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PiHKAL#168 TMPEA; SI#124 TMPEA-2
168
Variant: N α β R2 R3 R4 R5 R4,5 skeleton isomers all
Analogues: 1 3 1 3 1 81 4 1 5 36 136

IUPAC: 2-(2,4,5-Trimethoxyphenyl)ethanamine

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: GKATTZLSNLYADI-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-13-9-7-11(15-3)10(14-2)6-8(9)4-5-12/h6-7H,4-5,12H2,1-3H3

PubChem CID: 151954; ChemSpider: 133931; Wikipedia: 2C-O

Shulgin Index: #124 TMPEA-2; Table: 5 Page: 344 Row: 21

See also PiHKAL: #35 2C-O-4 #157 TMA #158 TMA-2  
See also TiHKAL: #13 Harmaline      

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. 36161 kB. Rhodium.

Clark, LC; Benington, F; Morin, RD. The effects of ring-methoxyl groups on biological deamination of phenethylamines. J. Med. Chem., 1 May 1965, 8 (3), 353–355. 389 kB. doi:10.1021/jm00327a016

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

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

Lewin, AH; Navarro, HA; Mascarella, SW. Structure-activity correlations for β-phenethylamines at human trace amine receptor 1. Bioorg. Med. Chem., 1 Aug 2008, 16 (15),. 366 kB. doi:10.1016/j.bmc.2008.06.009

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

Silva, ME. Theoretical study of the interaction of agonists with the 5-HT2A receptor. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 26 Aug 2008. 5904 kB.

Silva, ME; Heim, R; Strasser, A; Elz, S; Dove, S. Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor. J. Comput. Aided Mol. Des., 1 Jan 2011, 25 (1), 51–66. 834 kB. doi:10.1007/s10822-010-9400-2

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

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

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

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

One N analogue:
592
Analogue 1: Adding 2-Methoxybenzyl at N

245-NBOMe
NBOMe-2,4,5-TMPEA

IUPAC: N-(2-Methoxybenzyl)-2-(2,4,5-trimethoxyphenyl)ethanamine

Formula: C19H25NO4 Molecular weight: 331.4061 g/mol InChI Key: YWHPPSGTTPXYSD-UHFFFAOYSA-N

InChI=1S/C19H25NO4/c1-21-16-8-6-5-7-15(16)13-20-10-9-14-11-18(23-3)19(24-4)12-17(14)22-2/h5-8,11-12,20H,9-10,13H2,1-4H3

Silva, ME; Heim, R; Strasser, A; Elz, S; Dove, S. Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor. J. Comput. Aided Mol. Des., 1 Jan 2011, 25 (1), 51–66. 834 kB. doi:10.1007/s10822-010-9400-2

Anon. Personal communication of unpublished research. 1 Dec 2011.

Silva, ME. Theoretical study of the interaction of agonists with the 5-HT2A receptor. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 26 Aug 2008. 5904 kB.

Three α analogues:
158
Analogue 1: Adding Methyl at α

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 Pharmacology notes I: p. 54, TMA-2: Subacute evaluation
p. 55, 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

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

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

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

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

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

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

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

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

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. 36161 kB. Rhodium.

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.

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.

Anon. Report on the risk assessment of TMA-2 in the framework of the joint action on new synthetic drugs, European Monitoring Centre for Drugs and Drug Addiction, 2004.

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.

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.

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.

Fenderson5555. The Trimethoxylated Amphetamines (TMA-x). 9 Dec 2012.

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

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. 1175 kB. doi:10.1021/jm00256a016

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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; 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

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

7327
Analogue 2: Adding Ethyl at α

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

539
Analogue 3: Adding Carboxy at α

α-Carboxy-TMA-2
2,5-Dimethoxy-O-methyltyrosine

IUPAC: 2-Amino-3-(2,4,5-trimethoxyphenyl)propanoic acid

Formula: C12H17NO5 Molecular weight: 255.26708 g/mol InChI Key: UDNVWGVLPKFPLE-UHFFFAOYSA-N

InChI=1S/C12H17NO5/c1-16-9-6-11(18-3)10(17-2)5-7(9)4-8(13)12(14)15/h5-6,8H,4,13H2,1-3H3,(H,14,15)

PubChem CID: 3929285; ChemSpider: 3151339

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

One β analogue:
7322
Analogue 1: Adding Methoxy at β

BOT

IUPAC: 2-Methoxy-2-(2,4,5-trimethoxyphenyl)ethanamine

Formula: C12H19NO4 Molecular weight: 241.28356 g/mol InChI Key: RCJFHHAMXCSUBT-UHFFFAOYSA-N

InChI=1S/C12H19NO4/c1-14-9-6-11(16-3)10(15-2)5-8(9)12(7-13)17-4/h5-6,12H,7,13H2,1-4H3

PubChem CID: 10399437; ChemSpider: 8574875

Shulgin Index: See #14 BOB; Table: 5 Page: 344 Row: 22

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

Three R2 analogues:
197
Analogue 1: Substituting Bromo for Methoxy at R2

2,4,5-BMM
6-Br-DMPEA
2-Bromo-4,5-dimethoxyphenethylamine

IUPAC: 2-(2-Bromo-4,5-dimethoxyphenyl)ethanamine

Formula: C10H14BrNO2 Molecular weight: 260.12766 g/mol InChI Key: WGAFQMMKTNUYDH-UHFFFAOYSA-N

InChI=1S/C10H14BrNO2/c1-13-9-5-7(3-4-12)8(11)6-10(9)14-2/h5-6H,3-4,12H2,1-2H3

PubChem CID: 820370; ChemSpider: 716761

Shulgin Index: See #18 2C-B; Table: 5 Page: 344 Row: 15

See also PiHKAL: #20 2C-B      
7314
Analogue 2: Substituting Chloro for Methoxy at R2

2-Cl-4,5-DMPEA

IUPAC: 2-(2-Chloro-4,5-dimethoxyphenyl)ethanamine

Formula: C10H14ClNO2 Molecular weight: 215.67666 g/mol InChI Key: DHMSGUTWLHFESS-UHFFFAOYSA-N

InChI=1S/C10H14ClNO2/c1-13-9-5-7(3-4-12)8(11)6-10(9)14-2/h5-6H,3-4,12H2,1-2H3

PubChem CID: 15557188; ChemSpider: 14826767

Shulgin Index: See #19 2C-C; Table: 5 Page: 344 Row: 14

7330
Analogue 3: Substituting n-Propylthio for Methoxy at R2

4,5,2-2C-T-7

IUPAC: 2-[4,5-Dimethoxy-2-(propylsulfanyl)phenyl]ethanamine

Formula: C13H21NO2S Molecular weight: 255.37634 g/mol InChI Key: WBUPODDKBKBOOW-UHFFFAOYSA-N

InChI=1S/C13H21NO2S/c1-4-7-17-13-9-12(16-3)11(15-2)8-10(13)5-6-14/h8-9H,4-7,14H2,1-3H3

Shulgin Index: See #27 2C-T-7; Table: 5 Page: 344 Row: 30

One R3 analogue:
455
Analogue 1: Adding Methoxy at R3

TeMPEA

IUPAC: 2-(2,3,4,5-Tetramethoxyphenyl)ethanamine

Formula: C12H19NO4 Molecular weight: 241.28356 g/mol InChI Key: GJKJPCJLMHZZFK-UHFFFAOYSA-N

InChI=1S/C12H19NO4/c1-14-9-7-8(5-6-13)10(15-2)12(17-4)11(9)16-3/h7H,5-6,13H2,1-4H3

PubChem CID: 611405; ChemSpider: 531480

Shulgin Index: #114 TeMPEA; Table: 6 Page: 355 Row: 3

Clark, LC; Benington, F; Morin, RD. The effects of ring-methoxyl groups on biological deamination of phenethylamines. J. Med. Chem., 1 May 1965, 8 (3), 353–355. 389 kB. doi:10.1021/jm00327a016

Benington, F; Morin, RD; Clark, LC. Mescaline analogs. II. Tetra- and penta-methoxy-β-phenethylamines. J. Org. Chem., 1 Jan 1955, 20 (1), 102–108. 534 kB. doi:10.1021/jo01119a017

81 R4 analogues:
20
Analogue 1: Substituting Bromo for Methoxy at R4

2C-B
4-Bromo-2,5-dimethoxyphenethylamine

IUPAC: 2-(4-Bromo-2,5-dimethoxyphenyl)ethanamine

Formula: C10H14BrNO2 Molecular weight: 260.12766 g/mol InChI Key: YMHOBZXQZVXHBM-UHFFFAOYSA-N

InChI=1S/C10H14BrNO2/c1-13-9-6-8(11)10(14-2)5-7(9)3-4-12/h5-6H,3-4,12H2,1-2H3

PubChem CID: 98527; ChemSpider: 88978; Drugs Forum: 2C-B; Erowid: 2C-B; Wikipedia: 2C-B

Shulgin Index: #18 2C-B; Table: 5 Page: 340 Row: 23

See also PiHKAL: #9 ASB
#10 B
#14 BOD
#16 BOHD
#22 2C-C
#23 2C-D
#25 3C-E
#30 2C-G-5
#32 2C-H
#33 2C-I
#34 2C-N
#39 2C-T
#41 2C-T-4
#43 2C-T-7
#50 4-D
#65 DOEF
#72 E
#118 MDPR
#122 MEM
#170 5-TOET
See also TiHKAL: #5 α,O-DMS #37 5-MeO-DIPT    
See also Pharmacology notes I: p. 172, 2C-B: Trials
See also Pharmacology notes II: app. 2, Abuse week
p. 204, 2C-B
p. 211, 2C-B
p. 279, 2C-B
p. 303, 2C-B
p. 305, 2C-B
p. 309, 2C-B
p. 323, 2C-B

McGrane, O; Simmons, J; Jacobsen, E; Skinner, C. Alarming trends in a novel class of designer drugs. J. Clinic. Toxicol., 1 Nov 2011, 1 (2). 775 kB. doi:10.4172/2161-0494.1000108

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

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

Katagi, M; Tsuchihashi, H. Update on clandestine amphetamines and their analogues recently seen in Japan. J. Health Sci., 2002, 48 (1), 14–21. 181 kB. doi:10.1248/jhs.48.14

Caudevilla-Gálligo, F; Riba, J; Ventura, M; González, D; Farré, M; Barbanoj, MJ; Bouso, JC. 4-Bromo-2,5-dimethoxyphenethylamine (2C-B): presence in the recreational drug market in Spain, pattern of use and subjective effects. J. Psychopharmacol., 1 Jul 2012, 26 (7), 1026–1035. 586 kB. doi:10.1177/0269881111431752

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. doi:10.1124/jpet.106.117507

Lemaire, D; Jacob, P; Shulgin, AT. Ring substituted beta-methoxyphenethylamines: a new class of psychotomimetic agents active in man. J. Pharm. Pharmacol., 1 Jan 1985, 37 (8), 575–7. 1767 kB. doi:10.1111/j.2042-7158.1985.tb03072.x

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. 36161 kB. Rhodium.

Shulgin, AT; Shulgin, LA; Jacob, P. A protocol for the evaluation of new psychoactive drugs. Meth. Find. Exp. Clin. Pharmacol., 1 May 1986, 8 (5), 313. 7938 kB.

Parrish, JC. Toward a molecular understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2006. 5475 kB.

Shulgin, AT; Carter, MF. Centrally active phenethylamines. Psychopharmacol. Commun., 1 Jan 1975, 1 (1), 93–98. 6175 kB. Rhodium.

Cozzi, NV. Pharmacological studies of some psychoactive phenylalkylamines: entactogens, hallucinogens, and anorectics. Ph. D. Thesis, University Of Wisconsin-Madison, 1 Jan 1994. 10616 kB.

Silva, ME. Theoretical study of the interaction of agonists with the 5-HT2A receptor. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 26 Aug 2008. 5904 kB.

Theobald, DS. The 2C-series—A new class of designer drugs. Ph. D. Thesis, Universität des Saarlandes, Saarbrücken, Germany, 18 Dec 2006. 1370 kB.

Meyers-Riggs, B. The halogenated 2Cs. countyourculture: rational exploration of the underground, 29 Sep 2010.

Shulgin, AT. 2,5-Dimethoxy-4-bromophenethylamine (2C-B). Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 7 Feb 2003.

Parrish, JC; Braden, MR; Gundy, E; Nichols, DE. Differential phospholipase C activation by phenylalkylamine serotonin 5-HT2A receptor agonists. J. Neurochem., 1 Dec 2005, 95 (6), 1575–1584. 301 kB. doi:10.1111/j.1471-4159.2005.03477.x

Boer, D; Gijzels, MJ; Bosman, IJ; Maes, RAA. More data about the new psychoactive drug 2C-B. J. Anal. Toxicol., 0000, 23 (3), 227–228. 190 kB. doi:10.1093/jat/23.3.227

Makriyannis, A; Bowerman, D; Sze, PY; Fournier, D; Jong., APD. Structure activity correlations in the inhibition of brain synaptosomal 3H-norepinephrine uptake by phenethylamine analogs. The role of ?-alkyl side chain and methoxyl ring substitutions. Eur. J. Pharmacol., 9 Jul 1982, 81 (2), 337–340. 313 kB. doi:10.1016/0014-2999(82)90454-X

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. doi:10.1007/s11419-008-0041-2

Silva, ME; Heim, R; Strasser, A; Elz, S; Dove, S. Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor. J. Comput. Aided Mol. Des., 1 Jan 2011, 25 (1), 51–66. 834 kB. doi:10.1007/s10822-010-9400-2

Páleníček, T; Fujáková, M; Brunovský, M; Horáček, J; Gorman, I; Balíková, M; Rambousek, L; Syslová, K; Kačer, P; Zach, P; Bubeníková-Valešová, V; Tylš, F; Kubešová, A; Puskarčíková, J; Höschl, C. Behavioral, neurochemical and pharmaco-EEG profiles of the psychedelic drug 4-bromo-2,5-dimethoxyphenethylamine (2C-B) in rats. Psychopharmacology, 1 Jan 2013, 225 (1), 75–93. 1079 kB. doi:10.1007/s00213-012-2797-7

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

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

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

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

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

Lewin, AH; Navarro, HA; Mascarella, SW. Structure-activity correlations for β-phenethylamines at human trace amine receptor 1. Bioorg. Med. Chem., 1 Aug 2008, 16 (15),. 366 kB. doi:10.1016/j.bmc.2008.06.009

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. doi:10.1038/sj.bjp.0704747

Villalobos, CA; Bull, P; Sáez, P; Cassels, BK; Huidobro-Toro, JP. 4-Bromo-2,5-dimethoxyphenethylamine (2C-B) and structurally related phenylethylamines are potent 5-HT2A receptor antagonists in Xenopus laevis oocytes. Br. J. Pharmacol., 1 Apr 2004, 141 (7), 1167–1174. 271 kB. doi:10.1038/sj.bjp.0705722

Boer, D; Bosman, I. A new trend in drugs-of-abuse; the 2C-series of phenethylamine designer drugs. Pharm. World Sci., 1 Apr 2004, 26 (2), 110–113. 61 kB. doi:10.1023/B:PHAR.0000018600.03664.36

McLean, TH; Parrish, JC; Braden, MR; Marona-Lewicka, D; Gallardo-Godoy, A; Nichols, DE. 1-Aminomethylbenzocycloalkanes: Conformationally restricted hallucinogenic phenethylamine analogues as functionally selective 5-HT2A receptor agonists. J. Med. Chem., 1 Jan 2006, 49 (19), 5794–5803. 522 kB. doi:10.1021/jm060656o

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

Carmo, H; Hengstler, JG; Boer, D; Ringel, M; Remião, F; Carvalho, F; Fernandes, E; Reys, LA; Oesch, F; Bastos, ML. Metabolic pathways of 4-bromo-2,5-dimethoxyphenethylamine (2C-B): analysis of phase I metabolism with hepatocytes of six species including human. Toxicology, 5 Jan 2005, 206 (1), 75–89. 273 kB. doi:10.1016/j.tox.2004.07.004

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

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

22
Analogue 2: Substituting Chloro for Methoxy at R4

2C-C
4-Chloro-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-chlorophenethylamine

IUPAC: 2-(4-Chloro-2,5-dimethoxyphenyl)ethanamine

Formula: C10H14ClNO2 Molecular weight: 215.67666 g/mol InChI Key: CGKQFIWIPSIVAS-UHFFFAOYSA-N

InChI=1S/C10H14ClNO2/c1-13-9-6-8(11)10(14-2)5-7(9)3-4-12/h5-6H,3-4,12H2,1-2H3

PubChem CID: 29979100; ChemSpider: 21106221; Drugs Forum: 2C-C; Erowid: 2C-C; Wikipedia: 2C-C

Shulgin Index: #19 2C-C; Table: 5 Page: 340 Row: 19

See also PiHKAL: #32 2C-H #39 2C-T #64 DOC  

Meyers-Riggs, B. The halogenated 2Cs. countyourculture: rational exploration of the underground, 29 Sep 2010.

Cozzi, NV. Pharmacological studies of some psychoactive phenylalkylamines: entactogens, hallucinogens, and anorectics. Ph. D. Thesis, University Of Wisconsin-Madison, 1 Jan 1994. 10616 kB.

