4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4j-9100000000-3c5267564fda210cc134View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03dr-1900000000-ab951ea405c6154ef630View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0090000000-2527cae3cd95916624e4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-3910000000-f7ee26001f3fbe463baeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-01vk-9400000000-243fad64356c2d2c4864View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0592-9100000000-bbc78ee3e540bd560a88View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0aba-9000000000-1c4e7d6f8c8bbdc08335View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0090000000-0896fba0b89cb8cb6ff5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-2390000000-eaa608d1cc64b37d59dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9100000000-db54dcd1f4d6da575bf1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-3920000000-00258f4a6df2920817ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f8i-5790000000-dd0fbe214d13e5ebfde8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00l6-9300000000-18386f94d530fc45afc1View in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01424 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01424 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01424
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5787
KEGG Compound IDC07539
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAminophenazone
METLIN IDNot Available
PubChem Compound6009
PDB IDNot Available
ChEBI ID160246
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Rating D, Langhans CD: Breath tests: concepts, applications and limitations. Eur J Pediatr. 1997 Aug;156 Suppl 1:S18-23. [PubMed:9266210 ]