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PiHKAL#76 EMM
76
Variant: R2 R4 R5 R4,5 isomers all
Analogues: 9 3 1 1 37 51

IUPAC: 1-(2-Ethoxy-4,5-dimethoxyphenyl)propan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: SKRNTJDDBVAEGB-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-5-17-11-8-13(16-4)12(15-3)7-10(11)6-9(2)14/h7-9H,5-6,14H2,1-4H3

PubChem CID: 44719565; ChemSpider: 21106299; Wikipedia: EMM (psychedelic)

Shulgin Index: See #118 TMA-2; Table: 5 Page: 344 Row: 28

See also PiHKAL: #73 EEE #121 MEE #122 MEM #136 MME

See also Transcripts: 1.60

See also Pharmacology notes I: p. 60, EMM: Subacute evaluation

Shulgin, AT. The ethyl homologs of 2,4,5-trimethoxyphenylisopropylamine. J. Med. Chem., 1 Jan 1968, 11 (1), 186–187. 242 kB. doi:10.1021/jm00307a056

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

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. 8647 kB.

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; Vol. 11, pp 243–333. 2584 kB. doi:10.1007/978-1-4757-0510-2_6 Rhodium.

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. doi:10.1016/0014-2999(81)90106-0

Nine R2 analogues:
139
Analogue 1: Substituting Methylthio for Ethoxy at R2

ORTHO-DOT
o-DOT
2-Methylthio-4,5-dimethoxyamphetamine
4,5-Dimethoxy-2-methylthioamphetamine

IUPAC: 1-[4,5-Dimethoxy-2-(methylsulfanyl)phenyl]propan-2-amine

Formula: C12H19NO2S Molecular weight: 241.34976 g/mol InChI Key: GQUWSNDODZTHKC-UHFFFAOYSA-N

InChI=1S/C12H19NO2S/c1-8(13)5-9-6-10(14-2)11(15-3)7-12(9)16-4/h6-8H,5,13H2,1-4H3

PubChem CID: 144890; ChemSpider: 127831; Wikipedia: Ortho-DOT

Shulgin Index: See #3 ALEPH; Table: 5 Page: 344 Row: 29

See also PiHKAL: #3 ALEPH #125 META-DOT    

See also Transcripts: 1.181, 4.480

See also Pharmacology notes I: p. 181, ORTHO-DOT: Trials

Jacob, P; Anderson, G; Meshul, CK; Shulgin, AT; Castagnoli, N. Monomethylthio analogues of 1-(2,4,5-trimethoxyphenyl)-2-aminopropane. J. Med. Chem., 1 Jan 1977, 20 (10), 1235–1239. 717 kB. doi:10.1021/jm00220a001

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. doi:10.1021/jm00144a009

158
Analogue 2: Substituting Methoxy for Ethoxy at R2

TMA-2
2,4,5-Trimethoxyamphetamine

IUPAC: 1-(2,4,5-Trimethoxyphenyl)propan-2-amine

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: TVSIMAWGATVNGK-UHFFFAOYSA-N Properties: Essential amphetamine

InChI=1S/C12H19NO3/c1-8(13)5-9-6-11(15-3)12(16-4)7-10(9)14-2/h6-8H,5,13H2,1-4H3

PubChem CID: 31014; ChemSpider: 28773; Drugs Forum: TMA-2; Erowid: TMA-2; Wikipedia: Trimethoxyamphetamine

Shulgin Index: #118 TMA-2; Table: 5 Page: 344 Row: 23

See also PiHKAL: #35 2C-O-4
#42 Ψ-2C-T-4
#52 DESOXY
#69 Ψ-DOM
#73 EEE
#75 EME
#76 EMM
#93 IRIS
#120 MEDA
#121 MEE
#122 MEM
#136 MME
#138 MPM
#139 ORTHO-DOT
#145 TA
#157 TMA
#162 TMA-6
#167 4T-MMDA-2
#168 TMPEA
See also TiHKAL: #13 Harmaline #19 5-HO-DMT #46 5-MeS-DMT  

See also Transcripts: 1.54, 1.55, 1.55.2, 1.56, 1.64, 1.65, 1.72, 1.108, 1.151, 1.160, 1.161, 1.185, 2.224

See also Pharmacology notes I: p. 54, TMA-2: Subacute evaluation
p. 55.1, TMA-2: Subjective response
p. 56, TMA-2: Subjective response
p. 64, TMA-2: Subjective response
p. 65, TMA-2: Subjective response
p. 72, SARs
p. 108, TMA-2: Subjective response
p. 151, TMA-2
p. 160, TMA-2
p. 161, TMA-2
p. 185, TMA-2: Qualitative description
See also Pharmacology notes II: p. 224, TMA-2

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; Vol. 11, pp 243–333. 2584 kB. doi:10.1007/978-1-4757-0510-2_6 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., 2008, 51 (21), 6808–2828. 2229 kB. doi:10.1021/jm800771x

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. doi:10.1002/omr.1270210611

Thakur, M; Thakur, A; Khadikar, PV. QSAR studies on psychotomimetic phenylalkylamines. Bioorg. Med. Chem., 15 Feb 2004, 12 (4), 825–831. 323 kB. doi:10.1016/j.bmc.2003.10.027

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. 4445 kB. doi:10.1021/bk-1989-0413.ch018

Pirisi, MA; Nieddu, M; Burrai, L; Carta, A; Briguglio, I; Baralla, E; Demontis, MP; Varoni, MV; Boatto, G. An LC-MS-MS method for quantitative analysis of six trimethoxyamphetamine designer drugs in rat plasma, and its application to a pharmacokinetic study. Forensic Toxicol., 1 Jul 2013, 31 (2), 197–203. 305 kB. doi:10.1007/s11419-012-0177-y

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. doi:10.1007/BF02137743

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. doi:10.1021/jm00295a007

Tsujikawa, K; Kanamori, T; Kuwayama, K; Miyaguchi, H; Iwata, YT; Inoue, H. Analytical profiles for 3,4,5-, 2,4,5-, and 2,4,6-trimethoxyamphetamine. Microgram J., 1 Jan 2006, 4 (1–4), 12–23. 162 kB.

