archived from: http://blackroses.textfiles.com/drugs/ALT.DRUGS/notptryp.drg






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.