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MPTP: A Look at Deadly Synthesis Errors
Information Collected by Lamont Granquist
1993

In article <1992Dec23.073154.15839@u.washington.edu> Lamont Granquist writes:
>MPTP is produced by a synthetic error in making MPPP, which is an opiate
>whose chemical formula I don't seem to have on hand.  From what I read on

As well as I remember, from having looked into this a few years ago,
MPPP is the propanoate ester of 4-phenyl,4-hydroxy,N-methylpiperidine.


         Me                                     Me
         |                                      |
         N            this can lose             N
       /   \          propanoic acid          /   \
      CH2   CH2       to give                CH2   CH2
      |     |                                |     |
      CH2   CH2                              CH2   CH
       \   /                                  \  //
         C                                      C
       /   \ O                                  |
      Ph    OC3H5                               Ph

        MPPP                                   MPTP

MPTP is oxidized _in vivo_ to MPP+, the toxic species.  I think
deprenyl showed some indication in preventing the oxidation.
I don't think MPTP has any opiate activity itself, and I believe it
was produced simply by accident.  The reaction MPPP -> MPTP goes
rapidly as temperature is increased.

A technical note: I say MPPP loses propanoic acid rather than
water because I don't think the free hydroxy compound is ever
isolated in the synthesis.  And, of course, it is made via
everyone's favorite organic name reaction, the Grignard.
-- 
David J. Heisterberg (djh@osc.edu)       Hoeren Sie gut zu,
The Ohio Supercomputer Center            und wiederholen Sie!
Columbus, Ohio                             -- ALM German

=============================================================================

Newsgroups: alt.drugs
From: pbray@envy.reed.edu (Public account)
Date: Sun, 11 Apr 1993 01:52:02 GMT
Message-ID: <1993Apr11.015202.3963@reed.edu>

Okay I made a mistake after all.  I went and checked the source (Grilly,  
Drugs and Human Behaviour) and the story was about MPTP.  Here is the  
exerpt pertaining to this:

"Recently the danger of this was well illustrated by the discovery that  
the sloppy laboratory practices of a man attempting to synthesize analogs  
of the narcotic meperidine for street sale in nothern California resulted  
in the chemical l-methyl-4-phenyl-1,2,5,6-tetrahydropyridine (MPTP)  
(Lewin, 1984).  The substance has been found to metabolize in the brain  
into a compound that kills midbrain dopaminergic cells whose axons project  
to neurons in the basal ganglia.  This produces clinical symptoms  
essentially identical to those of parkinson's disease.  The phenomenon was  
first described in 1979 in the case of a 23-year-old graduate student who  
had developed parkinsonian-like condition after using a meperidine-like  
drug that he synthesized in his own laboratory. ... Unfortunatly, the  
student was not the only one who used the adulterated substance, and  
several dozen young users of this synthetic heroin [sic] have now  
succumbed to a similar fate- a lifetime (which could be quite short) of  
tremors, partial or complete paralysis, and abnormal posture."