Corrigall, WA; Coen, KM; Saouda, FM; Robertson, JM; Lodge, BA. Discriminative stimulus properties of substituted amphetamine derivatives. Pharmacol. Biochem. Behav., 1 Dec 1992, 43 (4), 1117–1119. 265 kB. doi:10.1016/0091-3057(92)90490-7

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. doi:10.1016/j.forsciint.2011.11.003

Takahashi, M; Nagashima, M; Suzuki, J; Seto, T; Yasuda, I; Yoshida, T. Analysis of phenethylamines and tryptamines in designer drugs using gas chromatography-mass spectrometry. J. Health Sci., 2008, 54 (1), 89–96. 1882 kB. doi:10.1248/jhs.54.89

Anon. Report on the risk assessment of TMA-2, European Monitoring Centre for Drugs and Drug Addiction, May 2004.

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. doi:10.1021/jm00177a017

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. doi:10.1016/S0968-0896(03)00437-1

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. 1054 kB. doi:10.1021/jm00082a014

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

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. 982 kB. doi:10.2478/s11532-008-0054-z

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. doi:10.1016/0014-2999(81)90106-0

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.

Sargent, T; Shulgin, AT; Kusubov, N. Quantitative measurement of demethylation of [14]C-methoxyl labeled DMPEA and TMA-2 in rats. Psychopharmacol. Commun., 1 Jan 1976, 2 (3), 199–206. 8643 kB.

Shulgin, AT. The six trimethoxyphenylisopropylamines (trimethoxyamphetamines). J. Med. Chem., 1 Jan 1966, 9 (3), 445–456. 362 kB. doi:10.1021/jm00321a058

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. 1188 kB. doi:10.1021/jm00256a016

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. doi:10.1002/cmdc.200800133

Ray, TS. Psychedelics and the human receptorome. PLOS ONE, 2 Feb 2010, 5 (2), e9019. 791 kB. doi:10.1371/journal.pone.0009019

Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 13 Dec 2011. 1038 kB. doi: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. doi:10.1016/j.neuropharm.2011.01.017

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. doi:10.1016/S0006-2952(97)00405-X

Zaitsu, K; Katagi, M; Kamata, H; Kamata, T; Shima, N; Miki, A; Iwamura, T; Tsuchihashi, H. Discrimination and identification of the six aromatic positional isomers of trimethoxyamphetamine (TMA) by gas chromatography-mass spectrometry (GC-MS). J. Mass Spectrom., 1 Apr 2008, 43 (4), 528–534. 147 kB. doi:10.1002/jms.1347

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. doi:10.1016/S0376-8716(99)00148-9

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. doi:10.1021/jm00144a009

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.

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. doi:10.1016/0027-5107(77)90210-X

Shulgin, AT. Profiles of psychedelic drugs. 1. DMT; 2. TMA-2. J. Psychedelic Drugs, 1 Jan 1976, 8 (2), 167–169. 2097 kB. doi:10.1080/02791072.1976.10471846

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. 8647 kB.

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

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. doi:10.1021/jm00165a023

242
Analogue 3: Substituting Methyl for Ethoxy at R2

o-DOM
2-DOM
F-320
4,5-Dimethoxy-2-methylamphetamine

IUPAC: 1-(4,5-Dimethoxy-2-methylphenyl)propan-2-amine

Formula: C12H19NO2 Molecular weight: 209.28476 g/mol InChI Key: YHJWDCSNMYYZAW-UHFFFAOYSA-N

InChI=1S/C12H19NO2/c1-8-5-11(14-3)12(15-4)7-10(8)6-9(2)13/h5,7,9H,6,13H2,1-4H3

PubChem CID: 143435; ChemSpider: 126545

Shulgin Index: See #60 DOM; Table: 5 Page: 344 Row: 19

See also PiHKAL: #68 DOM      

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. doi:10.1021/jm00144a009

287
Analogue 4: Substituting Bromo for Ethoxy at R2

o-DOB
ORTHO-DOB
2-Bromo-4,5-dimethoxyamphetamine

IUPAC: 1-(2-Bromo-4,5-dimethoxyphenyl)propan-2-amine

Formula: C11H16BrNO2 Molecular weight: 274.15424 g/mol InChI Key: JPDVAVONMYSOMF-UHFFFAOYSA-N

InChI=1S/C11H16BrNO2/c1-7(13)4-8-5-10(14-2)11(15-3)6-9(8)12/h5-7H,4,13H2,1-3H3

PubChem CID: 141685; ChemSpider: 124999

Shulgin Index: See #52 DOB; Table: 5 Page: 344 Row: 16

See also PiHKAL: #124 META-DOB      

Barfknecht, CF; Nichols, DE. Potential psychotomimetics. Bromomethoxyamphetamines. J. Med. Chem., 1 Jan 1971, 14 (4), 370–372. 377 kB. doi:10.1021/jm00286a026 Rhodium

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. doi:10.1016/S0006-2952(97)00405-X

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. doi:10.1021/jm00144a009

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. 1916 kB.

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. doi:10.1007/BF02137743

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. 1532 kB. doi:10.1002/dta.409

7313
Analogue 5: Substituting Fluoro for Ethoxy at R2

2-F-4,5-DMA

IUPAC: 1-(2-Fluoro-4,5-dimethoxyphenyl)propan-2-amine

Formula: C11H16FNO2 Molecular weight: 213.2486432 g/mol InChI Key: WHCXKZPZGWBQDL-UHFFFAOYSA-N

InChI=1S/C11H16FNO2/c1-7(13)4-8-5-10(14-2)11(15-3)6-9(8)12/h5-7H,4,13H2,1-3H3

PubChem CID: 10443198; ChemSpider: 8618617

Shulgin Index: See #118 TMA-2; Table: 5 Page: 344 Row: 13

Jara, AN; Torres, MA; Cassels, BK; Rezende, MC. Some fluoro and nitro analogues of hallucinogenic amphetamines. Synth. Commun., 1 Jan 1994, 24 (3), 417–426. 440 kB. doi:10.1080/00397919408011201 Rhodium.

