Go to PiHKAL • info home
Browse the short index of PiHKAL phenethylamines. Read book II of PiHKAL
Search for phenethylamines and related structures Beyond PiHKAL—Selected writings by Sasha and others. Explore phenethylamine structures and analogues
The essential oils and their amphetamine analogues How PiHKAL • info differs from the printed version
Go to TiHKAL • info home
You are currently exploring 3-DOB.
To explore a different substance, type its name: Help
3-DOB; 1-(3-Bromo-2,5-dimethoxyphenyl)propan-2-amine
7060
Variant: α R3 isomers all
Analogues: 1 5 19 25

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

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

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

PubChem CID: 12626552; ChemSpider: 23115301

Shulgin Index: See #52 DOB; Table: 5 Page: 339 Row: 10

Rasmussen, K; Glennon, RA; Aghajanian, GK. Phenethylamine hallucinogens in the locus coeruleus: potency of action correlates with rank order of 5-HT2 binding affinity. Eur. J. Pharmacol., 2 Dec 1986, 132 (1), 79–82. 267 kB. doi:10.1016/0014-2999(86)90014-2

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

Glennon, RA; Rosecrans, JA; Young, R. Behavioral properties of psychoactive phenylisopropylamines in rats. Eur. J. Pharmacol., 17 Dec 1981, 76 (4), 353–360. 964 kB. doi:10.1016/0014-2999(81)90106-0

One α analogue:
7059
Analogue 1: Removing Methyl at α

2,3,5-MBM

IUPAC: 2-(3-Bromo-2,5-dimethylphenyl)ethan-1-amine

Formula: C10H14BrN Molecular weight: 228.12886 g/mol InChI Key: PKHDQEALKJDESR-UHFFFAOYSA-N

InChI=1S/C10H14BrN/c1-7-5-9(3-4-12)8(2)10(11)6-7/h5-6H,3-4,12H2,1-2H3

Shulgin Index: See #18 2C-B; Table: 5 Page: 339 Row: 9

Five R3 analogues:
54
Analogue 1: Removing Bromo at R3

2,5-DMA
DMA
DOH
2,5-Dimethoxyamphetamine

IUPAC: 1-(2,5-Dimethoxyphenyl)propan-2-amine

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

InChI=1S/C11H17NO2/c1-8(12)6-9-7-10(13-2)4-5-11(9)14-3/h4-5,7-8H,6,12H2,1-3H3

PubChem CID: 62787; ChemSpider: 56526; Wikipedia: Dimethoxyamphetamine

Shulgin Index: #38 DMA; Table: 4 Page: 330 Row: 17, #36 2,5-DMA; Table: 4 Page: 335 Row: 22

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

See also Transcripts: 1.57, 1.58, 2.276, 4.462

See also Pharmacology notes I: p. 57, 2,5-DMA: Subacute evaluation
p. 58, 2,5-DMA: Subjective response
See also Pharmacology notes II: p. 276, 2,5-DMA

Bailey, K; Legauld, D; Verner, D. Spectroscopic and chromatographic identification of dimethoxyamphetamines. J. Assoc. Anal. Chem., 1974, 57 (1), 70–78. 426 kB.

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

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

Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017

Altun, A; Golcuk, K; Kumru, M; Jalbout, AF. Electron-conformation study for the structure-hallucinogenic activity relationships of phenylalkylamines. Bioorg. Med. Chem., 1 Dec 2003, 11 (24), 3861–3868. 577 kB. doi:10.1016/S0968-0896(03)00437-1

Glennon, RA; Raghupathi, R; Bartyzel, P; Teitler, M; Leonhardt, S. Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity. J. Med. Chem., 1 Feb 1992, 35 (4), 734–740. 1054 kB. doi:10.1021/jm00082a014

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

Fenderson5555. Shulgin’s syntheses of 2,5-DMA, DOB and DOEF. 5 Dec 2011. 3657 kB.

Nichols, DE; Snyder, SE; Oberlender, R; Johnson, MP; Huang, X. 2,3-Dihydrobenzofuran analogues of hallucinogenic phenethylamines. J. Med. Chem., 1 Jan 1991, 34 (1), 276–281. 833 kB. doi:10.1021/jm00105a043

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

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

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

Glennon, RA; Rosecrans, JA; Young, R. Behavioral properties of psychoactive phenylisopropylamines in rats. Eur. J. Pharmacol., 17 Dec 1981, 76 (4), 353–360. 964 kB. doi:10.1016/0014-2999(81)90106-0

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 2584 kB. doi:10.1007/978-1-4757-0510-2_6 Rhodium.

