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Volumn 5, Issue 7, 2013, Pages 549-559

Identification and characterization of 2,5-dimethoxy-3,4-dimethyl-β-phenethylamine (2C-G) - A new designer drug

Author keywords

Designer drugs; Identification; Legal highs; Phenethylamines

Indexed keywords

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

EID: 84880147510     PISSN: 19427603     EISSN: 19427611     Source Type: Journal    
DOI: 10.1002/dta.1396     Document Type: Article
Times cited : (22)

References (42)
  • 1
    • 79960631787 scopus 로고    scopus 로고
    • A brief history of 'new psychoactive substances'
    • L.A. King, A.T. Kicman. A brief history of 'new psychoactive substances'. Drug Test. Anal. 2011, 3, 401.
    • (2011) Drug Test. Anal. , vol.3 , pp. 401
    • King, L.A.1    Kicman, A.T.2
  • 2
    • 77956642096 scopus 로고    scopus 로고
    • Analyses of second generation 'legal highs' in the UK: initial findings
    • 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.
    • (2010) Drug Test. Anal. , vol.2 , pp. 377
    • Brandt, S.D.1    Sumnall, H.R.2    Measham, F.3    Cole, J.4
  • 3
    • 77957949654 scopus 로고    scopus 로고
    • Determination of piperazine derivatives in 'legal highs'
    • B. Byrska, D. Zuba, R. Stanaszek. Determination of piperazine derivatives in 'legal highs'. Probl. Forensic Sci. 2010, 82, 101.
    • (2010) Probl. Forensic Sci. , vol.82 , pp. 101
    • Byrska, B.1    Zuba, D.2    Stanaszek, R.3
  • 4
    • 79951517620 scopus 로고    scopus 로고
    • Naphyrone: Analytical profile of the new "legal high" substitute for mephedrone
    • G. De Paoli, P.D. Maskell, D.J. Pounder. Naphyrone: Analytical profile of the new "legal high" substitute for mephedrone. J. Forensic Legal Med. 2011, 18, 93.
    • (2011) J. Forensic Legal Med. , vol.18 , pp. 93
    • De Paoli, G.1    Maskell, P.D.2    Pounder, D.J.3
  • 5
    • 79959534957 scopus 로고    scopus 로고
    • Identification and characterization of the new designer drug 4-methylethcathinone (4-MEC) and elaboration of a novel liquid chromatography-tandem mass spectrometry (LC-MS/MS) screening method for seven different methcathinone analogs
    • P. Jankovics, A. Varadi, L. Tolgyesi, S. Lohner, J. Nemeth-Palotas, H. Koszegi-Szalai. Identification and characterization of the new designer drug 4-methylethcathinone (4-MEC) and elaboration of a novel liquid chromatography-tandem mass spectrometry (LC-MS/MS) screening method for seven different methcathinone analogs. Forensic Sci. Int. 2011, 210, 213.
    • (2011) Forensic Sci. Int. , vol.210 , pp. 213
    • Jankovics, P.1    Varadi, A.2    Tolgyesi, L.3    Lohner, S.4    Nemeth-Palotas, J.5    Koszegi-Szalai, H.6
  • 6
    • 80052336996 scopus 로고    scopus 로고
    • The analysis of substituted cathinones. Part 2: An investigation into the phenylacetone based isomers of 4-methylmethcathinone and N-ethylcathinone
    • S.D. McDermott, J.D. Power, P. Kavanagh, J. O'Brien. The analysis of substituted cathinones. Part 2: An investigation into the phenylacetone based isomers of 4-methylmethcathinone and N-ethylcathinone. Forensic Sci. Int. 2011, 212, 13.
    • (2011) Forensic Sci. Int. , vol.212 , pp. 13
    • McDermott, S.D.1    Power, J.D.2    Kavanagh, P.3    O'Brien, J.4
  • 7
    • 83055176351 scopus 로고    scopus 로고
    • Raman spectroscopy for forensic examination of β-ketophenethylamine 'legal highs': Reference and seized samples of cathinone derivatives
    • S.P. Stewart, S.E.J. Bell, N.C. Fletcher, S. Bouazzaoui, Y.C. Ho, S.J. Speers, et al. Raman spectroscopy for forensic examination of β-ketophenethylamine 'legal highs': Reference and seized samples of cathinone derivatives. Anal. Chim. Acta 2012, 711, 1.
    • (2012) Anal. Chim. Acta , vol.711 , pp. 1
    • Stewart, S.P.1    Bell, S.E.J.2    Fletcher, N.C.3    Bouazzaoui, S.4    Ho, Y.C.5    Speers, S.J.6
  • 8
    • 84858797283 scopus 로고    scopus 로고
    • Mass, NMR and IR spectroscopic characterization of pentedrone and pentylone and identification of their isocathinone by-products
