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PiHKAL book II entry DOI

ChemSpider 1192
PubChem 1229
Wikidata Q209251
Erowid DOI
Wikipedia 2,5-Dimethoxy-4-iodoamphetamine
PsychonautWiki DOI
swgdrug.org 2,5-Dimethoxy-4-iodoamphetamine (DOI)
bluelight.org DOI scraps
bluelight.org The Big & Dandy DOI Thread
Rhodium Shulgin: Synthesis of ¹²³I radioiodinated 4-iodo-2,5-dimethoxyamphetamine (DOI) (4)
Rhodium Shulgin: Synthesis of ¹²¹I and ¹²⁵I radioiodinated 4-iodo-2,5-dimethoxyamphetamine (DOI) (4)
Rhodium Iodination of methoxyamphetamines (I₂/AgSO₄)
bluelight.org DOI Effects and Ratings Survey Results

Shulgin Index #58 DOI · Table 5Page 341Row 12

PiHKAL #22 2C-C · #26 2C-F · #33 2C-I · #39 2C-T · #54 2,5-DMA · #62 DOB · #64 DOC · #65 DOEF · #71 DOPR · #72 E · #90 IDNNA · #105 MDDM · #162 TMA-6

TiHKAL #51 PRO-LAD

Phenethylamine: Von der Strucktur zur Funktion DOI: 7.5 (166) 562 · 8.5 (43) 769, 774, 778, 782, 785, 798, 799, 800, 801, 804, 807, 810, 813, 819, 836, 837, 838, 844, 849, 853 · 8.5 808

Braun, U; Shulgin, AT; Braun, G; Sargent, T. Synthesis and body distribution of several iodine-131-labeled central nervous system active drugs. J. Med. Chem., 1 Jan 1977, 20 (12), 1543–1546. 1.1 MB. https://doi.org/10.1021/jm00222a001 #3b NMR

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 #1g IR

Sargent, T; Budinger, TF; Braun, G; Shulgin, AT; Braun, U. An iodinated catecholamine congener for brain imaging and metabolic studies. J. Nucl. Med., 1 Jan 1978, 19 (1), 71–76. 922 kB.

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 #4 Rhodium.

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

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 #5

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 #DOI

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 #17

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

Sargent, T; Shulgin, AT; Mathis, CA. New iodinated amphetamines by rapid synthesis for use as brain blood flow indicators. J. Labelled Compd. Radiopharm., 1 Jan 1984, 19 (11–12), 1307–1308. 84 kB. https://doi.org/10.1002/jlcr.2580191102 #III

Sargent, T; Shulgin, AT; Mathis, CA. Radiohalogen-labeled imaging agents. 3. Compounds for measurement of brain blood flow by emission tomography. J. Med. Chem., 1 Jan 1984, 27 (8), 1071–1077. 1.9 MB. https://doi.org/10.1021/jm00374a023 #1r Rhodium. NMR,TLC

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

Schindler, EAD; Dave, KD; Smolock, EM; Aloyo, VJ; Harvey, JA. Serotonergic and dopaminergic distinctions in the behavioral pharmacology of (±)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Pharmacol. Biochem. Behav., 1 Mar 2012, 101 (1), 69–76. 722 kB. https://doi.org/10.1016/j.pbb.2011.12.002

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 #22

Fox, MA; French, HT; LaPorte, JL; Blackler, AR; Murphy, DL. The serotonin 5-HT_2A receptor agonist TCB-2: A behavioral and neurophysiological analysis. Psychopharmacology, 1 Sep 2010, 212 (1), 13–23. 240 kB. https://doi.org/10.1007/s00213-009-1694-1

Marona-Lewicka, D; Kurrasch-Orbaugh, DM; Selken, JR; Cumbay, MG; Lisnicchia, JG; Nichols, DE. Re-evaluation of lisuride pharmacology: 5-hydroxytryptamine 1A receptor-mediated behavioral effects overlap its other properties in rats. Psychopharmacology, 1 Oct 2002, 164 (1), 93–107. 293 kB. https://doi.org/10.1007/s00213-002-1141-z

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

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 #1h

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

Braden, MR; Parrish, JC; Naylor, JC; Nichols, DE. Molecular interaction of serotonin 5-HT_2A receptor residues Phe339^(6.51) and Phe340^(6.52) with superpotent N-benzyl phenethylamine agonists. Mol. Pharmacol., 1 Jan 2006, 70 (6), 1956–1964. 361 kB. https://doi.org/10.1124/mol.106.028720 #DOI

