Alloxan

[citation needed] Murexide results from the condensation of the unisolated intermediate uramil [de] with alloxan liberated during the course of the reaction.

William Prout investigated the compound in 1818 and he used boa constrictor excrement with up to 90% ammonium acid urate.

In the chapter "Nitrogen" of his memoir The Periodic Table, Primo Levi tells of his futile attempt to make alloxan for a cosmetics manufacturer who has read that it can cause permanent reddening of the lips.

[2] Alloxan monohydrate also undergoes one-electron reduction to form yellow salts containing a stable radical anion:[10] Alloxan is a toxic glucose analogue, which selectively destroys insulin-producing cells in the pancreas (that is, beta cells) when administered to rodents and many other animal species.

[12] Alloxan (C4H2N2O4) readily undergoes redox cycling with its one-electron (C4H3N2O4• semiquinone) and two-electron (dialuric acid, C4H4N2O4) reduction products.

In addition, alloxan has a high affinity to SH-containing cellular compounds and, as a result, reduces glutathione content.

Furthermore, alloxan inhibits glucokinase, a SH-containing protein essential for insulin secretion induced by glucose.

[17][18] Alloxan is, however, toxic to the liver and the kidneys in high doses, as these are tissues where the GLUT2 transporter is expressed in humans.

Murexide dye (right) from reaction of alloxantin (left)
Alloxane (left) with dialuric acid (center) and alloxantin (right)