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