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INBMeO; Cimbi-5-2
5380
Variant: N α R4 skeleton isomers all
Analogues: 28 1 17 1 4 51

IUPAC: 2-(4-Iodo-2,5-dimethoxyphenyl)-N-(2-methoxybenzyl)ethan-1-amine

Formula: C18H22INO3 Molecular weight: 427.27665 g/mol InChI Key: ZFUOLNAKPBFDIJ-UHFFFAOYSA-N

InChI=1S/C18H22INO3/c1-21-16-7-5-4-6-14(16)12-20-9-8-13-10-18(23-3)15(19)11-17(13)22-2/h4-7,10-11,20H,8-9,12H2,1-3H3

PubChem CID: 10251906; ChemSpider: 8427392; Drugs Forum: 25I-NBOMe; Erowid: 25I-NBOMe (2C-I-NBOMe); Wikipedia: 25I-NBOMe

Shulgin Index: See #58 DOI; Table: 5 Page: 341 Row: 9

Heim, R. Synthesis and pharmacology of potent 5-HT2A receptor agonists with N-2-methoxybenzyl partial structure. SC. D. Thesis, Freie Universität, Berlin, 1 Jan 2004. In German.

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.

Hansen, M. Design and synthesis of selective serotonin receptor agonists for positron emission tomography imaging of the brain. Ph. D. Thesis, University of Copenhagen, 16 Dec 2012. 7921 kB.

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

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

Casale, JF; Hays, PA. Characterization of eleven 2,5-dimethoxy-N-(2-methoxybenzyl)phenethylamine (NBOMe) derivatives and differentiation from their 3- and 4-methoxybenzyl analogues—Part I. Microgram J., 1 Jan 2012, 9 (2), 84–109. 4601 kB.

Anon. Report on the risk assessment of 2-(4-iodo-2,5-dimethoxyphenyl)-N-(2-methoxybenzyl)ethanamine (25I-NBOMe), European Monitoring Centre for Drugs and Drug Addiction, Apr 2014.

Heim, R; Pertz, HH; Elz, MZS. Stereoselective synthesis, absolute configuration and 5-HT2A-receptor agonism of chiral 2-methoxybenzylamines. Arch. Pharm. Pharm. Med. Chem., Oct 2002, 335 (Suppl. 1), 82. 573 kB. Poster abstract

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, 1 Apr 2011, 38 (4), 681–693. 752 kB. doi:10.1007/s00259-010-1686-8

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; Frescas, SP; Chemel, BR; Rehder, KS; Zhong, D; Lewin, AH. High specific activity tritium-labeled N-(2-methoxybenzyl)-2,5-dimethoxy-4-iodophenethylamine (INBMeO): A high-affinity 5-HT2A receptor-selective agonist radioligand. Bioorg. Med. Chem., 1 Jan 2008, 16 (10), 6116–6123. 251 kB. doi:10.1016/j.bmc.2008.04.050

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

Ettrup, A; Palner, M; Gillings, N; Santini, MA; Hansen, M; Kornum, BR; Rasmussen, LK; Nagren, K; Madsen, J; Begtrup, M; Knudsen, GM. Radiosynthesis and evaluation of 11C-CIMBI-5 as a 5-HT2A receptor agonist radioligand for PET. J. Nucl. Med., 1 Nov 2010, 51 (11), 1763–1770. 548 kB. doi:10.2967/jnumed.109.074021

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

Heim, R; Elz, S. Novel extremely potent partial 5-HT2A-receptor agonists: Successful application of a new structure-activity concept. Arch. Pharm. Pharm. Med. Chem., Mar 2000, 333 (Suppl. 1), 18. 566 kB. Poster abstract

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

28 N analogues:
33
Analogue 1: Removing 2-Methoxybenzyl at N

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

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

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 Transcripts: 1.179, 3.335

See also Pharmacology notes I: p. 179, 2C-I: Trials

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.

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

Anon. Report on the risk assessment of 2C-I, 2C-T-2 and 2C-T-7, European Monitoring Centre for Drugs and Drug Addiction, May 2004.

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

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

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

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

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

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.

Meyer, MR; Robert, A; Maurer, HH. Toxicokinetics of novel psychoactive substances: Characterization of N-acetyltransferase (NAT) isoenzymes involved in the phase II metabolism of 2C designer drugs. Toxicol. Lett., 5 Jun 2014, 227 (2), 124–128. 693 kB. doi:10.1016/j.toxlet.2014.03.010

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

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

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

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

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, 1 Apr 2011, 38 (4), 681–693. 752 kB. doi:10.1007/s00259-010-1686-8

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 halogenated 2Cs. countyourculture: rational exploration of the underground, 29 Sep 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

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

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

5379
Analogue 2: Substituting 2-Hydroxybenzyl for 2-Methoxybenzyl at N

25I-NBOH
NBOH-2CI
Cimbi-27
N-(2-Hydroxybenzyl)-4-iodo-2,5-dimethoxyphenethylamine

IUPAC: 2-({[2-(4-Iodo-2,5-dimethoxyphenyl)ethyl]amino}methyl)phenol

Formula: C17H20INO3 Molecular weight: 413.25007 g/mol InChI Key: FEUZHYRXGQTBRO-UHFFFAOYSA-N

InChI=1S/C17H20INO3/c1-21-16-10-14(18)17(22-2)9-12(16)7-8-19-11-13-5-3-4-6-15(13)20/h3-6,9-10,19-20H,7-8,11H2,1-2H3

PubChem CID: 10001761; ChemSpider: 8177342; Wikipedia: 25I-NBOH

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

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, 1 Apr 2011, 38 (4), 681–693. 752 kB. doi:10.1007/s00259-010-1686-8

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

Heim, R; Elz, S. Novel extremely potent partial 5-HT2A-receptor agonists: Successful application of a new structure-activity concept. Arch. Pharm. Pharm. Med. Chem., Mar 2000, 333 (Suppl. 1), 18. 566 kB. Poster abstract

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

Hansen, M. Design and synthesis of selective serotonin receptor agonists for positron emission tomography imaging of the brain. Ph. D. Thesis, University of Copenhagen, 16 Dec 2012. 7921 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.

Heim, R. Synthesis and pharmacology of potent 5-HT2A receptor agonists with N-2-methoxybenzyl partial structure. SC. D. Thesis, Freie Universität, Berlin, 1 Jan 2004. In German.

5394
Analogue 3: Substituting Naphthalen-2-ylmethyl for 2-Methoxybenzyl at N

25I-NNap
4-Iodo-2,5-dimethoxy-N-(naphthalen-2-ylmethyl)phenethylamine

IUPAC: 2-(4-Iodo-2,5-dimethoxyphenyl)-N-(naphthalen-2-ylmethyl)ethan-1-amine

Formula: C21H22INO2 Molecular weight: 447.30935 g/mol InChI Key: DWYOCCKOUPKDMW-UHFFFAOYSA-N

InChI=1S/C21H22INO2/c1-24-20-13-19(22)21(25-2)12-18(20)9-10-23-14-15-7-8-16-5-3-4-6-17(16)11-15/h3-8,11-13,23H,9-10,14H2,1-2H3

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.

