Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8.4 MB. #2CE; 2C-E
Blaazer, AR; Smid, P; Kruse, CG. Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT2A receptors. ChemMedChem, 15 Sep 2008, 3 (9), 1299–1309. 461 kB. https://doi.org/10.1002/cmdc.200800133 #13
Ray, TS. Psychedelics and the human receptorome. PLOS ONE, 2 Feb 2010, 5 (2), e9019. 791 kB. https://doi.org/10.1371/journal.pone.0009019
Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 1 Jul 2012, 4 (7-8), 577-590. 1.0 MB. https://doi.org/10.1002/dta.413
Meyers-Riggs, B. The alkylated 2Cs. countyourculture, countyourculture: rational exploration of the underground, 4 Oct 2010.
Glennon, RA; Kier, LB; Shulgin, AT. Molecular connectivity analysis of hallucinogenic mescaline analogs. J. Pharm. Sci., 1 Jan 1979, 68 (7), 906–907. 252 kB. https://doi.org/10.1002/jps.2600680733 #XV
Theobald, DS. The 2C-series—A new class of designer drugs. Ph. D. Thesis, Universität des Saarlandes, Saarbrücken, Germany, 18 Dec 2006. 1.4 MB.
Shulgin, AT. Abused substances. Tech. Rev., 1 Jan 2005, August, 80–81. 415 kB.
Altun, A; Golcuk, K; Kumru, M; Jalbout, AF. Electron-conformation study for the structure-hallucinogenic activity relationships of phenylalkylamines. Bioorg. Med. Chem., 1 Dec 2003, 11 (24), 3861–3868. 577 kB. https://doi.org/10.1016/S0968-0896(03)00437-1 #11
Lewin, AH; Navarro, HA; Mascarella, SW. Structure-activity correlations for β-phenethylamines at human trace amine receptor 1. Bioorg. Med. Chem., 1 Aug 2008, 16 (15), 7415-7423. 366 kB. https://doi.org/10.1016/j.bmc.2008.06.009
McGrane, O; Simmons, J; Jacobsen, E; Skinner, C. Alarming trends in a novel class of designer drugs. J. Clinic. Toxicol., 1 Nov 2011, 1 (2), 1000108. 775 kB. https://doi.org/10.4172/2161-0495.1000108
Kusin, S; Tesar, J; Hatten, B; Horowitz, BZ; Hendrickson, R; Leman, R; Buser, G. Severe methemoglobinemia and haemolytic anemia from aniline purchased as 2C-E (4-ethyl-2,5-dimethoxyphenethylamine), a recreational drug, on the internet – Oregon, 2011. MMWR, 10 Feb 2012, 61 (5), 85–88. 273 kB.
Thakur, M; Thakur, A; Khadikar, PV. QSAR studies on psychotomimetic phenylalkylamines. Bioorg. Med. Chem., 15 Feb 2004, 12 (4), 825–831. 323 kB. https://doi.org/10.1016/j.bmc.2003.10.027 #14
Meyer, MR; Robert, A; Maurer, HH. Toxicokinetics of novel psychoactive substances: Characterization of N-acetyltransferase (NAT) isoenzymes involved in the phase II metabolism of 2C designer drugs. Toxicol. Lett., 5 Jun 2014, 227 (2), 124–128. 865 kB. https://doi.org/10.1016/j.toxlet.2014.03.010
Chapman, SJ; Avanes, AA. PeakAL: Protons I Have Known and Loved — Fifty Shades of Grey-Market Spectra. BLOTTER, 1 Aug 2015, 1 (1). 2.6 MB. https://doi.org/10.16889/isomerdesign-1
Chapman, SJ; Avanes, AA. PeakAL: Protons I Have Known and Loved — Fifty Shades of Grey-Market Spectra. Supplementary Data. BLOTTER, 1 Aug 2015, 1 (1). 11.9 MB. https://doi.org/10.16889/isomerdesign-1-supp
Maurer, HH. Chemistry, pharmacology, and metabolism of emerging drugs of abuse. Ther. Drug Monit., 1 Oct 2010, 32 (5), 544–549. 142 kB. https://doi.org/10.1097/FTD.0b013e3181eea318 #2C-E
