Stereo effects in the chemical ionization mass spectrometry of galanthamine epimers

Eur. J. Mass Spectrom. 5, 77–80 (1999)
DOI: 10.1255/ejms.252

Stereo effects in the chemical ionization mass spectrometry of galanthamine epimers

Roumen Christov, Vassya Bankova, Ivayio Elenkov, Nedjalka Handjieva, Stefan Spassov and S.S. Popov^*
Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Sofia 1113, Bulgaria.

ABSTRACT:

Galanthamine and 2-epigalanthamine possess similar electron impact mass spectra (EI-MS), while their chemical ionization (CI) mass spectra with isobutane, acetone and diethyl ether as reagent gas show significant differences in the relative intensities of [M + H]⁺ and [M + H – H₂O]⁺ ions. Ionization with amines indicates lower basicity of galanthamine, compared with its epimer. Two modifications of a method for determination of the ratio galanthamine to 2-epigalanthamine in mixtures were developed.

Keywords: CI, MS, stereochemistry, alkaloids, galanthamine, epigalanthamine, diastereoisomers.

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