Mass spectrometric and nuclear magnetic resonance confirmation of a 3,3-spirocyclic indole derivative formed from melatonin and related acyl tryptamines

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Abstract
When melatonin is reacted with pentafluoropropionic anhydride for selected ion monitoring or electron capture gas chromatographic analysis a volatile product results. Examination of the product by combined gas chromatography mass spectrometry has established that the molecular weight of 360 corresponds to the addition of one molecule of pentafluoropropionic acid followed by dehydration. Further spectroscopic and chemical examination using mass spectrometry and nuclear magnetic resonance with isotopic labelling has established that the product is a 3,3-spirocyclic indole derivative. Several analogous compounds were also examined and their mass spectra studied.