Shulgin, AT. DOB and other possible prodrugs. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 3 May 2005.
Sargent, T; Kalbhen, DA; Shulgin, AT; Braun, G; Stauffer, H; Kusubov, N. In vivo human pharmacodynamics of the psychodysleptic 4-Br-2,5-dimethoxyphenylisopropylamine labelled with 82Br or 77Br. Neuropharmacology, 1 Jan 1975, 14 (3), 165–174. 1.0 MB. https://doi.org/10.1016/0028-3908(75)90001-5 #4-Br-DPIA
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 #1e IR
Barfknecht, CF; Nichols, DE. Potential psychotomimetics. Bromomethoxyamphetamines. J. Med. Chem., 1 Apr 1971, 14 (4), 370–372. 377 kB. https://doi.org/10.1021/jm00286a026 #6 Rhodium
Shulgin, AT; Sargent, T; Naranjo, C. 4-Bromo-2,5-dimethoxyphenylisopropylamine, a new centrally active amphetamine analog. Pharmacology, 1 Jan 1971, 5 (2), 103–107. 1.0 MB. https://doi.org/10.1159/000136181
Sargent, T; Kalbhen, DA; Shulgin, AT; Stauffer, H; Kusubov, N. A potential new brain-scanning agent: 4-77Br-2,5-dimethoxyphenylisopropylamine (4-Br-DPIA). J. Nucl. Med., 1 Jan 1975, 16 (3), 243–245. 443 kB. #4-Br-DPIA
Parker, MA; Kurrasch, DM; Nichols, DE. The role of lipophilicity in determining binding affinity and functional activity for 5-HT2A receptor ligands. Bioorg. Med. Chem., 1 Jan 2008, 16 (8), 4661–4669. 296 kB. https://doi.org/10.1016/j.bmc.2008.02.033 #7
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 #6 other
Schultz, DM; Prescher, JA; Kidd, S; Marona-Lewicka, D; Nichols, DE; Monte, A. ‘Hybrid’ benzofuran–benzopyran congeners as rigid analogs of hallucinogenic phenethylamines. Bioorg. Med. Chem., 1 Jan 2008, 16 (11), 6242–6251. 228 kB. https://doi.org/10.1016/j.bmc.2008.04.030
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 #DOB
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 #16
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
Halberstadt, AL; Geyer, MA. Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens. Neuropharmacology, 1 Sep 2011, 61 (3), 364–381. 817 kB. https://doi.org/10.1016/j.neuropharm.2011.01.017
Moya, PR; Berg, KA; Gutiérrez-Hernandez, MA; Sáez-Briones, P; Reyes-Parada, M; Cassels, BK; Clarke, WP. Functional selectivity of hallucinogenic phenethylamine and phenylisopropylamine derivatives at human 5-hydroxytryptamine (5-HT)2A and 5-HT2C receptors. J. Pharmacol. Exp. Ther., 1 Jun 2007, 321 (3), 1054–1061. 188 kB. https://doi.org/10.1124/jpet.106.117507
Urban, JD; Clarke, WP; von Zastrow, M; Nichols, DE; Kobilka, B; Weinstein, H; Javitch, JA; Roth, BL; Christopoulos, A; Sexton, PM; Miller,, KJ. Functional selectivity and classical concepts of quantitative pharmacology. J. Pharmacol. Exp. Ther., 1 Jan 2007, 320 (1), 1–13. 567 kB. https://doi.org/10.1124/jpet.106.104463
Scorza, MC; Carrau, C; Silveira, R; Zapata-Torres, G; Cassels, BK; Reyes-Parada, M. Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives. Biochem. Pharmacol., 15 Dec 1997, 54 (12), 1361–1369. 697 kB. https://doi.org/10.1016/S0006-2952(97)00405-X #19
da Costa, JL; Wang, AY; Micke, GA; Maldaner, AO; Romano, RL; Martins-Júnior, HA; Neto, ON; Magg, MF. Chemical identification of 2,5-dimethoxy-4-bromoamphetamine (DOB). Forensic Sci. Int., 20 Dec 2007, 173 (2–3), 130–136. 285 kB. https://doi.org/10.1016/j.forsciint.2007.02.018