7317
Analogue 6: Substituting Amino for Ethoxy at R2

2-NH2-4,5-DMA

IUPAC: 2-(2-Aminopropyl)-4,5-dimethoxyaniline

Formula: C11H18N2O2 Molecular weight: 210.27282 g/mol InChI Key: BEUBPILQBNLCJR-UHFFFAOYSA-N

InChI=1S/C11H18N2O2/c1-7(12)4-8-5-10(14-2)11(15-3)6-9(8)13/h5-7H,4,12-13H2,1-3H3

Shulgin Index: See #118 TMA-2; Table: 5 Page: 344 Row: 17

7318
Analogue 7: Substituting Nitro for Ethoxy at R2

o-DON

IUPAC: 1-(4,5-Dimethoxy-2-nitrophenyl)propan-2-amine

Formula: C11H16N2O4 Molecular weight: 240.25574 g/mol InChI Key: DQOIKAQFQOSIEA-UHFFFAOYSA-N

InChI=1S/C11H16N2O4/c1-7(12)4-8-5-10(16-2)11(17-3)6-9(8)13(14)15/h5-7H,4,12H2,1-3H3

Shulgin Index: See #61 DON; Table: 5 Page: 344 Row: 18

Nuñez-Vergara, LJ; Matus, C; Alvarez-Lueje, AF; Cassels, BK; Squella, JA. Nitro radical anion formation from nitro-substituted amphetamine derivatives. Electroanalysis, 1 May 1994, 6 (5–6), 509–513. 477 kB. doi:10.1002/elan.1140060525

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. doi:10.1016/S0006-2952(97)00405-X

Jara, AN; Torres, MA; Cassels, BK; Rezende, MC. Some fluoro and nitro analogues of hallucinogenic amphetamines. Synth. Commun., 1 Jan 1994, 24 (3), 417–426. 440 kB. doi:10.1080/00397919408011201 Rhodium.

7320
Analogue 8: Substituting Ethyl for Ethoxy at R2

2,4,5-DOET

IUPAC: 1-(2-Ethyl-4,5-dimethoxyphenyl)propan-2-amine

Formula: C13H21NO2 Molecular weight: 223.31134 g/mol InChI Key: AWDRRNOKPPRWMH-UHFFFAOYSA-N

InChI=1S/C13H21NO2/c1-5-10-7-12(15-3)13(16-4)8-11(10)6-9(2)14/h7-9H,5-6,14H2,1-4H3

PubChem CID: 57486951; ChemSpider: 26473102

Shulgin Index: See #56 DOET; Table: 5 Page: 344 Row: 20

1068
Analogue 9: Substituting Iodo for Ethoxy at R2

2-I-4,5-DMA

IUPAC: 1-(2-Iodo-4,5-dimethoxyphenyl)propan-2-amine

Formula: C11H16INO2 Molecular weight: 321.15471 g/mol InChI Key: IMLBVCRFUUUPRZ-UHFFFAOYSA-N

InChI=1S/C11H16INO2/c1-7(13)4-8-5-10(14-2)11(15-3)6-9(8)12/h5-7H,4,13H2,1-3H3

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. doi:10.1002/mrc.1260320913

Three R4 analogues:
74
Analogue 1: Substituting Ethoxy for Methoxy at R4

EEM
2,4-Diethoxy-5-methoxyamphetamine

IUPAC: 1-(2,4-Diethoxy-5-methoxyphenyl)propan-2-amine

Formula: C14H23NO3 Molecular weight: 253.33732 g/mol InChI Key: SAFDWWQYGOOGMX-UHFFFAOYSA-N

InChI=1S/C14H23NO3/c1-5-17-12-9-14(18-6-2)13(16-4)8-11(12)7-10(3)15/h8-10H,5-7,15H2,1-4H3

PubChem CID: 44719558; ChemSpider: 21106297; Wikipedia: EEM (psychedelic)

Shulgin Index: See #118 TMA-2; Table: 5 Page: 344 Row: 34

See also PiHKAL: #73 EEE #122 MEM    

Shulgin, AT. The ethyl homologs of 2,4,5-trimethoxyphenylisopropylamine. J. Med. Chem., 1 Jan 1968, 11 (1), 186–187. 242 kB. doi:10.1021/jm00307a056

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

2049
Analogue 2: Substituting Methyl for Methoxy at R4

FLORENCE
2-Et-DOM
2-Ethoxy-5-methoxy-4-methylamphetamine

IUPAC: 1-(2-Ethoxy-5-methoxy-4-methylphenyl)propan-2-amine

Formula: C13H21NO2 Molecular weight: 223.31134 g/mol InChI Key: JGTKJASRYQAIDY-UHFFFAOYSA-N

InChI=1S/C13H21NO2/c1-5-16-13-6-9(2)12(15-4)8-11(13)7-10(3)14/h6,8,10H,5,7,14H2,1-4H3

PubChem CID: 57486939

Shulgin Index: See #60 DOM; Table: 5 Page: 342 Row: 31

See also PiHKAL: #8 ARIADNE      

Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8442 kB.

Shulgin, AT. 4-Alkyl-dialkoxy-alpha-methyl-phenethylamines and their pharmacologically-acceptable salts. U S. Patent 3,547,999, 15 Dec 1970. 448 kB.

Ger, A; Ger, D. Triple Goddess of the Night. British Neuroscience Association Bulletin, 1 Mar 2011, 63, 28–30. 234 kB. Dmitri Ger is credited with the discovery of Jelena, also known as 2C-IP.

532
Analogue 3: Substituting Ethyl for Methoxy at R4

2-Ethoxy-4-ethyl-5-methoxyamphetamine

IUPAC: 1-(2-Ethoxy-4-ethyl-5-methoxyphenyl)propan-2-amine

Formula: C14H23NO2 Molecular weight: 237.33792 g/mol InChI Key: BUQOPIQJYPMXLL-UHFFFAOYSA-N

InChI=1S/C14H23NO2/c1-5-11-8-14(17-6-2)12(7-10(3)15)9-13(11)16-4/h8-10H,5-7,15H2,1-4H3

Shulgin, AT. 4-Alkyl-dialkoxy-alpha-methyl-phenethylamines and their pharmacologically-acceptable salts. U S. Patent 3,547,999, 15 Dec 1970. 448 kB.