Lewin, AH; Navarro, HA; Mascarella, SW. Structure-activity correlations for β-phenethylamines at human trace amine receptor 1. Bioorg. Med. Chem., 1 Aug 2008, 16 (15),. 366 kB. doi:10.1016/j.bmc.2008.06.009

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

23
Analogue 3: Substituting Methyl for Methoxy at R4

2C-D
LE-25
4-Methyl-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-methylphenethylamine

IUPAC: 2-(2,5-Dimethoxy-4-methylphenyl)ethanamine

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: UNQQFDCVEMVQHM-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-8-6-11(14-3)9(4-5-12)7-10(8)13-2/h6-7H,4-5,12H2,1-3H3

PubChem CID: 135740; ChemSpider: 119559; Drugs Forum: 2C-D; Erowid: 2C-D; Wikipedia: 2C-D

Shulgin Index: #20 2C-D; Table: 5 Page: 342 Row: 9

See also PiHKAL: #8 ARIADNE
#14 BOD
#16 BOHD
#20 2C-B
#25 3C-E
#56 DMCPA
#68 DOM
#85 GANESHA
#93 IRIS
 
See also TiHKAL: #16 4-HO-DET      
See also Pharmacology notes I: p. 94, 2C-D: Subacute evaluation
p. 175, 2C-D: Acute trials
See also Pharmacology notes II: p. 273, 2C-D
p. 280, 2C-D
p. 285, 2C-D: Report of experience
p. 310, 2C-D
p. 313, 2C-D
p. 316, 2C-D: Experiment with 2C-D

Theobald, DS. The 2C-series—A new class of designer drugs. Ph. D. Thesis, Universität des Saarlandes, Saarbrücken, Germany, 18 Dec 2006. 1370 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. 36161 kB. Rhodium.

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

Ho, B; Tansey, LW; Balster, RL; An, R; McIsaac, WM; Harris, RT. Amphetamine analogs. II. Methylated phenethylamines. J. Med. Chem., 1 Jan 1970, 13 (1), 134–135. 278 kB. doi:10.1021/jm00295a034

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

Lewin, AH; Navarro, HA; Mascarella, SW. Structure-activity correlations for β-phenethylamines at human trace amine receptor 1. Bioorg. Med. Chem., 1 Aug 2008, 16 (15),. 366 kB. doi:10.1016/j.bmc.2008.06.009

Allred, RA. Spectral characterization of 2,4-dimethoxy-3-methylphenethylamine and comparison to 2,5-dimethoxy-4-methylphenethylamine (“2C-D”). Microgram J., 1 Jan 2005, 3 (1–2), 16–26. 107 kB.

Villalobos, CA; Bull, P; Sáez, P; Cassels, BK; Huidobro-Toro, JP. 4-Bromo-2,5-dimethoxyphenethylamine (2C-B) and structurally related phenylethylamines are potent 5-HT2A receptor antagonists in Xenopus laevis oocytes. Br. J. Pharmacol., 1 Apr 2004, 141 (7), 1167–1174. 271 kB. doi:10.1038/sj.bjp.0705722

Lemaire, D; Jacob, P; Shulgin, AT. Ring substituted beta-methoxyphenethylamines: a new class of psychotomimetic agents active in man. J. Pharm. Pharmacol., 1 Jan 1985, 37 (8), 575–7. 1767 kB. doi:10.1111/j.2042-7158.1985.tb03072.x

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

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

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. doi:10.1038/sj.bjp.0704747

Shulgin, AT; Carter, MF. Centrally active phenethylamines. Psychopharmacol. Commun., 1 Jan 1975, 1 (1), 93–98. 6175 kB. Rhodium.

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

Meyers-Riggs, B. The alkylated 2Cs. countyourculture: rational exploration of the underground, 4 Oct 2010.

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. doi:10.1124/jpet.106.117507

Glennon, RA; Young, R; Jacyno, JM. Indolealkylamine and phenalkylamine hallucinogens: Effect of α-methyl and N-methyl substituents on behavioral activity. Biochem. Pharmacol., 1 Apr 1983, 32 (7), 1267–1273. 591 kB. doi:10.1016/0006-2952(83)90281-2

24
Analogue 4: Substituting Ethyl for Methoxy at R4

2C-E
4-Ethyl-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-ethylphenethylamine

IUPAC: 2-(4-Ethyl-2,5-dimethoxyphenyl)ethanamine

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

InChI=1S/C12H19NO2/c1-4-9-7-12(15-3)10(5-6-13)8-11(9)14-2/h7-8H,4-6,13H2,1-3H3

PubChem CID: 24729233; ChemSpider: 21106222; Drugs Forum: 2C-E; Erowid: 2C-E; Wikipedia: 2C-E

Shulgin Index: #21 2C-E; Table: 5 Page: 343 Row: 11

See also PiHKAL: #23 2C-D
#43 2C-T-7
#66 DOET
#72 E
#85 GANESHA  
See also Pharmacology notes II: app. 2, Abuse week
p. 236, 2C-E

McGrane, O; Simmons, J; Jacobsen, E; Skinner, C. Alarming trends in a novel class of designer drugs. J. Clinic. Toxicol., 1 Nov 2011, 1 (2). 775 kB. doi:10.4172/2161-0494.1000108

Lewin, AH; Navarro, HA; Mascarella, SW. Structure-activity correlations for β-phenethylamines at human trace amine receptor 1. Bioorg. Med. Chem., 1 Aug 2008, 16 (15),. 366 kB. doi:10.1016/j.bmc.2008.06.009

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. Abused substances. Tech. Rev., 1 Jan 2005, August, 80–81. 415 kB.

Theobald, DS. The 2C-series—A new class of designer drugs. Ph. D. Thesis, Universität des Saarlandes, Saarbrücken, Germany, 18 Dec 2006. 1370 kB.

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

Meyers-Riggs, B. The alkylated 2Cs. countyourculture: rational exploration of the underground, 4 Oct 2010.

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

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

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

Kusin, S; Tesar, J; Hatten, B; Horowitz, BZ; Hendrickson, R; Leman, R; Buser, G. Severe methemoglobinemia and haemolytic anemia from aniline purchased as 2C-E (4-ethyl-2,5-dimethoxyphenethylamine), a recreational drug, on the internet – Oregon, 2011. Morbidity and Mortality Weekly Report, 10 Feb 2012, 61 (5), 85–88. 273 kB.

26
Analogue 5: Substituting Fluoro for Methoxy at R4

2C-F
4-Fluoro-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-fluorophenethylamine

IUPAC: 2-(4-Fluoro-2,5-dimethoxyphenyl)ethanamine

Formula: C10H14FNO2 Molecular weight: 199.2220632 g/mol InChI Key: QAVFEDRVOUKIPM-UHFFFAOYSA-N

InChI=1S/C10H14FNO2/c1-13-9-6-8(11)10(14-2)5-7(9)3-4-12/h5-6H,3-4,12H2,1-2H3

PubChem CID: 44719499; ChemSpider: 21106223; Wikipedia: 2C-F

Shulgin Index: See #20 2C-D; Table: 5 Page: 340 Row: 17

See also PiHKAL: #22 2C-C      

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

Meyers-Riggs, B. The halogenated 2Cs. countyourculture: rational exploration of the underground, 29 Sep 2010.

32
Analogue 6: Removing Methoxy at R4

2C-H
25H
2,5-Dimethoxyphenethylamine

IUPAC: 2-(2,5-Dimethoxyphenyl)ethanamine

Formula: C10H15NO2 Molecular weight: 181.2316 g/mol InChI Key: WNCUVUUEJZEATP-UHFFFAOYSA-N

InChI=1S/C10H15NO2/c1-12-9-3-4-10(13-2)8(7-9)5-6-11/h3-4,7H,5-6,11H2,1-2H3

PubChem CID: 76632; ChemSpider: 69096; Wikipedia: 2C-H

Shulgin Index: #22 2C-H; Table: 4 Page: 335 Row: 7

See also PiHKAL: #16 BOHD
#20 2C-B
#22 2C-C
#33 2C-I
#34 2C-N
#35 2C-O-4
 

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

Silva, ME. Theoretical study of the interaction of agonists with the 5-HT2A receptor. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 26 Aug 2008. 5904 kB.

Cozzi, NV. Pharmacological studies of some psychoactive phenylalkylamines: entactogens, hallucinogens, and anorectics. Ph. D. Thesis, University Of Wisconsin-Madison, 1 Jan 1994. 10616 kB.

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

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-HT2A receptor. Mol. Pharmacol., 1 Jan 2007, 72 (5), 1200–1209. 487 kB. doi:10.1124/mol.107.039255

Braden, MR; Parrish, JC; Naylor, JC; Nichols, DE. Molecular interaction of serotonin 5-HT2A 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. doi:10.1124/mol.106.028720

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. doi:10.1124/jpet.106.117507

Maher, HM; Awad, T; DeRuiter, J; Clark, CR. GC-MS and GC-IRD studies on dimethoxyphenethylamines (DMPEA): Regioisomers related to 2,5-DMPEA. J. Chromatogr. Sci., 1 Jan 2012, 50 (1), 1–9. 594 kB. doi:10.1093/chromsci/bmr013

Villalobos, CA; Bull, P; Sáez, P; Cassels, BK; Huidobro-Toro, JP. 4-Bromo-2,5-dimethoxyphenethylamine (2C-B) and structurally related phenylethylamines are potent 5-HT2A receptor antagonists in Xenopus laevis oocytes. Br. J. Pharmacol., 1 Apr 2004, 141 (7), 1167–1174. 271 kB. doi:10.1038/sj.bjp.0705722

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. doi:10.1038/sj.bjp.0704747

Rangisetty, JB; Dukat, M; Dowd, CS; Herrick-Davis, K; DuPre, A; Gadepalli, S; Teitler, M; Kelley, CR; Sharif, NA; Glennon, RA. 1-[2-Methoxy-5-(3-phenylpropyl)]-2-aminopropane unexpectedly shows 5-HT2A serotonin receptor affinity and antagonist character. J. Med. Chem., 1 Jan 2001, 44 (20), 3283–3291. 115 kB. doi:10.1021/jm0100739

Clark, LC; Benington, F; Morin, RD. The effects of ring-methoxyl groups on biological deamination of phenethylamines. J. Med. Chem., 1 May 1965, 8 (3), 353–355. 389 kB. doi:10.1021/jm00327a016

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

Lewin, AH; Navarro, HA; Mascarella, SW. Structure-activity correlations for β-phenethylamines at human trace amine receptor 1. Bioorg. Med. Chem., 1 Aug 2008, 16 (15),. 366 kB. doi:10.1016/j.bmc.2008.06.009

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. doi:10.1007/s11419-008-0041-2

Silva, ME; Heim, R; Strasser, A; Elz, S; Dove, S. Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor. J. Comput. Aided Mol. Des., 1 Jan 2011, 25 (1), 51–66. 834 kB. doi:10.1007/s10822-010-9400-2

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

33
Analogue 7: Substituting Iodo for Methoxy at R4

2C-I
Cimbi-88
25I
4-Iodo-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-iodophenethylamine

IUPAC: 2-(4-Iodo-2,5-dimethoxyphenyl)ethanamine

Formula: C10H14INO2 Molecular weight: 307.12813 g/mol InChI Key: PQHQBRJAAZQXHL-UHFFFAOYSA-N

InChI=1S/C10H14INO2/c1-13-9-6-8(11)10(14-2)5-7(9)3-4-12/h5-6H,3-4,12H2,1-2H3

PubChem CID: 10267191; ChemSpider: 8442670; Drugs Forum: 2C-I; Erowid: 2C-I; Wikipedia: 2C-I

Shulgin Index: #23 2C-I; Table: 5 Page: 341 Row: 8

See also PiHKAL: #22 2C-C
#32 2C-H
#39 2C-T
#65 DOEF
#72 E  
See also Pharmacology notes I: p. 179, 2C-I: Trials

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

McGrane, O; Simmons, J; Jacobsen, E; Skinner, C. Alarming trends in a novel class of designer drugs. J. Clinic. Toxicol., 1 Nov 2011, 1 (2). 775 kB. doi:10.4172/2161-0494.1000108

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. 36161 kB. Rhodium.

Anon. Report on the risk assessment of 2C-I, 2C-T-2 and 2C-T-7 in the framework of the joint action on new synthetic drugs, European Monitoring Centre for Drugs and Drug Addiction, 2004.

Parrish, JC. Toward a molecular understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2006. 5475 kB.

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

Cozzi, NV. Pharmacological studies of some psychoactive phenylalkylamines: entactogens, hallucinogens, and anorectics. Ph. D. Thesis, University Of Wisconsin-Madison, 1 Jan 1994. 10616 kB.

Theobald, DS. The 2C-series—A new class of designer drugs. Ph. D. Thesis, Universität des Saarlandes, Saarbrücken, Germany, 18 Dec 2006. 1370 kB.

Meyers-Riggs, B. The halogenated 2Cs. countyourculture: rational exploration of the underground, 29 Sep 2010.

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-HT2A receptor. Mol. Pharmacol., 1 Jan 2007, 72 (5), 1200–1209. 487 kB. doi:10.1124/mol.107.039255

Braden, MR; Parrish, JC; Naylor, JC; Nichols, DE. Molecular interaction of serotonin 5-HT2A 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. doi:10.1124/mol.106.028720

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

Ettrup, A; Hansen, M; Santini, MA; Paine, J; Gillings, N; Palner, M; Lehel, S; Herth, MM; Madsen, J; Kristensen, JL; Begtrup, M; Knudsen, GM. Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT2A agonist PET tracers. Eur. J. Nucl. Med. Mol. Imaging, 21 Nov 2010. 752 kB. doi:10.1007/s00259-010-1686-8

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. doi:10.1007/s11419-008-0041-2

Johnson, MP; Mathis, CA; Shulgin, AT; Hoffman, AJ; Nichols, DE. [125I]-2-(2,5-Dimethoxy-4-iodophenyl)aminoethane ([125I]-2C-I) as a label for the 5-HT2 receptor in rat frontal cortex. Pharmacol. Biochem. Behav., 1 Jan 1990, 35 (1), 211–217. 724 kB. doi:10.1016/0091-3057(90)90228-A

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

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. 1124 kB. doi:10.1021/jm00222a001

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. doi:10.1038/sj.bjp.0704747

Villalobos, CA; Bull, P; Sáez, P; Cassels, BK; Huidobro-Toro, JP. 4-Bromo-2,5-dimethoxyphenethylamine (2C-B) and structurally related phenylethylamines are potent 5-HT2A receptor antagonists in Xenopus laevis oocytes. Br. J. Pharmacol., 1 Apr 2004, 141 (7), 1167–1174. 271 kB. doi:10.1038/sj.bjp.0705722

Parrish, JC; Braden, MR; Gundy, E; Nichols, DE. Differential phospholipase C activation by phenylalkylamine serotonin 5-HT2A receptor agonists. J. Neurochem., 1 Dec 2005, 95 (6), 1575–1584. 301 kB. doi:10.1111/j.1471-4159.2005.03477.x

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. doi:10.1124/jpet.106.117507

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

34
Analogue 8: Substituting Nitro for Methoxy at R4

2C-N
4-Nitro-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-nitrophenethylamine

IUPAC: 2-(2,5-Dimethoxy-4-nitrophenyl)ethanamine

Formula: C10H14N2O4 Molecular weight: 226.22916 g/mol InChI Key: ZMUSDZGRRJGRAO-UHFFFAOYSA-N

InChI=1S/C10H14N2O4/c1-15-9-6-8(12(13)14)10(16-2)5-7(9)3-4-11/h5-6H,3-4,11H2,1-2H3

PubChem CID: 10036637; ChemSpider: 8212202; Wikipedia: 2C-N

Shulgin Index: See #20 2C-D; Table: 5 Page: 342 Row: 1

See also PiHKAL: #32 2C-H #39 2C-T #72 E  

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. doi:10.1124/jpet.106.117507

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. doi:10.1038/sj.bjp.0704747

Zuba, D; Sekuła, K; Buczek, A. Identification and characterization of 2,5-dimethoxy-4-nitro-β-phenethylamine (2C-N)–A new member of 2C-series of designer drug. Forensic Sci. Int., 10 Oct 2012, 222 (1–3), 298–305. 588 kB. doi:10.1016/j.forsciint.2012.07.006

35
Analogue 9: Substituting Isopropoxy for Methoxy at R4

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

IUPAC: 2-[2,5-Dimethoxy-4-(propan-2-yloxy)phenyl]ethanamine

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

36
Analogue 10: Substituting n-Propyl for Methoxy at R4

2C-P
Selene
4-Propyl-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-n-propylphenethylamine

IUPAC: 2-(2,5-Dimethoxy-4-propylphenyl)ethanamine

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

InChI=1S/C13H21NO2/c1-4-5-10-8-13(16-3)11(6-7-14)9-12(10)15-2/h8-9H,4-7,14H2,1-3H3

PubChem CID: 44350080; ChemSpider: 21106226; Drugs Forum: 2C-P; Erowid: 2C-P; Wikipedia: 2C-P

Shulgin Index: See #20 2C-D; Table: 5 Page: 343 Row: 31

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

Meyers-Riggs, B. The alkylated 2Cs. countyourculture: rational exploration of the underground, 4 Oct 2010.

Fenderson5555. Mechanisms and named reactions in 2C-P synthesis. 7 Jan 2011.

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.

38
Analogue 11: Substituting Methylseleno for Methoxy at R4

2C-SE
4-Methylseleno-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-methylselenophenethylamine

IUPAC: 2-[2,5-Dimethoxy-4-(methylselanyl)phenyl]ethanamine

Formula: C11H17NO2Se Molecular weight: 274.21818 g/mol InChI Key: CXQUHXATPUFGMC-UHFFFAOYSA-N

InChI=1S/C11H17NO2Se/c1-13-9-7-11(15-3)10(14-2)6-8(9)4-5-12/h6-7H,4-5,12H2,1-3H3

PubChem CID: 44719515; ChemSpider: 21106227; Wikipedia: 2C-SE

Shulgin Index: See #124 TMPEA-2; Table: 5 Page: 346 Row: 17

39
Analogue 12: Substituting Methylthio for Methoxy at R4

2C-T
4-Methylthio-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-methylthiophenethylamine

IUPAC: 2-[2,5-Dimethoxy-4-(methylsulfanyl)phenyl]ethanamine

Formula: C11H17NO2S Molecular weight: 227.32318 g/mol InChI Key: UPZMYCMLLQTYEM-UHFFFAOYSA-N

InChI=1S/C11H17NO2S/c1-13-9-7-11(15-3)10(14-2)6-8(9)4-5-12/h6-7H,4-5,12H2,1-3H3

PubChem CID: 12315927; ChemSpider: 10438674; Wikipedia: 2C-T

Shulgin Index: #25 2C-T; Table: 5 Page: 345 Row: 12

See also PiHKAL: #3 ALEPH
#30 2C-G-5
#35 2C-O-4
#38 2C-SE
#40 2C-T-2
#49 2C-T-21
 
See also Pharmacology notes II: p. 315, 2C-T

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

Nichols, DE; Shulgin, AT. Sulfur analogs of psychotomimetic amines. J. Pharm. Sci., 1 Jan 1976, 65 (1), 1554–1556. 383 kB. doi:10.1002/jps.2600651040 Rhodium.

