Analytical characterization of three hallucinogenic N-(2-methoxy)benzyl derivatives of the 2C-series of phenethylamine drugs

Drug Testing and Analysis

Volumn 5, Issue 8, 2013, Pages 634-645

  Zuba, Dariusz ^a   Sekula, Karolina ^a  

^a INSTITUTE OF FORENSIC RESEARCH   (Poland)

Author keywords

Blotter paper; Hallucinogens; Identification; NBOMe

Indexed keywords

COMMERCE; DRUG PRODUCTS; ELECTROSPRAY IONIZATION; FOURIER TRANSFORM INFRARED SPECTROSCOPY; IONIZATION OF GASES; IONS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

4-METHYLPHENYL; BENZYL DERIVATIVES; BLOTTER PAPER; DERIVATIZATIONS; DRUG MARKETS; HALLUCINOGEN; IDENTIFICATION; METHOXY; NBOME; PHENETHYLAMINES;

GAS CHROMATOGRAPHY;

DOPAMINE DERIVATIVE; N (METHOXY)BENZYL DERIVATIVE; PHENETHYLAMINE DERIVATIVE; PSYCHEDELIC AGENT; TRIFLUOROACETIC ANHYDRIDE; UNCLASSIFIED DRUG; [2 (2,5 DIMETHOXY 3,4 DIMETHYLPHENYL) N (2 METHOXYBENZYL)ETHANAMINE]; [2 (2,5 DIMETHOXY 4 METHYLPHENYL) N (2 METHOXYBENZYL)ETHANAMINE]; [2 (4 ETHYL 2,5 DIMETHOXYPHENYL) N (2 METHOXYBENZYL)ETHANAMINE];

ANALYTIC METHOD; ARTICLE; DERIVATIZATION; DRUG MARKETING; DRUG SCREENING; DRUG STRUCTURE; GAS CHROMATOGRAPHY; HUMAN; INFRARED SPECTROSCOPY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; TANDEM MASS SPECTROMETRY;

BLOTTER PAPER; HALLUCINOGENS; IDENTIFICATION; NBOME;

BENZYL COMPOUNDS; CHROMATOGRAPHY, LIQUID; DESIGNER DRUGS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HALLUCINOGENS; MAGNETIC RESONANCE SPECTROSCOPY; PAPER; PHENETHYLAMINES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; SUBSTANCE ABUSE DETECTION;

EID: 84882262697     PISSN: 19427603     EISSN: 19427611     Source Type: Journal    
DOI: 10.1002/dta.1397     Document Type: Article

References (48)

