THE CONDENSATION OF AMINOANTIPYRINE. III. (1). THE SYNTHESIS OF METHYLRUBAZOIC ACID<sup>1</sup>

Emerson, Edgar; Beegle, Lindley Clair

doi:10.1021/jo01193a005

Cited by 10 publications

(6 citation statements)

References 3 publications

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“…Methylrubazoic acid was synthetized in our department by Dipl, Chern. D. Sackerer (9). 4-Methyl-3,5-dinitrobenzamide was a gift from Dr. Gaber.…”

Section: Methodsmentioning

confidence: 99%

On aminophenazone metabolism in the isolated perfused rat liver

Kampffmeyer

1976

European Journal of Drug Metabolism and Pharmacokinetics

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Isolated rat livers were perfused with recycling protein free Krebs-Henseleit solution for 80 min. Aminophenazone (0.87 mM, 1.7 mM), 4-methylaminoantipyrine (0.86 mM), 4-aminoantipyrine (1.6 mM), or 4-acetylaminoantipyrine (0.86 m M) was added to the perfusion medium.. 4-Methylaminoantipyrine was the major primary metabolite of aminophenazone detected following perfusion of livers from untreated and phenobarbital pretreated rats. The formation of 4-methylaminoantipyrine and elimination of aminophenazone and 4-methylaminoantipyrine following aminophenazone was faster in pretreated than in untreated livers. Fo~pr~treated rats the clearance rate (ml/min/g liver) of aminophenazone, 4-methylamino-, 4-amino-, and 4-acetylaminoant~pYfl~e was 0.99, 0.52, 0.25 and 0.08, respectively. Formation of 4-amino-and 4-acetylamino-antipyrine and methylarmne did not account for the loss of 4-methylamino-antipyrine.Following 80 min perfusion of pretreated liver only 20 % of the substrate, aminophenazone or 4-methylaminoantipyrine and its metabolites, was recovered as compared to 85 %found in the system with intreated livers.

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“…Methylrubazoic acid was synthetized in our department by Dipl, Chern. D. Sackerer (9). 4-Methyl-3,5-dinitrobenzamide was a gift from Dr. Gaber.…”

Section: Methodsmentioning

confidence: 99%

On aminophenazone metabolism in the isolated perfused rat liver

Kampffmeyer

1976

European Journal of Drug Metabolism and Pharmacokinetics

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“…Pyrazolin-4,5-dione (3-methyl-1-phenyl-2-pyrazolin-4,5-dione), CI0H8N2O2, 118.19, was prepared according to Knorr & Pschorr (1896) or by acid hydrolysis of methylrubazonic acid (Emerson & Beagle 1943). 4-Phenylazo-norantipyrine (3-methyl-l-phenyl-4phenylazo-2-pyrazolin-5-one) C16H14N40, 278.32, was synthesized according to Knorr (1887).…”

Section: Synthesismentioning

confidence: 99%

Quantitation of norantipyrine sulphate and norantipyrine glucuronide as major metabolites of antipyrine in man and rat

Böttcher

Bässmann

Schüppel

1984

Journal of Pharmacy and Pharmacology

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Two assay procedures are described for the quantitation of norantipyrine sulphate and norantipyrine glucuronide present in biological material. One, a selective acid hydrolytic assay procedure that affords the discriminative determination of both conjugates without prior separation, measures free norantipyrine by tlc-uv. The other is a tlc separation procedure for intact norantipyrine conjugates, which, in conjunction with radiolabelled material, derived from [3-14C]antipyrine, enables the direct quantitation of both conjugates independently. In man, about 25% of dose of antipyrine (1200 mg) was excreted as norantipyrine glucuronide within 48 h. The amount of norantipyrine sulphate was small. In the rat, norantipyrine sulphate represented about 15-20% of the dose of antipyrine (40-50 mg kg-1); no norantipyrine glucuronide was formed. Free norantipyrine has not been detected in urine of either species after antipyrine dosage. Pretreatment with 3-methylcholanthrene in the rat substantially enhanced excretion of norantipyrine sulphate, whereas induction with phenobarbitone was without effect on the microsomal N-demethylation of antipyrine. The lability of free norantipyrine was examined under different conditions and contrasted with the relative stability of norantipyrine conjugates. Two of the main degradation products of norantipyrine were identified as 4-phenylazo-norantipyrine and a 4,4'-bipyrazole-derivative.

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“…Only p-substituted phenols, however, were found to exhibit significantly reduced reactivities with 4-AAP in the presence of surfactant. The specificity of reaction inhibition by surfactants permitted a determination of phenol in the presence of hexachlorophene.Keyphrases Hexachlorophene, phenols analysis-4-aminoantipyrine method 0 Surfactants, interference-hexachlorophene, phenols analysis 0 Structure effect-phenol-dye interaction 0Colorimetric analysis-spectrophotometerThe colorimetric reaction between phenols and 4-aminoantipyrine (4-APP) was first described by Emerson et al (1)(2)(3)(4). The reaction involves the oxidative condensation of phenols with 4-AAP, in basic solution, to produce intensely colored pyrazolone dyes.…”

mentioning

confidence: 99%

“…The colorimetric reaction between phenols and 4-aminoantipyrine (4-APP) was first described by Emerson et al (1)(2)(3)(4). The reaction involves the oxidative condensation of phenols with 4-AAP, in basic solution, to produce intensely colored pyrazolone dyes.…”

mentioning

confidence: 99%

Interference by Surface-Active Agents with the 4-Aminoantipyrine Determination of Hexachlorophene and Other Phenols

Brown

Guttman²,

Anderson

1969

Journal of Pharmaceutical Sciences

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THE CONDENSATION OF AMINOANTIPYRINE. III. (1). THE SYNTHESIS OF METHYLRUBAZOIC ACID¹

Cited by 10 publications

References 3 publications

On aminophenazone metabolism in the isolated perfused rat liver

On aminophenazone metabolism in the isolated perfused rat liver

Quantitation of norantipyrine sulphate and norantipyrine glucuronide as major metabolites of antipyrine in man and rat

Interference by Surface-Active Agents with the 4-Aminoantipyrine Determination of Hexachlorophene and Other Phenols

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THE CONDENSATION OF AMINOANTIPYRINE. III. (1). THE SYNTHESIS OF METHYLRUBAZOIC ACID1

Cited by 10 publications

References 3 publications

On aminophenazone metabolism in the isolated perfused rat liver

On aminophenazone metabolism in the isolated perfused rat liver

Quantitation of norantipyrine sulphate and norantipyrine glucuronide as major metabolites of antipyrine in man and rat

Interference by Surface-Active Agents with the 4-Aminoantipyrine Determination of Hexachlorophene and Other Phenols

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THE CONDENSATION OF AMINOANTIPYRINE. III. (1). THE SYNTHESIS OF METHYLRUBAZOIC ACID¹