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

Meyers-Riggs, B. Shulgin’s sulfur symphony—part I. countyourculture: rational exploration of the underground, 15 Jan 2011.

Meyers-Riggs, B. 2C-T-x substitution size and potency. countyourculture: rational exploration of the underground, 1 Apr 2011.

40
Analogue 13: Substituting Ethylthio for Methoxy at R4

2C-T-2
4-Ethylthio-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-ethylthiophenethylamine

IUPAC: 2-[4-(Ethylsulfanyl)-2,5-dimethoxyphenyl]ethanamine

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

InChI=1S/C12H19NO2S/c1-4-16-12-8-10(14-2)9(5-6-13)7-11(12)15-3/h7-8H,4-6,13H2,1-3H3

PubChem CID: 12074193; ChemSpider: 16787961; Drugs Forum: 2C-T-2; Erowid: 2C-T-2; Wikipedia: 2C-T-2

Shulgin Index: #26 2C-T-2; Table: 5 Page: 345 Row: 17

See also PiHKAL: #4 ALEPH-2
#35 2C-O-4
#39 2C-T
#41 2C-T-4
#43 2C-T-7
#44 2C-T-8
#45 2C-T-9
#46 2C-T-13
#47 2C-T-15
#48 2C-T-17
#49 2C-T-21
#81 FLEA
#87 HOT-2
#118 MDPR

Parrish, JC. Toward a molecular understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2006. 5475 kB.

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

Theobald, DS. The 2C-series—A new class of designer drugs. Ph. D. Thesis, Universität des Saarlandes, Saarbrücken, Germany, 18 Dec 2006. 1370 kB.

Meyers-Riggs, B. Shulgin’s sulfur symphony—part I. countyourculture: rational exploration of the underground, 15 Jan 2011.

Meyers-Riggs, B. 2C-T-x substitution size and potency. countyourculture: rational exploration of the underground, 1 Apr 2011.

Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011.

Shulgin, AT. 2C-T-7. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 28 Jun 2001.

Anon. Report on the risk assessment of 2C-I, 2C-T-2 and 2C-T-7 in the framework of the joint action on new synthetic drugs, European Monitoring Centre for Drugs and Drug Addiction, 2004.

Stolaroff, MJ; Wells, CW. Preliminary results with new psychoactive agents 2C-T-2 and 2C-T-7. In Jahrbuch für Ethnomedizin und Bewußtseinsforschung (Yearbook of Ethnomedicine and the Study of Consciousness); Rätsch, C; Baker, J, Eds., 1 Jan 1993; Vol. 2, pp 99–117. 185 kB.

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

Boer, D; Bosman, I. A new trend in drugs-of-abuse; the 2C-series of phenethylamine designer drugs. Pharm. World Sci., 1 Apr 2004, 26 (2), 110–113. 61 kB. doi:10.1023/B:PHAR.0000018600.03664.36

Stolaroff, MJ. Letter to the editor (re: 2C-T-2 & 2C-T-7). J. Psychoactive Drugs, 1 Jan 1990, 22 (3), 379. 1090 kB. doi:10.1080/02791072.1990.10472568

Parrish, JC; Braden, MR; Gundy, E; Nichols, DE. Differential phospholipase C activation by phenylalkylamine serotonin 5-HT2A receptor agonists. J. Neurochem., 1 Dec 2005, 95 (6), 1575–1584. 301 kB. doi:10.1111/j.1471-4159.2005.03477.x

Katagi, M; Tsuchihashi, H. Update on clandestine amphetamines and their analogues recently seen in Japan. J. Health Sci., 2002, 48 (1), 14–21. 181 kB. doi:10.1248/jhs.48.14

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

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

McGrane, O; Simmons, J; Jacobsen, E; Skinner, C. Alarming trends in a novel class of designer drugs. J. Clinic. Toxicol., 1 Nov 2011, 1 (2). 775 kB. doi:10.4172/2161-0494.1000108

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

41
Analogue 14: Substituting Isopropylthio for Methoxy at R4

2C-T-4
4-Isopropylthio-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-isopropylthiophenethylamine

IUPAC: 2-[2,5-Dimethoxy-4-(propan-2-ylsulfanyl)phenyl]ethanamine

Formula: C13H21NO2S Molecular weight: 255.37634 g/mol InChI Key: HDYZSVKZKDPLDT-UHFFFAOYSA-N

InChI=1S/C13H21NO2S/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: 44350070; ChemSpider: 21106232; Erowid: 2C-T-4; Wikipedia: 2C-T-4

Shulgin Index: See #25 2C-T; Table: 5 Page: 345 Row: 33

See also PiHKAL: #5 ALEPH-4 #35 2C-O-4 #47 2C-T-15  

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

Meyers-Riggs, B. Shulgin’s sulfur symphony—part I. countyourculture: rational exploration of the underground, 15 Jan 2011.

Meyers-Riggs, B. 2C-T-x substitution size and potency. countyourculture: rational exploration of the underground, 1 Apr 2011.

43
Analogue 15: Substituting n-Propylthio for Methoxy at R4

2C-T-7
4-Propylthio-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-n-propylthiophenethylamine

IUPAC: 2-[2,5-Dimethoxy-4-(propylsulfanyl)phenyl]ethanamine

Formula: C13H21NO2S Molecular weight: 255.37634 g/mol InChI Key: OLEVEPDJOFPJTF-UHFFFAOYSA-N

InChI=1S/C13H21NO2S/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: 24728635; ChemSpider: 21106233; Drugs Forum: 2C-T-7; Erowid: 2C-T-7; Wikipedia: 2C-T-7

Shulgin Index: #27 2C-T-7; Table: 5 Page: 345 Row: 26

See also PiHKAL: #7 ALEPH-7
#35 2C-O-4
#40 2C-T-2
#81 FLEA
#88 HOT-7
#118 MDPR
 

Meyers-Riggs, B. 2C-T-x substitution size and potency. countyourculture: rational exploration of the underground, 1 Apr 2011.

Meyers-Riggs, B. Shulgin’s sulfur symphony—part I. countyourculture: rational exploration of the underground, 15 Jan 2011.

Theobald, DS. The 2C-series—A new class of designer drugs. Ph. D. Thesis, Universität des Saarlandes, Saarbrücken, Germany, 18 Dec 2006. 1370 kB.

Curtis, BD. The forensic toxicology of 2,5-dimethoxy-4-N-propylthiophenethylamine (2C-T-7). Ph. D. Thesis, University of Oklahoma, Oklahoma City, OK, USA, 2005. 726 kB.

Anon. Report on the risk assessment of 2C-I, 2C-T-2 and 2C-T-7 in the framework of the joint action on new synthetic drugs, European Monitoring Centre for Drugs and Drug Addiction, 2004.

McGrane, O; Simmons, J; Jacobsen, E; Skinner, C. Alarming trends in a novel class of designer drugs. J. Clinic. Toxicol., 1 Nov 2011, 1 (2). 775 kB. doi:10.4172/2161-0494.1000108

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

Stolaroff, MJ. Letter to the editor (re: 2C-T-2 & 2C-T-7). J. Psychoactive Drugs, 1 Jan 1990, 22 (3), 379. 1090 kB. doi:10.1080/02791072.1990.10472568

Boer, D; Bosman, I. A new trend in drugs-of-abuse; the 2C-series of phenethylamine designer drugs. Pharm. World Sci., 1 Apr 2004, 26 (2), 110–113. 61 kB. doi:10.1023/B:PHAR.0000018600.03664.36

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

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

Fantegrossi, WE; Harrington, AW; Eckler, JR; Arshad, S; Rabin, RA; Winter, JC; Coop, A; Rice, KC; Woods, JH. Hallucinogen-like actions of 2,5-dimethoxy-4-(n)-propylthiophenethylamine (2C-T-7) in mice and rats. Psychopharmacology, 1 Sep 2005, 181 (3), 496–503. 182 kB. doi:10.1007/s00213-005-0009-4

44
Analogue 16: Substituting Cyclopropylmethylthio for Methoxy at R4

2C-T-8
4-Cyclopropylmethylthio-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-cyclopropylmethylthiophenethylamine

IUPAC: 2-{4-[(Cyclopropylmethyl)sulfanyl]-2,5-dimethoxyphenyl}ethanamine

Formula: C14H21NO2S Molecular weight: 267.38704 g/mol InChI Key: AHMSSHCYIDBVQB-UHFFFAOYSA-N

InChI=1S/C14H21NO2S/c1-16-12-8-14(18-9-10-3-4-10)13(17-2)7-11(12)5-6-15/h7-8,10H,3-6,9,15H2,1-2H3

PubChem CID: 44350055; ChemSpider: 21106234; Wikipedia: 2C-T-8

Shulgin Index: See #25 2C-T; Table: 5 Page: 346 Row: 10

See also PiHKAL: #81 FLEA #104 MDCPM    

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

Stolaroff, MJ; Wells, CW. Preliminary results with new psychoactive agents 2C-T-2 and 2C-T-7. In Jahrbuch für Ethnomedizin und Bewußtseinsforschung (Yearbook of Ethnomedicine and the Study of Consciousness); Rätsch, C; Baker, J, Eds., 1 Jan 1993; Vol. 2, pp 99–117. 185 kB.

Meyers-Riggs, B. Shulgin’s sulfur symphony—part I. countyourculture: rational exploration of the underground, 15 Jan 2011.

Meyers-Riggs, B. 2C-T-x substitution size and potency. countyourculture: rational exploration of the underground, 1 Apr 2011.

Shulgin, AT. 2C-T-7. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 28 Jun 2001.

45
Analogue 17: Substituting tert-Butylthio for Methoxy at R4

2C-T-9
4-tert-Butylthio-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-tert-butylthiophenethylamine

IUPAC: 2-[4-(tert-Butylsulfanyl)-2,5-dimethoxyphenyl]ethanamine

Formula: C14H23NO2S Molecular weight: 269.40292 g/mol InChI Key: PSVDMTZXLJTPNX-UHFFFAOYSA-N

InChI=1S/C14H23NO2S/c1-14(2,3)18-13-9-11(16-4)10(6-7-15)8-12(13)17-5/h8-9H,6-7,15H2,1-5H3

PubChem CID: 44349799; ChemSpider: 23206245; Wikipedia: 2C-T-9

Shulgin Index: See #25 2C-T; Table: 5 Page: 346 Row: 8

Meyers-Riggs, B. 2C-T-x substitution size and potency. countyourculture: rational exploration of the underground, 1 Apr 2011.

46
Analogue 18: Substituting 2-Methoxyethylthio for Methoxy at R4

2C-T-13
4-(2-Methoxyethylthio)-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-(2-methoxyethylthio)phenethylamine

IUPAC: 2-{2,5-Dimethoxy-4-[(2-methoxyethyl)sulfanyl]phenyl}ethanamine

Formula: C13H21NO3S Molecular weight: 271.37574 g/mol InChI Key: PYJLRNOGMKMRTK-UHFFFAOYSA-N

InChI=1S/C13H21NO3S/c1-15-6-7-18-13-9-11(16-2)10(4-5-14)8-12(13)17-3/h8-9H,4-7,14H2,1-3H3

PubChem CID: 44350108; ChemSpider: 21106228; Wikipedia: 2C-T-13

Shulgin Index: See #25 2C-T; Table: 5 Page: 346 Row: 11

See also PiHKAL: #99 MAL      

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

Meyers-Riggs, B. 2C-T-x substitution size and potency. countyourculture: rational exploration of the underground, 1 Apr 2011.

Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011.

47
Analogue 19: Substituting Cyclopropylthio for Methoxy at R4

2C-T-15
SESQUI
4-Cyclopropylthio-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-cyclopropylthiophenethylamine

IUPAC: 2-[4-(Cyclopropylsulfanyl)-2,5-dimethoxyphenyl]ethanamine

Formula: C13H19NO2S Molecular weight: 253.36046 g/mol InChI Key: HHAPMOUVSYQKLK-UHFFFAOYSA-N

InChI=1S/C13H19NO2S/c1-15-11-8-13(17-10-3-4-10)12(16-2)7-9(11)5-6-14/h7-8,10H,3-6,14H2,1-2H3

PubChem CID: 44719534; ChemSpider: 21106229; Wikipedia: 2C-T-15

Shulgin Index: See #25 2C-T; Table: 5 Page: 345 Row: 35

See also PiHKAL: #48 2C-T-17 #49 2C-T-21    

Meyers-Riggs, B. 2C-T-x substitution size and potency. countyourculture: rational exploration of the underground, 1 Apr 2011.

Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011.

48
Analogue 20: Substituting sec-Butylthio for Methoxy at R4

2C-T-17
NIMITZ
4-sec-Butylthio-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-sec-butylthiophenethylamine

IUPAC: 2-[4-(Butan-2-ylsulfanyl)-2,5-dimethoxyphenyl]ethanamine

Formula: C14H23NO2S Molecular weight: 269.40292 g/mol InChI Key: KSZHVRPGICAZOA-UHFFFAOYSA-N

InChI=1S/C14H23NO2S/c1-5-10(2)18-14-9-12(16-3)11(6-7-15)8-13(14)17-4/h8-10H,5-7,15H2,1-4H3

PubChem CID: 44349798; ChemSpider: 21106230; Wikipedia: 2C-T-17

Shulgin Index: See #25 2C-T; Table: 5 Page: 346 Row: 6

See also PiHKAL: #81 FLEA #89 HOT-17    

Meyers-Riggs, B. 2C-T-x substitution size and potency. countyourculture: rational exploration of the underground, 1 Apr 2011.

Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011.

49
Analogue 21: Substituting 2-Fluoroethylthio for Methoxy at R4

2C-T-21
4-(2-Fluoroethylthio)-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-(2-fluoroethylthio)phenethylamine

IUPAC: 2-{4-[(2-Fluoroethyl)sulfanyl]-2,5-dimethoxyphenyl}ethanamine

Formula: C12H18FNO2S Molecular weight: 259.3402232 g/mol InChI Key: ZBUUUKBTOCTOPW-UHFFFAOYSA-N

InChI=1S/C12H18FNO2S/c1-15-10-8-12(17-6-4-13)11(16-2)7-9(10)3-5-14/h7-8H,3-6,14H2,1-2H3

PubChem CID: 44349972; ChemSpider: 21106231; Drugs Forum: 2C-T-21; Erowid: 2C-T-21; Wikipedia: 2C-T-21

Shulgin Index: See #25 2C-T; Table: 5 Page: 345 Row: 23

See also PiHKAL: #38 2C-SE #65 DOEF    

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

Meyers-Riggs, B. 2C-T-x substitution size and potency. countyourculture: rational exploration of the underground, 1 Apr 2011.

Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011.

200
Analogue 22: Substituting Cyano for Methoxy at R4

2C-CN
2,5-Dimethoxy-4-cyanophenethylamine

IUPAC: 4-(2-Aminoethyl)-2,5-dimethoxybenzonitrile

Formula: C11H14N2O2 Molecular weight: 206.24106 g/mol InChI Key: OGWCKYKYGQORLF-UHFFFAOYSA-N

InChI=1S/C11H14N2O2/c1-14-10-6-9(7-13)11(15-2)5-8(10)3-4-12/h5-6H,3-4,12H2,1-2H3

PubChem CID: 57474247

Shulgin Index: See #55 DOCN; Table: 5 Page: 343 Row: 7

See also PiHKAL: #22 2C-C      
201
Analogue 23: Substituting Carboxy for Methoxy at R4

2C-CA
2C-COOH
2,5-Dimethoxy-4-carboxyphenethylamine

IUPAC: 4-(2-Aminoethyl)-2,5-dimethoxybenzoic acid

Formula: C11H15NO4 Molecular weight: 225.2411 g/mol InChI Key: CGSVAQGHARVNCH-UHFFFAOYSA-N

InChI=1S/C11H15NO4/c1-15-9-6-8(11(13)14)10(16-2)5-7(9)3-4-12/h5-6H,3-4,12H2,1-2H3,(H,13,14)

PubChem CID: 57474249

Shulgin Index: See #55 DOCN; Table: 5 Page: 343 Row: 9

See also PiHKAL: #22 2C-C      
2040
Analogue 24: Substituting Trifluoromethyl for Methoxy at R4

2C-TFM
2C-CF3
4-Trifuouromethyl-2,5-dimethoxyphenethylamine

IUPAC: 2-[2,5-Dimethoxy-4-(trifluoromethyl)phenyl]ethanamine

Formula: C11H14F3NO2 Molecular weight: 249.2295696 g/mol InChI Key: LYXGNMLWYONZID-UHFFFAOYSA-N

InChI=1S/C11H14F3NO2/c1-16-9-6-8(11(12,13)14)10(17-2)5-7(9)3-4-15/h5-6H,3-4,15H2,1-2H3

PubChem CID: 10399795; ChemSpider: 8575233; Drugs Forum: 2C-TFM; Wikipedia: 2C-TFM

Shulgin Index: #28 2C-TFM; Table: 5 Page: 343 Row: 1

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

Nichols, DE; Frescas, SP; Marona-Lewicka, D; Huang, X; Roth, BL; Gudelsky, GA; Nash, JF. 1-(2,5-Dimethoxy-4-(trifluoromethyl)phenyl)-2-aminopropane: A potent serotonin 5-HT2A/2C agonist. J. Med. Chem., 1 Jan 1994, 37 (25), 4346–4351. 873 kB. doi:10.1021/jm00051a011

Parrish, JC; Braden, MR; Gundy, E; Nichols, DE. Differential phospholipase C activation by phenylalkylamine serotonin 5-HT2A receptor agonists. J. Neurochem., 1 Dec 2005, 95 (6), 1575–1584. 301 kB. doi:10.1111/j.1471-4159.2005.03477.x

Parrish, JC. Toward a molecular understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2006. 5475 kB.