Runyon, SP; Mosier, PD; Roth, BL; Glennon, RA; Westkaemper, RB. Potential modes of interaction of 9-aminomethyl-9,10-dihydroanthracene (AMDA) derivatives with the 5-HT2A receptor: A ligand structure-affinity relationship, receptor mutagenesis and receptor modeling investigation. J. Med. Chem., 2008, 51 (21), 6808–2828. 2229 kB. doi:10.1021/jm800771x

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

Antun, F; Smythies, JR; Benington, F; Morin, RD; Barfknecht, CF; Nichols, DE. Native fluorescence and hallucinogenic potency of some amphetamines. Experientia, 15 Jan 1971, 27 (1), 62–63. 248 kB. doi:10.1007/BF02137743

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

Nichols, DE; Barfknecht, CF; Rusterholz, DB; Benington, F; Morin, RD. Asymmetric synthesis of psychotomimetic phenylisopropylamines. J. Med. Chem., 1 Jan 1973, 16 (5), 480–483. 515 kB. doi:10.1021/jm00263a013

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

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

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

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

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

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

Nelson, DL; Lucaites, VL; Wainscott, DB; Glennon, RA. Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, 5-HT2B and 5-HT2C receptors. N-S. Arch. Pharmacol., 6 Sep 1998, 359 (1), 1–6. 66 kB. doi:10.1007/PL00005315

Aldous, FAB; Barrass, BC; Brewster, K; Buxton, DA; Green, DM; Pinder, RM; Rich, P; Skeels, PM; Tutt, KJ. Structure-activity relationships in psychotomimetic phenylalkylamines. J. Med. Chem., 1 Oct 1974, 17 (10),1100–1111. 1188 kB. doi:10.1021/jm00256a016

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

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

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

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

Dyer, DC; Nichols, DE; Rusterholz, DB; Barfknecht, CF. Comparative effects of stereoisomers of psychotomimetic phenylisopropylamines. Life Sci., 1 Oct 1973, 13 (7), 885–896. 398 kB. doi:10.1016/0024-3205(73)90079-9

Glennon, RA; Dukat, M; Grella, B; Hong, S; Costantino, L; Teitler, M; Smith, C; Egan, C; Davis, K; Mattson, MV. Binding of β-carbolines and related agents at serotonin (5-HT2 and 5-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

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

Glennon, RA; Bondarev, ML; Khorana, N; Young, R. β-Oxygenated analogues of the 5-HT2A serotonin receptor agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane. J. Med. Chem., 1 Jan 2004, 47 (24), 6034–6041. 146 kB. doi:10.1021/jm040082s

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

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

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

Shulgin, AT. Chemistry and structure-activity relationships of the psychotomimetics. In Psychotomimetic Drugs; Efron, DH, Ed., Raven Press, New York, 1 Jan 1970; pp 21–41. 8647 kB.

160
Analogue 2: Substituting Methoxy for Bromo at R3

TMA-4
2,3,5-Trimethoxyamphetamine

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

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

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

PubChem CID: 602804; ChemSpider: 523988; Wikipedia: Trimethoxyamphetamine

Shulgin Index: #120 TMA-4; Table: 5 Page: 339 Row: 22

See also PiHKAL: #42 Ψ-2C-T-4 #135 MMDA-3b #136 MME #158 TMA-2 #161 TMA-5

See also Transcripts: 1.61, 1.72

See also Pharmacology notes I: p. 61, TMA-4: Subacute evaluation
p. 72, SARs

Altun, A; Golcuk, K; Kumru, M; Jalbout, AF. Electron-conformation study for the structure-hallucinogenic activity relationships of phenylalkylamines. Bioorg. Med. Chem., 1 Dec 2003, 11 (24), 3861–3868. 577 kB. doi:10.1016/S0968-0896(03)00437-1

Glennon, RA; 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

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

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

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 2584 kB. doi:10.1007/978-1-4757-0510-2_6 Rhodium.

