R. Ransom, R. Kammerer, A. Cho
Jul 1, 1983
Citations
0
Influential Citations
4
Citations
Journal
Journal of Labelled Compounds and Radiopharmaceuticals
Abstract
Xylamine [N-(2-chloroethyl)-N-ethyl-2-methylbenzylamine], an irreversible inhibitor of neuronal norepinephrine uptake, has been synthesized with tritium incorporated in the aromatic nucleus. Initially, 2-methylbenzyl bromide was nonselectively mono-brominated on the ring and the resulting isomeric products were condensed with 2-(ethylamino)ethanol. Unequivocal identification of the products of each reaction was provided by mass spectral analysis. A mixture of mono-bromobenzylamine isomers was isolated for catalytic reduction with 3H2 at a commercial facility. Carrier N-(2-hydroxyethyl)-N-ethyl-2-methylbenzylamine was added to the crude tritiated product prior to refluxing in the presence of excess thionyl chloride. (3H)-Xylamine was obtained as the hydrochloride salt and repeated recrystallizations yielded a radiochemically pure product with a specific activity of 3.09 Ci/mmol. Several analytical procedures established that the radiolabel was associated with xylamine.