Dyer, DC; Nichols, DE; Rusterholz, DB; Barfknecht, CF. Comparative effects of stereoisomers of psychotomimetic phenylisopropylamines. Life Sci., 1 Oct 1973, 13 (7), 885–896. 398 kB. https://doi.org/10.1016/0024-3205(73)90079-9
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
McGraw, NP; Callery, PS; Castagnoli, N. In vitro stereoselective metabolism of the psychotomimetic amine, 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane. An apparent enantiomeric interaction. J. Med. Chem., 1 Jan 1977, 20 (2), 185–189. 661 kB. https://doi.org/10.1021/jm00212a001 #6
Acuña-Castillo, C; Villalobos, C; Moya, PR; Sáez, P; Cassels, BK; Huidobro-Toro, JP. Differences in potency and efficacy of a series of phenylisopropylamine/phenylethylamine pairs at 5-HT2A and 5-HT2C receptors. Br. J. Pharmacol., 1 Jun 2002, 136 (4), 510–519. 232 kB. https://doi.org/10.1038/sj.bjp.0704747
Glennon, RA; Bondarev, ML; Khorana, N; Young, R. β-Oxygenated analogues of the 5-HT2A serotonin receptor agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane. J. Med. Chem., 1 Jan 2004, 47 (24), 6034–6041. 146 kB. https://doi.org/10.1021/jm040082s #1a NMR
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 #1g
Nichols, DE; Shulgin, AT; Dyer, DC. Directional lipophilic character in a series of psychotomimetic phenethylamine derivatives. Life Sci., 15 Aug 1977, 21 (4), 569–576. 320 kB. https://doi.org/10.1016/0024-3205(77)90099-6 #9
White, TJ; Goodman, D; Shulgin, AT; Castagnoli, N; Lee, R; Petrakis, NL. Mutagenic activity of some centrally active aromatic amines in Salmonella typhimurium. Mutat. Res., 1 Jan 1977, 56 (2), 199–202. 256 kB. https://doi.org/10.1016/0027-5107(77)90210-X #8
Anderson, GM; Braun, G; Braun, U; Nichols, DE; Shulgin, AT. Absolute configuration and psychotomimetic activity. 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 8–15. 457 kB.
Domelsmith, LN; Eaton, TA; Houk, KN; Anderson, GM; Glennon, RA; Shulgin, AT; Castagnoli, N; Kollman, PA. Photoelectron spectra of psychotropic drugs. 6. Relationships between physical properties and pharmacological actions of amphetamine analogues. J. Med. Chem., 1 Jan 1981, 24 (12), 1414–1421. 963 kB. https://doi.org/10.1021/jm00144a009 other
Shulgin, AT. Profiles of psychedelic drugs. 10. DOB. J. Psychoactive Drugs, 1 Jan 1981, 13 (1), 99-99. 477 kB. https://doi.org/10.1080/02791072.1981.10471457
Lemaire, D; Jacob, P; Shulgin, AT. Ring substituted beta-methoxyphenethylamines: a new class of psychotomimetic agents active in man. J. Pharm. Pharmacol., 1 Jan 1985, 37 (8), 575–7. 1.8 MB. https://doi.org/10.1111/j.2042-7158.1985.tb03072.x #3d
Nichols, DE; Barfknecht, CF; Rusterholz, DB; Benington, F; Morin, RD. Asymmetric synthesis of psychotomimetic phenylisopropylamines. J. Med. Chem., 1 May 1973, 16 (5), 480–483. 515 kB. https://doi.org/10.1021/jm00263a013 #5o,p
Nichols, DE; Snyder, SE; Oberlender, R; Johnson, MP; Huang, X. 2,3-Dihydrobenzofuran analogues of hallucinogenic phenethylamines. J. Med. Chem., 1 Jan 1991, 34 (1), 276–281. 833 kB. https://doi.org/10.1021/jm00105a043 #5 MS,NMR
Silva, ME; Heim, R; Strasser, A; Elz, S; Dove, S. Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor. J. Comput. Aided Mol. Des., 1 Jan 2011, 25 (1), 51–66. 834 kB. https://doi.org/10.1007/s10822-010-9400-2
Parrish, JC. Toward a molecular understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2006. 5.5 MB.
