The hydrochloride salt of L -ecgonine, a congener of cocaine

The title compound, (1R,2R,3S,5S,8S)-3-hydroxy-8-methyl-8-azoniabicyclo[3.2.1]octane-2-carboxylic acid chloride, C9H16NO3+·Cl−, is both a metabolite and a precursor of the tropane alkaloid l-cocaine. The carboxyl group is not involved in dimerization, but instead donates a hydrogen bond to the chlor...

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Bibliographic Details
Published in:Acta crystallographica. Section E, Structure reports online Structure reports online, 2008-02, Vol.64 (2), p.o525-o525
Main Authors: Wood, Matthew R., Brettell, Thomas A., Thompson, Hugh W., Lalancette, Roger A.
Format: Article
Language:English
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Summary:The title compound, (1R,2R,3S,5S,8S)-3-hydroxy-8-methyl-8-azoniabicyclo[3.2.1]octane-2-carboxylic acid chloride, C9H16NO3+·Cl−, is both a metabolite and a precursor of the tropane alkaloid l-cocaine. The carboxyl group is not involved in dimerization, but instead donates a hydrogen bond to the chloride counter-ion, which participates in two additional hydrogen bonds. The chloride ion is thus trigonally hydrogen bonded to three l-ecgonine cations. The quarternary N proton is intramolecularly hydrogen bonded to the carboxyl C=O group, an arrangement identical to that reported for both (−)-norcocaine and the tetrachloroaurate(III) salt of l-cocaine. One close intermolecular C-H...O contact exists.
ISSN:1600-5368
1600-5368
DOI:10.1107/S1600536808002535