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

2068
Analogue 25: Substituting Ethoxy for Methoxy at R4

2C-O-2
2C-O-2
2,5-Dimethoxy-4-ethoxyphenethylamine

IUPAC: 2-(4-Ethoxy-2,5-dimethoxyphenyl)ethanamine

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: JFXGDWIZRPHJKN-UHFFFAOYSA-N

InChI=1S/C12H19NO3/c1-4-16-12-8-10(14-2)9(5-6-13)7-11(12)15-3/h7-8H,4-6,13H2,1-3H3

PubChem CID: 57474251

Shulgin Index: See #124 TMPEA-2; Table: 5 Page: 344 Row: 31

See also PiHKAL: #35 2C-O-4      
2069
Analogue 26: Substituting n-Propoxy for Methoxy at R4

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

IUPAC: 2-(2,5-Dimethoxy-4-propoxyphenyl)ethanamine

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      
2070
Analogue 27: Substituting n-Butoxy for Methoxy at R4

2C-O-19
2C-O-19
2,5-Dimethoxy-4-n-butoxyphenethylamine

IUPAC: 2-(4-Butoxy-2,5-dimethoxyphenyl)ethanamine

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

InChI=1S/C14H23NO3/c1-4-5-8-18-14-10-12(16-2)11(6-7-15)9-13(14)17-3/h9-10H,4-8,15H2,1-3H3

PubChem CID: 57474253

Shulgin Index: See #124 TMPEA-2; Table: 5 Page: 345 Row: 8

See also PiHKAL: #35 2C-O-4      
2072
Analogue 28: Substituting Ethylseleno for Methoxy at R4

2C-SE-2
2,5-Dimethoxy-4-ethylselenophenethylamine

IUPAC: 2-[4-(Ethylselanyl)-2,5-dimethoxyphenyl]ethanamine

Formula: C12H19NO2Se Molecular weight: 288.24476 g/mol InChI Key: HUFWOPLGIJKCJU-UHFFFAOYSA-N

InChI=1S/C12H19NO2Se/c1-4-16-12-8-10(14-2)9(5-6-13)7-11(12)15-3/h7-8H,4-6,13H2,1-3H3

PubChem CID: 57474255

See also PiHKAL: #38 2C-SE      
2073
Analogue 29: Substituting Isopropylseleno for Methoxy at R4

2C-SE-4
2,5-Dimethoxy-4-isopropylselenophenethylamine

IUPAC: 2-[2,5-Dimethoxy-4-(propan-2-ylselanyl)phenyl]ethanamine

Formula: C13H21NO2Se Molecular weight: 302.27134 g/mol InChI Key: UUGAXTBZOCLVOE-UHFFFAOYSA-N

InChI=1S/C13H21NO2Se/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: 57474257

See also PiHKAL: #38 2C-SE      
2074
Analogue 30: Substituting n-Propylseleno for Methoxy at R4

2C-SE-7
2,5-Dimethoxy-4-n-propylselenophenethylamine

IUPAC: 2-[2,5-Dimethoxy-4-(propylselanyl)phenyl]ethanamine

Formula: C13H21NO2Se Molecular weight: 302.27134 g/mol InChI Key: XMFDSLMFVAJUSR-UHFFFAOYSA-N

InChI=1S/C13H21NO2Se/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: 57474258

See also PiHKAL: #38 2C-SE      
2075
Analogue 31: Substituting 2-Fluoroethylseleno for Methoxy at R4

2C-SE-21
2,5-Dimethoxy-4-(2-fluoroethylseleno)phenethylamine

IUPAC: 2-{4-[(2-Fluoroethyl)selanyl]-2,5-dimethoxyphenyl}ethanamine

Formula: C12H18FNO2Se Molecular weight: 306.2352232 g/mol InChI Key: XSVWIVWPLWEQOK-UHFFFAOYSA-N

InChI=1S/C12H18FNO2Se/c1-15-10-8-12(17-6-4-13)11(16-2)7-9(10)3-5-14/h7-8H,3-6,14H2,1-2H3

PubChem CID: 57474261

See also PiHKAL: #38 2C-SE      
2076
Analogue 32: Substituting Methyltelluro for Methoxy at R4

2C-TE
2,5-Dimethoxy-4-methyltellurophenethylamine

IUPAC: 2-[2,5-Dimethoxy-4-(methyltellanyl)phenyl]ethanamine

Formula: C11H17NO2Te Molecular weight: 322.85818 g/mol InChI Key: OLHAAXPQNWOKOE-UHFFFAOYSA-N

InChI=1S/C11H17NO2Te/c1-13-9-7-11(15-3)10(14-2)6-8(9)4-5-12/h6-7H,4-5,12H2,1-3H3

PubChem CID: 57474263

See also PiHKAL: #38 2C-SE      
2079
Analogue 33: Substituting 2-Pyridylthio for Methoxy at R4

2C-T-10
2,5-Dimethoxy-4-(2-pyridylthio)phenethylamine

IUPAC: 2-[2,5-Dimethoxy-4-(pyridin-2-ylsulfanyl)phenyl]ethanamine

Formula: C15H18N2O2S Molecular weight: 290.38062 g/mol InChI Key: QGMVABLWTNWDAY-UHFFFAOYSA-N

InChI=1S/C15H18N2O2S/c1-18-12-10-14(20-15-5-3-4-8-17-15)13(19-2)9-11(12)6-7-16/h3-5,8-10H,6-7,16H2,1-2H3

PubChem CID: 57474265

See also PiHKAL: #45 2C-T-9      

Meyers-Riggs, B. Shulgin’s sulfur symphony—part I. countyourculture: rational exploration of the underground, 15 Jan 2011.

Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011.

2080
Analogue 34: Substituting 4-Bromophenylthio for Methoxy at R4

2C-T-11
4-(4-Bromophenylthio)-2,5-dimethoxyphenethylamine

IUPAC: 2-{4-[(4-Bromophenyl)sulfanyl]-2,5-dimethoxyphenyl}ethanamine

Formula: C16H18BrNO2S Molecular weight: 368.28862 g/mol InChI Key: YSYFWLXCMAVLOQ-UHFFFAOYSA-N

InChI=1S/C16H18BrNO2S/c1-19-14-10-16(15(20-2)9-11(14)7-8-18)21-13-5-3-12(17)4-6-13/h3-6,9-10H,7-8,18H2,1-2H3

PubChem CID: 57474267

See also PiHKAL: #45 2C-T-9      

Meyers-Riggs, B. Shulgin’s sulfur symphony—part I. countyourculture: rational exploration of the underground, 15 Jan 2011.

2081
Analogue 35: Substituting 1-Morpholinothio for Methoxy at R4

2C-T-12
2,5-Dimethoxy-4-(1-morpholinothio)phenethylamine

IUPAC: 2-[2,5-Dimethoxy-4-(morpholin-4-ylsulfanyl)phenyl]ethanamine

Formula: C14H22N2O3S Molecular weight: 298.40108 g/mol InChI Key: PHXFPOFFCCVTDK-UHFFFAOYSA-N

InChI=1S/C14H22N2O3S/c1-17-12-10-14(20-16-5-7-19-8-6-16)13(18-2)9-11(12)3-4-15/h9-10H,3-8,15H2,1-2H3

PubChem CID: 57474268

See also PiHKAL: #45 2C-T-9      

Meyers-Riggs, B. Shulgin’s sulfur symphony—part I. countyourculture: rational exploration of the underground, 15 Jan 2011.

2082
Analogue 36: Substituting 2-Methylthioethylthio for Methoxy at R4

2C-T-14
2,5-Dimethoxy-4-(2-methylthioethylthio)phenethylamine

IUPAC: 2-(2,5-Dimethoxy-4-{[2-(methylsulfanyl)ethyl]sulfanyl}phenyl)ethanamine

Formula: C13H21NO2S2 Molecular weight: 287.44134 g/mol InChI Key: YFENVCWPZGGJQO-UHFFFAOYSA-N

InChI=1S/C13H21NO2S2/c1-15-11-9-13(18-7-6-17-3)12(16-2)8-10(11)4-5-14/h8-9H,4-7,14H2,1-3H3

PubChem CID: 57474270

See also PiHKAL: #12 BIS-TOM #46 2C-T-13    

Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011.

2083
Analogue 37: Substituting Cyclohexylthio for Methoxy at R4

2C-T-5
4-Cyclohexylthio-2,5-dimethoxyphenethylamine

IUPAC: 2-[4-(Cyclohexylsulfanyl)-2,5-dimethoxyphenyl]ethanamine

Formula: C16H25NO2S Molecular weight: 295.4402 g/mol InChI Key: OABFYEYTJSTAMV-UHFFFAOYSA-N

InChI=1S/C16H25NO2S/c1-18-14-11-16(20-13-6-4-3-5-7-13)15(19-2)10-12(14)8-9-17/h10-11,13H,3-9,17H2,1-2H3

PubChem CID: 57474272; ChemSpider: 21375815

See also PiHKAL: #4 ALEPH-2 #47 2C-T-15    

Meyers-Riggs, B. Shulgin’s sulfur symphony—part I. countyourculture: rational exploration of the underground, 15 Jan 2011.

2086
Analogue 38: Substituting Allylthio for Methoxy at R4

2C-T-16
4-Allylthio-2,5-dimethoxyphenethylamine

IUPAC: 2-[2,5-Dimethoxy-4-(prop-2-en-1-ylsulfanyl)phenyl]ethanamine

Formula: C13H19NO2S Molecular weight: 253.36046 g/mol InChI Key: BXCMEIZBXNLJKM-UHFFFAOYSA-N

InChI=1S/C13H19NO2S/c1-4-7-17-13-9-11(15-2)10(5-6-14)8-12(13)16-3/h4,8-9H,1,5-7,14H2,2-3H3

PubChem CID: 12063256

Shulgin Index: See #25 2C-T; Table: 5 Page: 346 Row: 1

See also PiHKAL: #4 ALEPH-2      

Trachsel, D. Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 2. 4-Thio-substituted [2-(2,5-dimethoxyphenyl)ethyl]amines (=2,5-dimethoxybenzeneethanamines). Helv. Chim. Acta, 5 Aug 2003, 86 (7), 2610–2619. 133 kB. doi:10.1002/hlca.200390210 In German.

Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011.

2087
Analogue 39: Substituting Phenylthio for Methoxy at R4

2C-T-6
2,5-Dimethoxy-4-phenylthiophenethylamine

IUPAC: 2-[2,5-Dimethoxy-4-(phenylsulfanyl)phenyl]ethanamine

Formula: C16H19NO2S Molecular weight: 289.39256 g/mol InChI Key: JRDQLJCYERGHDJ-UHFFFAOYSA-N

InChI=1S/C16H19NO2S/c1-18-14-11-16(20-13-6-4-3-5-7-13)15(19-2)10-12(14)8-9-17/h3-7,10-11H,8-9,17H2,1-2H3

PubChem CID: 57474275

See also PiHKAL: #6 ALEPH-6      

Meyers-Riggs, B. Shulgin’s sulfur symphony—part I. countyourculture: rational exploration of the underground, 15 Jan 2011.

2089
Analogue 40: Substituting n-Butylthio for Methoxy at R4

2C-T-19
4-n-Butylthio-2,5-dimethoxyphenethylamine

IUPAC: 2-[4-(Butylsulfanyl)-2,5-dimethoxyphenyl]ethanamine

Formula: C14H23NO2S Molecular weight: 269.40292 g/mol InChI Key: LGUVDOBGXUFUAJ-UHFFFAOYSA-N

InChI=1S/C14H23NO2S/c1-4-5-8-18-14-10-12(16-2)11(6-7-15)9-13(14)17-3/h9-10H,4-8,15H2,1-3H3

PubChem CID: 12063257; ChemSpider: 21106235

Shulgin Index: See #25 2C-T; Table: 5 Page: 346 Row: 3

See also PiHKAL: #35 2C-O-4 #49 2C-T-21    

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

Trachsel, D. Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 2. 4-Thio-substituted [2-(2,5-dimethoxyphenyl)ethyl]amines (=2,5-dimethoxybenzeneethanamines). Helv. Chim. Acta, 5 Aug 2003, 86 (7), 2610–2619. 133 kB. doi:10.1002/hlca.200390210 In German.

Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011.

2090
Analogue 41: Substituting 2,2-Difluouroethylthio for Methoxy at R4

2C-T-21.5
4-(2,2-Difluouroethylthio)-2,5-dimethoxyphenethylamine

IUPAC: 2-{4-[(2,2-Difluoroethyl)sulfanyl]-2,5-dimethoxyphenyl}ethanamine

Formula: C12H17F2NO2S Molecular weight: 277.3306864 g/mol InChI Key: LVCSIKISADNGMR-UHFFFAOYSA-N

InChI=1S/C12H17F2NO2S/c1-16-9-6-11(18-7-12(13)14)10(17-2)5-8(9)3-4-15/h5-6,12H,3-4,7,15H2,1-2H3

PubChem CID: 12063258

Shulgin Index: See #25 2C-T; Table: 5 Page: 345 Row: 24

See also PiHKAL: #49 2C-T-21      

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

Trachsel, D. Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 2. 4-Thio-substituted [2-(2,5-dimethoxyphenyl)ethyl]amines (=2,5-dimethoxybenzeneethanamines). Helv. Chim. Acta, 5 Aug 2003, 86 (7), 2610–2619. 133 kB. doi:10.1002/hlca.200390210 In German.

Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011.

2091
Analogue 42: Substituting 2,2,2-Trifluoroethylthio for Methoxy at R4

2C-T-22
2,5-Dimethoxy-4-(2,2,2-trifluouroethylthio)phenethylamine

IUPAC: 2-{2,5-Dimethoxy-4-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}ethanamine

Formula: C12H16F3NO2S Molecular weight: 295.3211496 g/mol InChI Key: LDOOFVKAIHFXAR-UHFFFAOYSA-N

InChI=1S/C12H16F3NO2S/c1-17-9-6-11(19-7-12(13,14)15)10(18-2)5-8(9)3-4-16/h5-6H,3-4,7,16H2,1-2H3

PubChem CID: 12063259

Shulgin Index: See #25 2C-T; Table: 5 Page: 345 Row: 25

See also PiHKAL: #49 2C-T-21      

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

Trachsel, D. Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 2. 4-Thio-substituted [2-(2,5-dimethoxyphenyl)ethyl]amines (=2,5-dimethoxybenzeneethanamines). Helv. Chim. Acta, 5 Aug 2003, 86 (7), 2610–2619. 133 kB. doi:10.1002/hlca.200390210 In German.

Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011.

2108
Analogue 43: Substituting Cyclobutylthio for Methoxy at R4

2C-T-18
4-Cyclobutylthio-2,5-dimethoxyamphetamine

IUPAC: 2-[4-(Cyclobutylsulfanyl)-2,5-dimethoxyphenyl]ethanamine

Formula: C14H21NO2S Molecular weight: 267.38704 g/mol InChI Key: CSLQQULZSBSZTM-UHFFFAOYSA-N

InChI=1S/C14H21NO2S/c1-16-12-9-14(18-11-4-3-5-11)13(17-2)8-10(12)6-7-15/h8-9,11H,3-7,15H2,1-2H3

See also PiHKAL: #47 2C-T-15      
2109
Analogue 44: Substituting Cyclopentylthio for Methoxy at R4

2C-T-23
4-Cyclopentylthio-2,5-dimethoxyamphetamine

IUPAC: 2-[4-(Cyclopentylsulfanyl)-2,5-dimethoxyphenyl]ethanamine

Formula: C15H23NO2S Molecular weight: 281.41362 g/mol InChI Key: OVWHCXSUEIYTRY-UHFFFAOYSA-N

InChI=1S/C15H23NO2S/c1-17-13-10-15(19-12-5-3-4-6-12)14(18-2)9-11(13)7-8-16/h9-10,12H,3-8,16H2,1-2H3

PubChem CID: 57478605

See also PiHKAL: #47 2C-T-15      

Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011.