One R5 analogue:
75
Analogue 1: Substituting Ethoxy for Methoxy at R5

EME
2,5-Diethoxy-4-methoxyamphetamine

IUPAC: 1-(2,5-Diethoxy-4-methoxyphenyl)propan-2-amine

Formula: C14H23NO3 Molecular weight: 253.33732 g/mol InChI Key: IVHFHHXLFFHTTA-UHFFFAOYSA-N

InChI=1S/C14H23NO3/c1-5-17-12-9-13(16-4)14(18-6-2)8-11(12)7-10(3)15/h8-10H,5-7,15H2,1-4H3

PubChem CID: 44719562; ChemSpider: 21106298; Wikipedia: EME (psychedelic)

Shulgin Index: See #118 TMA-2; Table: 5 Page: 346 Row: 27

See also PiHKAL: #73 EEE #122 MEM #136 MME  

Shulgin, AT. The ethyl homologs of 2,4,5-trimethoxyphenylisopropylamine. J. Med. Chem., 1 Jan 1968, 11 (1), 186–187. 242 kB. doi:10.1021/jm00307a056

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

One R4,5 analogue:
300
Analogue 1: Substituting Methylenedioxy for Dimethoxy at R4,5

EMDA-2
2-Ethoxy-4,5-methylenedioxyamphetamine

IUPAC: 1-(6-Ethoxy-1,3-benzodioxol-5-yl)propan-2-amine

Formula: C12H17NO3 Molecular weight: 223.26828 g/mol InChI Key: OHOFHHFTTSOJCK-UHFFFAOYSA-N

InChI=1S/C12H17NO3/c1-3-14-10-6-12-11(15-7-16-12)5-9(10)4-8(2)13/h5-6,8H,3-4,7,13H2,1-2H3

PubChem CID: 61612198

See also PiHKAL: #133 MMDA-2      
37 isomers:
1
Isomer 1

AEM
α-Ethylmescaline
α-Ethyl-3,4,5-trimethoxyphenethylamine
2-Amino-1-(3,4,5-trimethoxyphenyl)butane
1-(3,4,5-Trimethoxyphenyl)-2-aminobutane

IUPAC: 1-(3,4,5-Trimethoxyphenyl)butan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: DCYONQVUAUEKAJ-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-5-10(14)6-9-7-11(15-2)13(17-4)12(8-9)16-3/h7-8,10H,5-6,14H2,1-4H3

PubChem CID: 204932; ChemSpider: 177522; Wikipedia: AEM (psychedelic)

Shulgin Index: #1 AEM; Table: 5 Page: 350 Row: 11

See also PiHKAL: #157 TMA      

See also Transcripts: 1.20

See also Pharmacology notes I: p. 20, AEM: Subacute evaluation

Shulgin, AT. Psychotomimetic agents related to mescaline. Experientia, 1 Jan 1963, 19 (3), 127–128. 264 kB. doi:10.1007/BF02171586

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

Daley, PF; Morris, H. Pages from the lab notebook of Alexander Shulgin: A glance through the history of psychedelic chemistry. Vice, 1 Oct 2012.

9
Isomer 2

ASB
Asymbescaline
3,4-Diethoxy-5-methoxyphenethylamine

IUPAC: 2-(3,4-Diethoxy-5-methoxyphenyl)ethan-1-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: VFOAVFQWZYUFQZ-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-4-16-12-9-10(6-7-14)8-11(15-3)13(12)17-5-2/h8-9H,4-7,14H2,1-3H3

PubChem CID: 45367; ChemSpider: 41279; Wikipedia: Asymbescaline

Shulgin Index: #8 ASB; Table: 5 Page: 351 Row: 2, #8 ASB; Table: 5 Page: 351 Row: 36

See also PiHKAL: #148 5-TASB #163 3-TME #178 3-T-TRIS  

Jacob, P; Shulgin, AT. Sulfur analogues of psychotomimetic agents. 3. Ethyl homologues of mescaline and their monothioanalogues. J. Med. Chem., 1 Jan 1984, 27 (7), 881–887. 1213 kB. doi:10.1021/jm00373a013

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. doi:10.1016/S0968-0896(03)00437-1

Thakur, M; Thakur, A; Khadikar, PV. QSAR studies on psychotomimetic phenylalkylamines. Bioorg. Med. Chem., 15 Feb 2004, 12 (4), 825–831. 323 kB. doi:10.1016/j.bmc.2003.10.027

25
Isomer 3

3C-E
4-Ethoxy-3,5-dimethoxyamphetamine
3,5-Dimethoxy-4-ethoxyamphetamine

IUPAC: 1-(4-Ethoxy-3,5-dimethoxyphenyl)propan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: AHLXCGRWNKUNTQ-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-5-17-13-11(15-3)7-10(6-9(2)14)8-12(13)16-4/h7-9H,5-6,14H2,1-4H3

PubChem CID: 44350137; ChemSpider: 21106237; Wikipedia: 3C-E

Shulgin Index: See #117 TMA; Table: 5 Page: 351 Row: 1

See also PiHKAL: #72 E      

See also Transcripts: 2.222

See also Pharmacology notes II: p. 222, 3C-E

Thakur, M; Thakur, A; Khadikar, PV. QSAR studies on psychotomimetic phenylalkylamines. Bioorg. Med. Chem., 15 Feb 2004, 12 (4), 825–831. 323 kB. doi:10.1016/j.bmc.2003.10.027

35
Isomer 4

2C-O-4
4-Isopropoxy-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-isopropoxyphenethylamine

IUPAC: 2-[2,5-Dimethoxy-4-(propan-2-yloxy)phenyl]ethan-1-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: KAKXJLWAEMHHTL-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-9(2)17-13-8-11(15-3)10(5-6-14)7-12(13)16-4/h7-9H,5-6,14H2,1-4H3

PubChem CID: 44719510; ChemSpider: 21106225; Wikipedia: 2C-O-4

Shulgin Index: See #124 TMPEA-2; Table: 5 Page: 345 Row: 5

92
Isomer 5

IP
Isoproscaline
3,5-Dimethoxy-4-isopropoxyphenethylamine

IUPAC: 2-[3,5-Dimethoxy-4-(propan-2-yloxy)phenyl]ethan-1-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: UBNHYNYMUORHAM-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-9(2)17-13-11(15-3)7-10(5-6-14)8-12(13)16-4/h7-9H,5-6,14H2,1-4H3

PubChem CID: 15102787; ChemSpider: 10439597; Wikipedia: Isoproscaline

Shulgin Index: See #91 Mescaline; Table: 5 Page: 351 Row: 13

See also Transcripts: 3.389, 3.418

Nichols, DE; Dyer, DC. Lipophilicity and serotonin agonist activity in a series of 4-substituted mescaline analogues. J. Med. Chem., 1 Jan 1977, 20 (2), 299–301. 409 kB. doi:10.1021/jm00212a022

Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 13 Dec 2011. 1038 kB. doi:10.1002/dta.413

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. doi:10.1016/0024-3205(77)90099-6

Kier, LB; Glennon, RA. Psychotomimetic phenalkylamines as serotonin agonists: An SAR analysis. Life Sci., 8 May 1978, 22 (18), 1589–1593. 238 kB. doi:10.1016/0024-3205(78)90053-X

122
Isomer 6

MEM
2,5-Dimethoxy-4-ethoxyamphetamine

IUPAC: 1-(4-Ethoxy-2,5-dimethoxyphenyl)propan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: ITZLAXJQDMGDEO-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-5-17-13-8-11(15-3)10(6-9(2)14)7-12(13)16-4/h7-9H,5-6,14H2,1-4H3

PubChem CID: 542053; ChemSpider: 472023; Wikipedia: 2,5-Dimethoxy-4-ethoxyamphetamine

Shulgin Index: #87 MEM; Table: 5 Page: 344 Row: 32

See also PiHKAL: #35 2C-O-4
#72 E
#73 EEE
#74 EEM
#76 EMM
#93 IRIS
#121 MEE
#136 MME
#138 MPM
 
See also TiHKAL: #19 5-HO-DMT #46 5-MeS-DMT    

See also Transcripts: 1.78, 1.78.2, 1.80, 1.112, 1.151, 2.229, 2.260, 2.270, 2.323.2, 2.323.4, 2.380, 3.380

See also Pharmacology notes I: p. 78, MEM: Subacute evaluation
p. 80, MEM: Marginal effects
p. 112, MEM: Subjective response
p. 151, MEM
See also Pharmacology notes II: app. 2, Abuse week
p. 229, MEM
p. 260, MEM
p. 270, MEM
p. 380, MEM

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. doi:10.1016/S0376-8716(99)00148-9

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. doi:10.1016/S0968-0896(03)00437-1

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; Vol. 11, pp 243–333. 2584 kB. doi:10.1007/978-1-4757-0510-2_6 Rhodium.

By, AW; Dawson, BA; Lodge, BA; Neville, GA; Sy, W; Zamecnik, J. Synthesis and spectral properties of 2,5-dimethoxy-4-ethoxyamphetamine and its precursors. J. Forensic Sci., 1 Mar 1990, 35 (2), 316–335. 538 kB. doi:10.1520/JFS12833J

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

Corrigall, WA; Coen, KM; Saouda, FM; Robertson, JM; Lodge, BA. Discriminative stimulus properties of substituted amphetamine derivatives. Pharmacol. Biochem. Behav., 1 Dec 1992, 43 (4), 1117–1119. 265 kB. doi:10.1016/0091-3057(92)90490-7

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. 4445 kB. doi:10.1021/bk-1989-0413.ch018

Thakur, M; Thakur, A; Khadikar, PV. QSAR studies on psychotomimetic phenylalkylamines. Bioorg. Med. Chem., 15 Feb 2004, 12 (4), 825–831. 323 kB. doi:10.1016/j.bmc.2003.10.027

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. doi:10.1016/0014-2999(81)90106-0

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. 8647 kB.

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

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. doi:10.1021/jm00165a023

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. 1054 kB. doi:10.1021/jm00082a014

Halberstadt, AL; Geyer, MA. Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens. Neuropharmacology, 1 Sep 2011, 61 (3) 364–381. 817 kB. doi:10.1016/j.neuropharm.2011.01.017

Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 13 Dec 2011. 1038 kB. doi:10.1002/dta.413

Ray, TS. Psychedelics and the human receptorome. PLOS ONE, 2 Feb 2010, 5 (2), e9019. 791 kB. doi:10.1371/journal.pone.0009019

Shulgin, AT. The ethyl homologs of 2,4,5-trimethoxyphenylisopropylamine. J. Med. Chem., 1 Jan 1968, 11 (1), 186–187. 242 kB. doi:10.1021/jm00307a056

136
Isomer 7

MME
2,4-Dimethoxy-5-ethoxyamphetamine

IUPAC: 1-(5-Ethoxy-2,4-dimethoxyphenyl)propan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: NAMNXRTWJMASNT-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-5-17-13-7-10(6-9(2)14)11(15-3)8-12(13)16-4/h7-9H,5-6,14H2,1-4H3

PubChem CID: 44719602; ChemSpider: 21106338; Wikipedia: MME (psychedelic)

Shulgin Index: See #118 TMA-2; Table: 5 Page: 346 Row: 26

See also PiHKAL: #73 EEE #75 EME #121 MEE #122 MEM

See also Transcripts: 1.77

See also Pharmacology notes I: p. 77, MME: Subacute evaluation

Shulgin, AT. The ethyl homologs of 2,4,5-trimethoxyphenylisopropylamine. J. Med. Chem., 1 Jan 1968, 11 (1), 186–187. 242 kB. doi:10.1021/jm00307a056

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

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. 8647 kB.

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; Vol. 11, pp 243–333. 2584 kB. doi:10.1007/978-1-4757-0510-2_6 Rhodium.

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. doi:10.1016/0014-2999(81)90106-0

137
Isomer 8

MP
Metaproscaline
3,4-Dimethoxy-5-propoxyphenethylamine
3,4-Dimethoxy-5-n-propoxyphenethylamine

IUPAC: 2-(3,4-Dimethoxy-5-propoxyphenyl)ethan-1-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: LRMHEQAATQTVRI-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-4-7-17-12-9-10(5-6-14)8-11(15-2)13(12)16-3/h8-9H,4-7,14H2,1-3H3

PubChem CID: 44375097; ChemSpider: 21106345; Wikipedia: Metaproscaline

Shulgin Index: See #91 Mescaline; Table: 5 Page: 352 Row: 5

See also PiHKAL: #119 ME #163 3-TME    

See also Transcripts: 3.430

Jacob, P; Shulgin, AT. Sulfur analogues of psychotomimetic agents. 3. Ethyl homologues of mescaline and their monothioanalogues. J. Med. Chem., 1 Jan 1984, 27 (7), 881–887. 1213 kB. doi:10.1021/jm00373a013

