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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.
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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.
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Newsgroups: alt.drugs
>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.