Rickli, A; Luethi, D; Reinisch, J; Buchy, D; Hoener, MC; Liechti, ME. Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs). Neuropharmacology, 1 Dec 2015, 99, 546–553. 625 kB. https://doi.org/10.1016/j.neuropharm.2015.08.034 #2C-E
McGonigal, MK; Wilhide, JA; Smith, PB; Elliott, NM; Dorman, FL. Analysis of synthetic phenethylamine street drugs using direct sample analysis coupled to accurate mass time of flight mass spectrometry. Forensic Sci. Int., 1 Jun 2017, 275, 83–89. 2.3 MB. https://doi.org/10.1016/j.forsciint.2017.02.025 #2C-E
Theobald, DS; Maurer, HH. Identification of monoamine oxidase and cytochrome P450 isoenzymes involved in the deamination of phenethylamine-derived designer drugs (2C-series). Biochem. Pharmacol., 1 Jan 2007, 73 (2), 287–297. 365 kB. https://doi.org/10.1016/j.bcp.2006.09.022 #2C-E
EMCDDA. New drugs in Europe, 2011, European Monitoring Centre for Drugs and Drug Addiction, Lisbon, 1 Apr 2012. 401 kB.
Zhang, S; Fan, Y; Shi, Z; Cheng, S. DFT-based QSAR and action mechanism of phenylalkylamine and tryptamine hallucinogens. Chin. J. Chem., 1 Apr 2011, 29 (4), 623–630. 166 kB. https://doi.org/10.1002/cjoc.201190132 #9
Montenarh, D; Hopf, M; Warth, S; Maurer, HH; Schmidt, P; Ewald, AH. A simple extraction and LC-MS/MS approach for the screening and identification of over 100 analytes in eight different matrices: Detection of 130 analytes in eight biosamples using only one LC-MS/MS method. Drug Test. Anal., 1 Mar 2015, 7 (3), 214-240. 593 kB. https://doi.org/10.1002/dta.1657
Vidal Giné, C; Espinosa, IF; Vilamala, MV. New psychoactive substances as adulterants of controlled drugs. A worrying phenomenon? Drug Test. Anal., 1 Jul 2014, 6 (7-8), 819-824. 113 kB. https://doi.org/10.1002/dta.1610
King, LA. New phenethylamines in Europe. Drug Test. Anal., 1 Jul 2014, 6 (7-8), 808-818. 472 kB. https://doi.org/10.1002/dta.1570
Takahashi, M; Nagashima, M; Suzuki, J; Seto, T; Yasuda, I; Yoshida, T. Creation and application of psychoactive designer drugs data library using liquid chromatography with photodiode array spectrophotometry detector and gas chromatography–mass spectrometry. Talanta, 15 Feb 2009, 77 (4), 1245–1272. 1.2 MB. https://doi.org/10.1016/j.talanta.2008.07.062 #2C-E
Shulgin, AT. Basic Pharmacology and Effects. In Hallucinogens. A Forensic Drug Handbook; Laing, R; Siegel, JA, Eds., Academic Press, London, 24 Apr 2003; pp 67–137. 6.3 MB.
Braun, U; Braun, G; Jacob, P; Nichols, DE; Shulgin, AT. Mescaline Analogs: Substitutions at the 4-Position. In QuaSAR: Quantitative Structure Activity Relationships of Analgesics, Narcotic Antagonists, and Hallucinogens. NIDA Research Monograph 22; Barnett, G; Trsic, M; Willette, RE, Eds., U.S. Department of Health and Human Services, National Institute of Health, U.S. Government Printing Office, Washington, DC, 1 Jan 1978; pp 27–37. 497 kB. Rhodium.
Jacob, P; Shulgin, AT. Structure-activity relationships of the classic hallucinogens and their analogs. In Hallucinogens: An update. NIDA Research Monograph 146; Lin, GC; Glennon, RA, Eds., U.S. Department of Health and Human Services, National Institute of Health, U.S. Government Printing Office, Washington, DC, 1 Jan 1994; pp 74–91. 51 kB.
