Aminopyrine

Title: Aminopyrine
CAS Registry Number: 58-15-1
CAS Name: 4-(Dimethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one
Additional Names: 4-(dimethylamino)antipyrine; dimethylaminophenyldimethylpyrazolone; 4-dimethylamino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one; aminophenazone; amidazophen; dipyrine; dimethylaminophenazone; amidopyrine
Trademarks: Mamallet-A (Showa); Pyramidon; Netsusarin (Ohta)
Molecular Formula: C13H17N3O
Molecular Weight: 231.29
Percent Composition: C 67.51%, H 7.41%, N 18.17%, O 6.92%
Literature References: Prepn: Beilstein 25, 452 (1936); T. Takahashi et al., J. Pharm. Soc. Jpn. 76, 1180 (1956); T. Takahashi, K. Kenematsu, Chem. Pharm. Bull. 6, 98 (1958). Metabolism: G. F. Lockwood, J. B. Houston, J. Pharm. Pharmacol. 31, 787 (1979). Hepatotoxicity: E. Bien et al., Pharmazie 36, 492 (1981). Toxicity studies: Hart, J. Pharmacol. Exp. Ther. 89, 205 (1947); Tubaro et al., Arzneim.-Forsch. 20, 1024 (1970). Use in breath test of hepatic function: G. W. Hepner, E. S. Vesell, N. Engl. J. Med. 291, 1384 (1974).
Properties: Leaflets from ligroin, mp 107-109°. The aq soln is slightly alkaline to litmus. Soly in water is increased by the addition of sodium benzoate. One gram dissolves in 1.5 ml alcohol, 12 ml benzene, 1 ml chloroform, 13 ml ether, 18 ml water. Stable in air, but affected by light. Readily attacked by mild oxidizing agents in the presence of water. LD50 orally in rats: 1.7 g/kg (Hart).
Melting point: mp 107-109°
Toxicity data: LD50 orally in rats: 1.7 g/kg (Hart)
Derivative Type: Hydrochloride
CAS Registry Number: 6170-29-2
Molecular Formula: C13H17N3O.HCl
Molecular Weight: 267.75
Percent Composition: C 58.32%, H 6.78%, N 15.69%, O 5.98%, Cl 13.24%
Properties: Deliquescent prisms, mp 143-144°. Freely sol in water with acid reaction.
Melting point: mp 143-144°
Derivative Type: Bicamphorate
CAS Registry Number: 94442-12-3
Molecular Formula: C13H17N3O.2C10H16O4
Molecular Weight: 631.76
Percent Composition: C 62.74%, H 7.82%, N 6.65%, O 22.79%
Properties: Crystalline powder, mp 94°. Sol in water with gradual decompn; sol in alcohol.
Melting point: mp 94°
Derivative Type: Salicylate
CAS Registry Number: 603-57-6
Molecular Formula: C13H17N3O.C7H6O3
Molecular Weight: 369.41
Percent Composition: C 65.03%, H 6.28%, N 11.37%, O 17.32%
Properties: Crystalline powder, mp 70°. One gram dissolves in 16 ml water, about 6 ml alcohol.
Melting point: mp 70°
CAUTION: Agranulocytosis may occur: E. Urbach, H. L. Goldburgh, J. Am. Med. Assoc. 131, 893 (1946); G. Discombe, Br. Med. J. 1, 1270 (1952).
Therap-Cat: Antipyretic; analgesic. Diagnostic aid (hepatic function).
Keywords: Analgesic (Non-Narcotic); Antipyretic.
Aminoquinuride Aminorex Amioca Amiodarone Amiphenazole

Aminophenazone
Aminophenazone-2d-skeletal.png
Aminophenazone-3D-balls.png
Systematic (IUPAC) name
4-Dimethylamino-1,5-dimethyl-2-phenylpyrazol-3-one
Clinical data
AHFS/Drugs.com International Drug Names
Legal status  ?
Identifiers
CAS number 58-15-1 YesY
ATC code N02BB03
PubChem CID 6009
DrugBank DB01424
ChemSpider 5787 YesY
UNII 01704YP3MO YesY
KEGG D00556 YesY
ChEBI CHEBI:160246 YesY
ChEMBL CHEMBL288470 YesY
Chemical data
Formula C13H17N3O 
Mol. mass 231.29358
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Aminophenazone (or aminopyrine) 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.[1]