The role of the aromatic amino group in deranged pigment metabolism

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Abstract
Chronic intoxication of rats with acetanilide, phenacetin, phenazone, amidopyrine, aspirin and para-aminophenol led to the urinary excretion of copro-pprphyrin. Equivalent doses of phenacetin and phenazone produced the same degree of porphyrinuria, amidopyrine and aspirin were twice as potent, acetanilide four times, while para-aminophenol was even more potent. These effects were parallel to the acute toxicity. These porphyrins were extracted, isolated, converted to methyl esters and identified as members of the series III isomers. These compounds gave rise to a common oxidation-reduction system which oxidised Hb to methemoglobin. The hypothesis is advanced that when methemoglobin is formed, the normal conversion to bilirubin cannot occur but is replaced by degradation to coproporphyrin III.

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