The hydrochloride and hydrobromide salt forms of (S)-amphetamine

Abstract

This version is available at https://strathprints.strath.ac.uk/54364/ Strathprints is designed to allow users to access the research output of the University of Strathclyde. Unless otherwise explicitly stated on the manuscript, Copyright © and Moral Rights for the papers on this site are retained by the individual authors and/or other copyright owners. Please check the manuscript for details of any other licences that may have been applied. You may not engage in further distribution of the material for any profitmaking activities or any commercial gain. You may freely distribute both the url (https://strathprints.strath.ac.uk/) and the content of this paper for research or private study, educational, or not-for-profit purposes without prior permission or charge.Any correspondence concerning this service should be sent to the Strathprints administrator: strathprints@strath.ac.ukThe Strathprints institutional repository (https://strathprints.strath.ac.uk) is a digital archive of University of Strathclyde research outputs. It has been developed to disseminate open access research outputs, expose data about those outputs, and enable the management and persistent access to Strathclyde's intellectual output. Abstract(S)-Amphetamine hydrochloride, C 9 H 14 ClN, has a Z′ = 6 structure with six independent cation, anion pairs. That these are indeed crystallographically independent is supported by different packing orientations of the cations and by observation of a wide range of cation conformations generated by rotation about the phenyl-CH 2 bond. The supramolecular contacts about the anions also differ such that both a wide variation in the geometry of the three N-H···Cl hydrogen bonds formed by each chloride anion and differences in C-H···Cl contacts are apparent. (S)-Amphetamine hydrobromide, C 9 H 14 BrN, is broadly similar to the chloride in terms of cation conformation, the existance of three N-H···X hydrogen bond contacts per anion and the overall 2 dimensional hydrogen bonded sheet motif. However, only the chloride structure features organic bilayers and Z′ > 1. CommentSalt selection or salt screening is a common technique used in the pharmacuetical industry to improve the physicochemical properties of potential Active Pharmaceutical Ingredients (APIs, Stahl & Wermuth 2008). Studies on systematic series of crystal structures of phenylethylamine salts have been instigated with a view to determining relationships between crystal structure and the physicochemical properties of APIs (see for example Kennedy et al., 2011;Black et al., 2007;Briggs et al., 2012;Cruickshank et al., 2013). The ultimate goal of such studies is to understand and improve the pharmaceutical salt selection process. A member of the phenylethylamine class of molecules, amphetamine is popularly known as a stimulant and as a drug of abuse (Kilminster et al., 1977), but it also has legitimate pharmaceutical roles for instance in the treatment of attention defecit hyperactivity disorder and of narcolepsy (Wood et al., 2014). Despite the high pro...

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