140
Isomer 9

P
Proscaline
Proscaline
3,5-Dimethoxy-4-propoxyphenethylamine
3,5-Dimethoxy-4-n-propoxyphenethylamine

IUPAC: 2-(3,5-Dimethoxy-4-propoxyphenyl)ethan-1-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: HYWLMSUAZVDUFW-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-4-7-17-13-11(15-2)8-10(5-6-14)9-12(13)16-3/h8-9H,4-7,14H2,1-3H3

PubChem CID: 15102790; ChemSpider: 10439596; Wikipedia: Proscaline

Shulgin Index: #104 Proscaline; Table: 5 Page: 351 Row: 11

See also PiHKAL: #72 E
#80 F-22
#123 MEPEA
#141 PE
#163 3-TME  

See also Transcripts: 2.209, 4.560

See also Pharmacology notes II: p. 209, Proscaline

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; Vol. 11, pp 243–333. 2584 kB. doi:10.1007/978-1-4757-0510-2_6 Rhodium.

Kier, LB; Glennon, RA. Psychotomimetic phenalkylamines as serotonin agonists: An SAR analysis. Life Sci., 8 May 1978, 22 (18), 1589–1593. 238 kB. doi:10.1016/0024-3205(78)90053-X

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. doi:10.1016/S0968-0896(03)00437-1

Thakur, M; Thakur, A; Khadikar, PV. QSAR studies on psychotomimetic phenylalkylamines. Bioorg. Med. Chem., 15 Feb 2004, 12 (4), 825–831. 323 kB. doi:10.1016/j.bmc.2003.10.027

Jacob, P; Shulgin, AT. Sulfur analogues of psychotomimetic agents. 3. Ethyl homologues of mescaline and their monothioanalogues. J. Med. Chem., 1 Jan 1984, 27 (7), 881–887. 1213 kB. doi:10.1021/jm00373a013

Glennon, RA; Kier, LB; Shulgin, AT. Molecular connectivity analysis of hallucinogenic mescaline analogs. J. Pharm. Sci., 1 Jan 1979, 68 (7), 906–907. 252 kB. doi:10.1002/jps.2600680733

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. doi:10.1016/0024-3205(77)90099-6

Meyers-Riggs, B. Leminger’s scalines. countyourculture: rational exploration of the underground, 4 May 2012.

Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 13 Dec 2011. 1038 kB. doi:10.1002/dta.413

Nichols, DE; Dyer, DC. Lipophilicity and serotonin agonist activity in a series of 4-substituted mescaline analogues. J. Med. Chem., 1 Jan 1977, 20 (2), 299–301. 409 kB. doi:10.1021/jm00212a022

144
Isomer 10

SB
Symbescaline
3,5-Diethoxy-4-methoxyphenethylamine

IUPAC: 2-(3,5-Diethoxy-4-methoxyphenyl)ethan-1-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: ROKMKYBLAPLLER-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-4-16-11-8-10(6-7-14)9-12(17-5-2)13(11)15-3/h8-9H,4-7,14H2,1-3H3

PubChem CID: 44374890; ChemSpider: 21106384; Wikipedia: Symbescaline

Shulgin Index: See #91 Mescaline; Table: 5 Page: 351 Row: 33

See also PiHKAL: #9 ASB #163 3-TME    

Jacob, P; Shulgin, AT. Sulfur analogues of psychotomimetic agents. 3. Ethyl homologues of mescaline and their monothioanalogues. J. Med. Chem., 1 Jan 1984, 27 (7), 881–887. 1213 kB. doi:10.1021/jm00373a013

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. doi:10.1016/S0968-0896(03)00437-1

189
Isomer 11

1-(2,5-Dimethoxy-4-methylphenyl)-N-hydroxy-2-aminobutane

IUPAC: 1-(2,5-Dimethoxy-4-methylphenyl)-N-hydroxybutan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: IODVUUDTFABAJR-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-5-11(14-15)7-10-8-12(16-3)9(2)6-13(10)17-4/h6,8,11,14-15H,5,7H2,1-4H3

See also PiHKAL: #8 ARIADNE      
190
Isomer 12

4C-TMPEA-6
1-(2,4,6-Trimethoxyphenyl)-2-aminobutane

IUPAC: 1-(2,4,6-Trimethoxyphenyl)butan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: RPZWJHJIKUKWKO-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-5-9(14)6-11-12(16-3)7-10(15-2)8-13(11)17-4/h7-9H,5-6,14H2,1-4H3

PubChem CID: 43565966

Shulgin Index: See #122 TMA-6; Table: 5 Page: 353 Row: 28

See also PiHKAL: #8 ARIADNE      
194
Isomer 13

BOED
2,5-Dimethoxy-β-ethoxy-4-methylphenethylamine

IUPAC: 2-(2,5-Dimethoxy-4-methylphenyl)-2-ethoxyethan-1-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: LZNFMACBNUDNGO-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-5-17-13(8-14)10-7-11(15-3)9(2)6-12(10)16-4/h6-7,13H,5,8,14H2,1-4H3

See also PiHKAL: #14 BOD      

Coutts, RT; Malicky, JL. The synthesis of analogs of the hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM). II. Some ring-methoxylated 1-amino- and 2-aminoindanes. Can. J. Chem., 1 Feb 1974, 52 (3), 381–389. 615 kB. doi:10.1139/v74-061

244
Isomer 14

Z-7.2
4-Methyl-2,3,6-trimethoxyamphetamine

IUPAC: 1-(2,3,6-Trimethoxy-4-methylphenyl)propan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: OIVHGEYWNKYFLE-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-8-6-11(15-3)10(7-9(2)14)13(17-5)12(8)16-4/h6,9H,7,14H2,1-5H3

See also PiHKAL: #69 Ψ-DOM      
263
Isomer 15

Trichocerine
Trichocereine
N,N-Dimethylmescaline
N,N-Dimethyl-3,4,5-trimethoxyphenethylamine

IUPAC: N,N-Dimethyl-2-(3,4,5-trimethoxyphenyl)ethan-1-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: BTSKBPJWJZFTPQ-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-14(2)7-6-10-8-11(15-3)13(17-5)12(9-10)16-4/h8-9H,6-7H2,1-5H3

PubChem CID: 420418; ChemSpider: 372161

Shulgin Index: #125 Trichocereine; Table: 5 Page: 350 Row: 25

See also PiHKAL: #96 M      

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; Vol. 11, pp 243–333. 2584 kB. doi:10.1007/978-1-4757-0510-2_6 Rhodium.

