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The synthesis of ( 3 H)‐xylamine, an irreversible inhibitor of norepinephrine uptake
Author(s) -
Ransom R. W.,
Kammerer R. C.,
Cho A. K.
Publication year - 1983
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580200708
Subject(s) - chemistry , thionyl chloride , tritium , ethanol , hydrochloride , norepinephrine , bromide , chloride , catalysis , medicinal chemistry , nuclear chemistry , chromatography , organic chemistry , physics , neuroscience , nuclear physics , dopamine , biology
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 3 H 2 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. ( 3 H)‐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.