    • F. Westphal, T. Junge, U. Girreser, W. Greibl, C. Doering. Mass, NMR and IR spectroscopic characterization of pentedrone and pentylone and identification of their isocathinone by-products. Forensic Sci. Int. 2012, 217, 157.
    • (2012) Forensic Sci. Int. , vol.217 , pp. 157
    • Westphal, F.1    Junge, T.2    Girreser, U.3    Greibl, W.4    Doering, C.5
  • 9
    • 34250359113 scopus 로고    scopus 로고
    • 1-(3-chlorophenyl)piperazine (mCPP)-a new designer drug that is still a legal substance
    • R. Stanaszek, D. Zuba. 1-(3-chlorophenyl)piperazine (mCPP)-a new designer drug that is still a legal substance. Probl. Forensic Sci. 2006, 66, 220.
    • (2006) Probl. Forensic Sci. , vol.66 , pp. 220
    • Stanaszek, R.1    Zuba, D.2
  • 10
    • 84856575678 scopus 로고    scopus 로고
    • Identification of cathinones and other active components of 'legal highs' by mass spectrometric methods
    • D. Zuba. Identification of cathinones and other active components of 'legal highs' by mass spectrometric methods, Trends Anal. Chem. 2012, 32, 15.
    • (2012) Trends Anal. Chem. , vol.32 , pp. 15
    • Zuba, D.1
  • 11
    • 0036826394 scopus 로고    scopus 로고
    • 4-Bromo-2,5-dimethoxyphenethylamine (2C-B): a review of the public domain literature
    • 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.
    • (2002) Sci. Justice , vol.42 , pp. 223
    • Cole, M.D.1    Lea, C.2    Oxley, N.3
  • 12
    • 85153167426 scopus 로고    scopus 로고
    • Wikipedia. Available at: [17 February ].
    • Wikipedia. Available at: http://en.wikipedia.org/wiki/2C-E [17 February 2012].
    • (2012)
  • 13
    • 1842427409 scopus 로고    scopus 로고
    • A new trend in drugs-of-abuse; the 2C-series of phenethylamine designer drugs
    • 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.
    • (2004) Pharm. World Sci. , vol.26 , pp. 110
    • de Boer, D.1    Bosman, I.2
  • 14
    • 34447255719 scopus 로고    scopus 로고
    • Determination of four thiophenethylamine designer drugs (2C-T-series) in human plasma by capillary electrophoresis with mass spectrometry detection
    • 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.
    • (2007) J. Chromatogr. A , vol.1159 , pp. 198
    • Boatto, G.1    Nieddu, M.2    Dessì, G.3    Manconi, P.4    Cerri, R.5
  • 15
    • 7444229150 scopus 로고    scopus 로고
    • 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
    • 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.
    • (2004) J. Chromatogr. B , vol.811 , pp. 27
    • Chiu, Y.C.1    Chou, S.H.2    Liu, J.T.3    Lin, C.H.4
  • 16
    • 33845191282 scopus 로고    scopus 로고
    • Identification of monoamine oxidase and cytochrome P450 isoenzymes involved in the deamination of phenethylamine-derived designer drugs (2C-series)
    • D.S. Theobald, H.H. Maurer. Identification of monoamine oxidase and cytochrome P450 isoenzymes involved in the deamination of phenethylamine-derived designer drugs (2C-series). Biochem. Pharmacol. 2007, 73, 287.
    • (2007) Biochem. Pharmacol. , vol.73 , pp. 287
    • Theobald, D.S.1    Maurer, H.H.2
  • 17
    • 0141682549 scopus 로고    scopus 로고
    • Postmortem identification and quantitation of 2,5-dimethoxy-4-n-propylthiophenethylamine using GC-MSD and GC-NPD
    • B. Curtis, P. Kemp, L. Harty, C. Choi, D. Christensen. Postmortem identification and quantitation of 2, 5-dimethoxy-4-n-propylthiophenethylamine using GC-MSD and GC-NPD. J. Anal. Toxicol. 2003, 27, 493.
    • (2003) J. Anal. Toxicol. , vol.27 , pp. 493
    • Curtis, B.1    Kemp, P.2    Harty, L.3    Choi, C.4    Christensen, D.5
  • 18
    • 85153141353 scopus 로고    scopus 로고
    • European Monitoring Centre for Drugs and Drug Addiction (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
    • European Monitoring Centre for Drugs and Drug Addiction (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.
    • (2004)
  • 19
    • 33748768184 scopus 로고    scopus 로고
    • 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
    • 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.
    • (2006) J. Chromatogr. B , vol.842 , pp. 76
    • Theobald, D.S.1    Maurer, H.H.2
