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PiHKAL book II entry 2,5-DMA

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Rhodium Shulgin: Synthesis of ¹²¹I and ¹²⁵I radioiodinated 4-iodo-2,5-dimethoxyamphetamine (DOI) (1)
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Shulgin Index #36 2,5-DMA · Table 4Page 335Row 22

PiHKAL #55 3,4-DMA · #62 DOB · #64 DOC · #67 DOI · #90 IDNNA · #124 META-DOB · #126 METHYL-DMA

Phenethylamine: Von der Strucktur zur Funktion 2,5-DMA: 3.15 (46) 283, 284 · 7.1 (34) 467 · 7.2 (46) 478, 479 · 7.3 (2) 489, 490, 491, 492, 494, 495, 496, 497, 504, 507, 509, 515 · 7.4 (3) 532, 533 · 8.5 (5) 758, 759, 819, 851, 852, 860 · DMA: 8.5 (5) 801

Shulgin, AT; Dyer, DC. Psychotomimetic phenylisopropylamines. 5. 4-Alkyl-2,5-dimethoxyphenylisopropylamines. J. Med. Chem., 1 Jan 1975, 18 (12), 1201–1204. 534 kB. https://doi.org/10.1021/jm00246a006 #6a

Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8.4 MB. #DOH (25DMA)

Parker, MA; Kurrasch, DM; Nichols, DE. The role of lipophilicity in determining binding affinity and functional activity for 5-HT_2A receptor ligands. Bioorg. Med. Chem., 1 Jan 2008, 16 (8), 4661–4669. 296 kB. https://doi.org/10.1016/j.bmc.2008.02.033 #19

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 #3 other

Nelson, DL; Lucaites, VL; Wainscott, DB; Glennon, RA. Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT_2A, 5-HT_2B and 5-HT_2C receptors. N-S. Arch. Pharmacol., 1 Jan 1999, 359 (1), 1–6. 66 kB. https://doi.org/10.1007/PL00005315 #DMA

Blaazer, AR; Smid, P; Kruse, CG. Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT_2A receptors. ChemMedChem, 15 Sep 2008, 3 (9), 1299–1309. 461 kB. https://doi.org/10.1002/cmdc.200800133 #20

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-HT_2C receptors. J. Pharmacol. Exp. Ther., 1 Jun 2007, 321 (3), 1054–1061. 188 kB. https://doi.org/10.1124/jpet.106.117507

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 #11

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-HT_1A), 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

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-HT_2A and 5-HT_2C 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-HT_2A 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 #4 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 #1a

Braden, MR; Nichols, DE. Assessment of the roles of serines 5.43(239) and 5.46(242) for binding and potency of agonist ligands at the human serotonin 5-HT_2A receptor. Mol. Pharmacol., 1 Jan 2007, 72 (5), 1200–1209. 487 kB. https://doi.org/10.1124/mol.107.039255

Shulgin, AT; Sargent, T; Naranjo, C. Structure-activity relationships of one-ring psychotomimetics. Nature, 1 Jan 1969, 221, 537–541. 537 kB. https://doi.org/10.1038/221537a0 #IV

Shulgin, AT. Chemistry and structure-activity relationships of the psychotomimetics. In Psychotomimetic Drugs; Efron, DH, Ed., Raven Press, New York, 1 Jan 1970; pp 21–41. 8.6 MB. #2,5-DMA

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 #18

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 #5

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

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 #5g,h

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 #3 MS,NMR

Guy, M; Freeman, S; Alder, JF; Brandt, SD. The Henry reaction: spectroscopic studies of nitrile and hydroxylamine by-products formed during synthesis of psychoactive phenylalkylamines. Cent. Eur. J. Chem., 1 Dec 2008, 6 (4), 526–534. 999 kB. https://doi.org/10.2478/s11532-008-0054-z #4d GC,MS,NMR

Glennon, RA; Raghupathi, R; Bartyzel, P; Teitler, M; Leonhardt, S. Binding of phenylalkylamine derivatives at 5-HT_1C 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 #21 NMR

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 #20

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 #18 NMR

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

Bailey, K; Legault, D. ¹³C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. https://doi.org/10.1002/omr.1270210611 #2,5-DMA NMR