Cozzi, NV. Pharmacological studies of some psychoactive phenylalkylamines: entactogens, hallucinogens, and anorectics. Ph. D. Thesis, University Of Wisconsin-Madison, 1 Jan 1994. 10.6 MB. #DOB LC,MS,NMR
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.
Silva, ME. Theoretical study of the interaction of agonists with the 5-HT2A receptor. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 26 Aug 2008. 5.9 MB. #35
Rasmussen, K; Glennon, RA; Aghajanian, GK. Phenethylamine hallucinogens in the locus coeruleus: potency of action correlates with rank order of 5-HT2 binding affinity. Eur. J. Pharmacol., 2 Dec 1986, 132 (1), 79–82. 267 kB. https://doi.org/10.1016/0014-2999(86)90014-2 #DOB
Bailey, K; Gagné, DR; Pike, RK. Investigation and identification of the bromination products of dimethoxyamphetamines. J. Assoc. Off. Anal. Chem., 1 Jan 1976, 59 (5), 1162–1169. 1.9 MB. GC,IR,TLC
Glennon, RA; Raghupathi, R; Bartyzel, P; Teitler, M; Leonhardt, S. Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity. J. Med. Chem., 1 Feb 1992, 35 (4), 734–740. 1.1 MB. https://doi.org/10.1021/jm00082a014 #2 NMR
Delliou, D. 4-Bromo-2,5-dimethoxyamphetamine: Psychoactivity, toxic effects and analytical methods. Forensic Sci. Int., 1 May 1983, 21 (3), 259–267. 1.4 MB. https://doi.org/10.1016/0379-0738(83)90131-7 #bromo-DMA GC,LC,IR,UV,TLC
Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. https://doi.org/10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B #S4, S5
Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. https://doi.org/10.1021/jm00177a017 #39 NMR
Parrish, JC; Braden, MR; Gundy, E; Nichols, DE. Differential phospholipase C activation by phenylalkylamine serotonin 5-HT2A receptor agonists. J. Neurochem., 1 Dec 2005, 95 (6), 1575–1584. 301 kB. https://doi.org/10.1111/j.1471-4159.2005.03477.x
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
Fenderson5555. Shulgin’s syntheses of 2,5-DMA, DOB and DOEF. , 5 Dec 2011. . Fenderson5555 3.7 MB.
Kanai, K; Takekawa, K; Kumamoto, T; Ishikawa, T; Ohmori, T. Simultaneous analysis of six phenethylamine-type designer drugs by TLC, LC-MS, and GC-MS. Forensic Toxicol., 1 Nov 2008, 26 (2), 6–12. 406 kB. https://doi.org/10.1007/s11419-008-0041-2
Antun, F; Smythies, JR; Benington, F; Morin, RD; Barfknecht, CF; Nichols, DE. Native fluorescence and hallucinogenic potency of some amphetamines. Experientia, 15 Jan 1971, 27 (1), 62–63. 248 kB. https://doi.org/10.1007/BF02137743 other
Kier, LB; Glennon, RA. Psychotomimetic phenalkylamines as serotonin agonists: An SAR analysis. Life Sci., 8 May 1978, 22 (18), 1589–1593. 238 kB. https://doi.org/10.1016/0024-3205(78)90053-X #9
McKenna, DJ; Saavedra, JM. Autoradiography of LSD and 2,5-dimethoxyphenylisopropylamine psychotomimetics demonstrates regional, specific cross-displacement in the rat brain. Eur. J. Pharmacol., 13 Oct 1987, 142 (2), 313–315. 263 kB. https://doi.org/10.1016/0014-2999(87)90121-X
Maher, HM; Awad, T; DeRuiter, J; Clark, CR. GC-MS and GC-IRD studies on brominated dimethoxyamphetamines: Regioisomers related to 4-Br-2,5-DMA (DOB). Drug Test. Anal., 1 Aug 2012, 4 (7–8), 591–600. 1.5 MB. https://doi.org/10.1002/dta.409
Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; pp 243–333. 2.6 MB. https://doi.org/10.1007/978-1-4757-0510-2_6 #82 Rhodium.
