From: dheister@magnus.acs.ohio-state.edu (David J Heisterberg)
Newsgroups: sci.chem
Subject: Re: What caused the famous case of Parkinsonism
Date: 12 Mar 1996 23:40:33 GMT

In article <delineDo5ywB.EHx@netcom.com>,
James Deline <deline@netcom.com> wrote:
>A chemist was trying to synthesize illicit demerol.  During one stage of 
>the synthesis he inadvertantly formed the "reverse" ester of demerol, 
>which is now called MPTP and is known to cause Parkinson's disease.  

I don't think that's exactly right.  He was purposely trying to
synthesize a propionate ester.  But the OH group in

        N-CH3     is very labile until it's esterified.  It
       / \        dehydrates very easily, losing the OH and
   H2C     CH2    a hydrogen at the *carbon to give a double
     |     |      bond.  It's the double bond compound that
   H2C    *CH2    is MPTP.  In vivo MPTP is easily oxidized
       \ /        to MPP+ which produces the Parkinson-like
        C         symptoms.
       / \ 
     Ph   OH

Dave Heisterberg