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The hydro-chloride salt of l-ecgonine, a congener of cocaine.

ABSTRACT: The title compound, (1R,2R,3S,5S,8S)-3-hydr-oxy-8-methyl-8-azoniabicyclo-[3.2.1]octane-2-carboxylic acid chloride, C(9)H(16)NO(3) (+)·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 intra-molecularly hydrogen bonded to the carboxyl C=O group, an arrangement identical to that reported for both (-)-nor-cocaine and the tetrachloroaurate(III) salt of l-cocaine. One close inter-molecular C-H⋯O contact exists.

SUBMITTER: Wood MR

PROVIDER: S-EPMC2960340 | biostudies-literature | 2008 Jan

REPOSITORIES: biostudies-literature

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The hydro-chloride salt of l-ecgonine, a congener of cocaine.

Wood Matthew R MR Brettell Thomas A TA Thompson Hugh W HW Lalancette Roger A RA

Acta crystallographica. Section E, Structure reports online 20080130 Pt 2

The title compound, (1R,2R,3S,5S,8S)-3-hydr-oxy-8-methyl-8-azoniabicyclo-[3.2.1]octane-2-carboxylic acid chloride, C(9)H(16)NO(3) (+)·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 intra-mo ...[more]

PMID: 21201544

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