Shulgin, AT. Chemistry of psychotomimetics. In Handbook of Experimental Pharmacology. Psychotropic Agents, Part III: Alcohol and Psychotomimetics, Psychotropic Effects of Central Acting Drugs; Hoffmeister, F; Stille, G, Eds., Springer-Verlag, Berlin, 1 Jan 1982; Vol. 55 (3), pp 3–29. 928 kB. https://doi.org/10.1007/978-3-642-67770-0_1 #10g
Li, Y; Wang, M; Li, A; Zheng, H; Wei, Y. Identification of the impurities in 2,5-dimethoxy-4-ethylphenethylamine tablets by high performance liquid chromatography mass spectrometry-ion trap-time of flight. Anal. Methods, 24 Nov 2016, 8 (46), 8179–8187. 1.1 MB. https://doi.org/10.1039/C6AY02162J #2C-E
Adamowicz, P; Zuba, D. Discrimination among designer drug isomers by chromatographic and spectrometric methods. In Chromatographic Techniques in the Forensic Analysis of Designer Drugs; Kowalska, T; Sajewicz, M; Sherma, J, Eds., CRC Press, Taylor & Francis Group, 1 Jan 2018; pp 211–232. 1.1 MB.
Nagai, F; Nonaka, R; Kamimura, KSH. The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain. Eur. J. Pharmacol., 22 Mar 2007, 559 (2), 132–137. 399 kB. https://doi.org/10.1016/j.ejphar.2006.11.075 #2C-E
Seto, T; Takahashi, M; Nagashima, M; Suzuki, J; Yasuda, I. The identifications and the aspects of the commercially available uncontrolled drugs purchased between Apr. 2003 and Mar. 2004. Ann. Rep. Tokyo Metr. Inst. P. H., 1 Jan 2005, 56 75–80. 1.2 MB. #2C-E MS,NMR,UV
Wagmann, L; Brandt, SD; Stratford, A; Maurer, HH; Meyer, MR. Interactions of phenethylamine-derived psychoactive substances of the 2C-series with human monoamine oxidases. Drug Test. Anal., 6 Sep 2018, 11 (2), 318-324. 650 kB. https://doi.org/10.1002/dta.2494 #2C-E
Zamberlan, F; Sanz, C; Vivot, RM; Pallavicini, C; Erowid, F; Erowid, E; Tagliazucchi, E. The varieties of the psychedelic experience: A preliminary study of the association between the reported subjective effects and the binding affinity profiles of substituted phenethylamines and tryptamines. Front. Integr. Neurosci., 8 Nov 2018, 12 (54). 5.0 MB. https://doi.org/10.3389/fnint.2018.00054 #2C-E
Passie, T; Brandt, SD. Self-experiments with psychoactive substances: A historical perspective. In New Psychoactive Substances: Pharmacology, Clinical, Forensic and Analytical Toxicology; Maurer, HH; Brandt, SD, Eds., Springer, Berlin, Heidelberg, 1 Jan 2018; pp 69-110. 563 kB. https://doi.org/10.1007/164_2018_177 #2C-E
Luethi, D; Liechti, ME. Monoamine transporter and receptor interaction profiles in vitro predict reported human doses of novel psychoactive stimulants and psychedelics. Int. J. Neuropsychoph., 1 Oct 2018, 21 (10), 926–931. 254 kB. https://doi.org/10.1093/ijnp/pyy047 #S2 Phenethylamines 2C-E
Bork, W; Dahlenburg, R; Gimbel, M; Jacobsen-Bauer, A; Zörntlein, S. Herleitung Von Grenzwerten Der „nicht Geringen Menge“ Im Sinne Des Btmg. Toxichem Krimtech, 1 Jan 2019, 86 (1), 5–91. 4.4 MB. #HP-010
Sexton, JD; Nichols, CD; Hendricks, PS. Population survey data informing the therapeutic potential of classic and novel phenethylamine, tryptamine, and lysergamide psychedelics. Front. Psychiatry, 11 Feb 2020, 10 (896). 529 kB. https://doi.org/10.3389/fpsyt.2019.00896 #2C-E
