64 lines
3.2 KiB
Plaintext
64 lines
3.2 KiB
Plaintext
In article <1992Dec23.073154.15839@u.washington.edu> lamontg@stein.u.washington.edu (Lamont Granquist) writes:
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>MPTP is produced by a synthetic error in making MPPP, which is an opiate
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>whose chemical formula I don't seem to have on hand. From what I read on
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As well as I remember, from having looked into this a few years ago,
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MPPP is the propanoate ester of 4-phenyl,4-hydroxy,N-methylpiperidine.
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Me Me
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N this can lose N
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/ \ propanoic acid / \
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CH2 CH2 to give CH2 CH2
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CH2 CH2 CH2 CH
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\ / \ //
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C C
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/ \ O |
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Ph OC3H5 Ph
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MPPP MPTP
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MPTP is oxidized _in vivo_ to MPP+, the toxic species. I think
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deprenyl showed some indication in preventing the oxidation.
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I don't think MPTP has any opiate activity itself, and I believe it
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was produced simply by accident. The reaction MPPP -> MPTP goes
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rapidly as temperature is increased.
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A technical note: I say MPPP loses propanoic acid rather than
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water because I don't think the free hydroxy compound is ever
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isolated in the synthesis. And, of course, it is made via
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everyone's favorite organic name reaction, the Grignard.
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--
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David J. Heisterberg (djh@osc.edu) Hoeren Sie gut zu,
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The Ohio Supercomputer Center und wiederholen Sie!
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Columbus, Ohio -- ALM German
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=============================================================================
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Newsgroups: alt.drugs
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From: pbray@envy.reed.edu (Public account)
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Date: Sun, 11 Apr 1993 01:52:02 GMT
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Message-ID: <1993Apr11.015202.3963@reed.edu>
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Okay I made a mistake after all. I went and checked the source (Grilly,
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Drugs and Human Behaviour) and the story was about MPTP. Here is the
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exerpt pertaining to this:
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"Recently the danger of this was well illustrated by the discovery that
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the sloppy laboratory practices of a man attempting to synthesize analogs
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of the narcotic meperidine for street sale in nothern California resulted
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in the chemical l-methyl-4-phenyl-1,2,5,6-tetrahydropyridine (MPTP)
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(Lewin, 1984). The substance has been found to metabolize in the brain
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into a compound that kills midbrain dopaminergic cells whose axons project
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to neurons in the basal ganglia. This produces clinical symptoms
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essentially identical to those of parkinson's disease. The phenomenon was
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first described in 1979 in the case of a 23-year-old graduate student who
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had developed parkinsonian-like condition after using a meperidine-like
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drug that he synthesized in his own laboratory. ... Unfortunatly, the
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student was not the only one who used the adulterated substance, and
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several dozen young users of this synthetic heroin [sic] have now
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succumbed to a similar fate- a lifetime (which could be quite short) of
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tremors, partial or complete paralysis, and abnormal posture."
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