Runyon, SP; Mosier, PD; Roth, BL; Glennon, RA; Westkaemper, RB. Potential modes of interaction of 9-aminomethyl-9,10-dihydroanthracene (AMDA) derivatives with the 5-HT2A receptor: A ligand structure-affinity relationship, receptor mutagenesis and receptor modeling investigation. J. Med. Chem., 13 Nov 2008, 51 (21), 6808–6828. 2.2 MB. https://doi.org/10.1021/jm800771x
Pigott, A; Frescas, SP; McCorvy, JD; Huang, X; Roth, BL; Nichols, DE. trans-2-(2,5-Dimethoxy-4-iodophenyl)cyclopropylamine and trans-2-(2,5-dimethoxy-4-bromophenyl)cyclopropylamine as potent agonists for the 5-HT2 receptor family. Beilstein J. Org. Chem., 8 Oct 2012, 8, 1705–1709. 298 kB. https://doi.org/10.3762/bjoc.8.194 #1b NMR,other
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 #7
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 #2
Ewald, AH; Fritschi, G; Bork, W; Maurer, HH. Designer drugs 2,5-dimethoxy-4-bromo-amphetamine (DOB) and 2,5-dimethoxy-4-bromo-methamphetamine (MDOB): studies on their metabolism and toxicological detection in rat urine using gas chromatographic/mass spectrometric techniques. J. Mass Spectrom., 1 Apr 2006, 41 (4), 487–498. 244 kB. https://doi.org/10.1002/jms.1007
Glennon, RA; Rosecrans, JA; Young, R. Behavioral properties of psychoactive phenylisopropylamines in rats. Eur. J. Pharmacol., 17 Dec 1981, 76 (4), 353–360. 964 kB. https://doi.org/10.1016/0014-2999(81)90106-0 #DOB
Shannon, M; Battaglia, G; Glennon, RA; Titeler, M. 5-HT1 and 5-HT2 binding properties of derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane (2,5-DMA). Eur. J. Pharmacol., 15 Jun 1984, 102 (1), 23–29. 461 kB. https://doi.org/10.1016/0014-2999(84)90333-9 #DOB
Glennon, RA; McKenney, JD; Lyon, RA; Titeler, M. 5-HT1 and 5-HT2 binding characteristics of 1-(2,5-dimethoxy-4-bromophenyl)-2-aminopropane analogs. J. Med. Chem., 1 Feb 1986, 29 (2), 194–199. 919 kB. https://doi.org/10.1021/jm00152a005 #1a NMR,IR
Glennon, RA; Titeler, M; McKenney, JD. Evidence for 5-HT2 involvement in the mechanism of action of hallucinogenic agents. Life Sci., 17 Dec 1984, 35 (25), 2505–2511. 332 kB. https://doi.org/10.1016/0024-3205(84)90436-3 #4,5,8
Halberstadt, AL. Pharmacology and Toxicology of N-Benzylphenethylamine (“NBOMe”) Hallucinogens. In Neuropharmacology of New Psychoactive Substances (NPS): The Science Behind the Headlines; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 18 Jan 2017; pp 283-311. 826 kB. https://doi.org/10.1007/7854_2016_64
Glennon, RA. Bath salts, mephedrone, and methylenedioxypyrovalerone as emerging illicit drugs that will need targeted therapeutic intervention. Adv. Pharmacol., 1 Jan 2014, 69, 581–620. 564 kB. https://doi.org/10.1016/B978-0-12-420118-7.00015-9
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
Isberg, V; Paine, J; Leth-Petersen, S; Kristensen, JL; Gloriam, DE. Structure-activity relationships of constrained phenylethylamine ligands for the serotonin 5-HT2 receptors. PLoS ONE, 7 Nov 2013, 8 (11), e78515. 2.3 MB. https://doi.org/10.1371/journal.pone.0078515