5395
Analogue 4: Substituting 1,3-Benzodioxol-4-ylmethyl for 2-Methoxybenzyl at N

INBMDO
25I-NBMD
NBMD-2CI
Cimbi-29
4-Iodo-2,5-dimethoxy-N-(2,3-methylenedioxybenzyl)phenethylamine

IUPAC: N-(1,3-Benzodioxol-4-ylmethyl)-2-(4-iodo-2,5-dimethoxyphenyl)ethan-1-amine

Formula: C18H20INO4 Molecular weight: 441.26017 g/mol InChI Key: NJNMIPDEUMTYNV-UHFFFAOYSA-N

InChI=1S/C18H20INO4/c1-21-16-9-14(19)17(22-2)8-12(16)6-7-20-10-13-4-3-5-15-18(13)24-11-23-15/h3-5,8-9,20H,6-7,10-11H2,1-2H3

PubChem CID: 57507899; ChemSpider: 26234932; Wikipedia: 25I-NBOMe

Shulgin Index: See #58 DOI; Table: 5 Page: 341 Row: 10

Sekuła, K; Zuba, D. Structural elucidation and identification of a new derivative of phenethylamine using quadrupole time-of-flight mass spectrometry. Rapid Commun. Mass Spectrom., 30 Sep 2013, 27 (18), 2081–2090. 2664 kB. doi:10.1002/rcm.6667

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, 1 Apr 2011, 38 (4), 681–693. 752 kB. doi:10.1007/s00259-010-1686-8

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.

Hansen, M. Design and synthesis of selective serotonin receptor agonists for positron emission tomography imaging of the brain. Ph. D. Thesis, University of Copenhagen, 16 Dec 2012. 7921 kB.

5506
Analogue 5: Substituting Furan-2-ylmethyl for 2-Methoxybenzyl at N

25I-NMeFur
N-(Furan-2-ylmethyl)-4-iodo-2,5-dimethoxyphenethylamine

IUPAC: N-(Furan-2-ylmethyl)-2-(4-iodo-2,5-dimethoxyphenyl)ethan-1-amine

Formula: C15H18INO3 Molecular weight: 387.21279 g/mol InChI Key: OCPXRKAITFONEF-UHFFFAOYSA-N

InChI=1S/C15H18INO3/c1-18-14-9-13(16)15(19-2)8-11(14)5-6-17-10-12-4-3-7-20-12/h3-4,7-9,17H,5-6,10H2,1-2H3

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

5507
Analogue 6: Substituting Thiophen-2-ylmethyl for 2-Methoxybenzyl at N

25I-NMeThiop
4-Iodo-2,5-dimethoxy-N-(thiophen-2-ylmethyl)phenethylamine

IUPAC: 2-(4-Iodo-2,5-dimethoxyphenyl)-N-(thiophen-2-ylmethyl)ethan-1-amine

Formula: C15H18INO2S Molecular weight: 403.27839 g/mol InChI Key: CPEQZELPZDGYNS-UHFFFAOYSA-N

InChI=1S/C15H18INO2S/c1-18-14-9-13(16)15(19-2)8-11(14)5-6-17-10-12-4-3-7-20-12/h3-4,7-9,17H,5-6,10H2,1-2H3

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

5508
Analogue 7: Substituting Pyridin-2-ylmethyl for 2-Methoxybenzyl at N

25I-NMePyr
4-Iodo-2,5-dimethoxy-N-(pyridin-2-ylmethyl)phenethylamine

IUPAC: 2-(4-Iodo-2,5-dimethoxyphenyl)-N-(pyridin-2-ylmethyl)ethan-1-amine

Formula: C16H19IN2O2 Molecular weight: 398.23873 g/mol InChI Key: WIGLUKMOENSTNX-UHFFFAOYSA-N

InChI=1S/C16H19IN2O2/c1-20-15-10-14(17)16(21-2)9-12(15)6-8-18-11-13-5-3-4-7-19-13/h3-5,7,9-10,18H,6,8,11H2,1-2H3

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

5509
Analogue 8: Substituting 2-Cyanobenzyl for 2-Methoxybenzyl at N

25I-NBCN
NBCN-2CI
N-(2-Cyanobenzyl)-4-iodo-2,5-dimethoxyphenethylamine

IUPAC: 2-({[2-(4-Iodo-2,5-dimethoxyphenyl)ethyl]amino}methyl)benzonitrile

Formula: C18H19IN2O2 Molecular weight: 422.26013 g/mol InChI Key: YYAXBDUAERMJJF-UHFFFAOYSA-N

InChI=1S/C18H19IN2O2/c1-22-17-10-16(19)18(23-2)9-13(17)7-8-21-12-15-6-4-3-5-14(15)11-20/h3-6,9-10,21H,7-8,12H2,1-2H3

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

5510
Analogue 9: Substituting 2-Carbamoylbenzyl for 2-Methoxybenzyl at N

25I-NBAm
NBAm-2CI
N-(2-Carbamoylbenzyl)-4-iodo-2,5-dimethoxyphenethylamine

IUPAC: 2-({[2-(4-Iodo-2,5-dimethoxyphenyl)ethyl]amino}methyl)benzamide

Formula: C18H21IN2O3 Molecular weight: 440.27541 g/mol InChI Key: DIZGFCCOWJQNDI-UHFFFAOYSA-N

InChI=1S/C18H21IN2O3/c1-23-16-10-15(19)17(24-2)9-12(16)7-8-21-11-13-5-3-4-6-14(13)18(20)22/h3-6,9-10,21H,7-8,11H2,1-2H3,(H2,20,22)

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

5511
Analogue 10: Substituting Indole-3-ylmethyl for 2-Methoxybenzyl at N

25I-NMeInd
N-(Indole-3-ylmethyl)-4-iodo-2,5-dimethoxyphenethylamine

IUPAC: N-(1H-Indol-3-ylmethyl)-2-(4-iodo-2,5-dimethoxyphenyl)ethan-1-amine

Formula: C19H21IN2O2 Molecular weight: 436.28671 g/mol InChI Key: CYNBAHOIZVVZMZ-UHFFFAOYSA-N

InChI=1S/C19H21IN2O2/c1-23-18-10-16(20)19(24-2)9-13(18)7-8-21-11-14-12-22-17-6-4-3-5-15(14)17/h3-6,9-10,12,21-22H,7-8,11H2,1-2H3

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

5512
Analogue 11: Substituting Naphthalen-1-ylmethyl for 2-Methoxybenzyl at N

25I-NNap2
4-Iodo-2,5-dimethoxy-N-(naphthalen-1-ylmethyl)phenethylamine

IUPAC: 2-(4-Iodo-2,5-dimethoxyphenyl)-N-(naphthalen-1-ylmethyl)ethan-1-amine

Formula: C21H22INO2 Molecular weight: 447.30935 g/mol InChI Key: IDERIEMRYLYMCD-UHFFFAOYSA-N

