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Nikolić D, Macias C, Lankin DC, et al. Collision-induced dissociation of phenethylamides: role of ion-neutral complexes. Rapid Commun Mass Spectrom. 2017;31(17):1385-1395doi: 10.1002/rcm.7915.
Nikolić, D., Macias, C., Lankin, D. C., & van Breemen, R. B. (2017). Collision-induced dissociation of phenethylamides: role of ion-neutral complexes. Rapid communications in mass spectrometry : RCM, 31(17), 1385-1395. https://doi.org/10.1002/rcm.7915
Nikolić, Dejan, et al. "Collision-induced dissociation of phenethylamides: role of ion-neutral complexes." Rapid communications in mass spectrometry : RCM vol. 31,17 (2017): 1385-1395. doi: https://doi.org/10.1002/rcm.7915
Nikolić D, Macias C, Lankin DC, van Breemen RB. Collision-induced dissociation of phenethylamides: role of ion-neutral complexes. Rapid Commun Mass Spectrom. 2017 Sep 15;31(17):1385-1395. doi: 10.1002/rcm.7915. PMID: 28558170; PMCID: PMC5555735.
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Rapid Commun Mass Spectrom. 2017 Sep 15;31(17):1385-1395. doi: 10.1002/rcm.7915.

Collision-induced dissociation of phenethylamides: role of ion-neutral complexes.

Rapid communications in mass spectrometry : RCM

Dejan Nikolić, Carmen Macias, David C Lankin, Richard B van Breemen

Affiliations

  1. Department of Medicinal Chemistry and Pharmacognosy, UIC/NIH Center for Botanical Dietary Supplements Research, College of Pharmacy, University of Illinois at Chicago, 833 S. Wood St., Chicago, IL, 60612-7231, USA.

PMID: 28558170 PMCID: PMC5555735 DOI: 10.1002/rcm.7915

Abstract

RATIONALE: Phenethylamides are a large group of naturally occurring molecules found both in the plant and animal kingdoms. In addition, they are used as intermediates for the synthesis of pharmaceutically important dihydro- and tetrahydroisoquinolines. To enable efficient characterization of this class of molecules, a detailed mass spectrometric fragmentation study of a broad series of analogs was carried out.

METHODS: The test compounds were synthesized using standard methods for amide bond formation. Low-energy high-resolution tandem mass spectra were acquired on a hybrid quadrupole/time-of-flight mass spectrometer using positive ion electrospray ionization.

RESULTS: A total of 26 analogs were investigated in the study. Fragmentation of phenethylamides was found to proceed via intermediate ion-neutral complexes. The complexes can break down via multiple pathways including dissociation, proton transfer, Friedel-Crafts acylation, and single electron transfer. The relative contribution of each of these pathways strongly depends on the structure of the coupling amine and acid.

CONCLUSIONS: A general scheme for the fragmentation of phenethylamides was developed. This study further extends the knowledge base of the ion-neutral complex by discovering Friedel-Crafts acylation as a novel reaction. The strong influence of minor structural modifications on the fragmentation patterns highlights the importance of testing many analogs in order to fully predict a fragmentation pattern of a particular class of molecules.

Copyright © 2017 John Wiley & Sons, Ltd.

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