title: Application of the extractive alkylation technique to the pentafluorobenzylation of morphine (a heroin metabolite) and surrogates, with special reference to the quantitative determination of plasma morphine levels using mass fragmentography.
abstract: The pentafluorobenzylation of morphine and related phenolic alkaloids by extractive alkylation is described. The alkylation is performed using tetrabutylammonium as counter ion and ethyl acetate as solvent. Optimum reaction conditions are presented together with the gas chromatographic properties of the derivatives formed. The technique is applied to the quantitation of plasma morphine levels. Using morphine-d3 as internal standard mass fragmentographic analysis of morphine as its pentafluorobenzyl- and pentafluorobenzyl, mono-trifluoroacetyl derivatives is demonstrated, and a case report is presented. Quantitation to a plasma morphine level of 5 ng/ml is readily attainable.
mesh_terms: D000478:Alkylation; D005464:Fluorobenzenes / Q000032:analysis; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods; D006801:Humans; D009020:Morphine / Q000097:blood*; D009022:Morphine Derivatives / Q000032:analysis*
chemical_list: D005464:Fluorobenzenes; D009022:Morphine Derivatives; D009020:Morphine