Site- and species-specific hydrolysis rates of cocaine.

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.

journal_name

J Pharm Biomed Anal

authors

Szöcs L,Völgyi G,Urai Á,Hosztafi S,Tóth G,Gergó L,Noszál B

doi

10.1016/j.jpba.2017.07.005

subject

Has Abstract

pub_date

2017-10-25 00:00:00

pages

372-378

eissn

0731-7085

issn

1873-264X

pii

S0731-7085(17)30849-X

journal_volume

145

pub_type

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