InChI=1S/C21H22INO2/c1-24-20-13-19(22)21(25-2)12-16(20)10-11-23-14-17-8-5-7-15-6-3-4-9-18(15)17/h3-9,12-13,23H,10-11,14H2,1-2H3

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

5513
Analogue 12: Substituting 2-(Hydroxymethyl)benzyl for 2-Methoxybenzyl at N

25I-NBMeOH
NBMeOH-2CI
N-[2-(Hydroxymethyl)benzyl]-4-iodo-2,5-dimethoxyphenethylamine

IUPAC: [2-({[2-(4-Iodo-2,5-dimethoxyphenyl)ethyl]amino}methyl)phenyl]methanol

Formula: C18H22INO3 Molecular weight: 427.27665 g/mol InChI Key: QSYQUZWORHKKKT-UHFFFAOYSA-N

InChI=1S/C18H22INO3/c1-22-17-10-16(19)18(23-2)9-13(17)7-8-20-11-14-5-3-4-6-15(14)12-21/h3-6,9-10,20-21H,7-8,11-12H2,1-2H3

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

5514
Analogue 13: Substituting Tetrahydrofuran-2-ylmethyl for 2-Methoxybenzyl at N

25I-NDHF
4-Iodo-2,5-dimethoxy-N-(tetrahydrofuran-2-ylmethyl)phenethylamine

IUPAC: 2-(4-Iodo-2,5-dimethoxyphenyl)-N-(tetrahydrofuran-2-ylmethyl)ethan-1-amine

Formula: C15H22INO3 Molecular weight: 391.24455 g/mol InChI Key: HRAFKXQRIJLRRU-UHFFFAOYSA-N

InChI=1S/C15H22INO3/c1-18-14-9-13(16)15(19-2)8-11(14)5-6-17-10-12-4-3-7-20-12/h8-9,12,17H,3-7,10H2,1-2H3

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

5515
Analogue 14: Substituting (3-Hydroxynaphthalen-2-yl)methyl for 2-Methoxybenzyl at N

25I-N2Nap3OH
N-(3-Hydroxynaphthalen-2-yl)-4-iodo-2,5-dimethoxyphenethylamine

IUPAC: 3-({[2-(4-Iodo-2,5-dimethoxyphenyl)ethyl]amino}methyl)naphthalen-2-ol

Formula: C21H22INO3 Molecular weight: 463.30875 g/mol InChI Key: AAIFMVPJPBCDCA-UHFFFAOYSA-N

InChI=1S/C21H22INO3/c1-25-20-12-18(22)21(26-2)11-16(20)7-8-23-13-17-9-14-5-3-4-6-15(14)10-19(17)24/h3-6,9-12,23-24H,7-8,13H2,1-2H3

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

5516
Analogue 15: Substituting (2-Hydroxynaphthalen-1-yl)methyl for 2-Methoxybenzyl at N

25I-N1Nap2OH
N-[(2-Hydroxynaphthalen-1-yl)methyl]-4-iodo-2,5-dimethoxyphenethylamine

IUPAC: 1-({[2-(4-Iodo-2,5-dimethoxyphenyl)ethyl]amino}methyl)naphthalen-2-ol

Formula: C21H22INO3 Molecular weight: 463.30875 g/mol InChI Key: CTGIMYIUEBZAGO-UHFFFAOYSA-N

InChI=1S/C21H22INO3/c1-25-20-12-18(22)21(26-2)11-15(20)9-10-23-13-17-16-6-4-3-5-14(16)7-8-19(17)24/h3-8,11-12,23-24H,9-10,13H2,1-2H3

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

5517
Analogue 16: Substituting (6-Hydroxy-1,3-benzodioxol-5-yl)methyl for 2-Methoxybenzyl at N

25I-NBOH45MD
NBOH45MD-2CI
N-(2-Hydroxy-4,5-methylenedioxybenzyl)-4-iodo-2,5-dimethoxyphenethylamine

IUPAC: 6-({[2-(4-Iodo-2,5-dimethoxyphenyl)ethyl]amino}methyl)-1,3-benzodioxol-5-ol

Formula: C18H20INO5 Molecular weight: 457.25957 g/mol InChI Key: BMXWVANOLDETPA-UHFFFAOYSA-N

InChI=1S/C18H20INO5/c1-22-15-7-13(19)16(23-2)5-11(15)3-4-20-9-12-6-17-18(8-14(12)21)25-10-24-17/h5-8,20-21H,3-4,9-10H2,1-2H3

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

5518
Analogue 17: Substituting (1-Hydroxynaphthalen-2-yl)methyl for 2-Methoxybenzyl at N

25I-N2Nap1OH
N-[(1-Hydroxynaphthalen-2-yl)methyl]-4-iodo-2,5-dimethoxyphenethylamine

IUPAC: 2-({[2-(4-Iodo-2,5-dimethoxyphenyl)ethyl]amino}methyl)naphthalen-1-ol

Formula: C21H22INO3 Molecular weight: 463.30875 g/mol InChI Key: FORLZYQTLAPSHJ-UHFFFAOYSA-N

InChI=1S/C21H22INO3/c1-25-19-12-18(22)20(26-2)11-15(19)9-10-23-13-16-8-7-14-5-3-4-6-17(14)21(16)24/h3-8,11-12,23-24H,9-10,13H2,1-2H3

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

5519
Analogue 18: Substituting 1,3-Benzodioxol-5-ylmethyl for 2-Methoxybenzyl at N

25I-NB34MD
NB34MD-2CI
4-Iodo-2,5-dimethoxy-N-(3,4-methylenedioxybenzyl)phenethylamine

IUPAC: N-(1,3-Benzodioxol-5-ylmethyl)-2-(4-iodo-2,5-dimethoxyphenyl)ethan-1-amine

Formula: C18H20INO4 Molecular weight: 441.26017 g/mol InChI Key: FWEBGKDUEZRMRQ-UHFFFAOYSA-N

InChI=1S/C18H20INO4/c1-21-16-9-14(19)17(22-2)8-13(16)5-6-20-10-12-3-4-15-18(7-12)24-11-23-15/h3-4,7-9,20H,5-6,10-11H2,1-2H3

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

5520
Analogue 19: Substituting 4-(Trifluoromethyl)benzyl for 2-Methoxybenzyl at N

25I-NBpTFM
NBpTFM-2CI
4-Iodo-2,5-dimethoxy-N-[4-(trifluoromethyl)benzyl]phenethylamine

IUPAC: 2-(4-Iodo-2,5-dimethoxyphenyl)-N-[4-(trifluoromethyl)benzyl]ethan-1-amine

Formula: C18H19F3INO2 Molecular weight: 465.2486396 g/mol InChI Key: AXTXOUFNMWSTLA-UHFFFAOYSA-N

