2026-04-27T22:10:14Zhttps://uvadoc.uva.es/oai/request

oai:uvadoc.uva.es:10324/565692025-03-04T09:48:49Zcom_10324_55675com_10324_954com_10324_894col_10324_55676

Aguado Vesperinas, Raúl Mata López, Santiago Sanz Novo, Miguel Alonso Alonso, Elena Rita León Ona, Iker Alonso Hernández, José Luis Producción Científica We report a detailed structural study of cytisine, an alkaloid used to help with smoking cessation, looking forward to unveiling its role as a nicotinic agonist. High-resolution rotational spectroscopy has allowed us to characterize two different conformers exhibiting axial and equatorial arrangements of the piperidinic NH group. Unexpectedly, the axial form has been found as the predominant configuration, in contrast to that observed for related molecules, such as piperidine. This anomalous behavior has been justified in terms of an intramolecular NH···N hydrogen bond. Moreover, this interaction justifies the overstabilization of the axial conformer over the equatorial one and is crucial for the mechanism of action of cytisine over the nicotinic receptor, further rationalizing its behavior as a nicotinic agonist. 2022-10-27 2022-10-27 2022 info:eu-repo/semantics/article Journal of Physical Chemistry Letters, 2022, vol. 13, p. 9991–9996 1948-7185 https://uvadoc.uva.es/handle/10324/56569 10.1021/acs.jpclett.2c02021 eng https://pubs.acs.org/doi/10.1021/acs.jpclett.2c02021 info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/4.0/ © 2022 The Authors Atribución 4.0 Internacional American Chemical Society