Foster, BC; McLeish, J; Wilson, DL; Whitehouse, LW; Zamecnik, J; Lodge, BA. Biotransformation of tri-substituted methoxyamphetamines by Cunninghamella echinulata. Xenobiotica, 1 Jan 1992, 22 (12), 1383–1394. 765 kB. https://doi.org/10.3109/00498259209056689 #1e MS,NMR

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 GC,LC,MS,NMR,IR,TLC

Ho, B; McIsaac, WM; An, R; Tansey, LW; Walker, KE; Englert, LF; Noel, MB. Analogs of α-methylphenethylamine (amphetamine). I. Synthesis and pharmacological activity of some methoxy and/or methyl analogs. J. Med. Chem., 1 Jan 1970, 13 (1), 26–30. 601 kB. https://doi.org/10.1021/jm00295a007 #5

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

Glennon, RA; Young, R; Rosecrans, JA. A comparison of the behavioral effects of DOM homologs. Pharmacol. Biochem. Behav., 1 Apr 1982, 16 (4), 557–559. 256 kB. https://doi.org/10.1016/0091-3057(82)90414-2 #2,5-DMA

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 #32 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-HT_2A 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 #2a NMR

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 #1

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 #2,5-DMA

Shaler, RC; Padden, JJ. Identification of hallucinogens in illicit seizures I: 2,5-dimethoxyamphetamine. J. Pharm. Sci., 1 Nov 1972, 61 (11), 1851–1855. 334 kB. https://doi.org/10.1002/jps.2600611142 GC,MS,NMR,IR

Bailey, K; Legauld, D; Verner, D. Spectroscopic and chromatographic identification of dimethoxyamphetamines. J. Assoc. Off. Anal. Chem., , 57 (1), 70–78. 426 kB. #2,5-DMA GC,LC,NMR,IR,UV,TLC

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 #2,5-DMA

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 #21

Sreenivasan, V. Problems in Identification of Methylenedioxy and Methoxy Amphetamines. J. Crim. Law Criminol., 1 Jan 1972, 63 (2), 304. 996 kB. #DMA MS,NMR,IR,UV

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. #DMA Japanese, English abstract GC,LC,MS,NMR,IR,UV

Baker, LE. Hallucinogens in drug discrimination. In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 201-219. 342 kB. https://doi.org/10.1007/7854_2017_476

Brimblecombe, RW; Pinder, RM. Hallucinogenic agents, Wright-Scientechnica, Bristol, UK, 1 Jan 1975. 46.2 MB. #3.7

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 #49

Maher, HM; Awad, T; DeRuiter, J; Clark, CR. GC–MS and GC–IRD studies on dimethoxyamphetamines (DMA): Regioisomers related to 2,5-DMA. Forensic Sci. Int., 1 Jan 2009, 192 (1-3), 115-125. 1.0 MB. https://doi.org/10.1016/j.forsciint.2009.08.010 GC,MS,IR

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

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 #13

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.

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. #2

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 #10k

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. #22i

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.

Biel, JH; Bopp, BA. Amphetamines: Structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; pp 1–39. 1.0 MB. https://doi.org/10.1007/978-1-4757-0510-2_1

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. #LXXI

Martins, D. Analysis of new psychoactive substances: A contribution to forensic chemistry. M. Sc. Thesis, Universidade do Porto, 1 Jan 2014. 2.5 MB. #7 MS,NMR,other

Ehlers, D; Schäning, J. Synthese von DOC (2,5-dimethoxy-4-chloramphetamin). Toxichem Krimtech, 1 Jan 2001, 68 (2), 62–68. 185 kB. #3 MS,NMR,IR,UV

Chambers, JJ; Kurrasch-Orbaugh, DM; Parker, MA; Nichols, DE. Enantiospecific synthesis and pharmacological evaluation of a series of super-potent, conformationally restricted 5-HT_2A/2C receptor agonists. J. Med. Chem., 1 Mar 2001, 44 (6), 1003–1010. 337 kB. https://doi.org/10.1021/jm000491y #4a 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 #1 NMR,other

Ho, B; Tansey, LW. Analogs of amphetamine. 4. Synthesis of metabolites of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM). J. Med. Chem., 1 Feb 1971, 14 (2), 156–157. 316 kB. https://doi.org/10.1021/jm00284a018 #6

