Theoretical study of cocaine and ecgonine methyl ester in gas phase and in aqueous solution

• Type: Article in International Scientific Journal
• Date: 2009

Authors

David A Rincon (Author) Other; Natalia N D S Cordeiro (Author) FCUP; Ricardo A Mosquera (Author) Other; Fernanda Borges (Author) FCUP

Journal

Title: Chemical Physics Letters

Vol. 467

Pages: 249-254

ISSN: 0009-2614

Publisher: Elsevier

Indexing

ISI Web of Knowledge - 8 Citations

Scopus - 8 Citations

Scientific classification

FOS: Natural sciences > Chemical sciences

Other information

Authenticus ID: P-003-NTX

DOI: 10.1016/j.cplett.2008.11.048

Abstract (EN): The conformational preferences of cocaine and ecgonine methyl ester were determined through ab initio and density functional theory calculations. They share the same preferred orientation of the acetate group with a hydrogen bond between the amine and carbonyl groups, and s-cis conformation for the methoxyl group. The benzoyloxy group of cocaine defines a specific accessible conformational region. In solution the most stable conformers are stabilized by internal hydrogen bonds in contrast to the lesser stables, which are stabilized by solute/solvent interactions. Overall, these conformational features explain why ecgonine methyl ester is the principal metabolite of cocaine in a human environment.

Language: English

Type (Professor's evaluation): Scientific