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

作者: Garry S.H. Lee , Renee C. Taylor , Michael Dawson , G.S.Kamali Kannangara , Michael A. Wilson

DOI: 10.1016/S0926-2040(00)00071-0

关键词: CrystallographyEnantiomerChemistryMoleculeHydrogen bondHydrochlorideNuclear magnetic resonanceLactoseCrystal structureChemical shiftSpectral line

摘要: Differences between solution and solid state 13C nuclear magnetic resonance spectra of some amphetamines namely, 3,4-methylenedioxyamphetamine·HCl, (R,S)-MDA·HCl, the methyl derivative 3,4-methylenedioxy-N-methylamphetamine·HCl, (R,S)-MDMA·HCl, ethyl derivative, (R,S)-MDEA·HCl, analogues (R,S)-methamphetamine·HCl, (−)-ephedrine·HCl (the 3R,2S enantiomer as numbered here), (+)-pseudo-ephedrine·HCl 3S,2S here) have been studied related to their crystal structure. For an interesting new finding is that observed chemical shifts changed when lactose monohydrate was added a dry powder thoroughly mixed at room temperature. This experiment mimicked illicit production “Ecstasy” tablets. The mixing phenomena with for (R,S)-MDMA·HCl not seen other compounds studied. results are discussed in terms hydrogen bonding possible polymorphs. It appears affects packing by reducing conformational rigidity so molecule more closely resembles solution.

参考文章(24)
A. M. van der Ark, A. M. A. Verweij, A. Sinnema, Weakly basic impurities in illicit amphetamine. Journal of Forensic Sciences. ,vol. 23, pp. 693- 700 ,(1978) , 10.1520/JFS10725J
Terry D. Cyr, Brian A. Dawson, Arnold W. By, George A. Neville, Herbert F. Shurvell, Structural Elucidation of Unusual Police Exhibits. II. Identification and Spectral Characterization of N-(2-Hydroxyethyl)amphetamine Hydrochloride Journal of Forensic Sciences. ,vol. 41, pp. 608- 611 ,(1996) , 10.1520/JFS13962J
Garry S. H. Lee, Don C. Craig, G. S. Kamali Kannangara, Michael Dawson, Costa Conn, James Robertson, Michael A. Wilson, ANALYSIS OF 3,4-METHYLENEDIOXY-N-METHYLAMPHETAMINE (MDMA) IN ECSTASY TABLETS BY 13C SOLID STATE NUCLEAR MAGNETIC RESONANCE (NMR) SPECTROSCOPY Journal of Forensic Sciences. ,vol. 44, pp. 761- 771 ,(1999) , 10.1520/JFS14550J
Christopher J. Groombridge, NMR Spectroscopy in Forensic Science Annual reports on NMR spectroscopy. ,vol. 32, pp. 215- 297 ,(1996) , 10.1016/S0066-4103(08)60080-0
KAZUO YAMASAKI, KIMIKO FUJITA, Qualitative and Quantitative Analysis of Ephedra Alkaloids in Ephedrae Herba by Carbon-13 Nuclear Magnetic Resonance Chemical & Pharmaceutical Bulletin. ,vol. 27, pp. 43- 47 ,(1979) , 10.1248/CPB.27.43
R. Bergin, Refinement of the structure of (−)-ephedrine hydrochloride Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry. ,vol. 27, pp. 381- 386 ,(1971) , 10.1107/S0567740871002267
S. Aml, B. Bomgren, H.B. Borén, H. Karlsson, A.C. Maehly, The use of 13C NMR spectroscopy in forensic drug analysis. Forensic Science International. ,vol. 19, pp. 271- 280 ,(1982) , 10.1016/0379-0738(82)90090-1
Jesús Ruiz-Cabello, Geerten W. Vuister, Chrit T.W. Moonen, Peter van Gelderen, Jack S. Cohen, Peter C.M. van Zijl, Gradient-enhanced heteronuclear correlation spectroscopy. Theory and experimental aspects Journal of Magnetic Resonance. ,vol. 100, pp. 282- 302 ,(1992) , 10.1016/J.JMR.2011.09.006
Ralph E Hurd, Boban K John, Gradient-enhanced proton-detected heteronuclear multiple-quantum coherence spectroscopy Journal of Magnetic Resonance. ,vol. 91, pp. 648- 653 ,(1991) , 10.1016/0022-2364(91)90395-A