Dowd, CS; Herrick-Davis, K; Egan, C; DuPre, A; Smith, C; Teitler, M; Glennon, RA. 1-[4-(3-Phenylalkyl)phenyl]-2-aminopropanes as 5-HT_2A partial agonists. J. Med. Chem., 10 Aug 2000, 43 (16), 3074–3084. 271 kB. https://doi.org/10.1021/jm9906062 #19 NMR,IR

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 #6 NMR,IR

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 #1a A different layout of the same paper

Glennon, RA; Schubert, E; Jacyno, JM; Rosecrans, JA. Studies on several 7-substituted N,N-dimethyltryptamines. J. Med. Chem., 1 Nov 1980, 23 (11), 1222–1226. 711 kB. https://doi.org/10.1021/jm00185a014 #4 NMR

Glennon, RA; Young, R; Rosecrans, JA; Kallman, MJ. Hallucinogenic agents as discriminative stimuli: A correlation with serotonin receptor affinities. Psychopharmacology, 1 May 1980, 68 (2), 155–158. 395 kB. https://doi.org/10.1007/BF00432133 #2,5-DMA

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 #5

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. #PP-028

Oberlender, RA. Stereoselective aspects of hallucinogenic drug action and drug discrimination studies of entactogens. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 May 1989. 8.2 MB. #2,5-DMA MS,NMR,IR,other

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 GC,LC,MS

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. #2,5-DMA MS,NMR

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 #2,5DMA

Fenderson5555. Shulgin’s syntheses of 2,5-DMA, DOB and DOEF. , 5 Dec 2011. . Fenderson5555 3.7 MB.

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 #A7 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 #DOH

Flanagan, TW; Billac, GB; Landry, AN; Sebastian, MN; Cormier, SA; Nichols, CD. Structure–activity relationship analysis of psychedelics in a rat model of asthma reveals the anti-inflammatory pharmacophore. ACS Pharmacol. Transl. Sci., 9 Apr 2021, 4 (2), 488-502. 13.3 MB. https://doi.org/10.1021/acsptsci.0c00063 #2,5-DMA

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 #2,5-dimethoxyamphetamine

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 #DMA TLC

Bailey, K; Legault, D. The use of carbon-13 nuclear magnetic resonance spectra in the identification and authentication of monomethoxyamphetamines and dimethoxyamphetamines. J. Forensic Sci., 1 Jan 1981, 26 (1), 27–34. 366 kB. https://doi.org/10.1520/JFS11326J #2,5-diOCH3 NMR

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 #2,5-Dimethoxyamphetamine MS,NMR,IR,spot

Benington, F; Morin, RD. The chemorelease of norepinephrine from mouse hearts by substituted amphetamines. J. Med. Chem., 1 Jul 1968, 11 (4), 896–897. 244 kB. https://doi.org/10.1021/jm00310a048 #2.25

Heim, R. Synthesis and pharmacology of potent 5-HT_2A receptor agonists with N-2-methoxybenzyl partial structure. SC. D. Thesis, Freie Universität, Berlin, 1 Jan 2004. 3.9 MB. #34 In German. MS,NMR,IR

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 #35

Shulgin, AT. Mescaline: the chemistry and pharmacology of its analogs. Lloydia, 1 Jan 1973, 36 (1), 46–58. 5.6 MB. #23

Braun, G; Shulgin, AT; Sargent, T. Synthesis of ¹²³I-labelled 4-iodo-2,5-dimethoxyphenylisopropylamine. J. Labelled Compd. Radiopharm., 1 Jan 1978, 14 (5), 767–773. 291 kB. https://doi.org/10.1002/jlcr.2580140515 #1 Rhodium.

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 #8l

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 #9

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 #21

Błachut, D; Wojtasiewicz, K; Czarnocki, Z; Szukalski, B. The analytical profile of some 4-methylthioamphetamine (4-MTA) homologues. Forensic Sci. Int., 20 Nov 2009, 192 (1–3), 98–114. 683 kB. https://doi.org/10.1016/j.forsciint.2009.08.009 #19, 2,5-DMA GC,MS,NMR,IR