McKenna, DJ; Mathis, CA; Shulgin, AT; Sargent, T; Saavedra, JM. Autoradiographic localization of binding sites for ¹²⁵I-DOI, a new psychotomimetic radioligand, in the rat brain. Eur. J. Pharmacol., 1 Jan 1987, 137 (2–3), 289–290. 232 kB. https://doi.org/10.1016/0014-2999(87)90239-1

Huang, X; Nichols, DE. 5-HT₂ receptor-mediated potentiation of dopamine synthesis and central serotonergic deficits. Eur. J. Pharmacol., 20 Jul 1993, 238 (2–3), 291–296. 553 kB. https://doi.org/10.1016/0014-2999(93)90859-G

Silva, ME; Heim, R; Strasser, A; Elz, S; Dove, S. Theoretical studies on the interaction of partial agonists with the 5-HT_2A receptor. J. Comput. Aided Mol. Des., 1 Jan 2011, 25 (1), 51–66. 834 kB. https://doi.org/10.1007/s10822-010-9400-2 #12

Moreno, JL; Holloway, T; Albizu, L; Sealfon, SC; González-Maeso, J. Metabotropic glutamate mGlu2 receptor is necessary for the pharmacological and behavioral effects induced by hallucinogenic 5-HT_2A receptor agonists. Neurosci. Lett., 15 Apr 2011, 493 (3), 76–79. 196 kB. https://doi.org/10.1016/j.neulet.2011.01.046

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. #DOI 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-HT_2A receptor. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 26 Aug 2008. 5.9 MB. #36

Sargent, T; Braun, G; Braun, U; Budinger, TF; Shulgin, AT. Brain and retina uptake of a radio-iodine labeled psychotomimetic in dog and monkey. Commun. Psychopharmacol., 1 Jan 1978, 2 (1), 1–10. 2.0 MB.

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 #3 NMR

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT_2A 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 #S7, S8

Parrish, JC; Braden, MR; Gundy, E; Nichols, DE. Differential phospholipase C activation by phenylalkylamine serotonin 5-HT_2A 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. DOC, DOB, DOI and DOET: Strategic considerations. , 7 Sep 2013. . Fenderson5555 9.5 MB. #DOI

Sy, W. Iodination of methoxyamphetamines with iodine and silver sulphate. Tetrahedron Lett., 24 Sep 1993, 34 (39), 6223–6224. 133 kB. https://doi.org/10.1016/S0040-4039(00)73715-4

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

Dawson, BA; Black, DB; Sy, W; Graham, K. ¹³C NMR of some iodinated methoxy-amphetamines. Magn. Reson. Chem., 1 Sep 1994, 32 (9), 557–558. 171 kB. https://doi.org/10.1002/mrc.1260320913 #6 NMR

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 #86 Rhodium.

Schindler, EAD. Behavioral and biochemical distinctions in the pharmacology of two common hallucinogens. Ph. D. Thesis, Drexel University, Philadelphia, PA, USA, 1 Apr 2010. 5.9 MB.

Ang, RLL. Molecular basis of the action of hallucinogens. Ph. D. Thesis, New York University, New York, NY, USA, . 2.4 MB. #DOI

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 #1a 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 #8

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Perez-Aguilar, JM; Shan, J; LeVine, MV; Khelashvili, G; Weinstein, H. A Functional Selectivity Mechanism at the Serotonin-2A GPCR Involves Ligand-Dependent Conformations of Intracellular Loop 2. J. Am. Chem. Soc., 12 Nov 2014, 136 (45), 16044–16054. 4.2 MB. https://doi.org/10.1021/ja508394x

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 #DOI

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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

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

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Jensen, AA; McCorvy, JD; Leth-Petersen, S; Bundgaard, C; Liebscher, G; Kenakin, TP; Bräuner-Osborne, H; Kehler, J; Kristensen, JL. Detailed characterization of the in vitro pharmacological and pharmacokinetic properties of N-(2-hydroxybenzyl)-2,5-dimethoxy-4-cyanophenylethylamine (25CN-NBOH), a highly selective and brain-penetrant 5-HT_2A receptor agonist. J. Pharmacol. Exp. Ther., 1 Jun 2017, 361 (3), 441–453. 4.1 MB. https://doi.org/10.1124/jpet.117.239905 #DOI

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Canal, CE; Morgan, D; Felsing, D; Kondabolu, K; Rowland, NE; Robertson, KL; Sakhuja, R; Booth, RG. A novel aminotetralin-type serotonin (5-HT) _2C receptor-specific agonist and 5-HT_2A competitive antagonist/5-HT_2B inverse agonist with preclinical efficacy for psychoses. J. Pharmacol. Exp. Ther., 1 May 2014, 349 (2), 310–318. 981 kB. https://doi.org/10.1124/jpet.113.212373 #DOI

