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The synthesis of (3H)-xylamine, an irreversible inhibitor of norepinephrine uptake

✍ Scribed by R. W. Ransom; R. C. Kammerer; A. K. Cho

Publisher
John Wiley and Sons
Year
1983
Tongue
French
Weight
293 KB
Volume
20
Category
Article
ISSN
0022-2135

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✦ Synopsis

Xylamine [N-(2-chloroethyl)-N-ethyl-2-methylbenzylamine], an irreversible inhibitor o f 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. 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.

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