  • 20
    • 0036663630 scopus 로고    scopus 로고
    • A homology-based model of the human 5-HT2A receptor derived from an in silico activated G-protein coupled receptor
    • J.J. Chambers, D.E. Nichols. A homology-based model of the human 5-HT2A receptor derived from an in silico activated G-protein coupled receptor. J. Comput. Aided Mol. Des. 2002, 16, 511.
    • (2002) J. Comput. Aided Mol. Des. , vol.16 , pp. 511
    • Chambers, J.J.1    Nichols, D.E.2
  • 21
    • 0031439559 scopus 로고    scopus 로고
    • Three-dimensional quantitative structure-activity relationships of hallucinogenic phenylalkanamine and tryptamine derivatives. Studies using comparative molecular field analysis (CoMFA)
    • 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. Relat. 1997, 16, 447.
    • (1997) Quant. Struct.-Act. Relat. , vol.16 , pp. 447
    • Beuerle, G.1    Kovar, K.A.2    Schulze-Alexandru, M.3
  • 22
    • 0032563976 scopus 로고    scopus 로고
    • The frontier orbital phase angles: novel QSAR descriptors for benzene derivatives, applied to phenylalkylamine hallucinogens
    • B.W. Clare. The frontier orbital phase angles: novel QSAR descriptors for benzene derivatives, applied to phenylalkylamine hallucinogens. J. Med. Chem. 1998, 41, 3845.
    • (1998) J. Med. Chem. , vol.41 , pp. 3845
    • Clare, B.W.1
  • 23
    • 0018745373 scopus 로고
    • Molecular connectivity analysis of halluciogenic mescaline analogs
    • R.A. Glennon, L.B. Kier, A.T. Shulgin. Molecular connectivity analysis of halluciogenic mescaline analogs. J. Pharm. Sci. 1979, 68, 906.
    • (1979) J. Pharm. Sci. , vol.68 , pp. 906
    • Glennon, R.A.1    Kier, L.B.2    Shulgin, A.T.3
  • 24
    • 0019949211 scopus 로고
    • Quantitative structure-activity studies on hallucinogenic mescaline analogs using modified first order valence connectivity
    • 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.
    • (1982) Arzneimittelforschung , vol.32 , pp. 1223
    • Gupta, S.P.1    Bindal, M.C.2    Singh, P.3
  • 25
    • 0018136424 scopus 로고
    • Progress with several models for the study of the SAR of hallucinogenic agents
    • 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.
    • (1978) NIDA Res. Monogr. , vol.22 , pp. 159
    • Kier, L.B.1    Glennon, R.A.2
  • 26
    • 0022412379 scopus 로고
    • Use of the Computer Automated Structure Evaluation program in determining quantitative structure-activity relationships within hallucinogenic phenylalkylamines
    • 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.
    • (1985) J. Theor. Biol. , vol.113 , pp. 637
    • Klopman, G.1    Macina, O.T.2
  • 27
    • 0041625695 scopus 로고    scopus 로고
    • QSAR study with steric (MTD), electronic and hydrophobicity parameters on psychotomimetic phenylalkylamines
    • 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.
    • (1996) Theochem , vol.367 , pp. 139
    • Mracec, M.1    Mracec, M.2    Kurunczi, L.3    Nusser, T.4    Simon, Z.5    Naray-Szabo, G.6
  • 29
    • 33646836082 scopus 로고    scopus 로고
    • Effect of 4-substitution on psychotomimetic activity of 2,5-dimethoxy amphetamines as studied by means of different substituent parameter scales
    • 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.
    • (2006) Bioorg. Med. Chem. Lett. , vol.16 , pp. 3495
    • Neuvonen, K.1    Neuvonen, H.2    Fulop, F.3
  • 30
    • 0028671876 scopus 로고
    • Structure-activity relationships of the classic hallucinogens and their analogs
    • P. Jacob III, A.T. Shulgin. Structure-activity relationships of the classic hallucinogens and their analogs. NIDA Res. Monogr. 1994, 146, 74.
    • (1994) NIDA Res. Monogr. , vol.146 , pp. 74
    • Jacob III, P.1    Shulgin, A.T.2
  • 31
    • 54849439730 scopus 로고    scopus 로고
    • Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT2A receptors
    • A.R. Blaazer, P. Smid, C.G. Kruse. Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT2A receptors. ChemMedChem 2008, 3, 1299.
    • (2008) ChemMedChem , vol.3 , pp. 1299
    • Blaazer, A.R.1    Smid, P.2    Kruse, C.G.3
  • 32
    • 0021269364 scopus 로고