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Marek, GJ. Interactions of hallucinogens with the glutamatergic system: Permissive network effects mediated through cortical layer V pyramidal neurons. In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 107-135. 1.2 MB. https://doi.org/10.1007/7854_2017_480

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 #39

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)

López-Giménez, JF; González-Maeso, J. Hallucinogens and serotonin 5-HT_2A 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

Lladó-Pelfort, L; Celada, P; Riga, MS; Troyano-Rodríguez,, E. Effect of hallucinogens on neuronal activity. In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 75-105. 902 kB. https://doi.org/10.1007/7854_2017_473

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

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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

Helm, K. Synthese und funktionelle In-vitro-Pharmakologie neuer Liganden des 5-HT_2A-Rezeptors aus der Klasse. Ph. D. Thesis, Universität Regensburg, Dresden, 1 Jan 2014. 3.2 MB. #35 LC,MS,NMR,IR

Nichols, DE. Structure-activity relationships of serotonin 5-HT_2A agonists. WIREs Membr. Transp. Signal, 1 Sep 2012, 1 (5), 559-579. 573 kB. https://doi.org/10.1002/wmts.42 #41

May, JA; Chen, H; Rusinko, A; Lynch, VM; Sharif, NA; McLaughlin, MA. A novel and selective 5-HT₂ receptor agonist with ocular hypotensive activity: (S)-(+)-1-(2-Aminopropyl)-8,9-dihydropyrano[3,2-e]indole. J. Med. Chem., 1 Sep 2003, 46 (19), 4188–4195. 126 kB. https://doi.org/10.1021/jm030205t #3 MS,NMR

May, JA; Dantanarayana, AP; Zinke, PW; McLaughlin, MA; Sharif, NA. 1-((S)-2-Aminopropyl)-1H-indazol-6-ol: A potent peripherally acting 5-HT₂ receptor agonist with ocular hypotensive activity. J. Med. Chem., 12 Jan 2006, 49 (1), 318–328. 124 kB. https://doi.org/10.1021/jm050663x #1 MS,NMR

Delille, HK; Mezler, M; Marek, GJ. The two faces of the pharmacological interaction of mGlu2 and 5-HT_2A – Relevance of receptor heterocomplexes and interaction through functional brain pathways. Neuropharmacology, 1 Jul 2013, 70, 296-305. 654 kB. https://doi.org/10.1016/j.neuropharm.2013.02.005

Ly, C; Greb, AC; Cameron, LP; Wong, JM; Barragan, EV; Wilson, PC; Burbach, KF; Zarandi, SS; Sood, A; Paddy, MR; Duim, WC; Dennis, MY; McAllister, AK; Ori-McKenney, KM; Gray, JA; Olson, DE. Psychedelics promote structural and functional neural plasticity. Cell Rep., 1 Jun 2018, 23 (11), 3170–3182. 6.0 MB. https://doi.org/10.1016/j.celrep.2018.05.022 #DOI

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.

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.

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. 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. #22gg

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. #41

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 #10nn

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

Flanagan, TW; Nichols, CD. Psychedelics as anti-inflammatory agents. Int. Rev. Psychiatry, 1 Sep 2012, 26 (3), 241-257. 1.3 MB. https://doi.org/10.1080/09540261.2018.1481827 #DOI

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 #DOI

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 #DOI GC,LC,MS,UV

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2-Ethoxy-4-iodo-5-methoxyphenethylamine · 2CI-2ETO

3-I-2,6-DMA · 3-Iodo-2,6-DMA · 3-Iodo-2,6-dimethoxyamphetamine

4-Iodo-2,6-dimethoxyamphetamine · ψ-DOI

2-I-3,5-DMA · 2-Iodo-3,5-dimethoxyamphetamine

5-I-2,4-DMA · 5-Iodo-2,4-dimethoxyamphetamine · META-DOI

6-I-2,3-DMA · 6-Iodo-2,3-dimethoxyamphetamine

2-I-4,5-DMA · 2-Iodo-4,5-dimethoxyamphetamine

4-I-3,5-DMA · 4-Iodo-3,5-dimethoxyamphetamine

N-Methyl-2C-I · N-Methyl-4-iodo-2,5-dimethoxyphenethylamine

p1-173: DOI: Trials
p4-469: 2C-E; DOI: J; LSD; MDMA; METHYL-MMDA-2