Site- and species-specific hydrolysis rates of cocaine

Levente Szöcs, Gergely Völgyi, Ákos Urai, Sándor Hosztafi, Gergő Tóth, Lajos Gergó, B. Noszál

Research output: Contribution to journalArticle

Abstract

The hydroxide-catalyzed non-enzymatic hydrolysis of cocaine is quantified in terms of ten site- and species-specific rate constants in connection with also ten site- and species-specific acid-base equilibrium constants, comprising all the twelve coexisting species in solution. This characterization involves the major and minor decomposition pathways via benzoylecgonine and ecgonine methyl ester, respectively, leading to ecgonine, the final product. Hydrolysis has been found to be 10–330 times faster at site 2 than at site 3, depending on the ionization status of the amino moiety and the rest of the molecule. Nitrogen protonation accelerates the hydrolyses approximately ten times both at site 2 and site 3.

Original languageEnglish
Pages (from-to)372-378
Number of pages7
JournalJournal of Pharmaceutical and Biomedical Analysis
Volume145
DOIs
Publication statusPublished - Oct 25 2017

Keywords

  • Cocaine
  • Ester hydrolysis
  • Microconstant
  • Protonation
  • Rate constant

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmaceutical Science
  • Drug Discovery
  • Spectroscopy
  • Clinical Biochemistry

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