InChI=1S/C18H19F3INO2/c1-24-16-10-15(22)17(25-2)9-13(16)7-8-23-11-12-3-5-14(6-4-12)18(19,20)21/h3-6,9-10,23H,7-8,11H2,1-2H3

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

5521
Analogue 20: Substituting 2-(Trifluoromethyl)benzyl for 2-Methoxybenzyl at N

25I-NBTFM
NBTFM-2CI
4-Iodo-2,5-dimethoxy-N-[2-(trifluoromethyl)benzyl]phenethylamine

IUPAC: 2-(4-Iodo-2,5-dimethoxyphenyl)-N-[2-(trifluoromethyl)benzyl]ethan-1-amine

Formula: C18H19F3INO2 Molecular weight: 465.2486396 g/mol InChI Key: QYBRDPIAMKDZDA-UHFFFAOYSA-N

InChI=1S/C18H19F3INO2/c1-24-16-10-15(22)17(25-2)9-12(16)7-8-23-11-13-5-3-4-6-14(13)18(19,20)21/h3-6,9-10,23H,7-8,11H2,1-2H3

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

5398
Analogue 21: Substituting 2-Fluorobenzyl for 2-Methoxybenzyl at N

25I-NBF
NBF-2CI
Cimbi-21
N-(2-Fluorobenzyl)-4-iodo-2,5-dimethoxyphenethylamine

IUPAC: N-(2-Fluorobenzyl)-2-(4-iodo-2,5-dimethoxyphenyl)ethan-1-amine

Formula: C17H19FINO2 Molecular weight: 415.2411332 g/mol InChI Key: LPBKNBHMWRBPHT-UHFFFAOYSA-N

InChI=1S/C17H19FINO2/c1-21-16-10-15(19)17(22-2)9-12(16)7-8-20-11-13-5-3-4-6-14(13)18/h3-6,9-10,20H,7-8,11H2,1-2H3

PubChem CID: 57469209; ChemSpider: 24751866; Wikipedia: 25I-NBF

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, 1 Apr 2011, 38 (4), 681–693. 752 kB. doi:10.1007/s00259-010-1686-8

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

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.

Hansen, M. Design and synthesis of selective serotonin receptor agonists for positron emission tomography imaging of the brain. Ph. D. Thesis, University of Copenhagen, 16 Dec 2012. 7921 kB.

5503
Analogue 22: Substituting 4-Fluorobenzyl for 2-Methoxybenzyl at N

25I-NBpF
NBpF-2CI

IUPAC: N-(4-Fluorobenzyl)-2-(4-iodo-2,5-dimethoxyphenyl)ethan-1-amine

Formula: C17H19FINO2 Molecular weight: 415.2411332 g/mol InChI Key: CMWOEGZDLUCCAW-UHFFFAOYSA-N

InChI=1S/C17H19FINO2/c1-21-16-10-15(19)17(22-2)9-13(16)7-8-20-11-12-3-5-14(18)6-4-12/h3-6,9-10,20H,7-8,11H2,1-2H3

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

5527
Analogue 23: Substituting Benzyl for 2-Methoxybenzyl at N

25I-NB
NB-2CI
N-Benzyl-4-iodo-2,5-dimethoxyphenethylamine

IUPAC: N-Benzyl-2-(4-iodo-2,5-dimethoxyphenyl)ethan-1-amine

Formula: C17H20INO2 Molecular weight: 397.25067 g/mol InChI Key: BRJJBCNYRXTWCY-UHFFFAOYSA-N

InChI=1S/C17H20INO2/c1-20-16-11-15(18)17(21-2)10-14(16)8-9-19-12-13-6-4-3-5-7-13/h3-7,10-11,19H,8-9,12H2,1-2H3

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

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.

2427
Analogue 24: Substituting 4-Methoxythiophen-3-ylmethyl for 2-Methoxybenzyl at N

N4MT3M-2C-I

IUPAC: 2-(4-Iodo-2,5-dimethoxyphenyl)-N-[(4-methoxythiophen-3-yl)methyl]ethan-1-amine

Formula: C16H20INO3S Molecular weight: 433.30437 g/mol InChI Key: UTMRVIAXDLNLDV-UHFFFAOYSA-N

InChI=1S/C16H20INO3S/c1-19-14-7-13(17)15(20-2)6-11(14)4-5-18-8-12-9-22-10-16(12)21-3/h6-7,9-10,18H,4-5,8H2,1-3H3

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

2426
Analogue 25: Substituting 3-Methoxythiophen-2-ylmethyl for 2-Methoxybenzyl at N

N3MT2M-2C-I

IUPAC: 2-(4-Iodo-2,5-dimethoxyphenyl)-N-[(3-methoxythiophen-2-yl)methyl]ethan-1-amine

Formula: C16H20INO3S Molecular weight: 433.30437 g/mol InChI Key: FVBHQWLJFNAWEM-UHFFFAOYSA-N

InChI=1S/C16H20INO3S/c1-19-13-5-7-22-16(13)10-18-6-4-11-8-15(21-3)12(17)9-14(11)20-2/h5,7-9,18H,4,6,10H2,1-3H3

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

587
Analogue 26: Substituting 2-Methoxyphenylethan-2-yl for 2-Methoxybenzyl at N

25I-NEPOMe

IUPAC: N-[2-(4-Iodo-2,5-dimethoxyphenyl)ethyl]-1-(2-methoxyphenyl)ethan-1-amine

Formula: C19H24INO3 Molecular weight: 441.30323 g/mol InChI Key: JGJOHZYRCCGXRR-UHFFFAOYSA-N

InChI=1S/C19H24INO3/c1-13(15-7-5-6-8-17(15)22-2)21-10-9-14-11-19(24-4)16(20)12-18(14)23-3/h5-8,11-13,21H,9-10H2,1-4H3

ChemSpider: 26599712

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

Heim, R; Pertz, HH; Elz, MZS. Stereoselective synthesis, absolute configuration and 5-HT2A-receptor agonism of chiral 2-methoxybenzylamines. Arch. Pharm. Pharm. Med. Chem., Oct 2002, 335 (Suppl. 1), 82. 573 kB. Poster abstract

2585
Analogue 27: Substituting 3-Methoxybenzyl for 2-Methoxybenzyl at N

25I-NB3OMe

IUPAC: 2-(4-Iodo-2,5-dimethoxyphenyl)-N-(3-methoxybenzyl)ethan-1-amine

Formula: C18H22INO3 Molecular weight: 427.27665 g/mol InChI Key: CJTZKPLDKCBUAF-UHFFFAOYSA-N

InChI=1S/C18H22INO3/c1-21-15-6-4-5-13(9-15)12-20-8-7-14-10-18(23-3)16(19)11-17(14)22-2/h4-6,9-11,20H,7-8,12H2,1-3H3

Casale, JF; Hays, PA. Characterization of eleven 2,5-dimethoxy-N-(2-methoxybenzyl)phenethylamine (NBOMe) derivatives and differentiation from their 3- and 4-methoxybenzyl analogues—Part I. Microgram J., 1 Jan 2012, 9 (2), 84–109. 4601 kB.