Palamar, JJ; Acosta, P. A qualitative descriptive analysis of effects of psychedelic phenethylamines and tryptamines. Hum. Psychopharmacol. Clin. Exp., 1 Jan 2020, 35 (1), e2719. 764 kB. https://doi.org/10.1002/hup.2719 #2C-E
Pottie, E; Cannaert, A; Stove, CP. In vitro structure–activity relationship determination of 30 psychedelic new psychoactive substances by means of β-arrestin 2 recruitment to the serotonin 2A receptor. Arch. Toxicol., 1 Oct 2020, 94 (10), 3449–3460. 919 kB. https://doi.org/10.1007/s00204-020-02836-w #2C-E
Clancy, L; Philp, M; Shimmon, R; Fu, S. Development and validation of a color spot test method for the presumptive detection of 25-NBOMe compounds. Drug Test. Anal., 19 Aug 2020, 13 (5), 929-943. 11.3 MB. https://doi.org/10.1002/dta.2905 #2C-E
Åstrand, A; Guerrieri, D; Vikingsson, S; Kronstrand, R; Green, H. In vitro characterization of new psychoactive substances at the μ-opioid, CB1, 5HT1A, and 5-HT2A receptors—On-target receptor potency and efficacy, and off-target effects. Forensic Sci. Int., 1 Dec 2020, 317, 110553. 1.7 MB. https://doi.org/10.1016/j.forsciint.2020.110553 #2C-E
Araneda, JF; Baumgarte, M; Lange, M; Maier, AFG; Riegel, SD. Identification of seven psychedelic 2,5‐dimethoxyphenylethylamine‐based designer drugs via benchtop 1H nuclear magnetic resonance spectroscopy. Magn. Reson. Chem., 23 Aug 2021, n/a. 1.2 MB. https://doi.org/10.1002/mrc.5205 #4 NMR
Zuba, D; Sekuła, K. Analytical characterization of three hallucinogenic N-(2-methoxy)benzyl derivatives of the 2C-series of phenethylamine drugs. Drug Test. Anal., 1 Aug 2013, 5 (8), 634–645. 1.1 MB. https://doi.org/10.1002/dta.1397 #2C-E MS,NMR,IR
Kikura-Hanajiri, R; Kawamura, M; Uchiyama, N; Ogata, J; Kamakura, H; Saisho, K; Goda, Y. Analytical data of designated substances (shitei-yakubutsu) controlled by the pharmaceutical affairs law in Japan, Part I: GC-MS and LC-MS. Yakugaku Zasshi, 1 Jun 2008, 128 (6), 971–979. 1.4 MB. https://doi.org/10.1248/yakushi.128.971 #2C-E Incorrect structures drawn. Corrected structures in errata page at end. GC,LC,MS,UV
Uchiyama, N; Kawamura, M; Kamakura, H; Kikura-Hanajiri, R; Goda, Y. Analytical data of designated substances (shitei-yakubutsu) controlled by the pharmaceutical affairs law in Japan, Part II: Color test and TLC. Yakugaku Zasshi, 1 Jan 2008, 128 (6), 981–987. 406 kB. https://doi.org/10.1248/yakushi.128.981 #2C-E TLC
Clare, BW. Structure-activity correlations for psychotomimetics. 1. Phenylalkylamines: electronic, volume, and hydrophobicity parameters. J. Med. Chem., 1 Feb 1990, 33 (2), 687–702. 2.8 MB. https://doi.org/10.1021/jm00164a036 #16
Gupta, SP; Singh, P; Bindal, MC. QSAR studies on hallucinogens. Chem. Rev., 1 Dec 1983, 83 (6), 633–649. 2.8 MB. https://doi.org/10.1021/cr00058a003 #47
Clare, BW. The frontier orbital phase angles: Novel QSAR descriptors for benzene derivatives, applied to phenylalkylamine hallucinogens. J. Med. Chem., 24 Sep 1998, 41 (20), 3845–3856. 239 kB. https://doi.org/10.1021/jm980144c #6