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Synthesis of tritium labelled metergoline, nicergoline, 1‐demethylnicergoline and of 3 H, 14 C double labelled nicergoline
Author(s) -
Vicario G. P.,
Perucca G. C.,
Ramella P. G.,
Arcamone F.
Publication year - 1978
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.2580150142
Subject(s) - chemistry , yield (engineering) , tritium , metergoline , radiosynthesis , radiochemistry , nuclear chemistry , chromatography , nuclear medicine , biochemistry , medicine , positron emission tomography , physics , materials science , receptor , 5 ht receptor , nuclear physics , serotonin , metallurgy
[9, 10‐ 3 H] Metergoline ( 9 ) has been prepared starting from 1‐methyllysergamide ( 6 ) which was reduced with tritium gas to 1‐methyl‐[9, 10‐ 3 H] dihydrolysergamide. The latter was converted to 9 in two steps with a 42% overall radiochemical yield. [G‐ 3 H] and [17‐ 3 H] nicergoline were prepared starting from generally labelled 11 and from 14 respectively. The latter was obtained by reducing the ester ( 13 ) with sodium boro [ 3 H]‐hydride. Similarly, 1‐demethyl‐[17‐ 3 H] nicergoline ( 15a ) was also obtained. [Carboxyl‐ 14 C] 5‐bromonicotinic acid ( 18 ) was prepared from K 14 CN via 3‐[ −14 C] cyanopyridine ( 16 ) which was converted into 17 and finally brominated. Double labelled nicergoline ( 15b ) was obtained by condensation of 14 and 18 . Radiochemical yield of 15 , 15a , and 15b from 14 and 14a was approximately 40% after the chromatographic purification step.