Ab initio calculations and raman and sers spectral analyses of amphetamine species

Applied Spectroscopy Reviews

Volumn 46, Issue 2, 2011, Pages 107-131

  Berg, Rolf W ^a   Nrbygaard, Thomas ^b   White, Peter C ^c   Abdali, Salim ^d  

^a TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

^b Allerd ^*  (Denmark)

^c ReForensics   (United Kingdom)

^d DANISH CANCER SOCIETY RESEARCH CENTER   (Denmark)

Author keywords

ab initio calculation; amphetamine; conformation; drugs; forensic; identification; IR; molecular orbital; Raman; SERS; Spectroscopy

Indexed keywords

AB INITIO CALCULATIONS; AMPHETAMINE; DRUGS; FORENSIC; IDENTIFICATION; IR; RAMAN; SERS;

CALCULATIONS; HYDROGEN BONDS; MOLECULAR MODELING; MOLECULAR ORBITALS; RAMAN SCATTERING; RAMAN SPECTROSCOPY; SPECTRUM ANALYSIS;

CONFORMATIONS;

EID: 79951939297     PISSN: 05704928     EISSN: 1520569X     Source Type: Journal    
DOI: 10.1080/05704928.2010.520180     Document Type: Article

References (44)

1. Rasmussen, L.B., Olsen, K.H., and Johansen, S.S. (2006) Chiral separation and quantification of R/S-amphetamine, R/S-methamphetamine, R/S-MDA, R/S-MDMA, and R/S-MDEA in whole blood by GC-EI-MS. J. Chrom. B Biomed. Sci. Appl., 842(2): 136-141. (Pubitemid 44416633)
2. Meyer, E., Van Bocxlaer, J.F., Dirinck, I.M., Lambert, W.E., Thienpont, L., and De Leenheer, A.P. (1997) Tissue distribution of amphetamine isomers in a fatal overdose. Belg. J. Anal. Toxicol., 21(3): 236-239. (Pubitemid 27218255)
3. Dirinck, I., Meyer, E., Van Bocxlaer, J., Lambert W., and De Leenheer, A. (1998) Application of gas chromatography-Fourier transform infrared spectrometry to the analysis of amphetamine analogues. J. Chrom., 819(1-2): 155-159. (Pubitemid 28401399)
4. Maurer, H.H., Kraemer, T., Springer, D., and Staack, R.F. (2004) Chemistry, pharmacology, toxicology, and hepatic metabolism of designer drugs of the amphetamine (ecstasy), piperazine, and pyrrolidinophenone types. A synopsis. Ther. Drug Monit., 26(2): 127-131. (Pubitemid 38501205)
5. Kraemer, T. and Maurer, H.H. (1998) Determination of amphetamine, methamphetamine and amphetamine-derived designer drugs or medicaments in blood and urine. J. Chrom., B713: 163-187. (Pubitemid 28346485)
6. Peters, F.T., Kraemer, T., and Maurer, H.H. (2002) Drug testing in blood: Validated negative-ion chemical ionization gas chromatographic-mass spectrometric assay for determination of amphetamine and methamphetamine enantiomers and its application to toxicology cases. Clin. Chem.,48(9): 1472-1485.
7. Hegedüs, H., Gergely, A., Veress, T., and Zsila, F. (1999) Determination of the enantiomeric purity of amphetamine after derivatization with Sanger's reagent (2,4-dinitrofluorobenzene) by simultaneous dual circular dichroism and ultraviolet spectroscopy. Fresen. J. Anal. Chem.,364(8): 749-752.
8. De Gelder, J., De Gussem, K., Vandenabeele, P., and Moens, L. (2007) Reference database of Raman spectra of biological molecules, J. Raman Spectros., 38: 1133-1147.
9. Kneipp, K., Kneipp, H., Abdali, S., Berg, R.W., and Bohr, H. (2004) Single molecule Raman detection of enkephalin on silver colloidal particles. Spectroscopy, 18(3): 433-440. (Pubitemid 39049873)
10. Bass, V.C. (1978) The identification of sympathomimetic amines by Raman spectroscopy. Foren-sicSci., 11(1): 57-65. (Pubitemid 8297515)
11. Hodges, C.M. and Akhavan, J. (1990) The use of Fourier transform Raman spectroscopy in the forensic identification of illicit drugs and explosives. Spectrochim. Acta Mol. Biomol. Spectros., 46A(2): 303-307.
