Synthesis of New d-Propoxyphene Derivatives and the Development of a Microparticle-Based Immunoassay for the Detection of Propoxyphene and Norpropoxyphene
Received May 6, 1996 Abstract: The synthesis of
[S-(R,S)]-4-[[methyl[2-methyl-3-(1-oxopropoxy)-3,4-diphenylbutyl]amino]-1-oxobutoxy]-2,5-pyrrolidinedione (propoxyphene active ester, 2) is
described. This was used as an intermediate to
prepare a propoxyphene immunogen,
[S-(R,S)]-4-[methyl[2-methyl-3-(1-oxopropoxy)-3,4-diphenylbutyl]amino]-1-oxobutyl-Bovine Thyroglobulin (3). This
immunogen was then used to generate antibodies
which demonstrate good cross-reactivity to d-propoxyphene,
d-norpropoxyphene, and other propoxyphene metabolites. In addition, these antibodies were shown to
have very low cross-reactivity to
methadone, a structurally related compound. The introduction of an
aminomethyl benzoate spacer
into the propoxyphene active ester (2), followed by the
activation of the carboxylic acid, provided for
a more stable active ester (5). This stable active
ester, together with the antibodies generated from
the propoxyphene immunogen, has led to the development of an
immunoassay based on the Kinetic
Interaction of Microparticles in Solution (KIMS).
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