    • The ethyl homologues of mescaline and their monothio analogues
    • P. Jacob III, A.T. Shulgin. The ethyl homologues of mescaline and their monothio analogues. J. Med. Chem. 1984, 27, 881.
    • (1984) J. Med. Chem. , vol.27 , pp. 881
    • Jacob III, P.1    Shulgin, A.T.2
  • 34
    • 85153147404 scopus 로고    scopus 로고
    • Wikipedia. Available at: [17 February ].
    • Wikipedia. Available at: http://en.wikipedia.org/wiki/2C-G [17 February 2012].
    • (2012)
  • 35
    • 0020401756 scopus 로고
    • Behavioral and serotonin receptor properties of 4-substituted derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane
    • R.A. Glennon, R. Young, F. Benington, R.D. Morin. Behavioral and serotonin receptor properties of 4-substituted derivatives of the hallucinogen 1-(2, 5-dimethoxyphenyl)-2-aminopropane. J. Med. Chem. 1982, 25, 1163.
    • (1982) J. Med. Chem. , vol.25 , pp. 1163
    • Glennon, R.A.1    Young, R.2    Benington, F.3    Morin, R.D.4
  • 36
    • 0014994480 scopus 로고
    • 4-Bromo-2,5-dimethoxyphenylisopropylamine - A new centrally active amphetamine analog
    • A.T. Shulgin, T. Sargent, C. Naranjo. 4-Bromo-2, 5-dimethoxyphenylisopropylamine - A new centrally active amphetamine analog. Pharmacology 1971, 5, 103.
    • (1971) Pharmacology , vol.5 , pp. 103
    • Shulgin, A.T.1    Sargent, T.2    Naranjo, C.3
  • 37
    • 48649110790 scopus 로고    scopus 로고
    • Structure-activity correlations for β-phenethylamines at human trace amine receptor 1
    • A.H. Lewin, H.A. Navarro, S.W. Mascarella. Structure-activity correlations for β-phenethylamines at human trace amine receptor 1. Bioorgan. Med. Chem. 2008, 16, 7415.
    • (2008) Bioorgan. Med. Chem. , vol.16 , pp. 7415
    • Lewin, A.H.1    Navarro, H.A.2    Mascarella, S.W.3
  • 38
    • 29144460257 scopus 로고    scopus 로고
    • Differential phospholipase C activation by phenylalkylamine serotonin 5-HT2A receptor agonists
    • J.C. Parrish, M.R. Braden, E. Gundy, D.E. Nichols. Differential phospholipase C activation by phenylalkylamine serotonin 5-HT2A receptor agonists. J. Neurochem. 2005, 95, 1575.
    • (2005) J. Neurochem. , vol.95 , pp. 1575
    • Parrish, J.C.1    Braden, M.R.2    Gundy, E.3    Nichols, D.E.4
  • 39
    • 37449031036 scopus 로고    scopus 로고
    • A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation
    • B.H. Chen, J.T. Liu, W.X. Chen, H.M. Chen, C.H. Lin. A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation. Talanta 2008, 74, 512.
    • (2008) Talanta , vol.74 , pp. 512
    • Chen, B.H.1    Liu, J.T.2    Chen, W.X.3    Chen, H.M.4    Lin, C.H.5
  • 40
    • 84863088980 scopus 로고    scopus 로고
    • Analytical characterization of three trifluoromethyl-substituted methcathinone isomers
    • S.D. Brandt, P.F. Daley, N.V. Cozzi. Analytical characterization of three trifluoromethyl-substituted methcathinone isomers. Drug Test. Anal. 2012, 4, 525.
    • (2012) Drug Test. Anal. , vol.4 , pp. 525
    • Brandt, S.D.1    Daley, P.F.2    Cozzi, N.V.3
  • 41
    • 0026544744 scopus 로고
    • Differentiation of side chain isomers of ring-substituted amphetamines using gas chromatography/infrared/mass spectrometry (GC/IR/MS)
    • W.H. Soine, W. Duncan, R. Lambert, R. Middleberg, H. Finley, D.J. O'Neil. Differentiation of side chain isomers of ring-substituted amphetamines using gas chromatography/infrared/mass spectrometry (GC/IR/MS). J. Forensic Sci. 1992, 37, 513.
    • (1992) J. Forensic Sci. , vol.37 , pp. 513
    • Soine, W.H.1    Duncan, W.2    Lambert, R.3    Middleberg, R.4    Finley, H.5    O'Neil, D.J.6
  • 42
    • 1442338459 scopus 로고    scopus 로고
    • Interpretation of Infrared Spectra, A Practical Approach
    • Ed. R.A. Meyers. John Wiley & Sons Ltd, Chichester, UK
    • J. Coates. Interpretation of Infrared Spectra, A Practical Approach. in Encyclopedia of Analytical Chemistry, (Ed. R.A. Meyers ). John Wiley & Sons Ltd, Chichester, UK, 2000, pp. 10815-10837.
    • (2000) Encyclopedia of Analytical Chemistry , pp. 10815-10837
    • Coates, J.1


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