Structural elucidation and identification of a new derivative of phenethylamine using quadrupole time-of-flight mass spectrometry

Rapid Communications in Mass Spectrometry

Volumn 27, Issue 18, 2013, Pages 2081-2090

  Sekuła, Karolina ^a   Zuba, Dariusz ^a  

^a INSTITUTE OF FORENSIC RESEARCH   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

COMMERCE; DRUG PRODUCTS; ELECTROSPRAY IONIZATION; GAS CHROMATOGRAPHY; IMPACT IONIZATION; IONIZATION OF GASES; LIQUID CHROMATOGRAPHY; MASS SPECTROMETERS; MASS SPECTROMETRY;

ANALYTICAL PROCEDURE; DESIGNER DRUGS; DRUG MARKETS; ELECTRON-IMPACT; ELECTROSPRAY IONIZATION-QUADRUPOLE TIME-OF-FLIGHT MASS SPECTROMETRY; MASS SPECTRA; PHENETHYLAMINES; QUADRUPOLE TIME OF FLIGHT MASS SPECTROMETRY; STRUCTURAL ELUCIDATION; STRUCTURAL IDENTIFICATION;

IONS;

EID: 84882258183     PISSN: 09514198     EISSN: 10970231     Source Type: Journal    
DOI: 10.1002/rcm.6667     Document Type: Article

References (38)

