High-resolution solid state C-13 nuclear magnetic resonance spectra of 3,4-methylenedioxyamphetamine hydrochloride and related compounds and their mixtures with lactose

Differences between solution and solid state C-13 nuclear magnetic resonanc e spectra of some amphetamines namely, 3,4-methylenedioxyamphetamine HCl, ( R,S)-MDA . HCl, the methyl derivative 3,4-methylenedioxy-N-methylamphetamin e . HCl, (R,S)-MDMA . HCl, the ethyl derivative, (R,S)-MDEA . HCl, and the analogues (R,S)-methamphetamine . HCl, (-)-ephedrine . HCl (the 3R,2S enant iomer as numbered here), and (+)-pseudo-ephedrine . HCl (the 3S,2S enantiom er as numbered here) have been studied and related to their crystal structu re. For (R,S)-MDMA . HCl, an interesting new finding is that the observed s olid state chemical shifts changed when lactose monohydrate was added as a dry powder and thoroughly mixed at room temperature. This experiment mimick ed the illicit production of "Ecstasy" tablets. The mixing: phenomena with lactose observed for (R,S)-MDMA . HCl was not seen for the other compounds studied. The results are discussed in terms of hydrogen bonding and possibl e polymorphs. It appears that lactose affects crystal packing by reducing c onformational rigidity so that the molecule more closely resembles that in solution. (C) 2000 Elsevier Science B.V. All rights reserved.