Shulgin, AT. Chemistry and structure-activity relationships of the psychotomimetics. In Psychotomimetic Drugs; Efron, DH, Ed., Raven Press, New York, 1 Jan 1970; pp 21–41. 8647 kB.

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

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

Shulgin, AT. MMDA (MMDA-4). Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 11 Apr 2003.

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

Fenderson5555. The trimethoxylated amphetamines (TMA-x). 9 Dec 2012. 7716 kB.

7061
Analogue 3: Substituting Nitro for Bromo at R3

3-DON

IUPAC: 1-(2,5-Dimethoxy-3-nitrophenyl)propan-2-amine

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

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

PubChem CID: 126982; ChemSpider: 112754

Shulgin Index: See #61 DON; Table: 5 Page: 339 Row: 11

7062
Analogue 4: Substituting Methyl for Bromo at R3

3-DOM

IUPAC: 1-(2,5-Dimethoxy-3-methylphenyl)propan-2-amine

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

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

PubChem CID: 12626548; ChemSpider: 23187896

Shulgin Index: See #60 DOM; Table: 5 Page: 339 Row: 12

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

Glennon, RA; Rosecrans, JA; Young, R. Behavioral properties of psychoactive phenylisopropylamines in rats. Eur. J. Pharmacol., 17 Dec 1981, 76 (4), 353–360. 964 kB. doi:10.1016/0014-2999(81)90106-0

7063
Analogue 5: Substituting Ethyl for Bromo at R3

3,2,5-DOET

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

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

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

PubChem CID: 57486947

Shulgin Index: See #56 DOET; Table: 5 Page: 339 Row: 13

19 isomers:
18
Isomer 1

4-Br-3,5-DMA
4,3,5-DOB
4-Bromo-3,5-dimethoxyamphetamine
3,5-Dimethoxy-4-bromoamphetamine

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

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

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

PubChem CID: 208044; ChemSpider: 180279; Wikipedia: 4-Bromo-3,5-dimethoxyamphetamine

Shulgin Index: See #52 DOB; Table: 5 Page: 349 Row: 11

See also Transcripts: 1.197

See also Pharmacology notes I: p. 197, 4-Br-3,5-DMA

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

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

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 2584 kB. doi:10.1007/978-1-4757-0510-2_6 Rhodium.

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

62
Isomer 2

DOB
Brolamphetamine
4-Bromo-2,5-dimethoxyamphetamine
2,5-Dimethoxy-4-bromoamphetamine

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

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

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

PubChem CID: 62065; ChemSpider: 55902; Drugs Forum: DOB; Erowid: DOB; Wikipedia: 2,5-Dimethoxy-4-bromoamphetamine

Shulgin Index: #52 DOB; Table: 5 Page: 340 Row: 28

See also PiHKAL: #8 ARIADNE
#10 B
#22 2C-C
#26 2C-F
#39 2C-T
#52 DESOXY
#54 2,5-DMA
#64 DOC
#65 DOEF
#67 DOI
#72 E
#124 META-DOB
#156 4-TM
#162 TMA-6

See also Transcripts: 1.152, 1.171, 2.226, 3.336, 3.337

See also Pharmacology notes I: p. 152, DOB
p. 171, DOB: Enantiomeric effects
See also Pharmacology notes II: p. 226, DOB

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

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

Delliou, D. 4-Bromo-2,5-dimethoxyamphetamine: Psychoactivity, toxic effects and analytical methods. Forensic Sci. Int., 1 May 1983, 21 (3), 259–267. 1358 kB. doi:10.1016/0379-0738(83)90131-7

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

Bailey, K; Gagné, DR; Pike, RK. Investigation and identification of the bromination products of dimethoxyamphetamines. J. Assoc. Off. Anal. Chem., 1 Jan 1976, 59 (5), 1162–1169. 1916 kB.

Rasmussen, K; Glennon, RA; Aghajanian, GK. Phenethylamine hallucinogens in the locus coeruleus: potency of action correlates with rank order of 5-HT2 binding affinity. Eur. J. Pharmacol., 2 Dec 1986, 132 (1), 79–82. 267 kB. doi:10.1016/0014-2999(86)90014-2

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.

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.