5378
Analogue 45: Substituting Ethynyl for Methoxy at R4

2C-YN
4-Ethynyl-2,5-dimethoxyphenethylamine

IUPAC: 2-(4-Ethynyl-2,5-dimethoxyphenyl)ethanamine

Formula: C12H15NO2 Molecular weight: 205.253 g/mol InChI Key: MLJHHYIJBZVUEA-UHFFFAOYSA-N

InChI=1S/C12H15NO2/c1-4-9-7-12(15-3)10(5-6-13)8-11(9)14-2/h1,7-8H,5-6,13H2,2-3H3

PubChem CID: 12063400; ChemSpider: 26234934; Wikipedia: 2C-YN

Shulgin Index: See #20 2C-D; Table: 5 Page: 343 Row: 21

Trachsel, D. Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 3. 4-Ethynyl-2,5-dimethoxyphenethylamine (= 4-Ethynyl-2,5-dimethoxybenzeneethanamine; 2C-YN). Helv. Chim. Acta, 28 Aug 2003, 86 (8), 2754–2759. 84 kB. doi:10.1002/hlca.200390224

5396
Analogue 46: Substituting 2-Hydroxyethyl for Methoxy at R4

2C-pEtOH
4-(2-Hydroxyethyl)-2,5-dimethoxyphenethylamine

IUPAC: [4-(2-Aminoethyl)-2,5-dimethoxyphenyl]methanol

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: AYJLNTOOEWDDBF-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-14-10-6-9(7-13)11(15-2)5-8(10)3-4-12/h5-6,13H,3-4,7,12H2,1-2H3

PubChem CID: 57474313

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

5397
Analogue 47: Substituting Acetoxy for Methoxy at R4

2C-pKet
4-Acetoxy-2,5-dimethoxyphenethylamine

IUPAC: Methyl 4-(2-aminoethyl)-2,5-dimethoxybenzoate

Formula: C12H17NO4 Molecular weight: 239.26768 g/mol InChI Key: NKPGPUBNFCEOAN-UHFFFAOYSA-N

InChI=1S/C12H17NO4/c1-15-10-7-9(12(14)17-3)11(16-2)6-8(10)4-5-13/h6-7H,4-5,13H2,1-3H3

PubChem CID: 57474315

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

2177
Analogue 48: Substituting Methallylthio for Methoxy at R4

2C-T-3
4-Methallylthio-2,5-dimethoxyphenethylamine

IUPAC: 2-{2,5-Dimethoxy-4-[(2-methylprop-2-en-1-yl)sulfanyl]phenyl}ethanamine

Formula: C14H21NO2S Molecular weight: 267.38704 g/mol InChI Key: JCDUUDQZKIXJJP-UHFFFAOYSA-N

InChI=1S/C14H21NO2S/c1-10(2)9-18-14-8-12(16-3)11(5-6-15)7-13(14)17-4/h7-8H,1,5-6,9,15H2,2-4H3

PubChem CID: 12063255

Shulgin Index: See #25 2C-T; Table: 5 Page: 346 Row: 9

See also PiHKAL: #4 ALEPH-2      

Trachsel, D. Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 2. 4-Thio-substituted [2-(2,5-dimethoxyphenyl)ethyl]amines (=2,5-dimethoxybenzeneethanamines). Helv. Chim. Acta, 5 Aug 2003, 86 (7), 2610–2619. 133 kB. doi:10.1002/hlca.200390210 In German.

Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011.

Meyers-Riggs, B. Shulgin’s sulfur symphony—part I. countyourculture: rational exploration of the underground, 15 Jan 2011.

2178
Analogue 49: Substituting Isobutylthio for Methoxy at R4

2C-T-25
4-Isobutylthio-2,5-dimethoxyphenethylamine

IUPAC: 2-{2,5-Dimethoxy-4-[(2-methylpropyl)sulfanyl]phenyl}ethanamine

Formula: C14H23NO2S Molecular weight: 269.40292 g/mol InChI Key: OEPKQBQEDYEXMC-UHFFFAOYSA-N

InChI=1S/C14H23NO2S/c1-10(2)9-18-14-8-12(16-3)11(5-6-15)7-13(14)17-4/h7-8,10H,5-6,9,15H2,1-4H3

PubChem CID: 12063260

Shulgin Index: See #25 2C-T; Table: 5 Page: 346 Row: 5

Trachsel, D. Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 2. 4-Thio-substituted [2-(2,5-dimethoxyphenyl)ethyl]amines (=2,5-dimethoxybenzeneethanamines). Helv. Chim. Acta, 5 Aug 2003, 86 (7), 2610–2619. 133 kB. doi:10.1002/hlca.200390210 In German.

Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011.

2179
Analogue 50: Substituting Benzylthio for Methoxy at R4

2C-T-27
4-Benzylthio-2,5-dimethoxyphenethylamine

IUPAC: 2-[4-(Benzylsulfanyl)-2,5-dimethoxyphenyl]ethanamine

Formula: C17H21NO2S Molecular weight: 303.41914 g/mol InChI Key: GRZVJRPTNCONNT-UHFFFAOYSA-N

InChI=1S/C17H21NO2S/c1-19-15-11-17(16(20-2)10-14(15)8-9-18)21-12-13-6-4-3-5-7-13/h3-7,10-11H,8-9,12,18H2,1-2H3

PubChem CID: 12063261

Trachsel, D. Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 2. 4-Thio-substituted [2-(2,5-dimethoxyphenyl)ethyl]amines (=2,5-dimethoxybenzeneethanamines). Helv. Chim. Acta, 5 Aug 2003, 86 (7), 2610–2619. 133 kB. doi:10.1002/hlca.200390210 In German.

Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011.

2180
Analogue 51: Substituting 3-Fluoropropylthio for Methoxy at R4

2C-T-28
4-(3-Fluoropropylthio)-2,5-dimethoxyphenethylamine

IUPAC: 2-{4-[(3-Fluoropropyl)sulfanyl]-2,5-dimethoxyphenyl}ethanamine

Formula: C13H20FNO2S Molecular weight: 273.3668032 g/mol InChI Key: XAFVGDRNPGLCMI-UHFFFAOYSA-N

InChI=1S/C13H20FNO2S/c1-16-11-9-13(18-7-3-5-14)12(17-2)8-10(11)4-6-15/h8-9H,3-7,15H2,1-2H3

PubChem CID: 12063262

Shulgin Index: See #25 2C-T; Table: 5 Page: 346 Row: 2

Trachsel, D. Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 2. 4-Thio-substituted [2-(2,5-dimethoxyphenyl)ethyl]amines (=2,5-dimethoxybenzeneethanamines). Helv. Chim. Acta, 5 Aug 2003, 86 (7), 2610–2619. 133 kB. doi:10.1002/hlca.200390210 In German.

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

Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011.

2181
Analogue 52: Substituting 4-Fluorobutylthio for Methoxy at R4

2C-T-30
4-(4-Fluorobutylthio)-2,5-dimethoxyphenethylamine

IUPAC: 2-{4-[(4-Fluorobutyl)sulfanyl]-2,5-dimethoxyphenyl}ethanamine

Formula: C14H22FNO2S Molecular weight: 287.3933832 g/mol InChI Key: BILSBDMCLLFSAV-UHFFFAOYSA-N

InChI=1S/C14H22FNO2S/c1-17-12-10-14(19-8-4-3-6-15)13(18-2)9-11(12)5-7-16/h9-10H,3-8,16H2,1-2H3

PubChem CID: 12063263

Shulgin Index: See #25 2C-T; Table: 5 Page: 346 Row: 12

Trachsel, D. Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 2. 4-Thio-substituted [2-(2,5-dimethoxyphenyl)ethyl]amines (=2,5-dimethoxybenzeneethanamines). Helv. Chim. Acta, 5 Aug 2003, 86 (7), 2610–2619. 133 kB. doi:10.1002/hlca.200390210 In German.

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

Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011.

2182
Analogue 53: Substituting 4-(Trifluoromethyl)benzylthio for Methoxy at R4

2C-T-31
2,5-Dimethoxy-4-[4-(trifluoromethyl)benzylthio]phenethylamine

IUPAC: 2-(2,5-Dimethoxy-4-{[4-(trifluoromethyl)benzyl]sulfanyl}phenyl)ethanamine

Formula: C18H20F3NO2S Molecular weight: 371.4171096 g/mol InChI Key: BDOJPUSYOLIGBS-UHFFFAOYSA-N

InChI=1S/C18H20F3NO2S/c1-23-15-10-17(16(24-2)9-13(15)7-8-22)25-11-12-3-5-14(6-4-12)18(19,20)21/h3-6,9-10H,7-8,11,22H2,1-2H3

PubChem CID: 12063264

Trachsel, D. Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 2. 4-Thio-substituted [2-(2,5-dimethoxyphenyl)ethyl]amines (=2,5-dimethoxybenzeneethanamines). Helv. Chim. Acta, 5 Aug 2003, 86 (7), 2610–2619. 133 kB. doi:10.1002/hlca.200390210 In German.

Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011.

2183
Analogue 54: Substituting 2,3,4,5,6-Pentafluorobenzylthio for Methoxy at R4

2C-T-32
2,5-Dimethoxy-4-(2,3,4,5,6-pentafluorobenzylthio)phenethylamine

IUPAC: 2-{2,5-Dimethoxy-4-[(pentafluorobenzyl)sulfanyl]phenyl}ethanamine

Formula: C17H16F5NO2S Molecular weight: 393.371456 g/mol InChI Key: SCZNXZRFVLLJGV-UHFFFAOYSA-N

InChI=1S/C17H16F5NO2S/c1-24-10-6-12(11(25-2)5-8(10)3-4-23)26-7-9-13(18)15(20)17(22)16(21)14(9)19/h5-6H,3-4,7,23H2,1-2H3

Trachsel, D. Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 2. 4-Thio-substituted [2-(2,5-dimethoxyphenyl)ethyl]amines (=2,5-dimethoxybenzeneethanamines). Helv. Chim. Acta, 5 Aug 2003, 86 (7), 2610–2619. 133 kB. doi:10.1002/hlca.200390210 In German.

Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011.

2184
Analogue 55: Substituting 3-Methoxybenzylthio for Methoxy at R4

2C-T-33
2,5-Dimethoxy-4-(3-methoxybenzylthio)phenethylamine

IUPAC: 2-{2,5-Dimethoxy-4-[(3-methoxybenzyl)sulfanyl]phenyl}ethanamine

Formula: C18H23NO3S Molecular weight: 333.44512 g/mol InChI Key: ADENDGINQJWQOK-UHFFFAOYSA-N

InChI=1S/C18H23NO3S/c1-20-15-6-4-5-13(9-15)12-23-18-11-16(21-2)14(7-8-19)10-17(18)22-3/h4-6,9-11H,7-8,12,19H2,1-3H3

PubChem CID: 12063266

Trachsel, D. Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 2. 4-Thio-substituted [2-(2,5-dimethoxyphenyl)ethyl]amines (=2,5-dimethoxybenzeneethanamines). Helv. Chim. Acta, 5 Aug 2003, 86 (7), 2610–2619. 133 kB. doi:10.1002/hlca.200390210 In German.

Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture: rational exploration of the underground, 3 Apr 2011.

2198
Analogue 56: Substituting Ethenyl for Methoxy at R4

2C-VI
2C-V
4-Ethenyl-2,5-dimethoxyphenethylamine

IUPAC: 2-(4-Ethenyl-2,5-dimethoxyphenyl)ethanamine

Formula: C12H17NO2 Molecular weight: 207.26888 g/mol InChI Key: LGLJOVNOGICITR-UHFFFAOYSA-N

InChI=1S/C12H17NO2/c1-4-9-7-12(15-3)10(5-6-13)8-11(9)14-2/h4,7-8H,1,5-6,13H2,2-3H3

PubChem CID: 57474284

Shulgin Index: See #20 2C-D; Table: 5 Page: 343 Row: 19

Trachsel, D. Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 3. 4-Ethynyl-2,5-dimethoxyphenethylamine (= 4-Ethynyl-2,5-dimethoxybenzeneethanamine; 2C-YN). Helv. Chim. Acta, 28 Aug 2003, 86 (8), 2754–2759. 84 kB. doi:10.1002/hlca.200390224

2300
Analogue 57: Substituting Phenyl for Methoxy at R4

2C-BI-1
2,5-Dimethoxy-4-phenylphenethylamine

IUPAC: 2-(2,5-Dimethoxybiphenyl-4-yl)ethanamine

Formula: C16H19NO2 Molecular weight: 257.32756 g/mol InChI Key: RMMCNNHGPNUXOX-UHFFFAOYSA-N

InChI=1S/C16H19NO2/c1-18-15-11-14(12-6-4-3-5-7-12)16(19-2)10-13(15)8-9-17/h3-7,10-11H,8-9,17H2,1-2H3

PubChem CID: 57474287

Trachsel, D; Nichols, DE; Kidd, S; Hadorn, M; Baumberger, F. 4-Aryl-substituted 2,5-dimethoxyphenethylamines: Synthesis and serotonin 5-HT2A receptor affinities. Chem. Biodiv., 28 May 2008, 6 (5), 692–704. 271 kB. doi:10.1002/cbdv.200800235

2301
Analogue 58: Substituting 2-Methoxyphenyl for Methoxy at R4

2C-BI-2
2,5-Dimethoxy-4-(2-methoxyphenyl)phenethylamine

IUPAC: 2-(2,2′,5-Trimethoxybiphenyl-4-yl)ethanamine

Formula: C17H21NO3 Molecular weight: 287.35354 g/mol InChI Key: WEQGJWJNANPJNP-UHFFFAOYSA-N

InChI=1S/C17H21NO3/c1-19-15-7-5-4-6-13(15)14-11-16(20-2)12(8-9-18)10-17(14)21-3/h4-7,10-11H,8-9,18H2,1-3H3

PubChem CID: 44219736

Trachsel, D; Nichols, DE; Kidd, S; Hadorn, M; Baumberger, F. 4-Aryl-substituted 2,5-dimethoxyphenethylamines: Synthesis and serotonin 5-HT2A receptor affinities. Chem. Biodiv., 28 May 2008, 6 (5), 692–704. 271 kB. doi:10.1002/cbdv.200800235

2302
Analogue 59: Substituting 2-Methylphenyl for Methoxy at R4

2C-BI-3
2,5-Dimethoxy-4-(2-methylphenyl)phenethylamine

IUPAC: 2-(2,5-Dimethoxy-2′-methylbiphenyl-4-yl)ethanamine

Formula: C17H21NO2 Molecular weight: 271.35414 g/mol InChI Key: INAUMGJNDBATML-UHFFFAOYSA-N

InChI=1S/C17H21NO2/c1-12-6-4-5-7-14(12)15-11-16(19-2)13(8-9-18)10-17(15)20-3/h4-7,10-11H,8-9,18H2,1-3H3

PubChem CID: 57474290

Trachsel, D; Nichols, DE; Kidd, S; Hadorn, M; Baumberger, F. 4-Aryl-substituted 2,5-dimethoxyphenethylamines: Synthesis and serotonin 5-HT2A receptor affinities. Chem. Biodiv., 28 May 2008, 6 (5), 692–704. 271 kB. doi:10.1002/cbdv.200800235

2303
Analogue 60: Substituting 2-(Trifluoromethyl)phenyl for Methoxy at R4

2C-BI-4
2,5-Dimethoxy-4-[2-(trifluoromethyl)phenyl]phenethylamine

IUPAC: 2-[2,5-Dimethoxy-2′-(trifluoromethyl)biphenyl-4-yl]ethanamine

Formula: C17H18F3NO2 Molecular weight: 325.3255296 g/mol InChI Key: XCNBZPCBVPDJFY-UHFFFAOYSA-N

InChI=1S/C17H18F3NO2/c1-22-15-10-13(16(23-2)9-11(15)7-8-21)12-5-3-4-6-14(12)17(18,19)20/h3-6,9-10H,7-8,21H2,1-2H3

PubChem CID: 57474292

Trachsel, D; Nichols, DE; Kidd, S; Hadorn, M; Baumberger, F. 4-Aryl-substituted 2,5-dimethoxyphenethylamines: Synthesis and serotonin 5-HT2A receptor affinities. Chem. Biodiv., 28 May 2008, 6 (5), 692–704. 271 kB. doi:10.1002/cbdv.200800235

2304
Analogue 61: Substituting Naphthalen-2-yl for Methoxy at R4

2C-BI-5
2,5-Dimethoxy-4-(naphthalen-2-yl)phenethylamine

IUPAC: 2-[2,5-Dimethoxy-4-(naphthalen-2-yl)phenyl]ethanamine

Formula: C20H21NO2 Molecular weight: 307.38624 g/mol InChI Key: KQKCTYPWGSPYLP-UHFFFAOYSA-N

InChI=1S/C20H21NO2/c1-22-19-13-18(20(23-2)12-17(19)9-10-21)16-8-7-14-5-3-4-6-15(14)11-16/h3-8,11-13H,9-10,21H2,1-2H3

PubChem CID: 57474294

Trachsel, D; Nichols, DE; Kidd, S; Hadorn, M; Baumberger, F. 4-Aryl-substituted 2,5-dimethoxyphenethylamines: Synthesis and serotonin 5-HT2A receptor affinities. Chem. Biodiv., 28 May 2008, 6 (5), 692–704. 271 kB. doi:10.1002/cbdv.200800235

2305
Analogue 62: Substituting 3-Methoxyphenyl for Methoxy at R4

2C-BI-6
2,5-Dimethoxy-4-(3-methoxyphenyl)phenethylamine

IUPAC: 2-(2,3′,5-Trimethoxybiphenyl-4-yl)ethanamine

Formula: C17H21NO3 Molecular weight: 287.35354 g/mol InChI Key: WMTQTFIOUBEGJW-UHFFFAOYSA-N

InChI=1S/C17H21NO3/c1-19-14-6-4-5-12(9-14)15-11-16(20-2)13(7-8-18)10-17(15)21-3/h4-6,9-11H,7-8,18H2,1-3H3

PubChem CID: 57474296

Trachsel, D; Nichols, DE; Kidd, S; Hadorn, M; Baumberger, F. 4-Aryl-substituted 2,5-dimethoxyphenethylamines: Synthesis and serotonin 5-HT2A receptor affinities. Chem. Biodiv., 28 May 2008, 6 (5), 692–704. 271 kB. doi:10.1002/cbdv.200800235

2306
Analogue 63: Substituting 3-Nitrophenyl for Methoxy at R4

2C-BI-7
2,5-Dimethoxy-4-(3-nitrophenyl)phenethylamine

IUPAC: 2-(2,5-Dimethoxy-3′-nitrobiphenyl-4-yl)ethanamine

Formula: C16H18N2O4 Molecular weight: 302.32512 g/mol InChI Key: YNWQIUDDSDYOFB-UHFFFAOYSA-N