2586
Analogue 28: Substituting 4-Methoxybenzyl for 2-Methoxybenzyl at N

25I-NB4OMe

IUPAC: 2-(4-Iodo-2,5-dimethoxyphenyl)-N-(4-methoxybenzyl)ethan-1-amine

Formula: C18H22INO3 Molecular weight: 427.27665 g/mol InChI Key: NWOROGLTELSWAZ-UHFFFAOYSA-N

InChI=1S/C18H22INO3/c1-21-15-6-4-13(5-7-15)12-20-9-8-14-10-18(23-3)16(19)11-17(14)22-2/h4-7,10-11,20H,8-9,12H2,1-3H3

Casale, JF; Hays, PA. Characterization of eleven 2,5-dimethoxy-N-(2-methoxybenzyl)phenethylamine (NBOMe) derivatives and differentiation from their 3- and 4-methoxybenzyl analogues—Part I. Microgram J., 1 Jan 2012, 9 (2), 84–109. 4601 kB.

One α analogue:
5387
Analogue 1: Adding Methyl at α

DOI-NBOMe
NBOMe-DOI
N-(2-Methoxybenzyl)-2,5-dimethoxyamphetamine
2,5-Dimethoxy-N-(2-methoxybenzyl)amphetamine

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

Formula: C19H24INO3 Molecular weight: 441.30323 g/mol InChI Key: XRQNUXKKHOVYIR-UHFFFAOYSA-N

InChI=1S/C19H24INO3/c1-13(21-12-14-7-5-6-8-17(14)22-2)9-15-10-19(24-4)16(20)11-18(15)23-3/h5-8,10-11,13,21H,9,12H2,1-4H3

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.

Heim, R. Synthesis and pharmacology of potent 5-HT2A receptor agonists with N-2-methoxybenzyl partial structure. SC. D. Thesis, Freie Universität, Berlin, 1 Jan 2004. In German.

17 R4 analogues:
5386
Analogue 1: Removing Iodo at R4

DMPEA-NBOMe
25H-NBOMe
NBOMe-2CH
N-(2-Methoxybenzyl)-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-N-(2-methoxybenzyl)phenethylamine

IUPAC: 2-(2,5-Dimethoxyphenyl)-N-(2-methoxybenzyl)ethan-1-amine

Formula: C18H23NO3 Molecular weight: 301.38012 g/mol InChI Key: RMLXCDMTGWSEOU-UHFFFAOYSA-N

InChI=1S/C18H23NO3/c1-20-16-8-9-18(22-3)14(12-16)10-11-19-13-15-6-4-5-7-17(15)21-2/h4-9,12,19H,10-11,13H2,1-3H3

PubChem CID: 39424372; ChemSpider: 25511924

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

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

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

Casale, JF; Hays, PA. Characterization of eleven 2,5-dimethoxy-N-(2-methoxybenzyl)phenethylamine (NBOMe) derivatives and differentiation from their 3- and 4-methoxybenzyl analogues—Part I. Microgram J., 1 Jan 2012, 9 (2), 84–109. 4601 kB.

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

5526
Analogue 2: Substituting Bromo for Iodo at R4

25B-NBOMe
NBOMe-2CB
Cimbi-36
4-Bromo-2,5-dimethoxy-N-(2-methoxybenzyl)phenethylamine
N-(2-Methoxybenzyl)-4-bromo-2,5-dimethoxyphenethylamine

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

Formula: C18H22BrNO3 Molecular weight: 380.27618 g/mol InChI Key: SUXGNJVVBGJEFB-UHFFFAOYSA-N

InChI=1S/C18H22BrNO3/c1-21-16-7-5-4-6-14(16)12-20-9-8-13-10-18(23-3)15(19)11-17(13)22-2/h4-7,10-11,20H,8-9,12H2,1-3H3

PubChem CID: 9977044; ChemSpider: 8152636; Drugs Forum: 25B-NBOMe; Wikipedia: 25B-NBOMe

Heim, R. Synthesis and pharmacology of potent 5-HT2A receptor agonists with N-2-methoxybenzyl partial structure. SC. D. Thesis, Freie Universität, Berlin, 1 Jan 2004. In German.

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.

Hansen, M. Design and synthesis of selective serotonin receptor agonists for positron emission tomography imaging of the brain. Ph. D. Thesis, University of Copenhagen, 16 Dec 2012. 7921 kB.

Casale, JF; Hays, PA. Characterization of eleven 2,5-dimethoxy-N-(2-methoxybenzyl)phenethylamine (NBOMe) derivatives and differentiation from their 3- and 4-methoxybenzyl analogues—Part I. Microgram J., 1 Jan 2012, 9 (2), 84–109. 4601 kB.

Heim, R; Pertz, HH; Elz, MZS. Stereoselective synthesis, absolute configuration and 5-HT2A-receptor agonism of chiral 2-methoxybenzylamines. Arch. Pharm. Pharm. Med. Chem., Oct 2002, 335 (Suppl. 1), 82. 573 kB. Poster abstract

Heim, R; Pertz, HH; Elz, S. Partial 5-HT2A-receptor agonists of the phenylethanamine series: Effect of a trifluoromethyl substituent. Arch. Pharm. Pharm. Med. Chem., 3 May 2000, 333 (Suppl. 2), 45. 542 kB. Poster abstract

Heim, R; Elz, S. Novel extremely potent partial 5-HT2A-receptor agonists: Successful application of a new structure-activity concept. Arch. Pharm. Pharm. Med. Chem., Mar 2000, 333 (Suppl. 1), 18. 566 kB. Poster abstract

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

Uchiyama, N; Shimokawa, Y; Matsuda, S; Kawamura, M; Kikura-Hanajiri, R; Goda, Y. Two new synthetic cannabinoids, AM-2201 benzimidazole analog (FUBIMINA) and (4-methylpiperazin-1-yl)(1-pentyl-1H-indol-3-yl)methanone (MEPIRAPIM), and three phenethylamine derivatives, 25H-NBOMe 3,4,5-trimethoxybenzyl analog, 25B-NBOMe, and 2C-N-NBOMe, identified in illegal products. Forensic Toxicol., 827 kB. doi:10.1007/s11419-013-0217-2

Ettrup, A; Holm, S; Hansen, M; Wasim, M; Santini, MA; Palner, M; Madsen, J; Svarer, C; Kristensen, JL; Knudsen, GM. Preclinical safety assessment of the 5-HT2A receptor agonist PET radioligand [11C]Cimbi-36. Mol. Imaging Biol., 1 Aug 2013, 15 (4), 376–383. 374 kB. doi:10.1007/s11307-012-0609-4

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

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, 1 Apr 2011, 38 (4), 681–693. 752 kB. doi:10.1007/s00259-010-1686-8