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

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

Nichols, DE; Snyder, SE; Oberlender, R; Johnson, MP; Huang, X. 2,3-Dihydrobenzofuran analogues of hallucinogenic phenethylamines. J. Med. Chem., 1 Jan 1991, 34 (1), 276–281. 833 kB. doi:10.1021/jm00105a043

Nichols, DE; Barfknecht, CF; Rusterholz, DB; Benington, F; Morin, RD. Asymmetric synthesis of psychotomimetic phenylisopropylamines. J. Med. Chem., 1 Jan 1973, 16 (5), 480–483. 515 kB. doi:10.1021/jm00263a013

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

Fenderson5555. Shulgin’s syntheses of 2,5-DMA, DOB and DOEF. 5 Dec 2011. 3657 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

Glennon, RA; Rosecrans, JA; Young, R. Behavioral properties of psychoactive phenylisopropylamines in rats. Eur. J. Pharmacol., 17 Dec 1981, 76 (4), 353–360. 964 kB. doi:10.1016/0014-2999(81)90106-0

Ewald, AH; Fritschi, G; Bork, W; Maurer, HH. Designer drugs 2,5-dimethoxy-4-bromo-amphetamine (DOB) and 2,5-dimethoxy-4-bromo-methamphetamine (MDOB): studies on their metabolism and toxicological detection in rat urine using gas chromatographic/mass spectrometric techniques. J. Mass. Spectrom., 1 Apr 2006, 41 (4), 487–498. 244 kB. doi:10.1002/jms.1007

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

Glennon, RA; Seggel, MR. Interaction of phenylisopropylamines with central 5-HT2 receptors. Analysis by quantitative structure-activity relationships. In Probing Bioactive Mechanisms; ACS Symposium Series; Magee, PS; Henry, DR; Block, JH, Eds., American Chemical Society, Washington, DC, 14 Nov 1989; Vol. 413, pp 264–280. 4445 kB. doi:10.1021/bk-1989-0413.ch018

Pigott, A; Frescas, SP; McCorvy, JD; Huang, X; Roth, BL; Nichols, DE. trans-2-(2,5-Dimethoxy-4-iodophenyl)cyclopropylamine and trans-2-(2,5-dimethoxy-4-bromophenyl)cyclopropylamine as potent agonists for the 5-HT2 receptor family. Beilstein J. Org. Chem, 8 Oct 2012, 8, 1705–1709. 298 kB. doi:10.3762/bjoc.8.194

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 2584 kB. doi:10.1007/978-1-4757-0510-2_6 Rhodium.

Runyon, SP; Mosier, PD; Roth, BL; Glennon, RA; Westkaemper, RB. Potential modes of interaction of 9-aminomethyl-9,10-dihydroanthracene (AMDA) derivatives with the 5-HT2A receptor: A ligand structure-affinity relationship, receptor mutagenesis and receptor modeling investigation. J. Med. Chem., 2008, 51 (21), 6808–2828. 2229 kB. doi:10.1021/jm800771x

Maher, HM; Awad, T; DeRuiter, J; Clark, CR. GC-MS and GC-IRD studies on brominated dimethoxyamphetamines: Regioisomers related to 4-Br-2,5-DMA (DOB). Drug Test. Anal., 1 Aug 2012, 4 (7–8), 591–600. 1532 kB. doi:10.1002/dta.409

McKenna, DJ; Saavedra, JM. Autoradiography of LSD and 2,5-dimethoxyphenylisopropylamine psychotomimetics demonstrates regional, specific cross-displacement in the rat brain. Eur. J. Pharmacol., 13 Oct 1987, 142 (2), 313–315. 263 kB. doi:10.1016/0014-2999(87)90121-X

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

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

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

Fenderson5555. DOC, DOB, DOI and DOET: Strategic considerations. 7 Sep 2013. Wanted! Please contact me if you find this video.

