Exploring DON. To explore a different substance…

IUPAC name:
70 · C11H16N2O4 · 240.256
JQJRESSXOVAECC-UHFFFAOYSA-N This stereoisomer Any stereoisomer

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

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

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

Scorza, M; 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 #21

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

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

Nichols, DE; Shulgin, AT; Dyer, DC. Directional lipophilic character in a series of psychotomimetic phenethylamine derivatives. Life Sci., 1 Jan 1977, 21 (4), 569–576. 320 kB. https://doi.org/10.1016/0024-3205(77)90099-6

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

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

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

Gomez-Jeria, JS; Cassels, BK; Carlos Saavedra-Aguilar, J. A quantum-chemical and experimental study of the hallucinogen (±)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropane (DON). Eur. J. Med. Chem., 1 Sep 1987, 22 (5), 433–437. 559 kB. https://doi.org/10.1016/0223-5234(87)90032-8

Gómez-Jeria, JS; Cassels, BK; Clavijo, R; Vargas, V; Quintana, R; Saavedra-Aguilar, JC. Spectroscopic characterization of a new hallucinogen: 1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropane (DON). Microgram, 1 Nov 1986, 19 (11), 153–161. 340 kB.

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

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

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 #39

Shulgin, AT. Basic Pharmacology and Effects. In Hallucinogens. A Forensic Drug Handbook; Laing, R; Siegel, JA, Eds., Academic Press, London, 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, 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, 1994; pp 3–41. 6.9 MB.

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