12. Tsuchihashi, H., Katagi, M., Nishikawa, M., Tatsuno, M., Nishioka, H., Nara, A., Nishio, E., and Petty, C. (1997) Determination ofmethamphetamine and its related compounds using Fourier transform Raman spectroscopy.Appl. Spectros., 51(12): 1796-1799. (Pubitemid 127643750)
13. Bell, S.E.J., Burns, D.T., Dennis, A.C., and Speers, J.S. (2000) Rapid analysis of ecstasy and related phenethylamines in seized tablets by Raman spectroscopy. Analyst, 125(3): 541-544. (Pubitemid 30179332)
14. Carter, J.C., Brewer, W.E., and Angel, S.M. (2000) Raman spectroscopy for the in situ identifi-cation ofcocaine and selected adulterants.Appl. Spectros., 54(12): 1876-1881. (Pubitemid 32133499)
15. Faulds, K., Smith, W.E., Graham, D., and Lacey, R.J. (2002) Assessment of silver and gold sub-strates for the detection of amphetamine sulfate by surface enhanced Raman scattering (SERS). Analyst, 127: 282-286. (Pubitemid 34151248)
16. Day, J.S., Edwards, H.G.M., Dobrowski, S.A., and Voice, A.M. (2004) The detection ofdrugs of abuse in fingerprints using Raman spectroscopy I: Latent fingerprints. Spectrochim. Acta, 60A(3): 563-568.
17. Day, J.S., Edwards, H.G.M., Dobrowski, S.A., and Voice, A.M. (2004) The detection ofdrugs of abuse in fingerprints using Raman spectroscopy II: Cyanoacrylate-fumed fingerprints. Spec-trochim. Acta, 60A(8-9): 1725-1730.
18. Sägmüller, B., Schwarze, B., Brehm, G., Trachta, G., and Schneider, S. (2003) Identification of illicit drugs by a combination of liquid chromatography and surface-enhanced Raman scattering spectroscopy. J. Mol. Struct., 661-662: 279-290. (Pubitemid 38169062)
19. Sägmüller, B., Schwarze, B., Brehm, G., and Schneider, S. (2001) Application of SERS spec-troscopy to the identification of (3,4-methylenedioxy)amphetamine in forensic samples utilizing matrix stabilized silverhalides.Analyst, 126(11): 2066-2071.
20. Ruperez, A., Montes, R., and Laserna, J.J. (1991) Identification of stimulant drugs by surface-enhanced Raman spectrometry on colloidal silver. Vib. Spectros., 2(2-3): 145-154.
21. Sulk, R.A., Corcoran, R.C., and Carron, K.T. (1999) Surface-enhanced Raman scattering de-tection of amphetamine and methamphetamine by modification with 2-mercaptonicotinic acid. Appl. Spectros., 53(8): 954-959.
22. Milhazes, N., Borges, F., Calheiros, R., and Marques, M.P.M. (2004) Identification of synthetic precursors of amphetamine-like drugs using Raman spectroscopy and ab initio calculations:/3-methyl-/3-nitrostyrenederivatives. Analyst, 129(11): 1106-1117.
23. Rasmussen, K.E. and Knutsen, P. (1985) Techniques for the detection and identification of amphetamines and amphetamine-like substances. Bull. Narc., 37(1): 95-112. (Pubitemid 15235655)
24. Hargreaves, M.D., Page, K., Munshi, T., Tomsett, R., Lynch, G., and Edwards, H.G.M. (2008) Analysis of seized drugs using portable Raman spectroscopy in an airport environment\A proof ofprinciple study. J. Raman Spectros., 39: 873-880.
25. Hargreaves, M.D., Burnett, A.D., Munshi, T., Cunningham, J.E., Linfield, E.H., Davies, A.G., and Edwards, H.G.M. (2009) Comparison of near infrared laser excitation wavelengths and its influence on the interrogation of seized drugs-of-abuse by Raman spectroscopy. J. Raman Spectros., 40: 1974-1983.
26. Katainen, E., Elomaa, M., Laakkonen, U.-M., Sippola, E., Niemelä, P., Suhonen, J., and Järvinen, K. (2007) Quantification of amphetamine content in seized street samples by Raman spectroscopy. J. ForensicSci., 52(1): 88-92. (Pubitemid 46018426)
27. West, M.J. and Went, M.J. (2009) The spectroscopic detection of drugs of abuse on textile fibers after recovery with adhesive lifters. Forensic Sci. Int., 189(1-3): 100-103.
28. (See also same article published in Spectrochim Acta. (2009) A71: 1984-1988).
