Coca­ethyl­ene, the in vivo product of cocaine and ethanol, is a narcotic more potent than its precursors

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dc.creatorAngélica Faleiros da Silva Maia
dc.creatorFelipe Terra Martins
dc.creatorLeonardo da Silva Neto
dc.creatorRosemeire Brondi Alves
dc.creatorÂngelo de Fátima
dc.date.accessioned2024-07-12T22:54:50Z
dc.date.accessioned2025-09-09T00:44:54Z
dc.date.available2024-07-12T22:54:50Z
dc.date.issued2017
dc.identifier.doihttps://doi.org/10.1107/S2053229617012852
dc.identifier.issn2053-2296
dc.identifier.urihttps://hdl.handle.net/1843/70506
dc.languageeng
dc.publisherUniversidade Federal de Minas Gerais
dc.relation.ispartofActa Crystallographica Section C: Structural Chemistry
dc.rightsAcesso Restrito
dc.subjectCocaina
dc.subjectNarcóticos
dc.subjectCristalografia
dc.subjectQuímica supramolecular
dc.subject.otherCrystal structure
dc.subject.otherCoca­ethyl­ene
dc.subject.otherCocaine
dc.subject.otherNarcotic
dc.subject.otherConformation
dc.subject.otherTransesterification
dc.subject.otherBenzoylecgonine ester
dc.titleCoca­ethyl­ene, the in vivo product of cocaine and ethanol, is a narcotic more potent than its precursors
dc.typeArtigo de periódico
local.citation.epage783
local.citation.spage780
local.citation.volume73
local.description.resumoThe 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.
local.identifier.orcidhttps://orcid.org/0000-0003-2344-5590
local.identifier.orcidhttps://orcid.org/0000-0003-4110-9670
local.identifier.orcidhttps://orcid.org/0000-0003-0546-2549
local.publisher.countryBrasil
local.publisher.departmentICX - DEPARTAMENTO DE QUÍMICA
local.publisher.initialsUFMG
local.url.externahttps://journals.iucr.org/paper?S2053229617012852

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