474. Aminopyrine

Nomenclature

CAS number: 58-15-1
4-(Dimethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one; 4-(dimethylamino)antipyrine; dimethylaminophenyldimethylpyrazolone; 4-dimethylamino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one; aminophenazone; amidazophen; dipyrine; dimethylaminophenazone; amidopyrine; Mamallet-A (Showa); Pyramidon; Netsusarin (Ohta).
C13H17N3O; mol wt 231.29.
C 67.51%, H 7.41%, N 18.17%, O 6.92%.

Description and 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).

Chemical structure

Properties

Leaflets from ligroin, mp 107-109°. Poisonous. 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).

Derivative

Hydrochloride.

Nomenclature

CAS number: 6170-29-2
C13H17N3O.HCl; mol wt 267.75.
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.

Derivative

Bicamphorate.

Nomenclature

CAS number: 94442-12-3
C13H17N3O.2C10H16O4; mol wt 631.76.
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.

Derivative

Salicylate.

Nomenclature

CAS number: 603-57-6
C13H17N3O.C7H6O3; mol wt 369.41.
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.

Caution

Agranulocytosis may occur: E. Urbach, H. L. Goldburgh, J. Am. Med. Assoc. 131, 893 (1946); G. Discombe, Br. Med. J. 1, 1270 (1952).

Therapeutic Category

Antipyretic; analgesic. Diagnostic aid (hepatic function).

Keywords

Antipyretic; Analgesic; Non-opioids; Pyrazolones