29. Godfrey, P.D., McGlone, S.J., and Brown, R.D. (2001) The shapes of neurotransmitters by millimetrewave spectroscopy: Amphetamine. J. Mol. Struct., 599(1-3): 139-152. (Pubitemid 34044695)
30. Bergin, R. and Carlström, D. (1971) Crystal and molecular structure of amphetamine sulfate. Acta Crystallogr., B27: 2146-2152.
31. Pogorzelec-Glaser, K., Kaszynska, J., Rachocki, A., Tritt-Goc, J., Pislewski, N., and Pietraszko, A. (2009) The crystal structure and evidence of the phase transition in d-amphetamine sulfate, as studied by X-ray crystallography, DSC and NMR spectroscopy. New J. Chem., 33: 1894-1900.
32. + H2PO4-. Acta Crystallogr., B34: 611-615.
33. Leopold, N. and Lendl, B. (2003) A new method for fast preparation of highly surface-enhanced Raman scattering (SERS) active silver colloids at room temperature by reduction of silver nitrate with hydroxylamine hydrochloride. J. Phys. Chem. B, 107: 5723-5727.
34. Berg, R.W., and Nørbygaard, T. (2006) Wavenumber calibration of CCD detector Raman spec-trometers controlled by a sinus arm drive. Appl. Spectros. Rev., 41(2): 165-183. (Pubitemid 43347973)
35. Frisch, M.J.T., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery, J., Jr., Vreven, T., Kudin, K.N., Burant, J.C., Millam, J.M., Iyengar, S.S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G.A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J.E., Hratchian, H.P., Cross, J.B., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Ayala, P.Y., Morokuma, K., Voth, G.A., Salvador, P., Dannenberg, J.J., Zakrzewski, V.G., Dapprich, S., Daniels, A.D., Strain, M.C., Farkas, O., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Ortiz, J.V., Cui, Q., Baboul, A.G., Clifford, S., Cioslowski, J., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Gonzalez, C., Pople, J.A. (2003) Gaussian 03, Rev. B.04, Gaussian, Inc.: Pittsburgh, PA.
36. Bremard, C., Laureyns, J., and Turrell, G. (1989) Polarization measurements in Raman mi-crospectroscopy. J. Chim. Phys., 86(6): 1245-1251.
37. Bremard, C., Dhamelincourt, P., Laureyns, J., and Turrell, G. (1985) The effect of objectivers on polarization measurements in micro-Raman spectrometry. Appl. Spectros., 39(6): 1036-1039. (Pubitemid 15604077)
38. Berg, R.W. and Thorup, N. (2005) The reaction between ZnO and molten Na2S2O7 or K2S2O7 forming Na2Zn(SO4)2 or K2Zn(SO4) 2, studied by Raman spectroscopy and X-ray diffraction. Inorg. Chem. 44(10) 3485-3493.
39. Irish, D.E. and Ozeki, T. (1991) Raman spectroscopy ofinorganic species in solution. InAnalyt-ical Raman Spectroscopy, Grasselli, J.G. and Bulkin, B.J., Eds. Chemical Analysis Series. New York: John Wiley & Sons. Table 4.1, p. 71; ch. 4, pp. 59-106.
40. Nakamoto, K. (1997) Infrared and Raman Spectra ofInorganic and Coordination Compounds, 5th ed. New York: John Wiley & Sons.
41. Knopf, D.A., Luo, B.P., Krieger, U.K., and Koop, T. (2003) Thermodynamic dissociation constant of the bisulphate ion from Raman studies. J. Phys. Chem. A, 107: 4322-4332.
42. Fehrmann, R., Hansen, N.H., and Bjerrum, N.J. (1983) Raman spectroscopic and spectrophoto-metric study of the system K2S2O7-KHSO4 in the temperature range 200-450"C. Inorg. Chem., 22: 4009-4014.
43. Rasmussen, S.B., Hamma, H., Lapina, O.B., Khabibulin, D.F., Eriksen, K.M., Berg, R.W., Hatem, G., and Fehrmann, R. (2003) Thermal, conductivity, NMR and Raman spectroscopic measurements and phase diagram of the Cs2S2O7-CsHSO4 System. J. Phys. Chem. B, 107: 13823-13830.
44. Knudsen, C.B., Kalampounias, A.G., Fehrmann, R., and Boghosian, S. (2008) Thermal disso-ciation of molten KHSO4: Temperature dependence of Raman spectra and thermodynamics. J. Phys. Chem. B, 112: 11996-12000.