Maruyama, Y; Matsumoto, Y; Noguchi, H; Yamazaki, M; Inde, S. Analysis of 2C-B and related compounds of 2C-B. JCCL, 1 Jan 2000, (39), 41–57. 476 kB. #DOB Japanese, English abstract GC,LC,MS,NMR,IR,UV
DeRuiter, J; Clark, R; Noggle, FT. LC and GC—MS analysis of 4-bromo-2,5-dimethoxyphenethylamine (Nexus) and 2-propanamine and 2-butanamine analogues. J. Chromatogr. Sci., 1 Oct 1995, 33 (10), 583–590. 1.2 MB. https://doi.org/10.1093/chromsci/33.10.583 #DOB GC,LC,MS
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
Ray, TS. Constructing the ecstasy of MDMA from its component mental organs: Proposing the primer/probe method. Med. Hypotheses, 1 Feb 2016, 87 (2016), 48–60. 455 kB. https://doi.org/10.1016/j.mehy.2015.12.018
Kalbhen, DA; Sargent, T; Shulgin, AT; Braun, G; Stauffer, H; Kusubov, N; Nohr, ML. Human pharmacodynamics of the psychodysleptic 4-bromo-2,5-dimethoxyphenylisopropylamine labelled with [82]Br. IRCS (Int. Res. Comm. Sys.), 1 Jan 1974, 2, 1091.
Brimblecombe, RW; Pinder, RM. Hallucinogenic agents, Wright-Scientechnica, Bristol, UK, 1 Jan 1975. 46.2 MB. #3.33
Titeler, M; Lyon, RA; Glennon, RA. Radioligand binding evidence implicates the brain 5-HT2 receptor as a site of action for LSD and phenylisopropylamine hallucinogens. Psychopharmacology, 1 Feb 1988, 94 (2), 213–216. 431 kB. https://doi.org/10.1007/BF00176847 #2,4,9
Collins, M. Some new psychoactive substances: Precursor chemical and synthesis-driver end-products. Drug Test. Anal., 1 Jul 2001, 3 (7–8), 404–416. 178 kB. https://doi.org/10.1002/dta.315
Monte, AP; Marona-Lewicka, D; Cozzi, NV; Nelson, DL; Nichols, DE. Conformationally restricted tetrahydro-1-benzoxepin analogs of hallucinogenic phenethylamines. Med. Chem. Res., 1 Sep 1995, 5 (9), 651–663. 2.0 MB. #1b NMR,IR
Nichols, DE. Chemistry and structure–activity relationships of psychedelics. In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 1-43. 2.6 MB. https://doi.org/10.1007/7854_2017_475 #38
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)
Halberstadt, AL; Geyer, MA. Effect of hallucinogens on unconditioned behavior. In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 159-199. 879 kB. https://doi.org/10.1007/7854_2016_466
López-Giménez, JF; González-Maeso, J. Hallucinogens and serotonin 5-HT2A receptor-mediated signaling pathways. In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 45-73. 712 kB. https://doi.org/10.1007/7854_2017_478
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
Nichols, DE. Structure-activity relationships of serotonin 5-HT2A agonists. WIREs Membr. Transp. Signal, 1 Sep 2012, 1 (5), 559-579. 573 kB. https://doi.org/10.1002/wmts.42 #40
Helm, K. Synthese und funktionelle In-vitro-Pharmakologie neuer Liganden des 5-HT2A-Rezeptors aus der Klasse. Ph. D. Thesis, Universität Regensburg, Dresden, 1 Jan 2014. 3.2 MB. #31 LC,MS,NMR,IR
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.