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. Profiles of psychedelic drugs. 10. DOB. J. Psychoactive Drugs, 1 Jan 1981, 13 (1), 99. 775 kB. doi:10.1080/02791072.1981.10471457

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

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

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

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

Nelson, DL; Lucaites, VL; Wainscott, DB; Glennon, RA. Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, 5-HT2B and 5-HT2C receptors. N-S. Arch. Pharmacol., 6 Sep 1998, 359 (1), 1–6. 66 kB. doi:10.1007/PL00005315

Schultz, DM; Prescher, JA; Kidd, S; Marona-Lewicka, D; Nichols, DE; Monte, A. ‘Hybrid’ benzofuran–benzopyran congeners as rigid analogs of hallucinogenic phenethylamines. Bioorg. Med. Chem., 1 Jan 2008, 16 (11), 6242–6251. 228 kB. doi:10.1016/j.bmc.2008.04.030

Aldous, FAB; Barrass, BC; Brewster, K; Buxton, DA; Green, DM; Pinder, RM; Rich, P; Skeels, PM; Tutt, KJ. Structure-activity relationships in psychotomimetic phenylalkylamines. J. Med. Chem., 1 Oct 1974, 17 (10),1100–1111. 1188 kB. doi:10.1021/jm00256a016

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

Sargent, T; Kalbhen, DA; Shulgin, AT; Stauffer, H; Kusubov, N. A potential new brain-scanning agent: 4-77Br-2,5-dimethoxyphenylisopropylamine (4-Br-DPIA). J. Nucl. Med., 1 Jan 1975, 16 (3), 243–245. 443 kB.

Shulgin, AT; Sargent, T; Naranjo, C. 4-Bromo-2,5-dimethoxyphenylisopropylamine, a new centrally active amphetamine analog. Pharmacology, 1 Jan 1971, 5 (2), 103–107. 1030 kB. doi:10.1159/000136181

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

Coutts, RT; Malicky, JL. The synthesis of some analogs of the hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM). Can. J. Chem., 1 Jan 1973, 51 (9), 1402–1409. 746 kB. doi:10.1139/v73-210

Sargent, T; Kalbhen, DA; Shulgin, AT; Braun, G; Stauffer, H; Kusubov, N. In vivo human pharmacodynamics of the psychodysleptic 4-Br-2,5-dimethoxyphenylisopropylamine labelled with 82Br or 77Br. Neuropharmacology, 1 Jan 1975, 14 (3), 165–174. 1157 kB. doi:10.1016/0028-3908(75)90001-5

Shulgin, AT. DOB and other possible prodrugs. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 3 May 2005.

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

Urban, JD; Clarke, WP; Zastrow, M; Nichols, DE; Kobilka, B; Weinstein, H; Javitch, JA; Roth, BL; Christopoulos, A; Sexton, PM; Miller, KJ; . Functional selectivity and classical concepts of quantitative pharmacology. J. Pharmacol. Exp. Ther., 1 Jan 2007, 320 (1), 1–13. 506 kB. doi:10.1124/jpet.106.104463

Scorza, M; Carrau, C; Silveira, R; Zapata-Torres, G; Cassels, BK; Reyes-Parada, M. Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives. Biochem. Pharmacol., 15 Dec 1997, 54 (12), 1361–1369. 697 kB. doi:10.1016/S0006-2952(97)00405-X

Domelsmith, LN; Eaton, TA; Houk, KN; Anderson, GM; Glennon, RA; Shulgin, AT; Castagnoli, N; Kollman, PA. Photoelectron spectra of psychotropic drugs. 6. Relationships between physical properties and pharmacological actions of amphetamine analogues. J. Med. Chem., 1 Jan 1981, 24 (12), 1414–1421. 963 kB. doi:10.1021/jm00144a009

Anderson, GM; Braun, G; Braun, U; Nichols, DE; Shulgin, AT. Absolute configuration and psychotomimetic activity. In QuaSAR: Quantitative Structure Activity Relationships of Analgesics, Narcotic Antagonists, and Hallucinogens. NIDA Research Monograph 22; Barnett, G; Trsic, M; Willette, RE, Eds., U.S. Department of Health and Human Services, National Institute of Health, U.S. Government Printing Office, Washington, DC, 1 Jan 1978; pp 8–15. 457 kB.