1. EMCDDA. 2011. Annual Report on the State of the Drugs Problem in Europe. Available at: http://www.emcdda.europa.eu/attachements.cfm/att_143743_EN_EMCDDA_AR2011_EN.pdf [30 June 2012].
2. EMCDDA. 2010. Annual Report on the State of the Drugs Problem in Europe. Available at: http://www.emcdda.europa.eu/attachements.cfm/att_120104_EN_EMCDDA_AR2010_EN.pdf [30 June 2012].
3. EMCDDA. 2009. Annual Report on the State of the Drugs Problem in Europe. Available at: http://www.emcdda.europa.eu/attachements.cfm/att_93236_EN_EMCDDA_AR2009_EN.pdf [30 June 2012].
4. EMCDDA. 2008. Annual Report on the State of the Drugs Problem in Europe. Available at: http://www.emcdda.europa.eu/attachements.cfm/att_64227_EN_EMCDDA_AR08_en.pdf [30 June 2012].
5. D. Zuba, B. Byrska . Prevalence and co-existence of active components of 'legal highs'. Drug Test. Anal. 2012, DOI: 10.1002/dta.1365
6. D. Zuba . Identification of cathinones and other active components of 'legal highs' by mass spectrometric methods. Trends Anal. Chem. 2012, 32, 15.
7. S.D. Brandt, H.R. Sumnall, F. Measham, J. Cole . Analyses of second-generation 'legal highs' in the UK: Initial findings. Drug Test. Anal. 2010, 2, 377.
8. D.M. Wood, S. Davies, G. Smith, J. Button, J. Ramsey, D.W. Holt, et al. Analytical findings of systematically purchased 'legal highs' from the Internet. Toxicol. Lett. 2010, 196, S296.
9. G.G. Davis . Drug abuse: Newly-emerging drugs and trends. Clin. Lab. Med. 2012, DOI: 10.1016/j.cll.2012.06.002
10. D.E. Nichols . Hallucinogens. Pharmacol. Ther. 2004, 101, 131.
11. R.A. Glennon, R. Raghupathi, P. Bartyzel, M. Teitler, S. Leonhardt . Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: Evidence for a lack of selectivity. J. Med. Chem. 1992, 35, 734.
12. W.A. Heller, J.M. Baraban . Potent agonist activity of DOB at 5-HT2 receptors in guinea pig trachea. Eur. J. Pharmacol. 1987, 138, 115.
13. E. Sanders-Bush, K.D. Burris, K. Knoth . Lysergic acid diethylamide and 2, 5-dimethoxy-4-methylamphetamine are partial agonists at serotonin receptors linked to phosphoinositide hydrolysis. J. Pharmacol. Exp. Ther. 1988, 246, 924.
14. M.R. Seggel, M.Y. Yousif, R.A. Lyon, M. Titeler, B.L. Roth, E.A. Suba, et al. A structure-affinity study of the binding of 4-substituted analogues of 1-(2, 5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors. J. Med. Chem. 1990, 33, 1032.
15. A. Shulgin, A. Shulgin, Phenethylamines I Have Known And Loved: A Chemical Love Story, Transform Press, Berkeley, CA, 1991.
16. G. Beuerle, K.A. Kovar, M. Schulze-Alexandru . Three-dimensional quantitative structure-activity relationships of hallucinogenic phenylalkanamine and tryptamine derivatives. Studies using comparative molecular field analysis (CoMFA). Quant. Struct-Act. Rel. 1997, 16, 447.
17. B.W. Clare . The frontier orbital phase angles: Novel QSAR descriptors for benzene derivatives, applied to phenylalkylamine hallucinogens. J. Med. Chem. 1998, 41, 3845.
18. R.A. Glennon, L.B. Kier, A.T. Shulgin . Molecular connectivity analysis of halluciogenic mescaline analogs. J. Pharm. Sci. 1979, 68, 906.
19. S.P Gupta, M.C Bindal, P. Singh . Quantitative structure-activity studies on hallucinogenic mescaline analogs using modified first order valence connectivity. Arzneimittelforschung 1982, 32, 1223.
20. L.B. Kier, R.A. Glennon . Progress with several models for the study of the SAR of hallucinogenic agents. NIDA Res. Monogr. 1978, 22, 159.
21. G. Klopman, O.T. Macina . Use of the computer automated structure evaluation program in determining quantitative structure-activity relationships within hallucinogenic phenylalkylamines. J. Theor. Biol. 1985, 113, 637.
22. M. Mracec, M. Mracec, L. Kurunczi, T. Nusser, Z. Simon, G. Naray-Szabo . QSAR study with steric (MTD), electronic and hydrophobicity parameters on psychotomimetic phenylalkylamines. Theochem. 1996, 367, 139.
23. M. Thakur, A. Thakur, P.V. Khadikar . QSAR studies on psychotomimetic phenylalkylamines. Bioorgan. Med. Chem. 2004, 12, 825.
24. 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.
25. M.D. Cole, C. Lea, N. Oxley . 4-Bromo-2, 5-dimethoxyphenethylamine (2C-B): A review of the public domain literature. Sci. Justice 2002, 42, 223.
26. 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.
27. G. Boatto, M. Nieddu, G. Dessì, P. Manconi, R. Cerri . Determination of four thiophenethylamine designer drugs (2C-T-series) in human plasma by capillary electrophoresis with mass spectrometry detection. J. Chromatogr. A 2007, 1159, 198.
28. D.S. Theobald, H.H. Maurer . Studies on the metabolism and toxicological detection of the designer drug 4-ethyl-2, 5-dimethoxy-β-phenethylamine (2C-E) in rat urine using gas chromatographic-mass spectrometric techniques. J. Chromatogr. B 2006, 842, 76.
29. D. Zuba, K. Sekula . Identification and characterization of 2, 5-dimethoxy-3, 4-dimethyl-β-phenethylamine (2C-G) - a new designer drug. Drug Test. Anal. 2012, DOI: 10.1002/dta.1396
30. D. Zuba, K. Sekula, 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, DOI: 10.1016/j.forsciint.2012.07.006
31. 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.
32. M.E. Silva, Theoretical Study of the Interaction of Agonists with the 5-HT2A Receptor, PhD thesis, University Regensburg, Regensburg, 2008.
33. R. Heim, Synthesis and Pharmacology of Potent 5-HT2A Receptor Agonists with N-2-Methoxybenzyl Partial Structure, PhD thesis, Free University, Berlin, 2003.
34. M.R. Braden, Towards a Biophysical Understanding of Hallucinogen Action, PhD thesis, Purdue University, West Lafayette, IN, USA, 2007.
35. C.C. Halter, Mescaline analogs as partial 5-HT2A receptor Agonists: Synthesis and Pharmacological In Vitro Testing, Dipl. Chem, Diploma thesis, University Regensburg, Regensburg, 2004.
36. R. Heim, H.H. Pertz, I. Walther, S. Elz . Congeners of 3-(2-benzylaminoethyl)-2, 4-quinazolindione: Partial agonists for rat vascular 5-HT2A receptors. Naunyn-Schmiedeberg's Arch. Pharmacol. 1998, 358, 105.
37. 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.
38. 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.
39. M.E. Silva, R. Heim, A. Strasser, S. Elz, S. Dove . Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor. J. Comput. Aided Mol. Des. 2011, 25, 51.
40. D.E. Nichols . Structure-activity relationships of serotonin 5-HT2A agonists. WIREs Membr. Transp. Signal. 2012, 1, 559.
41. J.C. Winter . Hallucinogens as discriminative stimuli in animals: LSD, phenethylamines, and tryptamines. Psychopharmacology 2009, 203, 251.
42. EROWID. NBOMe series. Available at: http://www.erowid.org/chemicals/nbome/ [30 June 2012].
43. Drugs Forum. 25C -NBOMe. Available at: http://www.drugs-forum.com/forum/showwiki.php?title=25C-NBOMe [30 June 2012].
44. EROWID. Definitely a winner: 2C.C NBOMe. Available at: http://www.erowid.org/experiences/exp.php?ID=90107 [30 June 2012].
45. EROWID. This is what I was looking for: 2C-I-NBOMe and Cannabis. Available at: http://www.erowid.org/experiences/exp.php?ID=95967 [30 June 2012].
46. NeuroSoup.com. NBOMe. Available at: http://www.neurosoup.com/nbome.html [30 June 2012].
47. Available at: http://tvnz.co.nz/national-news/new-legal-lsd-like-drug-under-investigation-4772881 [22 May 2012].
48. Stuff.co. Legal high may contain illegal ingredients. Available at: http://www.stuff.co.nz/national/health/6562612/Legal-high-may-contain-illegal-ingredient [22 May 2012].