288
Isomer 16

N-Me-TMA
METHYL-TMA
N-Methyl-3,4,5-trimethoxyamphetamine

IUPAC: N-Methyl-1-(3,4,5-trimethoxyphenyl)propan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: XYKHBBWJSFSLRF-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-9(14-2)6-10-7-11(15-3)13(17-5)12(8-10)16-4/h7-9,14H,6H2,1-5H3

PubChem CID: 24257271; ChemSpider: 23900079

Shulgin Index: See #117 TMA; Table: 5 Page: 350 Row: 2

See also PiHKAL: #126 METHYL-DMA      

Clark, CC. The identification of methoxy-N-methylamphetamines. J. Forensic Sci., 1 Oct 1984, 29 (4), 1056–1071. 423 kB. doi:10.1520/JFS11772J

289
Isomer 17

N-Me-TMA-2
METHYL-TMA-2
N-Methyl-2,4,5-trimethoxyamphetamine

IUPAC: N-Methyl-1-(2,4,5-trimethoxyphenyl)propan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: USTLBRBKMWJINX-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-9(14-2)6-10-7-12(16-4)13(17-5)8-11(10)15-3/h7-9,14H,6H2,1-5H3

PubChem CID: 69454104

Shulgin Index: See #118 TMA-2; Table: 5 Page: 344 Row: 24

See also PiHKAL: #126 METHYL-DMA      

See also Transcripts: 1.59

See also Pharmacology notes I: p. 59, N-Me-TMA-2: Subacute evaluation

Clark, CC. The identification of methoxy-N-methylamphetamines. J. Forensic Sci., 1 Oct 1984, 29 (4), 1056–1071. 423 kB. doi:10.1520/JFS11772J

290
Isomer 18

N-Me-TMA-6
METHYL-TMA-6
N-Methyl-2,4,6-trimethoxyamphetamine

IUPAC: N-Methyl-1-(2,4,6-trimethoxyphenyl)propan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: VSIUFWGLSWJBHU-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-9(14-2)6-11-12(16-4)7-10(15-3)8-13(11)17-5/h7-9,14H,6H2,1-5H3

PubChem CID: 69393054

Shulgin Index: See #122 TMA-6; Table: 5 Page: 353 Row: 27

See also PiHKAL: #126 METHYL-DMA      

Clark, CC. The identification of methoxy-N-methylamphetamines. J. Forensic Sci., 1 Oct 1984, 29 (4), 1056–1071. 423 kB. doi:10.1520/JFS11772J

2069
Isomer 19

2C-O-7
2C-O-7
2,5-Dimethoxy-4-n-propoxyphenethylamine

IUPAC: 2-(2,5-Dimethoxy-4-propoxyphenyl)ethan-1-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: RRKXVAQJHSSQHK-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-4-7-17-13-9-11(15-2)10(5-6-14)8-12(13)16-3/h8-9H,4-7,14H2,1-3H3

PubChem CID: 57474252

Shulgin Index: See #124 TMPEA-2; Table: 5 Page: 344 Row: 35

See also PiHKAL: #35 2C-O-4      
5549
Isomer 20

Salbutamol
N-tert-Butyl-β,4-dihydroxy-3-(hydroxymethyl)phenethylamine

IUPAC: 4-[2-(tert-Butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: NDAUXUAQIAJITI-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-13(2,3)14-7-12(17)9-4-5-11(16)10(6-9)8-15/h4-6,12,14-17H,7-8H2,1-3H3

PubChem CID: 2083; ChemSpider: 1999; Wikipedia: Salbutamol

620
Isomer 21

homo-TMA-2

IUPAC: 4-(2,4,5-Trimethoxyphenyl)butan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: PDUFRZLKPVMEJH-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-9(14)5-6-10-7-12(16-3)13(17-4)8-11(10)15-2/h7-9H,5-6,14H2,1-4H3

PubChem CID: 3839009; ChemSpider: 3064644

Shulgin Index: See #91 Mescaline; Table: 10 Page: 358 Row: 27

622
Isomer 22

homo-TMA-3

IUPAC: 4-(2,3,4-Trimethoxyphenyl)butan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: JZNQOQZDPWRYGP-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-9(14)5-6-10-7-8-11(15-2)13(17-4)12(10)16-3/h7-9H,5-6,14H2,1-4H3

PubChem CID: 3041182; ChemSpider: 2304487

Shulgin Index: See #91 Mescaline; Table: 10 Page: 358 Row: 29

623
Isomer 23

homo-TMA-6

IUPAC: 4-(2,4,6-Trimethoxyphenyl)butan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: XCOSLSXZEMZDEY-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-9(14)5-6-11-12(16-3)7-10(15-2)8-13(11)17-4/h7-9H,5-6,14H2,1-4H3

PubChem CID: 3041180; ChemSpider: 2304485

Shulgin Index: See #91 Mescaline; Table: 10 Page: 358 Row: 30

6613
Isomer 24

N,N-Me-β,3,4-TMPEA

IUPAC: 2-(3,4-Dimethoxyphenyl)-2-methoxy-N,N-dimethylethan-1-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: JDECRXOMHIGGFQ-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-14(2)9-13(17-5)10-6-7-11(15-3)12(8-10)16-4/h6-8,13H,9H2,1-5H3

Shulgin Index: See #49 DMPEA; Table: 4 Page: 330 Row: 13

6870
Isomer 25

β-HO-β,N,N-Me-2,5-DMPEA

IUPAC: 2-(2,5-Dimethoxyphenyl)-1-(dimethylamino)propan-2-ol

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: NDKCLAODTZQRKW-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-13(15,9-14(2)3)11-8-10(16-4)6-7-12(11)17-5/h6-8,15H,9H2,1-5H3

PubChem CID: 50632; ChemSpider: 45892

Shulgin Index: See #22 2C-H; Table: 4 Page: 335 Row: 20

6878
Isomer 26

β-HO-N,N-Me-2,5-DMA

IUPAC: 1-(2,5-Dimethoxyphenyl)-2-(dimethylamino)propan-1-ol

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: IGNNPUVUCCOGBL-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-9(14(2)3)13(15)11-8-10(16-4)6-7-12(11)17-5/h6-9,13,15H,1-5H3

