Identification of decomposition products of 1,1'-ethylidenebis [L-tryptophan], a compound associated with eosinophilia-myalgia syndrome

At the end of 1989 a new disease called eosinophiliamyalgia syndrome (EMS) appeared in America and West Germany. Epidemiologic investigators traced the cause to an unknown contaminant in L-tryptophan (LT) dietary supplement tablets. Of the more than 50 contaminants found in the LT material by high-p...

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Bibliographic Details
Published in:Bulletin of environmental contamination and toxicology 1992-05, Vol.48 (5), p.679-687
Main Authors: DRISKELL, W. J, ASHLEY, D. L, GRAINGER, J, SIRIMANNE, S. R, MAZZOLA, E. P, PAGE, S. W, NEEDHAM, L. L, HILL, R. H
Format: Article
Language:English
Subjects:
Biological and medical sciences
Chromatography, Liquid
Drug toxicity and drugs side effects treatment
Eosinophilia-Myalgia Syndrome - chemically induced
Gastric Juice - metabolism
Magnetic Resonance Spectroscopy
Mass Spectrometry
Medical sciences
Miscellaneous (drug allergy, mutagens, teratogens...)
Models, Biological
Pharmacology. Drug treatments
Spectrum Analysis
Tryptophan - analogs & derivatives
Tryptophan - metabolism
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Summary:At the end of 1989 a new disease called eosinophiliamyalgia syndrome (EMS) appeared in America and West Germany. Epidemiologic investigators traced the cause to an unknown contaminant in L-tryptophan (LT) dietary supplement tablets. Of the more than 50 contaminants found in the LT material by high-performance liquid chromatography (HPLC) analysis, a contaminant identified as 1,1'-ethylidenebis (L-tryptophan) (EBT), also known as "peak 97" and "peak E", was the only one that had a marked association with EMS cases. In this report we describe studies in which we incubated EBT in simulated gastric fluid, followed the course of its breakdown into other products, and identified all of those products.
ISSN:0007-4861
1432-0800
DOI:10.1007/BF00195987