InChI=1S/C16H18N2O4/c1-21-15-10-14(16(22-2)9-12(15)6-7-17)11-4-3-5-13(8-11)18(19)20/h3-5,8-10H,6-7,17H2,1-2H3

PubChem CID: 57474298

Trachsel, D; Nichols, DE; Kidd, S; Hadorn, M; Baumberger, F. 4-Aryl-substituted 2,5-dimethoxyphenethylamines: Synthesis and serotonin 5-HT2A receptor affinities. Chem. Biodiv., 28 May 2008, 6 (5), 692–704. 271 kB. doi:10.1002/cbdv.200800235

2307
Analogue 64: Substituting 4-Methoxyphenyl for Methoxy at R4

2C-BI-8
2,5-Dimethoxy-4-(4-methoxyphenyl)phenethylamine

IUPAC: 2-(2,4′,5-Trimethoxybiphenyl-4-yl)ethanamine

Formula: C17H21NO3 Molecular weight: 287.35354 g/mol InChI Key: ZALWHJKGZWNFNR-UHFFFAOYSA-N

InChI=1S/C17H21NO3/c1-19-14-6-4-12(5-7-14)15-11-16(20-2)13(8-9-18)10-17(15)21-3/h4-7,10-11H,8-9,18H2,1-3H3

PubChem CID: 57474300

Trachsel, D; Nichols, DE; Kidd, S; Hadorn, M; Baumberger, F. 4-Aryl-substituted 2,5-dimethoxyphenethylamines: Synthesis and serotonin 5-HT2A receptor affinities. Chem. Biodiv., 28 May 2008, 6 (5), 692–704. 271 kB. doi:10.1002/cbdv.200800235

2308
Analogue 65: Substituting 4-Butylphenyl for Methoxy at R4

2C-BI-9
4-(4-Butylphenyl)-2,5-dimethoxyphenethylamine

IUPAC: 2-(4′-Butyl-2,5-dimethoxybiphenyl-4-yl)ethanamine

Formula: C20H27NO2 Molecular weight: 313.43388 g/mol InChI Key: NDHZIVILVFWOSE-UHFFFAOYSA-N

InChI=1S/C20H27NO2/c1-4-5-6-15-7-9-16(10-8-15)18-14-19(22-2)17(11-12-21)13-20(18)23-3/h7-10,13-14H,4-6,11-12,21H2,1-3H3

PubChem CID: 57474302

Trachsel, D; Nichols, DE; Kidd, S; Hadorn, M; Baumberger, F. 4-Aryl-substituted 2,5-dimethoxyphenethylamines: Synthesis and serotonin 5-HT2A receptor affinities. Chem. Biodiv., 28 May 2008, 6 (5), 692–704. 271 kB. doi:10.1002/cbdv.200800235

2309
Analogue 66: Substituting 4-(Trifluoromethyl)phenyl for Methoxy at R4

2C-BI-10
2,5-Dimethoxy-4-[4-(trifluoromethyl)phenyl]phenethylamine

IUPAC: 2-[2,5-Dimethoxy-4′-(trifluoromethyl)biphenyl-4-yl]ethanamine

Formula: C17H18F3NO2 Molecular weight: 325.3255296 g/mol InChI Key: BFFLBYIGPNMJQH-UHFFFAOYSA-N

InChI=1S/C17H18F3NO2/c1-22-15-10-14(16(23-2)9-12(15)7-8-21)11-3-5-13(6-4-11)17(18,19)20/h3-6,9-10H,7-8,21H2,1-2H3

PubChem CID: 57474304

Trachsel, D; Nichols, DE; Kidd, S; Hadorn, M; Baumberger, F. 4-Aryl-substituted 2,5-dimethoxyphenethylamines: Synthesis and serotonin 5-HT2A receptor affinities. Chem. Biodiv., 28 May 2008, 6 (5), 692–704. 271 kB. doi:10.1002/cbdv.200800235

2310
Analogue 67: Substituting 4-Phenylphenyl for Methoxy at R4

2C-BI-11
2,5-Dimethoxy-4-(4-phenylphenyl)phenethylamine

IUPAC: 2-(2,5-Dimethoxy-1,1′:4′,1′′-terphenyl-4-yl)ethanamine

Formula: C22H23NO2 Molecular weight: 333.42352 g/mol InChI Key: ZQEKXNJKMUWVBC-UHFFFAOYSA-N

InChI=1S/C22H23NO2/c1-24-21-15-20(22(25-2)14-19(21)12-13-23)18-10-8-17(9-11-18)16-6-4-3-5-7-16/h3-11,14-15H,12-13,23H2,1-2H3

Trachsel, D; Nichols, DE; Kidd, S; Hadorn, M; Baumberger, F. 4-Aryl-substituted 2,5-dimethoxyphenethylamines: Synthesis and serotonin 5-HT2A receptor affinities. Chem. Biodiv., 28 May 2008, 6 (5), 692–704. 271 kB. doi:10.1002/cbdv.200800235

2311
Analogue 68: Substituting 1,3-Benzodioxol-5-yl for Methoxy at R4

2C-BI-12
2,5-Dimethoxy-4-(3,4-methylenedioxyphenyl)phenethylamine

IUPAC: 2-[4-(1,3-Benzodioxol-5-yl)-2,5-dimethoxyphenyl]ethanamine

Formula: C17H19NO4 Molecular weight: 301.33706 g/mol InChI Key: QNWIOBZDXFFFLT-UHFFFAOYSA-N

InChI=1S/C17H19NO4/c1-19-15-9-13(16(20-2)8-12(15)5-6-18)11-3-4-14-17(7-11)22-10-21-14/h3-4,7-9H,5-6,10,18H2,1-2H3

PubChem CID: 57474306

Trachsel, D; Nichols, DE; Kidd, S; Hadorn, M; Baumberger, F. 4-Aryl-substituted 2,5-dimethoxyphenethylamines: Synthesis and serotonin 5-HT2A receptor affinities. Chem. Biodiv., 28 May 2008, 6 (5), 692–704. 271 kB. doi:10.1002/cbdv.200800235

2326
Analogue 69: Substituting Phenylpropyl for Methoxy at R4

2,5-Dimethoxy-4-phenylpropylphenethylamine

IUPAC: 2-[2,5-Dimethoxy-4-(3-phenylpropyl)phenyl]ethanamine

Formula: C19H25NO2 Molecular weight: 299.4073 g/mol InChI Key: UCMBNCAZQUWZLT-UHFFFAOYSA-N

InChI=1S/C19H25NO2/c1-21-18-14-17(11-12-20)19(22-2)13-16(18)10-6-9-15-7-4-3-5-8-15/h3-5,7-8,13-14H,6,9-12,20H2,1-2H3

PubChem CID: 10542173; ChemSpider: 8717564

Dowd, CS; Herrick-Davis, K; Egan, C; DuPre, A; Smith, C; Teitler, M; Glennon, RA. 1-[4-(3-Phenylalkyl)phenyl]-2-aminopropanes as 5-HT2A partial agonists. J. Med. Chem., 10 Aug 2000, 43 (16), 3074–3084. 271 kB. doi:10.1021/jm9906062

2324
Analogue 70: Substituting 2-Phenylethyl for Methoxy at R4

2,5-Dimethoxy-4-phenethylphenethylamine

IUPAC: 2-[2,5-Dimethoxy-4-(2-phenylethyl)phenyl]ethanamine

Formula: C18H23NO2 Molecular weight: 285.38072 g/mol InChI Key: YIMMOGDNQSRZTF-UHFFFAOYSA-N

InChI=1S/C18H23NO2/c1-20-17-13-16(10-11-19)18(21-2)12-15(17)9-8-14-6-4-3-5-7-14/h3-7,12-13H,8-11,19H2,1-2H3

PubChem CID: 10827012; ChemSpider: 9002312

Dowd, CS; Herrick-Davis, K; Egan, C; DuPre, A; Smith, C; Teitler, M; Glennon, RA. 1-[4-(3-Phenylalkyl)phenyl]-2-aminopropanes as 5-HT2A partial agonists. J. Med. Chem., 10 Aug 2000, 43 (16), 3074–3084. 271 kB. doi:10.1021/jm9906062

2327
Analogue 71: Substituting Phenylbutyl for Methoxy at R4

2,5-Dimethoxy-4-phenylbutylphenethylamine

IUPAC: 2-[2,5-Dimethoxy-4-(4-phenylbutyl)phenyl]ethanamine

Formula: C20H27NO2 Molecular weight: 313.43388 g/mol InChI Key: SUAFIELOZLKXOQ-UHFFFAOYSA-N

InChI=1S/C20H27NO2/c1-22-19-15-18(12-13-21)20(23-2)14-17(19)11-7-6-10-16-8-4-3-5-9-16/h3-5,8-9,14-15H,6-7,10-13,21H2,1-2H3

PubChem CID: 10805159; ChemSpider: 8980464

Dowd, CS; Herrick-Davis, K; Egan, C; DuPre, A; Smith, C; Teitler, M; Glennon, RA. 1-[4-(3-Phenylalkyl)phenyl]-2-aminopropanes as 5-HT2A partial agonists. J. Med. Chem., 10 Aug 2000, 43 (16), 3074–3084. 271 kB. doi:10.1021/jm9906062

2361
Analogue 72: Substituting Isopropyl for Methoxy at R4

2C-IP
Jelena
4-Isopropyl-2,5-dimethoxyphenethylamine

IUPAC: 2-[2,5-Dimethoxy-4-(propan-2-yl)phenyl]ethanamine

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

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

PubChem CID: 57474311; ChemSpider: 27750188

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.

Meyers-Riggs, B. The alkylated 2Cs. countyourculture: rational exploration of the underground, 4 Oct 2010.

370
Analogue 73: Substituting 2-Fluoroethyl for Methoxy at R4

2C-EF
4-(2-Fluoroethyl)-2,5-dimethoxyphenethylamine

IUPAC: 2-[4-(2-Fluoroethyl)-2,5-dimethoxyphenyl]ethanamine

Formula: C12H18FNO2 Molecular weight: 227.2752232 g/mol InChI Key: KXPMRPNOYIOXFY-UHFFFAOYSA-N

InChI=1S/C12H18FNO2/c1-15-11-8-10(4-6-14)12(16-2)7-9(11)3-5-13/h7-8H,3-6,14H2,1-2H3

PubChem CID: 44350106; ChemSpider: 23206505

Shulgin Index: See #20 2C-D; Table: 5 Page: 343 Row: 23

See also PiHKAL: #65 DOEF      
7179
Analogue 74: Substituting Amino for Methoxy at R4

2C-NH

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

Formula: C10H16N2O2 Molecular weight: 196.24624 g/mol InChI Key: GAEPEBLGEFMUAZ-UHFFFAOYSA-N

InChI=1S/C10H16N2O2/c1-13-9-6-8(12)10(14-2)5-7(9)3-4-11/h5-6H,3-4,11-12H2,1-2H3

PubChem CID: 10330310; ChemSpider: 8505771

Shulgin Index: See #124 TMPEA-2; Table: 5 Page: 341 Row: 29

7253
Analogue 75: Substituting Hydroxymethyl for Methoxy at R4

2C-HM

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

Formula: C11H15NO3 Molecular weight: 209.2417 g/mol InChI Key: ZDHYVCBZXIAZEJ-UHFFFAOYSA-N

InChI=1S/C11H15NO3/c1-14-10-6-9(7-13)11(15-2)5-8(10)3-4-12/h5-7H,3-4,12H2,1-2H3

PubChem CID: 57486930

Shulgin Index: See #20 2C-D; Table: 5 Page: 343 Row: 3

7302
Analogue 76: Substituting Isobutyl for Methoxy at R4

2C-IB

IUPAC: 2-[2,5-Dimethoxy-4-(2-methylpropyl)phenyl]ethanamine

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

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

PubChem CID: 57486931

Shulgin Index: See #20 2C-D; Table: 5 Page: 344 Row: 2

472
Analogue 77: Substituting 2,2,2-Trifluoroethyl for Methoxy at R4

2C-TFE

IUPAC: 2-[2,5-Dimethoxy-4-(2,2,2-trifluoroethyl)phenyl]ethanamine

Formula: C12H16F3NO2 Molecular weight: 263.2561496 g/mol InChI Key: DVENUPQPPXYSLN-UHFFFAOYSA-N

InChI=1S/C12H16F3NO2/c1-17-10-6-9(7-12(13,14)15)11(18-2)5-8(10)3-4-16/h5-6H,3-4,7,16H2,1-2H3

PubChem CID: 57498513

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

466
Analogue 78: Substituting 2,2,2-Trifluoroethoxy for Methoxy at R4

2C-O-22

IUPAC: 2-[2,5-Dimethoxy-4-(2,2,2-trifluoroethoxy)phenyl]ethanamine

Formula: C12H16F3NO3 Molecular weight: 279.2555496 g/mol InChI Key: WXMPTDDEIHHBRM-UHFFFAOYSA-N

InChI=1S/C12H16F3NO3/c1-17-9-6-11(19-7-12(13,14)15)10(18-2)5-8(9)3-4-16/h5-6H,3-4,7,16H2,1-2H3

PubChem CID: 57498514

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

465
Analogue 79: Substituting 2,2-Difluoroethoxy for Methoxy at R4

2C-O-21.5

IUPAC: 2-[4-(2,2-Difluoroethoxy)-2,5-dimethoxyphenyl]ethanamine

Formula: C12H17F2NO3 Molecular weight: 261.2650864 g/mol InChI Key: USTOBZVLZKAMKI-UHFFFAOYSA-N

InChI=1S/C12H17F2NO3/c1-16-9-6-11(18-7-12(13)14)10(17-2)5-8(9)3-4-15/h5-6,12H,3-4,7,15H2,1-2H3

PubChem CID: 57498515

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

464
Analogue 80: Substituting 2-Fluoroethyoxy for Methoxy at R4

2C-O-21

IUPAC: 2-[4-(2-Fluoroethoxy)-2,5-dimethoxyphenyl]ethanamine

Formula: C12H18FNO3 Molecular weight: 243.2746232 g/mol InChI Key: QFEAVTWEYZNLIS-UHFFFAOYSA-N

InChI=1S/C12H18FNO3/c1-15-10-8-12(17-6-4-13)11(16-2)7-9(10)3-5-14/h7-8H,3-6,14H2,1-2H3

PubChem CID: 57498516

2474
Analogue 81: Substituting Astato for Methoxy at R4

2C-A
2,5-Dimethoxy-4-astatophenethylamine

IUPAC: [4-(2-Aminoethyl)-2,5-dimethoxyphenyl]astatine

Formula: C10H14AtNO2 Molecular weight: 390.22366 g/mol InChI Key: ULHVWCPOZNGWMU-UHFFFAOYSA-N

InChI=1S/C10H14AtNO2/c1-13-9-6-8(11)10(14-2)5-7(9)3-4-12/h5-6H,3-4,12H2,1-2H3

See also PiHKAL: #33 2C-I      

Meyers-Riggs, B. The halogenated 2Cs. countyourculture: rational exploration of the underground, 29 Sep 2010.

Four R5 analogues:
5392
Analogue 1: Removing Methoxy at R5

24
2,4-DMPEA
2,4-Dimethoxyphenethylamine

IUPAC: 2-(2,4-Dimethoxyphenyl)ethanamine

Formula: C10H15NO2 Molecular weight: 181.2316 g/mol InChI Key: YDTQAPOROITHCN-UHFFFAOYSA-N

InChI=1S/C10H15NO2/c1-12-9-4-3-8(5-6-11)10(7-9)13-2/h3-4,7H,5-6,11H2,1-2H3

PubChem CID: 417604; ChemSpider: 369665

Shulgin Index: #47 2,4-DMPEA; Table: 4 Page: 327 Row: 9

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

Clark, LC; Benington, F; Morin, RD. The effects of ring-methoxyl groups on biological deamination of phenethylamines. J. Med. Chem., 1 May 1965, 8 (3), 353–355. 389 kB. doi:10.1021/jm00327a016

Maher, HM; Awad, T; DeRuiter, J; Clark, CR. GC-MS and GC-IRD studies on dimethoxyphenethylamines (DMPEA): Regioisomers related to 2,5-DMPEA. J. Chromatogr. Sci., 1 Jan 2012, 50 (1), 1–9. 594 kB. doi:10.1093/chromsci/bmr013

Braden, MR; Parrish, JC; Naylor, JC; Nichols, DE. Molecular interaction of serotonin 5-HT2A 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. doi:10.1124/mol.106.028720

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

7079
Analogue 2: Substituting Bromo for Methoxy at R5

2,4,5-MMB

IUPAC: 2-(5-Bromo-2,4-dimethoxyphenyl)ethanamine

Formula: C10H14BrNO2 Molecular weight: 260.12766 g/mol InChI Key: FEAKOSWVJXEIIK-UHFFFAOYSA-N

InChI=1S/C10H14BrNO2/c1-13-9-6-10(14-2)8(11)5-7(9)3-4-12/h5-6H,3-4,12H2,1-2H3

ChemSpider: 25529597

Shulgin Index: See #18 2C-B; Table: 5 Page: 339 Row: 29

7101
Analogue 3: Substituting Amino for Methoxy at R5

5-NH2-2,4-DMPEA

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

Formula: C10H16N2O2 Molecular weight: 196.24624 g/mol InChI Key: HUJXOQJDJLWIEV-UHFFFAOYSA-N

InChI=1S/C10H16N2O2/c1-13-9-6-10(14-2)8(12)5-7(9)3-4-11/h5-6H,3-4,11-12H2,1-2H3

PubChem CID: 10035582; ChemSpider: 8211147

Shulgin Index: See #124 TMPEA-2; Table: 5 Page: 340 Row: 1

7504
Analogue 4: Substituting n-Propylthio for Methoxy at R5

2,4,5-2C-T-7

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

Formula: C14H23NO2S Molecular weight: 269.40292 g/mol InChI Key: WPEOSQBUHPSLAM-UHFFFAOYSA-N

