Conformational impact of aliphatic side chains in local anaesthetics: benzocaine, butamben and isobutamben

A. Insausti; C. Calabrese; M. Parra; I. Usabiaga; M. Vallejo-López; P. Écija; F. J. Basterretxea; J.-U. Grabow; W. Caminati; A. Lesarri; E. J. Cocinero

doi:10.1039/D0CC00760A

Conformational impact of aliphatic side chains in local anaesthetics: benzocaine, butamben and isobutamben†

A. Insausti,^ab C. Calabrese,

^ab M. Parra,^ab I. Usabiaga,

^ac M. Vallejo-López,^a P. Écija,^a F. J. Basterretxea,^a J.-U. Grabow,

^d W. Caminati,

^c A. Lesarri

^e and E. J. Cocinero

*^ab

Author affiliations

* Corresponding authors

^a Departamento de Química Física, Facultad de Ciencia y Tecnología, Universidad del País Vasco (UPV/EHU), Leioa, Spain
E-mail: emiliojose.cocinero@ehu.es
Web: http://grupodeespectroscopia.es/MW/

^b Instituto Biofisika (CSIC, UPV/EHU), Leioa, Spain

^c Dipartimento di Chimica “G. Ciamician”, Università di Bologna, via Selmi 2, Bologna 40126, Italy

^d Institut für Physikalische Chemie und Elektrochemie, Gottfried Wilhelm Leibniz Universität Hannover, Hannover, Germany

^e Departamento de Química Física y Química Inorgánica – IU CINQUIMA, Universidad de Valladolid, Valladolid, Spain

Abstract

We studied the impact of aliphatic side chains on the stability and conformational landscape of the local anaesthetics benzocaine, butamben and isobutamben, combining high-resolution rotational spectroscopy in the microwave and millimetre regions and molecular modelling. The study reveals the connections between alkyl chain flexibility and molecular conformations.

Chemical Communications

Conformational impact of aliphatic side chains in local anaesthetics: benzocaine, butamben and isobutamben†

Abstract

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Conformational impact of aliphatic side chains in local anaesthetics: benzocaine, butamben and isobutamben

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