- DOC
- 4-Chloro-2,5-dimethoxyamphetamine
- 2,5-Dimethoxy-4-chloroamphetamine
Coutts, RT; Malicky, JL. The synthesis of some analogs of the hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM) Can. J. Chem., 1 Jan 1973, 51 (9), 1402–1409. 746 kB. https://doi.org/10.1139/v73-210 #1f IR
Aldous, FAB; Barrass, BC; Brewster, K; Buxton, DA; Green, DM; Pinder, RM; Rich, P; Skeels, PM; Tutt, KJ. Structure-activity relationships in psychotomimetic phenylalkylamines J. Med. Chem., 1 Oct 1974, 17 (10), 1100–1111. 1.2 MB. https://doi.org/10.1021/jm00256a016 #5 other
Nelson, DL; Lucaites, VL; Wainscott, DB; Glennon, RA. Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, 5-HT2B and 5-HT2C receptors N-S. Arch. Pharmacol., 1 Jan 1999, 359 (1), 1–6. 66 kB. https://doi.org/10.1007/PL00005315 #DOC
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 #28
Glennon, RA; Dukat, M; Grella, B; Hong, S; Costantino, L; Teitler, M; Smith, C; Egan, C; Davis, K; Mattson, MV. Binding of β-carbolines and related agents at serotonin (5-HT2 and 5-HT1A), dopamine (D2) and benzodiazepine receptors Drug Alcohol Depend., 1 Aug 2000, 60 (2), 121–132. 276 kB. https://doi.org/10.1016/S0376-8716(99)00148-9
Seggel, MR; Yousif, MY; Lyon, RA; Titeler, M; Roth, BL; Suba, EA; Glennon, RA. 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., 1 Mar 1990, 33 (3), 1032–1036. 807 kB. https://doi.org/10.1021/jm00165a023 #1f
Ewald, AH. The 2,5-Dimethoxyamphetamines—A new class of designer drugs Ph. D. Thesis, Universität des Saarlandes, Saarbrücken, Germany, 1 Jan 2008. 195 kB.
Fenderson5555. DOC, DOB, DOI and DOET: Strategic considerations , 7 Sep 2013. . Fenderson5555 9.5 MB. #DOC
Nakanishi, K; Miki, A; Zaitsu, K; Kamata, H; Shima, N; Kamata, T; Katagi, M; Tatsuno, M; Tsuchihashi, H; Suzuki, K. Cross-reactivities of various phenethylamine-type designer drugs to immunoassays for amphetamines, with special attention to the evaluation of the one-step urine drug test Instant-View™, and the Emit® assays for use in drug enforcement Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 174–181. 397 kB. https://doi.org/10.1016/j.forsciint.2011.11.003
Glennon, RA; Seggel, MR. Interaction of phenylisopropylamines with central 5-HT2 receptors. Analysis by quantitative structure-activity relationships In Probing Bioactive Mechanisms; ACS Symposium Series; Magee, PS; Henry, DR; Block, JH, Eds., American Chemical Society, Washington, DC, 14 Nov 1989; Vol. 413, pp 264–280. 4.4 MB. https://doi.org/10.1021/bk-1989-0413.ch018 #6
Ehlers, D; Schäning, J. Synthese von DOC (2,5-dimethoxy-4-chloramphetamin) Toxichem Krimtech, 1 Jan 2001, 68 (2), 62–68. 185 kB. #8 MS,NMR,IR,UV
Ovaska, H; Viljoen, A; Puchnarewicz, M; Button, J; Ramsey, J; Holt, DW; Dargan, PI; Wood, DM. First case report of recreational use of 2,5-dimethoxy-4-chloroamphetamine confirmed by toxicological screening: Eur. J. Emerg. Med., 1 Dec 2008, 15 (6), 354–356. 55 kB. https://doi.org/10.1097/MEJ.0b013e3282fc765b
Martins, D; Barratt, MJ; Pires, CV; Carvalho, H; Ventura, M; Fornís, I; Valente, H. The detection and prevention of unintentional consumption of DOx and 25x-NBOMe at Portugal’s Boom Festival Hum. Psychopharmacol. Clin. Exp., 1 May 2017, 32 (3), e2608. 400 kB. https://doi.org/10.1002/hup.2608
Ogino, M; Naiki, T; Orui, H; Kosone, K; Yamazaki, M. Study of method for identifying phenethylamine drugs JCCL, 11 Feb 2011, 50, 63-82. 627 kB. Japanese, English abstract LC,MS,NMR,IR
Brimblecombe, RW; Pinder, RM. Hallucinogenic agents, Wright-Scientechnica, Bristol, UK, 1 Jan 1975. 46.2 MB. #3.34
Nichols, DE. Psychedelics Pharmacol. Rev., 1 Apr 2016, 68 (2), 264-355. 1.9 MB. https://doi.org/10.1124/pr.115.011478 Updated with published correction to Figure 4 (the α-methyl group was missing in the original)
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
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.
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.
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 #DOC
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 #DOC GC,LC,MS,UV
Takahashi, M; Suzuki, J; Nagashima, M; Seto, T; Yasuda, I. Newly detected compounds in uncontrolled drugs purchased in Tokyo between April 2006 and March 2007 Ann. Rep. Tokyo Metr. Inst. P. H., 1 Jan 2007, 58 83–87. 1.1 MB. #DOC MS,NMR,IR,UV
Chapman, SJ. Novel Psychoactive Spectra: NMR of (mostly) Novel Psychoactive Substances BLOTTER, 25 Jun 2018, 3 (2). https://doi.org/10.16889/isomerdesign-6 #DOC NMR
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-016
Halberstadt, AL; Chatha, M; Klein, AK; Wallach, J; Brandt, SD. Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species Neuropharmacology, 1 May 2020, 167, 107933. 2.4 MB. https://doi.org/10.1016/j.neuropharm.2019.107933 #DOC
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 #DOC
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 #DOC
Hägele, JS; Basrak, M; Schmid, MG. Enantioselective separation of novel psychoactive substances using a Lux® AMP 3 μm column and HPLC-UV J. Pharm. Biomed. Anal., 5 Feb 2020, 179, 112967. 3.6 MB. https://doi.org/10.1016/j.jpba.2019.112967 #A2 LC
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 #DOC
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 #4-chloro-2,5-DMA spot
King, LA. Designer drugs related to amphetamine (1990–1996) JCLIC, 1 Jul 1996, 6 (3), 15-16. 562 kB. #17
de Oliveira Magalhães, L; Arantes, LC; Braga, JWB. Identification of NBOMe and NBOH in blotter papers using a handheld NIR spectrometer and chemometric methods Microchem. J., 1 Jan 2019, 144, 151–158. 2.7 MB. https://doi.org/10.1016/j.microc.2018.08.051 #DOC
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 #DOC TLC
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 #58
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 #42
Duan, W; Cao, D; Wang, S; Cheng, J. Serotonin 2A receptor (5-HT2AR) agonists: Psychedelics and non-hallucinogenic analogues as emerging antidepressants Chem. Rev., 10 Jan 2024, 124 (1), 124–163. 12.6 MB. https://doi.org/10.1021/acs.chemrev.3c00375 #88