Poklis, JL; Nanco, CR; Troendle, MM; Wolf, CE; Poklis, A. Determination of 4-bromo-2,5-dimethoxy-N-[(2-methoxyphenyl)methyl]-benzeneethanamine (25B-NBOMe) in serum and urine by high performance liquid chromatography with tandem mass spectrometry in a case of severe intoxication. Drug Test. Anal., 2 Sep 2013. 292 kB. doi:10.1002/dta.1522

342
Analogue 3: Substituting Methyl for Iodo at R4

25D-NBOMe
NBOMe-2CD
N-(2-Methoxybenzyl)-2,5-dimethoxy-4-methylphenethylamine
2,5-Dimethoxy-N-(2-methoxybenzyl)-4-methylphenethylamine

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

Formula: C19H25NO3 Molecular weight: 315.4067 g/mol InChI Key: UTVHBNXCFSATDB-UHFFFAOYSA-N

InChI=1S/C19H25NO3/c1-14-11-19(23-4)15(12-18(14)22-3)9-10-20-13-16-7-5-6-8-17(16)21-2/h5-8,11-12,20H,9-10,13H2,1-4H3

Drugs Forum: 25D-NBOMe

Casale, JF; Hays, PA. Characterization of eleven 2,5-dimethoxy-N-(2-methoxybenzyl)phenethylamine (NBOMe) derivatives and differentiation from their 3- and 4-methoxybenzyl analogues—Part I. Microgram J., 1 Jan 2012, 9 (2), 84–109. 4601 kB.

Hansen, M. Design and synthesis of selective serotonin receptor agonists for positron emission tomography imaging of the brain. Ph. D. Thesis, University of Copenhagen, 16 Dec 2012. 7921 kB.

343
Analogue 4: Substituting Chloro for Iodo at R4

25C-NBOMe
NBOMe-2CC
Cimbi-82
N-(2-Methoxybenzyl)-4-chloro-2,5-dimethoxyphenethylamine
4-Chloro-2,5-dimethoxy-N-(2-methoxybenzyl)phenethylamine

IUPAC: 2-(4-Chloro-2,5-dimethoxyphenyl)-N-(2-methoxybenzyl)ethan-1-amine

Formula: C18H22ClNO3 Molecular weight: 335.82518 g/mol InChI Key: FJFPOGCVVLUYAQ-UHFFFAOYSA-N

InChI=1S/C18H22ClNO3/c1-21-16-7-5-4-6-14(16)12-20-9-8-13-10-18(23-3)15(19)11-17(13)22-2/h4-7,10-11,20H,8-9,12H2,1-3H3

PubChem CID: 46856354; ChemSpider: 24583389; Drugs Forum: 25C-NBOMe; Erowid: 25C-NBOMe (2C-C-NBOMe)

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, 1 Apr 2011, 38 (4), 681–693. 752 kB. doi:10.1007/s00259-010-1686-8

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

Hansen, M. Design and synthesis of selective serotonin receptor agonists for positron emission tomography imaging of the brain. Ph. D. Thesis, University of Copenhagen, 16 Dec 2012. 7921 kB.

Zuba, D; Sekuła, K; Buczek, A. 25C-NBOMe – New potent hallucinogenic substance identified on the drug market. Forensic Sci. Int., Apr 2013. 638 kB. doi:10.1016/j.forsciint.2012.08.027

Casale, JF; Hays, PA. Characterization of eleven 2,5-dimethoxy-N-(2-methoxybenzyl)phenethylamine (NBOMe) derivatives and differentiation from their 3- and 4-methoxybenzyl analogues—Part I. Microgram J., 1 Jan 2012, 9 (2), 84–109. 4601 kB.

5543
Analogue 5: Substituting Ethyl for Iodo at R4

25E-NBOMe
NBOMe-2CE
4-Ethyl-2,5-dimethoxy-N-(2-methoxybenzyl)phenethylamine

IUPAC: 2-(4-Ethyl-2,5-dimethoxyphenyl)-N-(2-methoxybenzyl)ethan-1-amine

Formula: C20H27NO3 Molecular weight: 329.43328 g/mol InChI Key: PXDVGFGXPVCNAB-UHFFFAOYSA-N

InChI=1S/C20H27NO3/c1-5-15-12-20(24-4)16(13-19(15)23-3)10-11-21-14-17-8-6-7-9-18(17)22-2/h6-9,12-13,21H,5,10-11,14H2,1-4H3

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

Casale, JF; Hays, PA. Characterization of eleven 2,5-dimethoxy-N-(2-methoxybenzyl)phenethylamine (NBOMe) derivatives and differentiation from their 3- and 4-methoxybenzyl analogues—Part I. Microgram J., 1 Jan 2012, 9 (2), 84–109. 4601 kB.

Hansen, M. Design and synthesis of selective serotonin receptor agonists for positron emission tomography imaging of the brain. Ph. D. Thesis, University of Copenhagen, 16 Dec 2012. 7921 kB.

5544
Analogue 6: Substituting Isopropylthio for Iodo at R4

25T4-NBOMe
NBOMe-2CT4
4-Isopropylthio-2,5-dimethoxy-N-(2-methoxybenzyl)phenethylamine

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

Formula: C21H29NO3S Molecular weight: 375.52486 g/mol InChI Key: BOWHVFJVXBVJCU-UHFFFAOYSA-N

InChI=1S/C21H29NO3S/c1-15(2)26-21-13-19(24-4)16(12-20(21)25-5)10-11-22-14-17-8-6-7-9-18(17)23-3/h6-9,12-13,15,22H,10-11,14H2,1-5H3

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

Casale, JF; Hays, PA. Characterization of eleven 2,5-dimethoxy-N-(2-methoxybenzyl)phenethylamine (NBOMe) derivatives and differentiation from their 3- and 4-methoxybenzyl analogues—Part I. Microgram J., 1 Jan 2012, 9 (2), 84–109. 4601 kB.

5562
Analogue 7: Substituting 2-Fluoroethyl for Iodo at R4

25EF-NBOMe
NBOMe-2CEF
4-(2-Fluoroethyl)-2,5-dimethoxy-N-(2-methoxybenzyl)phenethylamine

IUPAC: 2-[4-(2-Fluoroethyl)-2,5-dimethoxyphenyl]-N-(2-methoxybenzyl)ethan-1-amine

Formula: C20H26FNO3 Molecular weight: 347.4237432 g/mol InChI Key: NCIWUIMJACBUAO-UHFFFAOYSA-N

InChI=1S/C20H26FNO3/c1-23-18-7-5-4-6-17(18)14-22-11-9-16-13-19(24-2)15(8-10-21)12-20(16)25-3/h4-7,12-13,22H,8-11,14H2,1-3H3

5551
Analogue 8: Substituting Trifluoromethyl for Iodo at R4

25TFM-NBOMe
NBOMe-2CTFM
Cimbi-138
2,5-Dimethoxy-N-(2-methoxybenzyl)-4-(trifluoromethyl)phenethylamine

IUPAC: 2-[2,5-Dimethoxy-4-(trifluoromethyl)phenyl]-N-(2-methoxybenzyl)ethan-1-amine

Formula: C19H22F3NO3 Molecular weight: 369.3780896 g/mol InChI Key: FBHVTQIAHOTPAM-UHFFFAOYSA-N

InChI=1S/C19H22F3NO3/c1-24-16-7-5-4-6-14(16)12-23-9-8-13-10-18(26-3)15(19(20,21)22)11-17(13)25-2/h4-7,10-11,23H,8-9,12H2,1-3H3

PubChem CID: 10067667; ChemSpider: 8243207

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.

