The synthesis of (3H)-xylamine, an irreversible inhibitor of norepinephrine uptake
| Autor: | R. W. Ransom, R. C. Kammerer, Arthur K. Cho |
|---|---|
| Rok vydání: | 1983 |
| Předmět: |
chemistry.chemical_classification
Ethanol Hydrochloride Organic Chemistry Salt (chemistry) Biochemistry Analytical Chemistry Norepinephrine uptake chemistry.chemical_compound Thionyl chloride chemistry Bromide Drug Discovery Organic chemistry Radiology Nuclear Medicine and imaging Tritium Specific activity Spectroscopy Nuclear chemistry |
| Zdroj: | Journal of Labelled Compounds and Radiopharmaceuticals. 20:833-841 |
| ISSN: | 0362-4803 |
| DOI: | 10.1002/jlcr.2580200708 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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