White, TJ; Goodman, D; Shulgin, AT; Castagnoli, N; Lee, R; Petrakis, NL. Mutagenic activity of some centrally active aromatic amines in Salmonella typhimurium. Mutat. Res., 1 Jan 1977, 56 (2), 199–202. 256 kB. doi:10.1016/0027-5107(77)90210-X

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

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; Bondarev, ML; Khorana, N; Young, R. β-Oxygenated analogues of the 5-HT2A serotonin receptor agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane. J. Med. Chem., 1 Jan 2004, 47 (24), 6034–6041. 146 kB. doi:10.1021/jm040082s

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

Costa, JL; Wang, AY; Micke, GA; Maldaner, AO; Romano, RL; Martins-Júnior, HA; Neto, ON; Magg, MF. Chemical identification of 2,5-dimethoxy-4-bromoamphetamine (DOB). Forensic Sci. Int., 20 Dec 2007, 173 (2–3), 130–136. 285 kB. doi:10.1016/j.forsciint.2007.02.018

McGraw, NP; Callery, PS; Castagnoli, N. In vitro stereoselective metabolism of the psychotomimetic amine, 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane. An apparent enantiomeric interaction. J. Med. Chem., 1 Jan 1977, 20 (2), 185–189. 661 kB. doi:10.1021/jm00212a001

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

Dyer, DC; Nichols, DE; Rusterholz, DB; Barfknecht, CF. Comparative effects of stereoisomers of psychotomimetic phenylisopropylamines. Life Sci., 1 Oct 1973, 13 (7), 885–896. 398 kB. doi:10.1016/0024-3205(73)90079-9

124
Isomer 3

META-DOB
m-DOB
5-Bromo-2,4-dimethoxyamphetamine

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

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

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

PubChem CID: 143750; ChemSpider: 126826; Wikipedia: Meta-DOB

Shulgin Index: See #52 DOB; Table: 5 Page: 339 Row: 30

See also PiHKAL: #53 2,4-DMA #55 3,4-DMA #62 DOB    

Scorza, M; Carrau, C; Silveira, R; Zapata-Torres, G; Cassels, BK; Reyes-Parada, M. Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives. Biochem. Pharmacol., 15 Dec 1997, 54 (12), 1361–1369. 697 kB. doi:10.1016/S0006-2952(97)00405-X

Domelsmith, LN; Eaton, TA; Houk, KN; Anderson, GM; Glennon, RA; Shulgin, AT; Castagnoli, N; Kollman, PA. Photoelectron spectra of psychotropic drugs. 6. Relationships between physical properties and pharmacological actions of amphetamine analogues. J. Med. Chem., 1 Jan 1981, 24 (12), 1414–1421. 963 kB. doi:10.1021/jm00144a009

Bailey, K; Gagné, DR; Pike, RK. Investigation and identification of the bromination products of dimethoxyamphetamines. J. Assoc. Off. Anal. Chem., 1 Jan 1976, 59 (5), 1162–1169. 1916 kB.

Maher, HM; Awad, T; DeRuiter, J; Clark, CR. GC-MS and GC-IRD studies on brominated dimethoxyamphetamines: Regioisomers related to 4-Br-2,5-DMA (DOB). Drug Test. Anal., 1 Aug 2012, 4 (7–8), 591–600. 1532 kB. doi:10.1002/dta.409

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 2584 kB. doi:10.1007/978-1-4757-0510-2_6 Rhodium.

195
Isomer 4

2C-B-2-EtO
2CB-2ETO
4-Bromo-2-ethoxy-5-methoxyphenethylamine

IUPAC: 2-(4-Bromo-2-ethoxy-5-methoxyphenyl)ethan-1-amine

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

InChI=1S/C11H16BrNO2/c1-3-15-10-7-9(12)11(14-2)6-8(10)4-5-13/h6-7H,3-5,13H2,1-2H3

Shulgin Index: See #18 2C-B; Table: 5 Page: 346 Row: 21

See also PiHKAL: #20 2C-B        
198
Isomer 5

N-Me-2-Br-DMPEA
2-Bromo-4,5-dimethoxy-N-methylphenethylamine

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

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

InChI=1S/C11H16BrNO2/c1-13-5-4-8-6-10(14-2)11(15-3)7-9(8)12/h6-7,13H,4-5H2,1-3H3

PubChem CID: 60697533; ChemSpider: 27209759

See also PiHKAL: #20 2C-B        
287
Isomer 6

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

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

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

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

PubChem CID: 141685; ChemSpider: 124999

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

See also PiHKAL: #124 META-DOB        

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

Scorza, M; Carrau, C; Silveira, R; Zapata-Torres, G; Cassels, BK; Reyes-Parada, M. Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives. Biochem. Pharmacol., 15 Dec 1997, 54 (12), 1361–1369. 697 kB. doi:10.1016/S0006-2952(97)00405-X