Heim, R; Pertz, HH; Elz, S. Partial 5-HT2A-receptor agonists of the phenylethanamine series: Effect of a trifluoromethyl substituent. Arch. Pharm. Pharm. Med. Chem., 3 May 2000, 333 (Suppl. 2), 45. 542 kB. Poster abstract

Hansen, M. Design and synthesis of selective serotonin receptor agonists for positron emission tomography imaging of the brain. Ph. D. Thesis, University of Copenhagen, 16 Dec 2012. 7921 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.

Heim, R. Synthesis and pharmacology of potent 5-HT2A receptor agonists with N-2-methoxybenzyl partial structure. SC. D. Thesis, Freie Universität, Berlin, 1 Jan 2004. In German.

5557
Analogue 9: Substituting Isopropyl for Iodo at R4

25IP-NBOMe
NBOMe-2CIP
4-Isopropyl-2,5-dimethoxy-N-(2-methoxybenzyl)phenethylamine

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

Formula: C21H29NO3 Molecular weight: 343.45986 g/mol InChI Key: KMZZEEDFQLXSQF-UHFFFAOYSA-N

InChI=1S/C21H29NO3/c1-15(2)18-13-20(24-4)16(12-21(18)25-5)10-11-22-14-17-8-6-7-9-19(17)23-3/h6-9,12-13,15,22H,10-11,14H2,1-5H3

2432
Analogue 10: Substituting Cyano for Iodo at R4

25CN-NBOMe
NBOMe-2CCN

IUPAC: 2,5-Dimethoxy-4-{2-[(2-methoxybenzyl)amino]ethyl}benzonitrile

Formula: C19H22N2O3 Molecular weight: 326.38958 g/mol InChI Key: QBJWOIWLBRLGKZ-UHFFFAOYSA-N

InChI=1S/C19H22N2O3/c1-22-17-7-5-4-6-15(17)13-21-9-8-14-10-19(24-3)16(12-20)11-18(14)23-2/h4-7,10-11,21H,8-9,13H2,1-3H3

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

Hansen, M. Design and synthesis of selective serotonin receptor agonists for positron emission tomography imaging of the brain. Ph. D. Thesis, University of Copenhagen, 16 Dec 2012. 7921 kB.

2431
Analogue 11: Substituting Fluoro for Iodo at R4

25F-NBOMe
NBOMe-2CF

IUPAC: 2-(4-Fluoro-2,5-dimethoxyphenyl)-N-(2-methoxybenzyl)ethan-1-amine

Formula: C18H22FNO3 Molecular weight: 319.3705832 g/mol InChI Key: DFTJMIFNIHIWAJ-UHFFFAOYSA-N

InChI=1S/C18H22FNO3/c1-21-16-7-5-4-6-14(16)12-20-9-8-13-10-18(23-3)15(19)11-17(13)22-2/h4-7,10-11,20H,8-9,12H2,1-3H3

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

Hansen, M. Design and synthesis of selective serotonin receptor agonists for positron emission tomography imaging of the brain. Ph. D. Thesis, University of Copenhagen, 16 Dec 2012. 7921 kB.

2422
Analogue 12: Substituting Nitro for Iodo at R4

25N-NBOMe
NBOMe-2CN

IUPAC: 2-(2,5-Dimethoxy-4-nitrophenyl)-N-(2-methoxybenzyl)ethan-1-amine

Formula: C18H22N2O5 Molecular weight: 346.37768 g/mol InChI Key: TXCKTIBHURMASQ-UHFFFAOYSA-N

InChI=1S/C18H22N2O5/c1-23-16-7-5-4-6-14(16)12-19-9-8-13-10-18(25-3)15(20(21)22)11-17(13)24-2/h4-7,10-11,19H,8-9,12H2,1-3H3

Uchiyama, N; Shimokawa, Y; Matsuda, S; Kawamura, M; Kikura-Hanajiri, R; Goda, Y. Two new synthetic cannabinoids, AM-2201 benzimidazole analog (FUBIMINA) and (4-methylpiperazin-1-yl)(1-pentyl-1H-indol-3-yl)methanone (MEPIRAPIM), and three phenethylamine derivatives, 25H-NBOMe 3,4,5-trimethoxybenzyl analog, 25B-NBOMe, and 2C-N-NBOMe, identified in illegal products. Forensic Toxicol., 827 kB. doi:10.1007/s11419-013-0217-2

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

Casale, JF; Hays, PA. Characterization of eleven 2,5-dimethoxy-N-(2-methoxybenzyl)phenethylamine (NBOMe) derivatives and differentiation from their 3- and 4-methoxybenzyl analogues—Part I. Microgram J., 1 Jan 2012, 9 (2), 84–109. 4601 kB.

592
Analogue 13: Substituting Methoxy for Iodo at R4

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

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

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.

1248
Analogue 14: Substituting Propyl for Iodo at R4

25P-NBOMe
NBOMe-2CP

IUPAC: 2-(2,5-Dimethoxy-4-propylphenyl)-N-(2-methoxybenzyl)ethan-1-amine

Formula: C21H29NO3 Molecular weight: 343.45986 g/mol InChI Key: QHEBYIJRKGDFGH-UHFFFAOYSA-N

InChI=1S/C21H29NO3/c1-5-8-16-13-21(25-4)17(14-20(16)24-3)11-12-22-15-18-9-6-7-10-19(18)23-2/h6-7,9-10,13-14,22H,5,8,11-12,15H2,1-4H3

Casale, JF; Hays, PA. Characterization of eleven 2,5-dimethoxy-N-(2-methoxybenzyl)phenethylamine (NBOMe) derivatives and differentiation from their 3- and 4-methoxybenzyl analogues—Part I. Microgram J., 1 Jan 2012, 9 (2), 84–109. 4601 kB.

Hansen, M. Design and synthesis of selective serotonin receptor agonists for positron emission tomography imaging of the brain. Ph. D. Thesis, University of Copenhagen, 16 Dec 2012. 7921 kB.

1249
Analogue 15: Substituting Methylthio for Iodo at R4

25T-NBOMe
NBOMe-2CT

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

Formula: C19H25NO3S Molecular weight: 347.4717 g/mol InChI Key: ZWPIZVVOKGWMFW-UHFFFAOYSA-N

InChI=1S/C19H25NO3S/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

Hansen, M. Design and synthesis of selective serotonin receptor agonists for positron emission tomography imaging of the brain. Ph. D. Thesis, University of Copenhagen, 16 Dec 2012. 7921 kB.