PubChem CID: 46240; ChemSpider: 42098

Shulgin Index: See #36 2,5-DMA; Table: 4 Page: 335 Row: 28

6913
Isomer 27

β-HO-N-Me-2,5-DEPEA

IUPAC: 1-(2,5-Diethoxyphenyl)-2-(methylamino)ethanol

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: ZTNAVFBSHZSJTJ-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-4-16-10-6-7-13(17-5-2)11(8-10)12(15)9-14-3/h6-8,12,14-15H,4-5,9H2,1-3H3

Shulgin Index: See #22 2C-H; Table: 4 Page: 336 Row: 13

6915
Isomer 28

β-HO-2,5-DEA

IUPAC: 2-Amino-1-(2,5-diethoxyphenyl)propan-1-ol

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: BGSGDJXRVUYFFR-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-4-16-10-6-7-12(17-5-2)11(8-10)13(15)9(3)14/h6-9,13,15H,4-5,14H2,1-3H3

PubChem CID: 11253430; ChemSpider: 9428457

Shulgin Index: See #36 2,5-DMA; Table: 4 Page: 336 Row: 15

7016
Isomer 29

N-Me-TMA-3

IUPAC: N-Methyl-1-(2,3,4-trimethoxyphenyl)propan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: HHLOEWSDUOAEAF-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-9(14-2)8-10-6-7-11(15-3)13(17-5)12(10)16-4/h6-7,9,14H,8H2,1-5H3

ChemSpider: 21476716

Shulgin Index: See #119 TMA-3; Table: 5 Page: 338 Row: 16

Clark, CC. The identification of methoxy-N-methylamphetamines. J. Forensic Sci., 1 Oct 1984, 29 (4), 1056–1071. 423 kB. doi:10.1520/JFS11772J

7017
Isomer 30

4C-TMPEA-3

IUPAC: 1-(2,3,4-Trimethoxyphenyl)butan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: QMRNVOUMUIECKP-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-5-10(14)8-9-6-7-11(15-2)13(17-4)12(9)16-3/h6-7,10H,5,8,14H2,1-4H3

PubChem CID: 43566032

Shulgin Index: See #119 TMA-3; Table: 5 Page: 338 Row: 17

7255
Isomer 31

4C-HM

IUPAC: 4-(2-Aminobutyl)-2,5-dimethoxybenzaldehyde

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: SHHGHSUAGKMYFL-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-4-11(14)5-9-6-13(17-3)10(8-15)7-12(9)16-2/h6-7,11,15H,4-5,8,14H2,1-3H3

PubChem CID: 20315288

Shulgin Index: See #118 TMA-2; Table: 5 Page: 343 Row: 5

7262
Isomer 32

BOE

IUPAC: 2-(4-Ethyl-2,5-dimethoxyphenyl)-2-methoxyethan-1-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: IJTKRVQOZAXRFT-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-5-9-6-12(16-3)10(7-11(9)15-2)13(8-14)17-4/h6-7,13H,5,8,14H2,1-4H3

PubChem CID: 10331826; ChemSpider: 8507286

Shulgin Index: See #14 BOB; Table: 5 Page: 343 Row: 12

Torres, MA; Cassels, BK; Rezende, MC. The preparation of potentially psychoactive β-alkoxyphenethylamines. Synth. Commun., 1 Jan 1995, 25 (8), 1239–1247. 415 kB. doi:10.1080/00397919508012687

7275
Isomer 33

DOEH

IUPAC: 2-[4-(2-Aminopropyl)-2,5-dimethoxyphenyl]ethanol

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: XXLDJSGSZKURAM-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-9(14)6-11-8-12(16-2)10(4-5-15)7-13(11)17-3/h7-9,15H,4-6,14H2,1-3H3

PubChem CID: 14201978; ChemSpider: 21415075

Shulgin Index: See #60 DOM; Table: 5 Page: 343 Row: 25

7327
Isomer 34

4C-MeO

IUPAC: 1-(2,4,5-Trimethoxyphenyl)butan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: AJLCTEZQDLTABS-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-5-10(14)6-9-7-12(16-3)13(17-4)8-11(9)15-2/h7-8,10H,5-6,14H2,1-4H3

PubChem CID: 43566022

Shulgin Index: See #118 TMA-2; Table: 5 Page: 344 Row: 27

7570
Isomer 35

DESMETHYL-iPr

IUPAC: 2,6-Dimethoxy-4-[2-(propan-2-ylamino)ethyl]phenol

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: MQVBLDXCDVGWQB-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-9(2)14-6-5-10-7-11(16-3)13(15)12(8-10)17-4/h7-9,14-15H,5-6H2,1-4H3

Shulgin Index: See #29 DESMETHYL; Table: 5 Page: 349 Row: 20

Short, JH; Dunnigan, DA; Ours, CW. Synthesis of phenethylamines from phenylacetonitriles obtained by alkylation of cyanide ion with Mannich bases from phenols and other benzylamines. Tetrahedron, 1973, 29 (14), 1931–1939. 791 kB. doi:10.1016/0040-4020(73)80127-9

7609
Isomer 36

α-MM-M

IUPAC: 2-Methyl-1-(3,4,5-trimethoxyphenyl)propan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: XCMXEBPTBOCOFV-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-13(2,14)8-9-6-10(15-3)12(17-5)11(7-9)16-4/h6-7H,8,14H2,1-5H3

PubChem CID: 3029803; ChemSpider: 2295076

Shulgin Index: See #117 TMA; Table: 5 Page: 350 Row: 9

1520
Isomer 37

DOMOM

IUPAC: 1-[2,5-Dimethoxy-4-(methoxymethyl)phenyl]propan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: IACSUTUTFQAPTC-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-9(14)5-10-6-13(17-4)11(8-15-2)7-12(10)16-3/h6-7,9H,5,8,14H2,1-4H3

PubChem CID: 10934687; ChemSpider: 9109923

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. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

Harms, A; Ulmer, E; Kovar, K. Synthesis and 5-HT2A radioligand receptor binding assays of DOMCl and DOMOM, two novel 5-HT2A receptor ligands. Arch. Pharm. Pharm. Med. Chem., 16 Jun 2003, 336 (3), 155–158. 69 kB. doi:10.1002/ardp.200390014

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