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Volume 3, Number 35 November 4, 1990 Update: Analysis of L-Tryptophan for the Etiology of Eosinophilia-Myalgia Syndrome In August 1990, CDC and the Food and Drug Administration proposed a structure for peak 97 (Figure 1A), the high performance liquid chromatographic (HPLC) peak that was most predictive of L-tryptophan (LT) lots associated with eosinophilia-myalgia syndrome (EMS) cases(1). This report updates those findings. Analyses of the product of LT and acetaldehyde show that the product is the di-L-tryptophan aminal of acetaldehyde (DTAA), with the methine bridge coupling the two tryptophan molecules across the indolenitrogens (Figure 1B) rather than the amino nitrogens (Figure 1A). Thissynthesized product has the same proton nuclear magnetic resonance(NMR) spectra, mass spectra, and HPLC chromatographic properties aspeak 97. [...] 1. CDC. Analysis of L-tryptophan for the etiology of eosinophilia-myalgia syndrome. MMWR 1990;39:589-91. 2. Reynolds WF, McClean S, Perpick-Dumont M, Enriquez RG.Improved 13C-1H shift correlation spectra for indirectly bonded carbons and hydrogens: the FLOCK sequence. Magn ResonChem 1989;27:162-9. 3. Crofford LJ, Rader JI, Dalakas MC, et al. L-Tryptophan implicated in human eosinophilia-myalgia syndrome causes fasciitis and perimyositis in the Lewis rat. JClin Invest 1990;86:1757-63. Health InfoCom Network News Page 28 ****************************** Article Separation ***************************** L-tryptophan eosinophilia-myalgia synrome (L-TRP-EMS) references: Belongia-E-A, et al. "An investigation of the cause of the eosinophilia- myalgia syndrome associated with tryptophan use" N-Engl-J-Med. 1990 Aug 9. 323(6). P 357-365 (see also N-Engl-J-Med. 1990 Oct 4. 323(14). P 992-993 "CONCLUSIONS. The outbreak of the eosinophilia-myalgia syndrome in 1989 resulted from the ingestion of a chemical constituent that was associated with specific tryptophan-manufacturing conditions at one company. The chemical constituent represented by peak E may contribute to the pathogenesis of the eosinophilia-myalgia syndrome, or it may be a surrogate for another chemical that induces the syndrome." Mayeno-A-N, et al. "Characterization of "peak E," a novel amino acid associated with eosinophilia-myalgia syndrome." Science. 1990 Dec 21. 250(4988). P 1707-1708. Spectral and chemical studies now demonstrate that peak E is 1,1'-ethylidenebis[tryptophan]. This novel amino acid may be the etiological agent responsible for EMS, or it may be a marker of a still unidentified causal agent. Slutsker-L, et al. "Eosinophilia-myalgia syndrome associated with exposure to tryptophan from a single manufacturer." JAMA. 1990 Jul 11. 264(2). P 213-217. ****************************** Article Separation ***************************** From: eesnyder@boulder.Colorado.EDU (Eric E. Snyder) Date: 10 Feb 92 14:29:21 GMT Newsgroups: alt.drugs Subject: Re: Tryptophan malcolm@basser.cs.su.oz.au (Malcolm Bjorn Gillies) writes: >Has anyone else heard the rumour that it was withdrawn from general >availability becuase it was being used as a precursor for the synthesis of >hallucinogenic tryptamine derivatives? Tryptophan is a possible precursor of DMT. More than likely, however, tryptamine itself would be the preferred precursor for DMT. I would wager that anyone capable of making DMT from either precursor would have access to both compounds through the usual channels and would not try extracting the amino acid from store-bought tablets. Has anyone found LiAlH4 at a healthfood store? Judging from the amount of DMT on the street these days (none), I don't think it is a big public health problem. 5-MeODMT is not even a controlled substance and is pharmacologically very similar.