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 #10mm
Nichols, DE; Oberlender, R. Structure-activity relationships of MDMA-like substances. In Pharmacology and Toxicology of Amphetamine and Related Designer Drugs. NIDA Research Monograph 94; Asghar, K; De Souza, E, Eds., U.S. Department of Health and Human Services, National Institute of Health, U.S. Government Printing Office, Washington, DC, 1 Jan 1989; pp 1-29. 282 kB.
Nichols, DE; Weintraub, HJR; Pfister, WR; Yim, GKW. The use of rigid analogues to probe hallucinogen receptors. 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 70–83. 717 kB.
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.
Anderson, GM; Castagnoli, N; Kollman, PA. Quantitative structure-activity relationships in the 2,4,5-ring-substituted phenylisopropylamines. 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 199–217. 623 kB. #11
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.
Nichols, DE. Medicinal chemistry and structure-activity relationships. In Amphetamine and its Analogs; Cho, AK; Segal, DS, Eds., Academic Press, San Diego, CA, 1 Jan 1994; pp 3–41. 8.1 MB.
Shulgin, AT. Hallucinogens. In Burger’s Medicinal Chemistry, 4th ed., Part III; Wolff, ME, Ed., John Wiley & Sons, Inc., 1 Jan 1981; pp 1109–1137. 4.7 MB. #22ff
Hoffman, AJ. Synthesis and pharmacological evaluation of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives. Ph. D. Thesis, Purdue University, 1 Aug 1987. 9.3 MB. NMR
Shulgin, AT. Psychotomimetic agents. In Psychopharmacological Agents; Gordon, M, Ed., Academic Press, New York, 1 Jan 1976; Vol. 4, pp 59–146. 3.1 MB. #LXXXIV
Martins, D. Analysis of new psychoactive substances: A contribution to forensic chemistry. M. Sc. Thesis, Universidade do Porto, 1 Jan 2014. 2.5 MB. #9 MS,NMR,other
Nichols, DE. Potential psychotomimetics: Bromomethoxyamphetamines and structural congeners of lysergic acid. Ph. D. Thesis, University of Iowa, Iowa City, IA, 1 May 1973. 13.0 MB. #43f NMR,IR,other
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 #DOB
Cole, MD; Lea, C; Oxley, N. 4-Bromo-2,5-dimethoxyphenethylamine (2C-B): a review of the public domain literature. Sci. Justice, 1 Oct 2002, 42 (4), 223–224. 2.0 MB. https://doi.org/10.1016/S1355-0306(02)71832-7 #DOB
Chambers, JJ; Kurrasch-Orbaugh, DM; Parker, MA; Nichols, DE. Enantiospecific synthesis and pharmacological evaluation of a series of super-potent, conformationally restricted 5-HT2A/2C receptor agonists. J. Med. Chem., 1 Mar 2001, 44 (6), 1003–1010. 337 kB. https://doi.org/10.1021/jm000491y #4b NMR
Monte, AP; Marona-Lewicka, D; Parker, MA; Wainscott, DB; Nelson, DL; Nichols, DE. Dihydrobenzofuran analogues of hallucinogens. 3. 1 Models of 4-substituted (2,5-dimethoxyphenyl)alkylamine derivatives with rigidified methoxy groups. J. Med. Chem., 1 Jan 1996, 39 (15), 2953–2961. 290 kB. https://doi.org/10.1021/jm960199j #1b
Parker, MA; Marona-Lewicka, D; Lucaites, VL; Nelson, DL; Nichols, DE. A novel (benzodifuranyl)aminoalkane with extremely potent activity at the 5-HT2A receptor. J. Med. Chem., 1 Dec 1998, 41 (26), 5148–5149. 382 kB. https://doi.org/10.1021/jm9803525 #1 NMR