1250
Analogue 16: Substituting Ethylthio for Iodo at R4

25T2-NBOMe
NBOMe-2CT2

IUPAC: 2-[4-(Ethylsulfanyl)-2,5-dimethoxyphenyl]-N-(2-methoxybenzyl)ethan-1-amine

Formula: C20H27NO3S Molecular weight: 361.49828 g/mol InChI Key: OZEBFZPAWCXEGK-UHFFFAOYSA-N

InChI=1S/C20H27NO3S/c1-5-25-20-13-18(23-3)15(12-19(20)24-4)10-11-21-14-16-8-6-7-9-17(16)22-2/h6-9,12-13,21H,5,10-11,14H2,1-4H3

Casale, JF; Hays, PA. Characterization of eleven 2,5-dimethoxy-N-(2-methoxybenzyl)phenethylamine (NBOMe) derivatives and differentiation from their 3- and 4-methoxybenzyl analogues—Part I. Microgram J., 1 Jan 2012, 9 (2), 84–109. 4601 kB.

Hansen, M. Design and synthesis of selective serotonin receptor agonists for positron emission tomography imaging of the brain. Ph. D. Thesis, University of Copenhagen, 16 Dec 2012. 7921 kB.

1251
Analogue 17: Substituting Propylthio for Iodo at R4

25T7-NBOMe
NBOMe-2CT7

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

Formula: C21H29NO3S Molecular weight: 375.52486 g/mol InChI Key: CPVMNHOHOSNFOP-UHFFFAOYSA-N

InChI=1S/C21H29NO3S/c1-5-12-26-21-14-19(24-3)16(13-20(21)25-4)10-11-22-15-17-8-6-7-9-18(17)23-2/h6-9,13-14,22H,5,10-12,15H2,1-4H3

Casale, JF; Hays, PA. Characterization of eleven 2,5-dimethoxy-N-(2-methoxybenzyl)phenethylamine (NBOMe) derivatives and differentiation from their 3- and 4-methoxybenzyl analogues—Part I. Microgram J., 1 Jan 2012, 9 (2), 84–109. 4601 kB.

Hansen, M. Design and synthesis of selective serotonin receptor agonists for positron emission tomography imaging of the brain. Ph. D. Thesis, University of Copenhagen, 16 Dec 2012. 7921 kB.

One skeleton analogue:
551
Analogue 1: With 2,3,4,5-Tetrahydro-1-benzoxepin-4-amine skeleton

IBOX

IUPAC: 8-Iodo-7-methoxy-2,3,4,5-tetrahydro-1-benzoxepin-4-amine

Formula: C11H14INO2 Molecular weight: 319.13883 g/mol InChI Key: PAQLHNYBWOPNGV-UHFFFAOYSA-N

InChI=1S/C11H14INO2/c1-14-11-5-7-4-8(13)2-3-15-10(7)6-9(11)12/h5-6,8H,2-4,13H2,1H3

Monte, AP; Marona-Lewicka, D; Cozzi, NV; Nelson, DL; Nichols, DE. Conformationally restricted tetrahydro-1-benzoxepin analogs of hallucinogenic phenethylamines. Med. Chem. Res., 1 Jan 1995, 5, 651–663. 2040 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.

Four isomers:
5513
Isomer 1

25I-NBMeOH
NBMeOH-2CI
N-[2-(Hydroxymethyl)benzyl]-4-iodo-2,5-dimethoxyphenethylamine

IUPAC: [2-({[2-(4-Iodo-2,5-dimethoxyphenyl)ethyl]amino}methyl)phenyl]methanol

Formula: C18H22INO3 Molecular weight: 427.27665 g/mol InChI Key: QSYQUZWORHKKKT-UHFFFAOYSA-N

InChI=1S/C18H22INO3/c1-22-17-10-16(19)18(23-2)9-13(17)7-8-20-11-14-5-3-4-6-15(14)12-21/h3-6,9-10,20-21H,7-8,11-12H2,1-2H3

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

387
Isomer 2

DOI-NBOH
NBOH-DOI
N-(2-Hydroxybenzyl)-4-iodo-2,5-dimethoxyamphetamine

IUPAC: 2-({[1-(4-Iodo-2,5-dimethoxyphenyl)propan-2-yl]amino}methyl)phenol

Formula: C18H22INO3 Molecular weight: 427.27665 g/mol InChI Key: XDAKXIFEZODALS-UHFFFAOYSA-N

InChI=1S/C18H22INO3/c1-12(20-11-13-6-4-5-7-16(13)21)8-14-9-18(23-3)15(19)10-17(14)22-2/h4-7,9-10,12,20-21H,8,11H2,1-3H3

Heim, R. Synthesis and pharmacology of potent 5-HT2A receptor agonists with N-2-methoxybenzyl partial structure. SC. D. Thesis, Freie Universität, Berlin, 1 Jan 2004. In German.

2585
Isomer 3

25I-NB3OMe

IUPAC: 2-(4-Iodo-2,5-dimethoxyphenyl)-N-(3-methoxybenzyl)ethan-1-amine

Formula: C18H22INO3 Molecular weight: 427.27665 g/mol InChI Key: CJTZKPLDKCBUAF-UHFFFAOYSA-N

InChI=1S/C18H22INO3/c1-21-15-6-4-5-13(9-15)12-20-8-7-14-10-18(23-3)16(19)11-17(14)22-2/h4-6,9-11,20H,7-8,12H2,1-3H3

Casale, JF; Hays, PA. Characterization of eleven 2,5-dimethoxy-N-(2-methoxybenzyl)phenethylamine (NBOMe) derivatives and differentiation from their 3- and 4-methoxybenzyl analogues—Part I. Microgram J., 1 Jan 2012, 9 (2), 84–109. 4601 kB.

2586
Isomer 4

25I-NB4OMe

IUPAC: 2-(4-Iodo-2,5-dimethoxyphenyl)-N-(4-methoxybenzyl)ethan-1-amine

Formula: C18H22INO3 Molecular weight: 427.27665 g/mol InChI Key: NWOROGLTELSWAZ-UHFFFAOYSA-N

InChI=1S/C18H22INO3/c1-21-15-6-4-13(5-7-15)12-20-9-8-14-10-18(23-3)16(19)11-17(14)22-2/h4-7,10-11,20H,8-9,12H2,1-3H3

Casale, JF; Hays, PA. Characterization of eleven 2,5-dimethoxy-N-(2-methoxybenzyl)phenethylamine (NBOMe) derivatives and differentiation from their 3- and 4-methoxybenzyl analogues—Part I. Microgram J., 1 Jan 2012, 9 (2), 84–109. 4601 kB.

Show all 51 analogues and isomers Show only the 28 N analogues Show only the one α analogues Show only the 17 R4 analogues Show only the one skeleton analogues
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