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Iodinated melatonin: Preparation and characterization of the molecular structure by mass and 1H NMR spectroscopy

✍ Scribed by Olli Vakkuri; Erkki Lämsä; Erkki Rahkamaa; Heikki Ruotsalainen; Juhani Leppäluoto

Publisher
Elsevier Science
Year
1984
Tongue
English
Weight
490 KB
Volume
142
Category
Article
ISSN
0003-2697

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✦ Synopsis

Synthetic melatonin was iodinated by treatment with potassium iodide in the presence of an oxidizing agent, Iodo-Gen. The iodination products of melatonin were extracted with chloroform and separated by HPLC. The fraction showing immunoreactivity with respect to melatonin antisera was characterized as iodomelatonin by mass spectrometry, so that the substitution of iodine had occurred at a ring carbon atom. 'H NMR spectra showed the iodine to be incorporated at the C-2 position of the indole moiety. The N-[2-(2-iodo&methoxy-lH-indol-3-yl)ethyl]acetamide (Ziodomelatonin) reported here is more useful than [3H]melatonin as a tracer in melatonin radioimmunoassay. This method offers also the possibility of preparing iodinated serotonin and other indoleamines for biological studies. o 1984 Academic PBS, IIIC.

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