2,5-Dimethoxy-4-methylphenethylamine · 2C-D · LE-25

3,5-Dimethoxy-4-methylphenethylamine · DESOXY

2,4-DMA · 2,4-Dimethoxyamphetamine

3,4-DMA · 3,4-Dimethoxyamphetamine · DMA · EA-1316

3-Methoxy-4-ethoxyphenethylamine · MEPEA

3,5-DMA · 3,5-Dimethoxyamphetamine

2,3-DMA · 2,3-Dimethoxyamphetamine

2,6-DMA · 2,6-Dimethoxyamphetamine

3-Methoxy-N,N-dimethyltyramine · MM-GEA

25H-NMe · N-Me-2,5-DMPEA

2,5-MH-MMA · 5-Hydroxy-2-methoxymethamphetamine · 5HMP

2-DES-Me-DOM · 2-DM-DOM · 2-HMMP

5-DES-Me-DOM · 5-DM-DOM

4-Me-2,6-DMPEA · ψ-2C-D

2407

4-Ethoxynorephedrine · β-Hydroxy-4-ethoxyamphetamine

N-Methyl-β,3-dimethoxyphenethylamine · BO3MM

BO3ME · β-Ethoxy-3-methoxyphenethylamine

BO3MA · β,3-Dimethoxyamphetamine

BO3E · β-Methoxy-3-ethoxyphenethylamine

N-Me-DMPEA-2 · N-Methyl-2,3-dimethoxyphenethylamine

2,3-EMPEA · 2-Ethoxy-3-methoxyphenethylamine

N-Me-DMPEA-3 · N-Methyl-2,4-dimethoxyphenethylamine

2,4-EMPEA · 2-Ethoxy-4-methoxyphenethylamine

N,N,N-Trimethyl-3,4-dihydroxyphenethylamine⁺ · Coryneine

N,N-Dimethyl-3,4-dihydroxyamphetamine · N,N-Me-DHA

N-Ethyl-3,4-dihydroxyamphetamine · DHEA

4-HO-3-MeO-MA · 4-Hydroxy-3-methoxymethamphetamine · HMMA · MHMA

MH-α-Et-PEA · α-Ethyl-4-hydroxy-3-methoxyphenethylamine

3-Hydroxy-4-methoxymethamphetamine · HMMA

β-Me-DMPEA · β-Methyl-3,4-dimethoxyphenethylamine

N-Me-DMPEA · N-Methyl-3,4-dimethoxyphenethylamine

3-Ethoxy-4-methoxyphenethylamine · EMPEA

β,2-Dihydroxy-5-methylmethamphetamine · β,2-HO-5,N-DMeA

β-HO-N-Me-2-M-5-MePEA · β-Hydroxy-2-methoxy-N,5-dimethylphenethylamine

β-HO-2-M-5-MeA · β-Hydroxy-2-methoxy-5-methylamphetamine

N,N-Dimethyl-2-hydroxy-5-methoxyphenethylamine · N,N-Me-2,5-HMPEA

β-Me-2,5-DMPEA · β-Methyl-2,5-dimethoxyphenethylamine

N-Me-3,5-DMPEA · N-Methyl-3,5-dimethoxyphenethylamine

N-Me-2,6-DMPEA · N-Methyl-2,6-dimethoxyphenethylamine

2,4-Dimethoxy-6-methylphenethylamine · 6-Me-2,4-DMPEA

3-Methyl-2,4-dimethoxyphenethylamine · iso-2C-D

3-Hydroxy-2-methoxymethamphetamine · HMP

N,4-Dimethoxyamphetamine · N-MeO-PMA

homo-3,4-DMPEA

N-Isopropyl-2,3-dihydroxyphenethylamine · N-iPr-2,3-DHPEA

5,2-EMPEA · 5-Ethoxy-2-methoxyphenethylamine

N-Pr-3,4-DHPEA · N-Propyl-3,4-dihydroxyphenethylamine

N-Isopropyl-4-hydroxyphenethylamine N-oxide · N-iPr-4-MPEA N-oxide

N-Isopropyl-β,4-dihyydroxyphenethylamine · Deterenol

6948

β-O-Ethyl-synephrine

12680

p1-57: 2,5-DMA: Subacute evaluation
p1-58: 2,5-DMA: Subjective response
p2-276: 2,5-DMA
p4-462: α-CP-2C-D; 2C-C; 4-HO-DET; 4-HO-DPT; 4-MeO-DET; 5,6-MDO-MIPT; BOAD; BOD; DMA; DOIB; DPT; ORTHO-MDA