Characterization of ephedrine HCl and pseudoephedrine HCl using quadrupolar NMR crystallography guided crystal structure prediction

Fleischer, Carl H.; Holmes, Sean T.; Levin, Kirill; Veinberg, Stanislav L.; Schurko, Robert W.

doi:10.1039/D4FD00089G

Title: Characterization of ephedrine HCl and pseudoephedrine HCl using quadrupolar NMR crystallography guided crystal structure prediction

Journal Article · 07 January 2025 · Faraday Discussions

DOI: https://doi.org/10.1039/D4FD00089G · OSTI ID:2447637

^[1];

^[2]; Veinberg, Stanislav L. ^[2];

^[1]

Department of Chemistry & Biochemistry, Florida State University, Tallahassee, FL 32306, USA, National High Magnetic Field Laboratory, Tallahassee, FL, 32310, USA
Department of Chemistry & Biochemistry, University of Windsor, Windsor, ON, N9B 3P4, Canada

We report a quadrupolar guided NMR crystallography crystal structure prediction protocol as applied for pseudoephedrine HCl and ephedrine HCl. We explore the crystal structure prediction of pseudoephedrine HCl in the dosage form.

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Sponsoring Organization:: USDOE

Grant/Contract Number:: SC0022310

OSTI ID:: 2447637

Journal Information:: Faraday Discussions, Journal Name: Faraday Discussions Vol. 255; ISSN 1359-6640; ISSN FDISE6

Publisher:: Royal Society of Chemistry (RSC)Copyright Statement

Country of Publication:: United Kingdom

Language:: English

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A third blind test of crystal structure prediction Day, G. M.; Motherwell, W. D. S.; Ammon, H. L. Acta Crystallographica Section B Structural Science, Vol. 61, Issue 5 https://doi.org/10.1107/S0108768105016563	journal	September 2005
17 salts of ephedrine: crystal structures and packing analysis Collier, Edwin A.; Davey, Roger J.; Black, Simon N. Acta Crystallographica Section B Structural Science, Vol. 62, Issue 3 https://doi.org/10.1107/S0108768106012018	journal	May 2006
Significant progress in predicting the crystal structures of small organic molecules – a report on the fourth blind test Day, Graeme M.; Cooper, Timothy G.; Cruz-Cabeza, Aurora J. Acta Crystallographica Section B Structural Science, Vol. 65, Issue 2 https://doi.org/10.1107/S0108768109004066	journal	March 2009
Towards crystal structure prediction of complex organic compounds – a report on the fifth blind test Bardwell, David A.; Adjiman, Claire S.; Arnautova, Yelena A. Acta Crystallographica Section B Structural Science, Vol. 67, Issue 6 https://doi.org/10.1107/S0108768111042868	journal	November 2011
The crystal and molecular structures of (+)-pseudoephedrine and (+)-pseudoephedrine hydrochloride Mathew, M.; Palenik, G. J. Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry, Vol. 33, Issue 4 https://doi.org/10.1107/S0567740877005287	journal	April 1977
Mercury 4.0 : from visualization to analysis, design and prediction Macrae, Clare F.; Sovago, Ioana; Cottrell, Simon J. Journal of Applied Crystallography, Vol. 53, Issue 1 https://doi.org/10.1107/S1600576719014092	journal	February 2020
NMR crystallography: structure and properties of materials from solid-state nuclear magnetic resonance observables Bryce, David L. IUCrJ, Vol. 4, Issue 4 https://doi.org/10.1107/S2052252517006042	journal	May 2017
The Cambridge Structural Database Groom, Colin R.; Bruno, Ian J.; Lightfoot, Matthew P. Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials, Vol. 72, Issue 2, p. 171-179 https://doi.org/10.1107/S2052520616003954	journal	April 2016
Report on the sixth blind test of organic crystal structure prediction methods Reilly, Anthony M.; Cooper, Richard I.; Adjiman, Claire S. Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials, Vol. 72, Issue 4 https://doi.org/10.1107/S2052520616007447	journal	August 2016
A multinuclear NMR and quantum chemical study of solid trimethylammonium chloride Penner, Glenn H.; Webber, Renee; O’Dell, Luke A. Canadian Journal of Chemistry, Vol. 89, Issue 9 https://doi.org/10.1139/v11-034	journal	September 2011
Crystal Structure Prediction Methods for Organic Molecules: State of the Art Bowskill, David H.; Sugden, Isaac J.; Konstantinopoulos, Stefanos Annual Review of Chemical and Biomolecular Engineering, Vol. 12, Issue 1 https://doi.org/10.1146/annurev-chembioeng-060718-030256	journal	June 2021
Using the Cambridge Structural Database to validate powder structures Barr, G.; Dong, W.; Gilmore, C. J. Zeitschrift für Kristallographie, Vol. 2007, Issue suppl_26 https://doi.org/10.1524/zkri.2007.2007.suppl_26.209	journal	November 2007
First principles methods using CASTEP Clark, Stewart J.; Segall, Matthew D.; Pickard, Chris J. Zeitschrift für Kristallographie - Crystalline Materials, Vol. 220, Issue 5/6 https://doi.org/10.1524/zkri.220.5.567.65075	journal	January 2005
NMR Crystallography as a Vital Tool in Assisting Crystal Structure Determination from Powder XRD Data Harris, Kenneth D. M. Crystals, Vol. 12, Issue 9 https://doi.org/10.3390/cryst12091277	journal	September 2022
Zwitterionic or Not? Fast and Reliable Structure Determination by Combining Crystal Structure Prediction and Solid-State NMR Bravetti, Federica; Russo, Raffaele E.; Bordignon, Simone Molecules, Vol. 28, Issue 4 https://doi.org/10.3390/molecules28041876	journal	February 2023

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