1. EMCDDA, Europol. EU drug markets report. A strategic analysis, 2012. Available: http://www.emcdda.europa.eu/attachements.cfm/att-194336-EN- TD3112366ENC.pdf (accessed January 2013).
2. EMCDDA. Annual Report on the State of the Drugs Problem in Europe, 2011. Available: http://www.emcdda.europa.eu/attachements.cfm/att-143743-EN-EMCDDA- AR2011-EN.pdf (accessed January 2013).
3. EMCDDA. Annual Report on the State of the Drugs Problem in Europe, 2010. Available: http://www.emcdda.europa.eu/attachements.cfm/att-120104-EN-EMCDDA- AR2010-EN.pdf (accessed January 2013).
4. EMCDDA. Annual Report on the State of the Drugs Problem in Europe, 2009. Available: http://www.emcdda.europa.eu/attachements.cfm/att-93236-EN-EMCDDA- AR2009-EN.pdf (accessed January 2013).
5. A. Shulgin, A. Shulgin,. Phenethylamines I Have Known And Loved: A Chemical Love Story, Transform Press, Berkeley, CA, 1991.
6. 125I]-2C-I) as a label for the 5-HT 2 receptor in rat frontal cortex. Pharmacol. Biochem. Behav. 1990, 35, 211.
7. M. Thakur, A. Thakur, P. V. Khadikar,. QSAR studies on psychotomimetic phenylalkylamines. Bioorg. Med. Chem. 2004, 12, 825.
8. K. Neuvonen, H. Neuvonen, F. Fulop,. Effect of 4-substitution on psychotomimetic activity of 2,5-dimethoxy amphetamines as studied by means of different substituent parameter scales. Bioorg. Med. Chem. Lett. 2006, 16, 3495.
9. M. D. Cole, C. Lea, N. Oxley,. 4-Bromo-2,5-dimethoxy-phenethylamine (2C-B): a review of the public domain literature. Sci. Justice 2002, 42, 223.
10. D. de Boer, I. Bosman,. A new trend in drugs-of-abuse; the 2C-series of phenethylamine designer drugs. Pharm. World Sci. 2004, 26, 110.
11. G. Boatto, M. Nieddu, G. Dessì, P. Manconi, R. Cerri,. Determination of four thiophenethylamine designer drugs (2C-T-series) inhuman plasma by capillary electrophoresis with mass spectrometry detection. J. Chromatogr. A 2007, 1159, 198.
12. Y. C. Chiu, S.H. Chou, J.T. Liu, C.H. Lin,. The bioactivity of 2,5-dimethoxy-4-ethylthiophenethylamine (2C-T-2) and its detection in rat urine by capillary electrophoresis combined with an on-line sample concentration technique. J. Chromatogr. B 2004, 811, 27.
13. EMCDDA. Report on the risk assessment of 2C-I, 2C-T-2 and 2C-T-7 in the framework of the joint action on new synthetic drugs, 2004.
14. D. S. Theobald, H. H. Maurer,. Studies on the metabolism and toxicological detection of the designer drug 4-ethyl-2,5-dimethoxy- bphenethylamine (2C-E) in rat urine using gas chromatographic-mass spectrometric techniques. J. Chromatogr. B 2006, 842, 76.
15. D. Zuba, K. Sekuła,. Identification and characterization of 2,5-dimethoxy-3,4-dimethyl-β-phenethylamine (2C-G)-a new designer drug. Drug Test. Anal. 2013, 5, 549.
16. D. Zuba, K. Sekuła, A. Buczek,. Identification and characterization of 2,5-dimethoxy-4-nitro-β-phenethylamine (2C-N)-a new member of 2C-series of designer drug. Forensic Sci. Int. 2012, 222, 298.
17. H. H. Pertz, R. Heim, S. Elz,. N-Benzylated phenylethanamines are highly potent partial agonists at 5-HT2A receptors. Arch. Pharm. Pharm. Med. Chem. 2000, 333, 30.
18. M. E. Silva,. Theoretical study of the interaction of agonists with the 5-HT2A receptor. PhD thesis, University of Regensburg, Regensburg, Germany, 2008.
19. R. Heim,. Synthesis and pharmacology of potent 5-HT2A receptor agonists with N-2-methoxybenzyl partial structure. PhD thesis, Free University, Berlin, 2003.
20. M. R. Braden,. Towards a biophysical understanding of hallucinogen action. PhD thesis, Purdue University, West Lafayette, IN, USA, 2007.
21. C. C. Halter,. Mescaline analogs as partial 5-HT2A receptor agonists: synthesis and pharmacological in vitro testing. Dipl. Chem, Diploma thesis, University of Regensburg, Regensburg, Germany, 2004.
22. R. Heim, H. H. Pertz, M. Zabel, S. Elz,. Stereoselective synthesis, absolute configuration and 5-HT2A agonism of chiral 2-methoxybenzylamines. Arch. Pharm. Pharm. Med. Chem. 2002, 335, 82.
23. M. R. Braden, J. C. Parrish, J. C. Naylor, D. E. Nichols,. Molecular interaction of serotonin 5-HT2A receptor residues Phe339(6.51) and Phe340(6.52) with superpotent N-benzyl phenethylamine agonists. Mol. Pharmacol. 2006, 70, 1956.
24. D. E. Nichols,. Structure-activity relationships of serotonin 5-HT2A agonists. WIREs Membr. Transp. Signal. 2012, 1, 559.
25. M. Hansen,. Design and synthesis of selective serotonin receptor agonists for positron emission tomography imaging of the brain. PhD Thesis, University of Copenhagen, Copenhagen, Denmark, 2011.
26. http://www.shroomery.org/forums/showflat.php/Number/15695659 (accessed January 2013).
27. http://www.drugs-forum.com/forum/showthread.php?t=127848 (accessed January 2013).
28. http://talk.hyperreal.info/25i-nbmd-t34180.html (accessed January 2013).
29. http://murtibing.blog.com/2011/09/10/25i-nbmd-nowa-zabawka-ze-stajni- nicholsa/ (accessed January 2013).
30. http://www.bluelight.ru/vb/threads/601990-The-Main-25I-NBMD-Thread (accessed January 2013).
31. D. Zuba, K. Sekuła,. Analytical characterization of three hallucinogenic N-(2-methoxy)benzyl derivatives of the 2C-series of phenethylamine drugs. Drug Test. Anal. 2012, DOI: 10.1002/dta.1397.
32. D. Zuba, K. Sekuła, A. Buczek,. 25C-NBOMe-New potent hallucinogenic substance identified on the drug market. Forensic Sci. Int. 2013, 227, 7.
33. F. Westphal, P. Rösner, Th. Junge,. Differentiation of regioisomeric ring-substituted fluorophenethylamines with product ion spectrometry. Forensic Sci. Int. 2010, 194, 53.
34. J. Lee, S. Choe, H. Choi, S. Heo, E. Kim, H. Kim, E. Bang, H. Chung,. Identification of N-ethyl-α-ethylphenethylamine in crystalline powder seized for suspected drug trafficking: A research chemical or a new designer drug? Forensic Toxicol. 2013, 31, 54.
35. S. P. Stewart, S. E. J. Bell, N. C. Fletcher, S. Bouazzaoui, Y. C. Ho, S. J. Speers, K. L. Peters,. Raman spectroscopy for forensic examination of β-ketophenethylamine " legal highs": Reference and seized samples of cathinone derivatives. Anal. Chim. Acta 2012, 711, 1.
36. A. M. Al-Hossaini, T. Awad, J. DeRuiter, C. R. Clark,. GC/MS and GC/IRD analysis of ring and side chain regioisomers of ethoxyphenethylamines related to the controlled substances MDEA, MDMMA and MBDB. Forensic Sci. Int. 2010, 200, 73.
37. M. Praisler, I. Dirinck, J. Van Bocxlaer, A. De Leenheer, D. L. Massart,. Identification of novel illicit amphetamines from vapor-phase FTIR spectra-A chemometrical solution. Talanta 2000, 53, 155.
38. S. Castiglioni, E. Zuccato, Ch. Chiabrando, R. Fanelli, R. Bagnati,. Mass spectrometric analysis of illicit drugs in wastewater and surface water. Mass Spectrom. Rev. 2008, 27, 378.