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

• Tipo: Artigo em Revista Científica Internacional
• Data: 2009

Autores

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

Revista

Título: Chemical Physics Letters

Vol. 467

Páginas: 249-254

ISSN: 0009-2614

Editora: Elsevier

Indexação

ISI Web of Knowledge - 8 Citações

Scopus - 8 Citações

Classificação Científica

FOS: Ciências exactas e naturais > Química

Outras Informações

ID Authenticus: 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.

Idioma: Inglês

Tipo (Avaliação Docente): Científica