Domelsmith, LN; Eaton, TA; Houk, KN; Anderson, GM; Glennon, RA; Shulgin, AT; Castagnoli, N; Kollman, PA. Photoelectron spectra of psychotropic drugs. 6. Relationships between physical properties and pharmacological actions of amphetamine analogues. J. Med. Chem., 1 Jan 1981, 24 (12), 1414–1421. 963 kB. doi:10.1021/jm00144a009

Bailey, K; Gagné, DR; Pike, RK. Investigation and identification of the bromination products of dimethoxyamphetamines. J. Assoc. Off. Anal. Chem., 1 Jan 1976, 59 (5), 1162–1169. 1916 kB.

Antun, F; Smythies, JR; Benington, F; Morin, RD; Barfknecht, CF; Nichols, DE. Native fluorescence and hallucinogenic potency of some amphetamines. Experientia, 15 Jan 1971, 27 (1), 62–63. 248 kB. doi:10.1007/BF02137743

Maher, HM; Awad, T; DeRuiter, J; Clark, CR. GC-MS and GC-IRD studies on brominated dimethoxyamphetamines: Regioisomers related to 4-Br-2,5-DMA (DOB). Drug Test. Anal., 1 Aug 2012, 4 (7–8), 591–600. 1532 kB. doi:10.1002/dta.409

2166
Isomer 7

5,2,3-DOB
5-Br-2,3-DMA
5-Bromo-2,3-dimethoxyamphetamine

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

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

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

PubChem CID: 69396115; ChemSpider: 26472392

Shulgin Index: See #52 DOB; Table: 5 Page: 339 Row: 4

See also PiHKAL: #124 META-DOB        
2168
Isomer 8

6,2,3-DOB
6-Br-2,3-DMA
6-Bromo-2,3-dimethoxyamphetamine

IUPAC: 1-(6-Bromo-2,3-dimethoxyphenyl)propan-2-amine

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

InChI=1S/C11H16BrNO2/c1-7(13)6-8-9(12)4-5-10(14-2)11(8)15-3/h4-5,7H,6,13H2,1-3H3

PubChem CID: 69396333

Shulgin Index: See #52 DOB; Table: 5 Page: 352 Row: 16

See also PiHKAL: #124 META-DOB        

Maher, HM; Awad, T; DeRuiter, J; Clark, CR. GC-MS and GC-IRD studies on brominated dimethoxyamphetamines: Regioisomers related to 4-Br-2,5-DMA (DOB). Drug Test. Anal., 1 Aug 2012, 4 (7–8), 591–600. 1532 kB. doi:10.1002/dta.409

Bailey, K; Gagné, DR; Pike, RK. Investigation and identification of the bromination products of dimethoxyamphetamines. J. Assoc. Off. Anal. Chem., 1 Jan 1976, 59 (5), 1162–1169. 1916 kB.

2169
Isomer 9

3,2,6-DOB
3-Br-2,6-DMA
3-Bromo-2,6-dimethoxyamphetamine

IUPAC: 1-(3-Bromo-2,6-dimethoxyphenyl)propan-2-amine

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

InChI=1S/C11H16BrNO2/c1-7(13)6-8-10(14-2)5-4-9(12)11(8)15-3/h4-5,7H,6,13H2,1-3H3

PubChem CID: 69390368

Shulgin Index: See #52 DOB; Table: 5 Page: 352 Row: 22

See also PiHKAL: #124 META-DOB        

Maher, HM; Awad, T; DeRuiter, J; Clark, CR. GC-MS and GC-IRD studies on brominated dimethoxyamphetamines: Regioisomers related to 4-Br-2,5-DMA (DOB). Drug Test. Anal., 1 Aug 2012, 4 (7–8), 591–600. 1532 kB. doi:10.1002/dta.409

Bailey, K; Gagné, DR; Pike, RK. Investigation and identification of the bromination products of dimethoxyamphetamines. J. Assoc. Off. Anal. Chem., 1 Jan 1976, 59 (5), 1162–1169. 1916 kB.