Glennon, RA; Young, R; Benington, F; Morin, RD. Behavioral and serotonin receptor properties of 4-substituted derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane. J. Med. Chem., 1 Oct 1982, 25 (10), 1163–1168. 780 kB. https://doi.org/10.1021/jm00352a013 #7 NMR,other
Dowd, CS; Herrick-Davis, K; Egan, C; DuPre, A; Smith, C; Teitler, M; Glennon, RA. 1-[4-(3-Phenylalkyl)phenyl]-2-aminopropanes as 5-HT2A partial agonists. J. Med. Chem., 10 Aug 2000, 43 (16), 3074–3084. 271 kB. https://doi.org/10.1021/jm9906062 #1a NMR,IR
Rangisetty, JB; Dukat, M; Dowd, CS; Herrick-Davis, K; DuPre, A; Gadepalli, S; Teitler, M; Kelley, CR; Sharif, NA; Glennon, RA. 1-[2-Methoxy-5-(3-phenylpropyl)]-2-aminopropane unexpectedly shows 5-HT2A serotonin receptor affinity and antagonist character. J. Med. Chem., 1 Jan 2001, 44 (20), 3283–3291. 115 kB. https://doi.org/10.1021/jm0100739 #1a NMR
Glennon, RA; Dukat, M; El-Bermawy, M; Law, H; De Los Angeles, J; Teitler, M; King, A; Herrick-Davis, K. Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines. J. Med. Chem., 1 Jun 1994, 37 (13), 1929–1935. 1.1 MB. https://doi.org/10.1021/jm00039a004 #1 NMR,IR
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 #DOB
Shulgin, AT; Nichols, DE. Characterization of three new psychotomimetics. In The Psychopharmacology of Hallucinogens; Stillman, RC; Willette, RE, Eds., Pergamon, 1 Jan 1978; pp 74–83. 210 kB. https://doi.org/10.1016/B978-0-08-021938-7.50010-2 #1e A different layout of the same paper
Glennon, RA; Liebowitz, SM; Mack, EC. Serotonin receptor binding affinities of several hallucinogenic phenylalkylamine and N,N-dimethyltryptamine analogs. J. Med. Chem., 1 Aug 1978, 21 (8), 822–825. 597 kB. https://doi.org/10.1021/jm00206a022 #4
McCorvy, JD. Mapping the binding site of the 5-HT2A receptor using mutagenesis and ligand libraries: Insights into the molecular actions of psychedelics. Ph. D. Thesis, Purdue University, 1 Jan 2012. 3.9 MB. #DOB
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-017
Julian, EA. Microcrystalline identification of drugs of abuse: The psychedelic amphetamines. J. Forensic Sci., 1 Jul 1990, 35 (4), 821–830. 632 kB. https://doi.org/10.1520/JFS12894J #DOB other
Monte, AP. Structure-activity relationships of hallucinogens: Design, synthesis, and pharmacological evaluation of a series of conformationally restricted phenethylamines. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Aug 1995. 10.7 MB. #DOB MS,NMR
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 #DOB
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 #DOB
Sadzot, B; Baraban, JM; Glennon, RA; Lyon, RA; Leonhardt, S; Jan, C; Titeler, M. Hallucinogenic drug interactions at human brain 5-HT2 receptors: implications for treating LSD-induced hallucinogenesis. Psychopharmacology, 1 Aug 1989, 98 (4), 495–499. 895 kB. https://doi.org/10.1007/BF00441948 #DOB
Sáez-Briones, P; Hernández, A. MDMA (3,4-Methylenedioxymethamphetamine) Analogues as Tools to Characterize MDMA-Like Effects: An Approach to Understand Entactogen Pharmacology. Curr. Neuropharmacol., 1 Sep 2013, 11 (5), 521–534. 1.4 MB. https://doi.org/10.2174/1570159X11311050007 #DOB