InChI=1S/C14H23NO2S/c1-5-6-18-14-8-11(7-10(2)15)12(16-3)9-13(14)17-4/h8-10H,5-7,15H2,1-4H3

Shulgin Index: See #27 2C-T-7; Table: 5 Page: 348 Row: 4

One R4,5 analogue:
298
Analogue 1: Substituting Methylenedioxy for Dimethoxy at R4,5

2C-2
2C-MMDA-2
2-Methoxy-4,5-methylenedioxyphenethylamine

IUPAC: 2-(6-Methoxy-1,3-benzodioxol-5-yl)ethanamine

Formula: C10H13NO3 Molecular weight: 195.21512 g/mol InChI Key: VHBCQDKBQRHHPZ-UHFFFAOYSA-N

InChI=1S/C10H13NO3/c1-12-8-5-10-9(13-6-14-10)4-7(8)2-3-11/h4-5H,2-3,6,11H2,1H3

PubChem CID: 21831819; ChemSpider: 13802346

Shulgin Index: See #98 MMDA-2; Table: 5 Page: 339 Row: 24, See #98 MMDA-2; Table: 5 Page: 347 Row: 19

See also PiHKAL: #133 MMDA-2      
See also Pharmacology notes I: p. 75, 2C-2: Subacute evaluation
Five skeleton analogues:
1061
Analogue 1: With Prop-2-en-1-ylbenzene skeleton

γ-Asarone
2,4,5-Trimethoxyphenylprop-2-ene

IUPAC: 1,2,4-Trimethoxy-5-(prop-2-en-1-yl)benzene

Formula: C12H16O3 Molecular weight: 208.25364 g/mol InChI Key: AUNAUZZQBAIQFJ-UHFFFAOYSA-N Properties: Essential oil

InChI=1S/C12H16O3/c1-5-6-9-7-11(14-3)12(15-4)8-10(9)13-2/h5,7-8H,1,6H2,2-4H3

PubChem CID: 636750; ChemSpider: 552473

See also PiHKAL: #157 TMA #158 TMA-2    

Shulgin, AT. The separation and identification of the components of the aromatic ether fraction of essential oils by gas-liquid chromatography. J. Chromatogr., 1 Jan 1967, 30, 54–61. 769 kB. doi:10.1016/S0021-9673(00)84112-6

Monte, AP; Marona-Lewicka, D; Cozzi, NV; Nichols, DE. Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4-(methylenedioxy)amphetamine. J. Med. Chem., 1 Jan 1993, 36 (23), 3700–3706. 1026 kB. doi:10.1021/jm00075a027

Shulgin, AT. Synthesis of the trimethoxyphenylpropenes. Can. J. Chem., 1 Jan 1965, 43 (12), 3437–3440. 295 kB. doi:10.1139/v65-478

1062
Analogue 2: With (1Z)-Prop-1-en-1-ylbenzene skeleton

β-Asarone
cis-2,4,5-Trimethoxyphenylprop-1-ene

IUPAC: 1,2,4-Trimethoxy-5-[(1Z)-prop-1-en-1-yl]benzene

Formula: C12H16O3 Molecular weight: 208.25364 g/mol InChI Key: RKFAZBXYICVSKP-WAYWQWQTSA-N Properties: Essential oil

InChI=1S/C12H16O3/c1-5-6-9-7-11(14-3)12(15-4)8-10(9)13-2/h5-8H,1-4H3/b6-5-

PubChem CID: 636822; ChemSpider: 4445072

See also PiHKAL: #157 TMA #158 TMA-2    
See also Pharmacology notes I: p. 154, β-Asarone

Shulgin, AT. Possible implication of myristicin as a psychotropic substance. Nature, 1 Jan 1966, 210, 380–384. 707 kB. doi:10.1038/210380a0

Shulgin, AT. Synthesis of the trimethoxyphenylpropenes. Can. J. Chem., 1 Jan 1965, 43 (12), 3437–3440. 295 kB. doi:10.1139/v65-478

Shulgin, AT. The separation and identification of the components of the aromatic ether fraction of essential oils by gas-liquid chromatography. J. Chromatogr., 1 Jan 1967, 30, 54–61. 769 kB. doi:10.1016/S0021-9673(00)84112-6

Zuba, D; Byrska, B. Alpha- and beta-asarone in herbal medicinal products. A case study. Forensic Sci. Int., 229 kB. doi:10.1016/j.forsciint.2012.08.015

1063
Analogue 3: With (1E)-Prop-1-en-1-ylbenzene skeleton

α-Asarone
Asarone
trans-2,4,5-Trimethoxyphenylprop-1-ene

IUPAC: 1,2,4-Trimethoxy-5-[(1E)-prop-1-en-1-yl]benzene

Formula: C12H16O3 Molecular weight: 208.25364 g/mol InChI Key: RKFAZBXYICVSKP-AATRIKPKSA-N Properties: Essential oil

InChI=1S/C12H16O3/c1-5-6-9-7-11(14-3)12(15-4)8-10(9)13-2/h5-8H,1-4H3/b6-5+

PubChem CID: 636822; ChemSpider: 552532; Wikipedia: Asarone

See also PiHKAL: #157 TMA #158 TMA-2    

Shulgin, AT. The separation and identification of the components of the aromatic ether fraction of essential oils by gas-liquid chromatography. J. Chromatogr., 1 Jan 1967, 30, 54–61. 769 kB. doi:10.1016/S0021-9673(00)84112-6

Zuba, D; Byrska, B. Alpha- and beta-asarone in herbal medicinal products. A case study. Forensic Sci. Int., 229 kB. doi:10.1016/j.forsciint.2012.08.015

Shulgin, AT. Possible implication of myristicin as a psychotropic substance. Nature, 1 Jan 1966, 210, 380–384. 707 kB. doi:10.1038/210380a0

Shulgin, AT. Synthesis of the trimethoxyphenylpropenes. Can. J. Chem., 1 Jan 1965, 43 (12), 3437–3440. 295 kB. doi:10.1139/v65-478

7326
Analogue 4: With 2-Phenylcyclopropan-1-amine skeleton

TMCPA

IUPAC: 2-(2,4,5-Trimethoxyphenyl)cyclopropanamine

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

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

PubChem CID: 21151752; ChemSpider: 27941063

Shulgin Index: See #41 DMCPA; Table: 5 Page: 344 Row: 26

522
Analogue 5: With 2-Phenylcyclobutan-1-amine skeleton

TMCBA

IUPAC: 2-(2,4,5-Trimethoxyphenyl)cyclobutanamine

Formula: C13H19NO3 Molecular weight: 237.29486 g/mol InChI Key: FVHLLYXOSNOULA-UHFFFAOYSA-N

InChI=1S/C13H19NO3/c1-15-11-7-13(17-3)12(16-2)6-9(11)8-4-5-10(8)14/h6-8,10H,4-5,14H2,1-3H3

PubChem CID: 146232; ChemSpider: 128991

Nichols, DE; Jadhav, KP; Oberlender, RA; Zabik, JE; Bossart, JF; Hamada, A; Miller, DD. Synthesis and evaluation of substituted 2-phenylcyclobutylamines as analogues of hallucinogenic phenethylamines: Lack of LSD-like biological activity. J. Med. Chem., 1 Jan 1984, 27 (9), 1108–1111. 617 kB. doi:10.1021/jm00375a004

36 isomers:
16
Isomer 1

BOHD
2,5-Dimethoxy-β-hydroxy-4-methylphenethylamine

IUPAC: 2-Amino-1-(2,5-dimethoxy-4-methylphenyl)ethanol

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: WCURBUJUIMRCCJ-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-7-4-11(15-3)8(9(13)6-12)5-10(7)14-2/h4-5,9,13H,6,12H2,1-3H3

PubChem CID: 44719489; ChemSpider: 21106263; Wikipedia: BOHD (psychedelic)

See also PiHKAL: #14 BOD #57 DME    

Ho, B; Tansey, LW; McIsaac, WM. Derivatives of 2,5-dimethoxy-4-methylamphetamine (DOM). J. Med. Chem., 1 Sep 1970, 13 (5), 1022. 99 kB. doi:10.1021/jm00299a071

50
Isomer 2

4-D
4-Trideuteromethoxy-3,5-dimethoxyphenethylamine
3,5-Dimethoxy-4-trideuteromethoxyphenethylamine

IUPAC: 2-{3,5-Dimethoxy-4-[(2H3)methyloxy]phenyl}ethanamine

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: RHCSKNNOAZULRK-HPRDVNIFSA-N

InChI=1S/C11H17NO3/c1-13-9-6-8(4-5-12)7-10(14-2)11(9)15-3/h6-7H,4-5,12H2,1-3H3/i3D3

ChemSpider: 23553050; Wikipedia: 4-D (psychedelic)

Shulgin Index: See #91 Mescaline; Table: 5 Page: 350 Row: 35

See also PiHKAL: #51 β-D      
51
Isomer 3

β-D
β,β-Dideutero-3,4,5-trimethoxyphenethylamine
3,4,5-Trimethoxy-β,β-dideuterophenethylamine

IUPAC: 2-(3,4,5-Trimethoxyphenyl)(2,2-2H2)ethanamine

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: RHCSKNNOAZULRK-APZFVMQVSA-N

InChI=1S/C11H17NO3/c1-13-9-6-8(4-5-12)7-10(14-2)11(9)15-3/h6-7H,4-5,12H2,1-3H3/i4D2

PubChem CID: 44719547; ChemSpider: 21106267; Wikipedia: Beta-D

Shulgin Index: See #91 Mescaline; Table: 5 Page: 350 Row: 19

See also PiHKAL: #50 4-D #96 M    
91
Isomer 4

IM
Isomescaline
2,3,4-Trimethoxyphenethylamine

IUPAC: 2-(2,3,4-Trimethoxyphenyl)ethanamine

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: PVLFQRLVSMMSQK-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-13-9-5-4-8(6-7-12)10(14-2)11(9)15-3/h4-5H,6-7,12H2,1-3H3

PubChem CID: 414332; ChemSpider: 366878; Wikipedia: Isomescaline

Shulgin Index: #72 IM; Table: 5 Page: 338 Row: 14

See also PiHKAL: #92 IP #153 3-TIM    

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

Silva, ME; Heim, R; Strasser, A; Elz, S; Dove, S. Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor. J. Comput. Aided Mol. Des., 1 Jan 2011, 25 (1), 51–66. 834 kB. doi:10.1007/s10822-010-9400-2

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

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

Clark, LC; Benington, F; Morin, RD. The effects of ring-methoxyl groups on biological deamination of phenethylamines. J. Med. Chem., 1 May 1965, 8 (3), 353–355. 389 kB. doi:10.1021/jm00327a016

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. 36161 kB. Rhodium.

Makriyannis, A; Bowerman, D; Sze, PY; Fournier, D; Jong., APD. Structure activity correlations in the inhibition of brain synaptosomal 3H-norepinephrine uptake by phenethylamine analogs. The role of ?-alkyl side chain and methoxyl ring substitutions. Eur. J. Pharmacol., 9 Jul 1982, 81 (2), 337–340. 313 kB. doi:10.1016/0014-2999(82)90454-X

96
Isomer 5

M
Mescaline
EA-1306
Mescaline
3,4,5-Trimethoxyphenethylamine

IUPAC: 2-(3,4,5-Trimethoxyphenyl)ethanamine

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: RHCSKNNOAZULRK-UHFFFAOYSA-N Properties: Peyote alkaloid

InChI=1S/C11H17NO3/c1-13-9-6-8(4-5-12)7-10(14-2)11(9)15-3/h6-7H,4-5,12H2,1-3H3

PubChem CID: 4076; ChemSpider: 3934; Drugs Forum: Mescaline; Erowid: Mescaline; Wikipedia: Mescaline

Shulgin Index: #91 Mescaline; Table: 5 Page: 349 Row: 26

See also PiHKAL: #1 AEM
#9 ASB
#10 B
#16 BOHD
#17 BOM
#25 3C-E
#27 2C-G
#37 CPM
#41 2C-T-4
#43 2C-T-7
#44 2C-T-8
#50 4-D
#51 β-D
#52 DESOXY
#55 3,4-DMA
#58 DMMDA
#59 DMMDA-2
#68 DOM
#72 E
#91 IM
#92 IP
#93 IRIS
#95 LOPHOPHINE
#99 MAL
#100 MDA
#115 MDPEA
#119 ME
#125 META-DOT
#132 MMDA
#135 MMDA-3b
#142 PEA
#144 SB
#150 3-TE
#151 4-TE
#156 4-TM
#157 TMA
#158 TMA-2
#159 TMA-3
#160 TMA-4
#161 TMA-5
#162 TMA-6
#163 3-TME
#168 TMPEA
#175 TRIS
#178 3-T-TRIS
See also TiHKAL: #8 α,N-DMT
#9 DPT
#13 Harmaline
#17 4-HO-DIPT
#45 5-MeO-TMT
#48 α-MT
#53 T
See also Pharmacology notes I: p. 1, Mescaline: Subjective response
p. 2, Mescaline: Subjective response
p. 3, Mescaline: Subjective response
p. 4, Mescaline: Subjective response
p. 5, Mescaline: Subjective response
p. 6, Mescaline: Subjective response
p. 7, Mescaline: Basis for M.U. calculation
See also Pharmacology notes II: app. 5, Untitled
p. 321, Mescaline

Daly, J; Axelrod, J; Witkop, B. Methylation and demethylation in relation to the in vitro metabolism of mescaline. Ann. N.Y. Acad. Sci., 1 Jan 1962, 96, 37–43. 397 kB. doi:10.1111/j.1749-6632.1962.tb50099.x

Friedhoff, AJ; Goldstein, M. New developments in metabolism of mescaline and related amines. Ann. N.Y. Acad. Sci., 1 Jan 1962, 96, 5–13. 506 kB. doi:10.1111/j.1749-6632.1962.tb50097.x

Smythies, JR. The mescaline phenomena. Br. J. Philos. Sci., 1 Feb 1953, 3 (12), 339–347. 72 kB. doi:10.1093/bjps/III.12.339

Shulgin, AT. Profiles of psychedelic drugs. 7. Mescaline. J. Psychedelic Drugs, 1 Jan 1979, 11 (4), 355. 713 kB. doi:10.1080/02791072.1979.10471421

Reviriego, F; Navarro, P; Domènech, A; García-España, E. Effective complexation of psychotropic phenethylammonium salts from a disodium dipyrazolate salt of macrocyclic structure. J. Chem. Soc. Perkin Trans. 2, 2002, 1634–1638. 115 kB. doi:10.1039/b200607c

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

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

Lemaire, D; Jacob, P; Shulgin, AT. Ring substituted beta-methoxyphenethylamines: a new class of psychotomimetic agents active in man. J. Pharm. Pharmacol., 1 Jan 1985, 37 (8), 575–7. 1767 kB. doi:10.1111/j.2042-7158.1985.tb03072.x

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. doi:10.1124/jpet.106.117507

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

McGrane, O; Simmons, J; Jacobsen, E; Skinner, C. Alarming trends in a novel class of designer drugs. J. Clinic. Toxicol., 1 Nov 2011, 1 (2). 775 kB. doi:10.4172/2161-0494.1000108

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. 36161 kB. Rhodium.

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.

Silva, ME. Theoretical study of the interaction of agonists with the 5-HT2A receptor. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 26 Aug 2008. 5904 kB.

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

Fenderson5555. Two syntheses of mescaline. 21 Mar 2011.