2170
Isomer 10

2,3,5-DOB
2-Br-3,5-DMA
2-Bromo-3,5-dimethoxyamphetamine

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

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

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

PubChem CID: 69396730

Shulgin Index: See #52 DOB; Table: 5 Page: 339 Row: 16

See also PiHKAL: #124 META-DOB        

Maher, HM; Awad, T; DeRuiter, J; Clark, CR. GC-MS and GC-IRD studies on brominated dimethoxyamphetamines: Regioisomers related to 4-Br-2,5-DMA (DOB). Drug Test. Anal., 1 Aug 2012, 4 (7–8), 591–600. 1532 kB. doi:10.1002/dta.409

Bailey, K; Gagné, DR; Pike, RK. Investigation and identification of the bromination products of dimethoxyamphetamines. J. Assoc. Off. Anal. Chem., 1 Jan 1976, 59 (5), 1162–1169. 1916 kB.

374
Isomer 11

4,2,6-DOB
Ψ-DOB
4-Bromo-2,6-dimethoxyamphetamine

IUPAC: 1-(4-Bromo-2,6-dimethoxyphenyl)propan-2-amine

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

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

PubChem CID: 158251; ChemSpider: 139237

Shulgin Index: See #52 DOB; Table: 5 Page: 353 Row: 15

See also PiHKAL: #162 TMA-6        

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

391
Isomer 12

2C-B-M
4-Bromo-2,5-dimethoxy-N-methylphenethylamine

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

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

InChI=1S/C11H16BrNO2/c1-13-5-4-8-6-11(15-3)9(12)7-10(8)14-2/h6-7,13H,4-5H2,1-3H3

PubChem CID: 9970546; ChemSpider: 8146138

Shulgin Index: See #18 2C-B; Table: 5 Page: 340 Row: 24

Glennon, RA; Dukat, M; El-Bermawy, M; Law, H; De Los Angeles, J; Teitler, M; King, A; Herrick-Davis, K. Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines. J. Med. Chem., 1 Jun 1994, 37 (13), 1929–1935. 1058 kB. doi:10.1021/jm00039a004

6977
Isomer 13

4,2,3-DOB

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

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

InChI=1S/C11H16BrNO2/c1-7(13)6-8-4-5-9(12)11(15-3)10(8)14-2/h4-5,7H,6,13H2,1-3H3

PubChem CID: 69730008

Shulgin Index: See #52 DOB; Table: 5 Page: 337 Row: 27

7005
Isomer 14

3,2,4-DOB

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

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

InChI=1S/C11H16BrNO2/c1-7(13)6-8-4-5-9(14-2)10(12)11(8)15-3/h4-5,7H,6,13H2,1-3H3

Shulgin Index: See #52 DOB; Table: 5 Page: 338 Row: 5

7011
Isomer 15

2,3,4-DOB

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

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

InChI=1S/C11H16BrNO2/c1-7(13)6-8-4-5-9(14-2)11(15-3)10(8)12/h4-5,7H,6,13H2,1-3H3

Shulgin Index: See #52 DOB; Table: 5 Page: 338 Row: 11

7420
Isomer 16

2C-B-5-EtO

IUPAC: 2-(4-Bromo-5-ethoxy-2-methoxyphenyl)ethan-1-amine

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

InChI=1S/C11H16BrNO2/c1-3-15-11-6-8(4-5-13)10(14-2)7-9(11)12/h6-7H,3-5,13H2,1-2H3

Shulgin Index: See #18 2C-B; Table: 5 Page: 346 Row: 20

7574
Isomer 17

3,4,5-DOB

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

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

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

PubChem CID: 60907710; ChemSpider: 26495735

Shulgin Index: See #52 DOB; Table: 5 Page: 349 Row: 24

7730
Isomer 18

2,3,6-DOB

IUPAC: 1-(2-Bromo-3,6-dimethoxyphenyl)propan-2-amine

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

InChI=1S/C11H16BrNO2/c1-7(13)6-8-9(14-2)4-5-10(15-3)11(8)12/h4-5,7H,6,13H2,1-3H3

Shulgin Index: See #52 DOB; Table: 5 Page: 352 Row: 30

7772
Isomer 19

2,4,6-DOB

IUPAC: 1-(2-Bromo-4,6-dimethoxyphenyl)propan-2-amine

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

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

Shulgin Index: See #52 DOB; Table: 5 Page: 353 Row: 22

Show all 25 analogues and isomers Show only the one α analogues Show only the five R3 analogues
Page updated 21 October 2014 · This work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License ·