Iodine-containing organic carbonates as investigative radiopaque compounds

Carbonates containing an iodinated aromatic ring on one side of the carbonate linkage and an alkyl group on the other were prepared. The aromatic side consisted of p-iodophenyl, p-iodobenzyl, m-iodobenzyl, 3,5-diiodobenzyl, m-amino-2,4,6-triiodobenzyl, m-acetamido-2,4,6-triiodobenzyl, p-iodophenethyl, p-iodo-sec-phenethyl, 3-(p-iodophenyl)propyl, 3-(p-iodophenyl)butyl, 2-(p-iodobenzyl)butyl, and 2-(iodobenzyl)hexyl groups. The alkyl portion of the carbonates was derived from alkyl alcohols containing from two to ten carbon atoms. The approximate lethal dose of intraperitoneal injections ranged from less than 1 ml/kg to more than 15 ml/kg. An investigation into the use of these compounds as radiopaques for myelography, lymphography, bronchography, and salpingography is underway.