Fenderson5555. DOC, DOB, DOI and DOET: Strategic considerations. , 7 Sep 2013. . Fenderson5555 9.5 MB. #DOB
Marcher-Rørsted, E; Halberstadt, AL; Klein, AK; Chatha, M; Jademyr, S; Jensen, AA; Kristensen, JL. Investigation of the 2,5-dimethoxy motif in phenethylamine serotonin 2A receptor agonists. ACS Chem. Neurosci., 26 Mar 2020, 11 (9), 1238-1244. 3.8 MB. https://doi.org/10.1021/acschemneuro.0c00129 #2 LC,MS,NMR
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 #DOB
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 #DOB
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-bromo-2,5-dimethoxyamphetamine
Cumming, P; Scheidegger, M; Dornbierer, D; Palner, M; Quednow, BB; Martin-Soelch, C. Molecular and functional imaging studies of psychedelic drug action in animals and humans. Molecules, 1 Jan 2021, 26 (9), 2451. 3.5 MB. https://doi.org/10.3390/molecules26092451 #12
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 #DOB TLC
Canfield, DV; Lorimer, P; Epstein, RL. Gas chromatographic analysis of amphetamine derivatives and morpholine-related drugs. J. Forensic Sci., 1 Apr 1977, 22 (2), 429–433. 303 kB. https://doi.org/10.1520/JFS10605J #4-bromo-2,5-dimethoxyamphetamine GC
Philp, M; Shimmon, R; Stojanovska, N; Tahtouh, M; Fu, S. Development and validation of a presumptive colour spot test method for the detection of piperazine analogues in seized illicit materials. Anal. Methods, 1 Jan 2013, 5 (20), 5402. 783 kB. https://doi.org/10.1039/c3ay40511g #4-Bromo-2,5-dimethoxyamphetamine MS,NMR,IR,spot
Heim, R. Synthesis and pharmacology of potent 5-HT2A receptor agonists with N-2-methoxybenzyl partial structure. SC. D. Thesis, Freie Universität, Berlin, 1 Jan 2004. 3.9 MB. #35 In German. MS,NMR,IR
Halberstadt, AL. Recent advances in the neuropsychopharmacology of serotonergic hallucinogens. Behav. Brain Res., 15 Jan 2015, 277, 99–120. 4.1 MB. https://doi.org/10.1016/j.bbr.2014.07.016 #DOB
Shulgin, AT. Mescaline: the chemistry and pharmacology of its analogs. Lloydia, 1 Jan 1973, 36 (1), 46–58. 5.6 MB. #37
Glennon, RA; Rosecrans, JA. Indolealkylamine and phenalkylamine hallucinogens: A brief overview. Neurosci. Biobehav. Rev., 1 Jan 1982, 6 (4), 489–497. 895 kB. https://doi.org/10.1016/0149-7634(82)90030-6 #8c,d,e
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 #29
Gerdes, JM; Mathis, CA; Shulgin, AT. Synthesis of 1-[2′,5′-dimethoxy-4′-(β-fluoroethyl)phenyl]-2-aminopropane: Studies related to 18F-labeled serotonin receptor ligands. Tetrahedron Lett., 1 Jan 1988, 129 (50), 6537–6540. 268 kB. https://doi.org/10.1016/S0040-4039(00)82391-6 #1a
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 #40
Kurrasch-Orbaugh, DM. Elucidation of the serotonin 5-HT2A receptor-coupled phospholipase A2 signaling pathway. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 May 2002. 7.9 MB. #DOB
Trachsel, D. Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 3. 4-Ethynyl-2,5-dimethoxyphenethylamine (= 4-Ethynyl-2,5-dimethoxybenzeneethanamine; 2C-YN). Helv. Chim. Acta, 28 Aug 2003, 86 (8), 2754–2759. 84 kB. https://doi.org/10.1002/hlca.200390224 #2a NMR,IR