Clark, LC; Benington, F; Morin, RD. The effects of ring-methoxyl groups on biological deamination of phenethylamines. J. Med. Chem., 1 May 1965, 8 (3), 353–355. 389 kB. doi:10.1021/jm00327a016

Ho, B; Tansey, LW; Balster, RL; An, R; McIsaac, WM; Harris, RT. Amphetamine analogs. II. Methylated phenethylamines. J. Med. Chem., 1 Jan 1970, 13 (1), 134–135. 278 kB. doi:10.1021/jm00295a034

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

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

Makriyannis, A; Bowerman, D; Sze, PY; Fournier, D; Jong., APD. Structure activity correlations in the inhibition of brain synaptosomal 3H-norepinephrine uptake by phenethylamine analogs. The role of ?-alkyl side chain and methoxyl ring substitutions. Eur. J. Pharmacol., 9 Jul 1982, 81 (2), 337–340. 313 kB. doi:10.1016/0014-2999(82)90454-X

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

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

Desantis, F; Nieforth, KA. Synthesis of potential mescaline antagonists. J. Pharm. Sci., 1 Jan 1976, 65 (10), 1479–1484. 704 kB. doi:10.1002/jps.2600651016

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

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

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

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

Battersby, AR; Binks, R; Huxtable, R. Biosynthesis of cactus alkaloids. Tetrahedron Lett., 1 Jan 1967, 8 (6), 563–565. 134 kB. doi:10.1016/S0040-4039(00)90548-3

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

Parker, MA; Kurrasch, DM; Nichols, DE. The role of lipophilicity in determining binding affinity and functional activity for 5-HT2A receptor ligands. Bioorg. Med. Chem., 1 Jan 2008, 16 (8), 4661–4669. 296 kB. doi:10.1016/j.bmc.2008.02.033

Ogunbodede, O; McCombs, D; Trout, K; Daley, PF; Terry, M. New mescaline concentrations from 14 taxa/cultivars of Echinopsis spp. (Cactaceae) (“San Pedro”) and their relevance to shamanic practice. J. Ethnopharmacol., 15 Sep 2010, 131 (2), 356–362. 324 kB. doi:10.1016/j.jep.2010.07.021

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

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

Marona-Lewicka, D; Nichols, DE. Further evidence that the delayed temporal dopaminergic effects of LSD are mediated by a mechanism different than the first temporal phase of action. Pharmacol. Biochem. Behav., 1 Jan 2007, 87 (4), 453–461. 266 kB. doi:10.1016/j.pbb.2007.06.001

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

307
Isomer 6

TMPEA-5
2C-TMA-5
2,3,6-Trimethoxyphenethylamine

IUPAC: 2-(2,3,6-Trimethoxyphenyl)ethanamine

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: SOARXDWNNULVNL-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-13-9-4-5-10(14-2)11(15-3)8(9)6-7-12/h4-5H,6-7,12H2,1-3H3

PubChem CID: 414331; ChemSpider: 366877

Shulgin Index: See #121 TMA-5; Table: 5 Page: 353 Row: 1

See also PiHKAL: #161 TMA-5      

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

Clark, LC; Benington, F; Morin, RD. The effects of ring-methoxyl groups on biological deamination of phenethylamines. J. Med. Chem., 1 May 1965, 8 (3), 353–355. 389 kB. doi:10.1021/jm00327a016

Matsuhiro, B; Furst, A. 2,3,6-Trimethoxynitrostyrene and its β-phenethylamine. J. Med. Chem., 1 Sep 1970, 13 (5), 973. 140 kB. doi:10.1021/jm00299a042

308
Isomer 7

TMPEA-6
2C-TMA-6
2,4,6-TMPEA
Ψ-2C-O
2,4,6-Trimethoxyphenethylamine

IUPAC: 2-(2,4,6-Trimethoxyphenyl)ethanamine

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: CGUNKAXAEZSOFA-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-13-8-6-10(14-2)9(4-5-12)11(7-8)15-3/h6-7H,4-5,12H2,1-3H3

PubChem CID: 21679959; ChemSpider: 10296635

Shulgin Index: See #122 TMA-6; Table: 5 Page: 353 Row: 25

See also PiHKAL: #162 TMA-6      

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

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

Clark, LC; Benington, F; Morin, RD. The effects of ring-methoxyl groups on biological deamination of phenethylamines. J. Med. Chem., 1 May 1965, 8 (3), 353–355. 389 kB. doi:10.1021/jm00327a016

Benington, F; Morin, RD; Clark, LC. Mescaline analogs. I. 2,4,6-Trialkoxy-β-phenethylamines. J. Org. Chem., 1 Jan 1954, 19 (1), 11–16. 436 kB. doi:10.1021/jo01366a003

2092
Isomer 8

3,5-D
4-Methoxy-3,5-di(trideuteromethoxy)phenethylamine

IUPAC: 2-{4-Methoxy-3,5-bis[(2H3)methyloxy]phenyl}ethanamine

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: RHCSKNNOAZULRK-WFGJKAKNSA-N

InChI=1S/C11H17NO3/c1-13-9-6-8(4-5-12)7-10(14-2)11(9)15-3/h6-7H,4-5,12H2,1-3H3/i1D3,2D3

See also PiHKAL: #50 4-D #51 β-D    
2093
Isomer 9

2,6-D
2,6-Dideutero-3,4,5-trimethoxyphenethylamine

IUPAC: 2-[3,4,5-Trimethoxy(2H2)phenyl]ethanamine

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: RHCSKNNOAZULRK-QFIQSOQBSA-N

InChI=1S/C11H17NO3/c1-13-9-6-8(4-5-12)7-10(14-2)11(9)15-3/h6-7H,4-5,12H2,1-3H3/i6D,7D

See also PiHKAL: #51 β-D      
2094
Isomer 10

α-D
α,α-Dideutero-3,4,5-trimethoxyphenethylamine

IUPAC: 2-(3,4,5-Trimethoxyphenyl)(1,1-2H2)ethanamine

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: RHCSKNNOAZULRK-BFWBPSQCSA-N

InChI=1S/C11H17NO3/c1-13-9-6-8(4-5-12)7-10(14-2)11(9)15-3/h6-7H,4-5,12H2,1-3H3/i5D2

See also PiHKAL: #51 β-D      
2213
Isomer 11

N-Me-3-DESMETHYL
N-Methyl-3-demethylmescaline
3-Hydroxy-4,5-dimethoxy-N-methylphenethylamine

IUPAC: 2,3-Dimethoxy-5-[2-(methylamino)ethyl]phenol

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: ZIXMCYWHHXSJOK-UHFFFAOYSA-N Properties: Peyote alkaloid

InChI=1S/C11H17NO3/c1-12-5-4-8-6-9(13)11(15-3)10(7-8)14-2/h6-7,12-13H,4-5H2,1-3H3

PubChem CID: 57478610

Shulgin Index: See #30 3-DESMETHYL; Table: 5 Page: 349 Row: 6

5396
Isomer 12

2C-pEtOH
4-(2-Hydroxyethyl)-2,5-dimethoxyphenethylamine

IUPAC: [4-(2-Aminoethyl)-2,5-dimethoxyphenyl]methanol

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: AYJLNTOOEWDDBF-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-14-10-6-9(7-13)11(15-2)5-8(10)3-4-12/h5-6,13H,3-4,7,12H2,1-2H3

PubChem CID: 57474313

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

2414
Isomer 13

DOOH
4-Hydroxy-2,5-dimethoxyamphetamine

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

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: XZYTWVYCADLTTI-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-7(12)4-8-5-11(15-3)9(13)6-10(8)14-2/h5-7,13H,4,12H2,1-3H3

PubChem CID: 44265202; ChemSpider: 23108622

Shulgin Index: See #118 TMA-2; Table: 5 Page: 344 Row: 11

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

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

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

2394
Isomer 14

β-HO-2,5-DMA
2,5-Dimethoxynorephedrine

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

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: WJAJPNHVVFWKKL-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-7(12)11(13)9-6-8(14-2)4-5-10(9)15-3/h4-7,11,13H,12H2,1-3H3

PubChem CID: 6082; ChemSpider: 5857

Shulgin Index: See #36 2,5-DMA; Table: 4 Page: 335 Row: 26

Rusterholz, DB; Dryer, SE; Long, JP; Barfknecht, CF; Mott, J. Sedative and analgesic actions of methoxylated 2-aminotetralins; involvement of α1- and α2-adrenoreceptors. Eur. J. Pharmacol., 25 Jul 1980, 65 (2–3), 201–211. 870 kB. doi:10.1016/0014-2999(80)90393-3

Osorio-Olivares, M; Rezende, MC; Sepúlveda-Boza, S; Cassels, BK; Fierro, A. MAO inhibition by arylisopropylamines: the effect of oxygen substituents at the β-position. Bioorg. Med. Chem., 1 Jan 2004, 12 (15), 4055–4066. 412 kB. doi:10.1016/j.bmc.2004.05.033

Warren, RJ; Begosh, PP; Zarembo, JE. Identification of amphetamines and related sympathomimetic amines. J. Assoc. Off. Anal. Chem., 1971, 54 (5), 1179–1191. 3851 kB.

6522
Isomer 15

β,3,4-HO-N-iPr-DHPEA

IUPAC: 4-[1-Hydroxy-2-(propan-2-ylamino)ethyl]benzene-1,2-diol

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: JWZZKOKVBUJMES-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-7(2)12-6-11(15)8-3-4-9(13)10(14)5-8/h3-5,7,11-15H,6H2,1-2H3

PubChem CID: 3779; ChemSpider: 3647

Shulgin Index: See #49 DMPEA; Table: 4 Page: 328 Row: 22

6565
Isomer 16

MHMAOH

IUPAC: 4-{2-[Hydroxy(methyl)amino]propyl}-2-methoxyphenol

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: CFCCDEBKSDYMQE-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-8(12(2)14)6-9-4-5-10(13)11(7-9)15-3/h4-5,7-8,13-14H,6H2,1-3H3

Shulgin Index: See #33 DHA; Table: 4 Page: 329 Row: 15

6584
Isomer 17

N,N-Me-HME

IUPAC: 5-[2-(Dimethylamino)-1-hydroxyethyl]-2-methoxyphenol

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: VDYIKJCBMMLENB-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-12(2)7-10(14)8-4-5-11(15-3)9(13)6-8/h4-6,10,13-14H,7H2,1-3H3

Shulgin Index: See #49 DMPEA; Table: 4 Page: 329 Row: 34

6608
Isomer 18

N-Me-DME

IUPAC: 1-(3,4-Dimethoxyphenyl)-2-(methylamino)ethanol

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: QSUCQAULQIAOEP-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-12-7-9(13)8-4-5-10(14-2)11(6-8)15-3/h4-6,9,12-13H,7H2,1-3H3

PubChem CID: 3084840; ChemSpider: 2341843

Shulgin Index: See #49 DMPEA; Table: 4 Page: 330 Row: 8

Ghosal, S; Srivastava, RS. β-Phenethylamine, tetrahydroisoquinoline and indole alkaloids of Desmodium tiliaefolium. Phytochemistry, 1 Jan 1973, 12 (1), 193–197. 552 kB. doi:10.1016/S0031-9422(00)84646-4

Butterick, JR. Synthesis of O-transmethylated catecholamines and psychodysleptic β-phenylisopropylamines. Ph. D. Thesis, Simon Faser University, Burnaby, BC, Canada, 11 Mar 1975. 6069 kB. External examiner: A. T. Shulgin!

6611
Isomer 19

β,3,4-TMPEA

IUPAC: 2-(3,4-Dimethoxyphenyl)-2-methoxyethanamine

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: CFEHWNSMGUKJEU-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-13-9-5-4-8(6-10(9)14-2)11(7-12)15-3/h4-6,11H,7,12H2,1-3H3

PubChem CID: 3014315; ChemSpider: 2282798

Shulgin Index: See #49 DMPEA; Table: 4 Page: 330 Row: 11

6619
Isomer 20

DMAOH
HOT-DMA

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

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: QESZBOZKJCHKCL-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-8(12-13)6-9-4-5-10(14-2)11(7-9)15-3/h4-5,7-8,12-13H,6H2,1-3H3

PubChem CID: 5190226; ChemSpider: 4361999

Shulgin Index: See #38 DMA; Table: 4 Page: 330 Row: 19

Benington, F; Morin, RD; Clark, LC. Behavioral and neuropharmacological actions of N-aralkylhydroxylamines and their O-methyl ethers. J. Med. Chem., 1 Jan 1965, 8 (1), 100–104. 634 kB. doi:10.1021/jm00325a020

6626
Isomer 21

β-HO-DMA

IUPAC: 2-Amino-1-(3,4-dimethoxyphenyl)propan-1-ol

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: JTIPLNDENHDFNZ-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-7(12)11(13)8-4-5-9(14-2)10(6-8)15-3/h4-7,11,13H,12H2,1-3H3

PubChem CID: 13585934; ChemSpider: 12956236

Shulgin Index: See #38 DMA; Table: 4 Page: 330 Row: 26

6634
Isomer 22

β-HO-4,3-EMPEA

IUPAC: 2-Amino-1-(4-ethoxy-3-methoxyphenyl)ethanol

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: TYSLQHFYCCDHQF-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-3-15-10-5-4-8(9(13)7-12)6-11(10)14-2/h4-6,9,13H,3,7,12H2,1-2H3

PubChem CID: 16768023; ChemSpider: 11852804

Shulgin Index: See #49 DMPEA; Table: 4 Page: 330 Row: 34

6856
Isomer 23

β,2-HO-N-Me-5-MA

IUPAC: 2-[1-Hydroxy-2-(methylamino)propyl]-4-methoxyphenol

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: OZBWNQQJAATCCF-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-7(12-2)11(14)9-6-8(15-3)4-5-10(9)13/h4-7,11-14H,1-3H3

Shulgin Index: See #36 2,5-DMA; Table: 4 Page: 335 Row: 6

6865
Isomer 24

β-HO-N-Me-2,5-DMPEA

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

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: AFGIOLGUENMUPF-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-12-7-10(13)9-6-8(14-2)4-5-11(9)15-3/h4-6,10,12-13H,7H2,1-3H3

PubChem CID: 46244; ChemSpider: 42102

Shulgin Index: See #22 2C-H; Table: 4 Page: 335 Row: 15

6867
Isomer 25

BODM

IUPAC: 2-(2,5-Dimethoxyphenyl)-2-methoxyethanamine

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: HRQOYIJXQHSHOE-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-13-8-4-5-10(14-2)9(6-8)11(7-12)15-3/h4-6,11H,7,12H2,1-3H3

PubChem CID: 10420680; ChemSpider: 8596110

Shulgin Index: See #14 BOB; Table: 4 Page: 335 Row: 17

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

6868
Isomer 26

β-HO,Me-2,5-DMPEA

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

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: AURMVDWBJNLYHE-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-11(13,7-12)9-6-8(14-2)4-5-10(9)15-3/h4-6,13H,7,12H2,1-3H3

PubChem CID: 46246; ChemSpider: 42104

Shulgin Index: See #22 2C-H; Table: 4 Page: 335 Row: 18

6906
Isomer 27

β,2-HO-N-Me-5-EPEA

IUPAC: 4-Ethoxy-2-[1-hydroxy-2-(methylamino)ethyl]phenol

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: YOIOXOFQHDQNEP-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-3-15-8-4-5-10(13)9(6-8)11(14)7-12-2/h4-6,11-14H,3,7H2,1-2H3

Shulgin Index: See #22 2C-H; Table: 4 Page: 336 Row: 6

6909
Isomer 28

β,2-HO-5-EA

IUPAC: 2-(2-Amino-1-hydroxypropyl)-4-ethoxyphenol

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: LQFDWMDHTDNEFB-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-3-15-8-4-5-10(13)9(6-8)11(14)7(2)12/h4-7,11,13-14H,3,12H2,1-2H3

Shulgin Index: See #36 2,5-DMA; Table: 4 Page: 336 Row: 9

6926
Isomer 29

β-HO-N-Me-3,5-DMPEA

IUPAC: 1-(3,5-Dimethoxyphenyl)-2-(methylamino)ethanol

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: RJKGQUALUZJVGM-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-12-7-11(13)8-4-9(14-2)6-10(5-8)15-3/h4-6,11-13H,7H2,1-3H3

PubChem CID: 62774486

Shulgin Index: See #50 3,5-DMPEA; Table: 4 Page: 336 Row: 26

6972
Isomer 30

β-HO-N-Me-2,6-DMPEA

IUPAC: 1-(2,6-Dimethoxyphenyl)-2-(methylamino)ethanol

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: HSYSLTPRNLNOAG-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-12-7-8(13)11-9(14-2)5-4-6-10(11)15-3/h4-6,8,12-13H,7H2,1-3H3

PubChem CID: 22574395; ChemSpider: 11474127

Shulgin Index: See #48 2,6-DMPEA; Table: 4 Page: 337 Row: 22

7071
Isomer 31

TMPEA-4

IUPAC: 2-(2,3,5-Trimethoxyphenyl)ethanamine

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: GERNGXILVRWWGB-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-13-9-6-8(4-5-12)11(15-3)10(7-9)14-2/h6-7H,4-5,12H2,1-3H3

PubChem CID: 413872; ChemSpider: 366438

Shulgin Index: See #120 TMA-4; Table: 5 Page: 339 Row: 21

Clark, LC; Benington, F; Morin, RD. The effects of ring-methoxyl groups on biological deamination of phenethylamines. J. Med. Chem., 1 May 1965, 8 (3), 353–355. 389 kB. doi:10.1021/jm00327a016

7210
Isomer 32

N-HO-2C-D

IUPAC: 2-(2,5-Dimethoxy-4-methylphenyl)-N-hydroxyethanamine

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: YRZMJKDZPVHTBF-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-8-6-11(15-3)9(4-5-12-13)7-10(8)14-2/h6-7,12-13H,4-5H2,1-3H3

Shulgin Index: See #20 2C-D; Table: 5 Page: 342 Row: 10

7559
Isomer 33

α-Me-3-DESMETHYL

IUPAC: 5-(2-Aminopropyl)-2,3-dimethoxyphenol

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: CEDBRNZPRXITHE-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-7(12)4-8-5-9(13)11(15-3)10(6-8)14-2/h5-7,13H,4,12H2,1-3H3

ChemSpider: 26495745

Shulgin Index: See #117 TMA; Table: 5 Page: 349 Row: 9

7568
Isomer 34

DESMETHYL-M

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

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: CQRXQNMRCIMDPZ-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-12-5-4-8-6-9(14-2)11(13)10(7-8)15-3/h6-7,12-13H,4-5H2,1-3H3

Shulgin Index: See #29 DESMETHYL; Table: 5 Page: 349 Row: 18

7572
Isomer 35

α-Me-DESMETHYL

IUPAC: 4-(2-Aminopropyl)-2,6-dimethoxyphenol

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: NCPDWXQFKKIRGY-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-7(12)4-8-5-9(14-2)11(13)10(6-8)15-3/h5-7,13H,4,12H2,1-3H3

ChemSpider: 26495039

Shulgin Index: See #117 TMA; Table: 5 Page: 349 Row: 22

933
Isomer 36

N-Methyl-3,4,5-trimethoxybenzylamine

IUPAC: N-Methyl-1-(3,4,5-trimethoxyphenyl)methanamine

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: LFULMNRPABTDDQ-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-12-7-8-5-9(13-2)11(15-4)10(6-8)14-3/h5-6,12H,7H2,1-4H3

Benington, F; Morin, RD; Clark, LC. Mescaline analogs. VI. Mescaline homologs. J. Org. Chem., 1 Dec 1956, 21 (12), 1545–1546. 282 kB. doi:10.1021/jo01118a635

Show all 136 analogues and isomers Show only the one N analogues Show only the three α analogues Show only the one β analogues Show only the three R2 analogues Show only the one R3 analogues Show only the 81 R4 analogues Show only the four R5 analogues Show only the one R4,5 analogues Show only the five skeleton analogues
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