2023-12-142023-12-142017MAIA, Angélica Faleiros da Silva et al. Coca­ethyl­ene, the in vivo product of cocaine and ethanol, is a narcotic more potent than its precursors. Acta Crystallographica. Section C: structural chemistry, Chester, v. 73, p. 780-783, 2017. DOI: 10.1107/S2053229617012852. Disponível em: https://scripts.iucr.org/cgi-bin/paper?S2053229617012852. Acesso em: 28 nov. 2023.e- 2053-2296https://scripts.iucr.org/cgi-bin/paper?S2053229617012852The molecular conformation and supramolecular architecture of cocaethylene [systematic name: eth­yl (1R,2R,3S,5S)-3-benzo­yloxy-8-methyl-8-aza­bicyclo­[3.2.1]octane-2-carboxyl­ate], C18H23NO4, have been determined for the first time. Cocaethylene is a narcotic produced in vivo when cocaine and ethanol are administered concomitantly. The intra- and inter­molecular features of coca­ethyl­ene and its less potent narcotic precursor cocaine are very similar. The only mol­ecular difference is in the conformation of the methyl group of the ethoxycarbonyl group. Similar to cocaine, the carboxyl­ate atoms and the α-C atom are coplanar in coca­ethyl­ene, but the methyl C atom of the ethyl group is bent by ca 90° away from this plane in the narcotic reported here. The main supra­molecular motif is a one-dimensional chain stabilized by weak C—H...O contacts.engAcesso RestritoCrystal structureBenzoylecgonine esterTransesterificationConformationNarcoticCocaineCoca­ethyl­eneArtigo10.1107/S2053229617012852