Exploring 25I-NBOMe. To explore a different substance…

Names:
25I-NB2OMe · 25I-NBOMe · INBMeO · NBOMe-2CI · Cimbi-5-2 · Cimbi-5 · N-(2-Methoxybenzyl)-4-iodo-2,5-dimethoxyphenethylamine · 4-Iodo-2,5-dimethoxy-N-(2-methoxybenzyl)phenethylamine
IUPAC names:
2-(4-Iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethan-1-amine
2-(4-Iodo-2,5-dimethoxyphenyl)-N-(2-methoxybenzyl)ethan-1-amine
ID: 5380 · Formula: C18H22INO3 · Molecular weight: 427.277
InChI: 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

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. http://dx.doi.org/10.1002/cmdc.200800133

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.

Hays, PA; Casale, JF. Characterization of eleven 2,5-dimethoxy-N-(2-methoxybenzyl)phenethylamine (NBOMe) derivatives and differentiation from their 3-and 4-methoxybenzyl analogues - Part II. Microgram J., 1 Jan 2014, 11 (1–4), 3–22. 8079 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.

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.

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.

Heim, R; Pertz, H; 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; 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. JW, Personal communication of unpublished research. 1 Dec 2011.

Brandt, SD; Elliott, SP; Kavanagh, PV; Dempster, NM; Meyer, MR; Maurer, HH; Nichols, DE. Analytical characterization of bioactive N-benzyl-substituted phenethylamines and 5-methoxytryptamines. Rapid Commun. Mass Spectrom., 2 Mar 2015, 29 (7), 573–584. 2154 kB. http://dx.doi.org/10.1002/rcm.7134

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. http://dx.doi.org/10.1007/s00259-010-1686-8

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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. http://dx.doi.org/10.1016/j.bmc.2008.04.050

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Chapman, SJ; Avanes, AA. PeakAL: Protons I Have Known and Loved — Fifty Shades of Grey-Market Spectra. Supplementary Data. BLOTTER, 1 Aug 2015. 11879 kB. http://dx.doi.org/10.16889/isomerdesign-1-supp Open access DOI

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. http://dx.doi.org/10.2967/jnumed.109.074021

2C-I
25I-NBOH
25I-NNap
INBMDO · 25I-NBMD
25I-NMeFur
25I-NMeThiop
25I-NMePyr
25I-NBCN
25I-NBAm
25I-NMeInd
25I-NNap2
25I-NBMeOH
25I-NDHF
25I-N2Nap3OH
25I-N1Nap2OH
25I-NBOH45MD
25I-N2Nap1OH
25I-NB34MD
25I-NBpTFM
25I-NBTFM
25I-NBF
25I-NB4F · 25I-NBpF
25I-NB
N4MT3M-2C-I
N3MT2M-2C-I
25I-NEPOMe
25I-NB3OMe
25I-NB4OMe
25I-NB4B
25I-NB3B
25I-NBBr · 25I-NB2B
DOI-NBOMe
DMPEA-NBOMe · 25H-NBOMe
25B-NB2OMe · 25B-NBOMe
25D-NBOMe
25C-NB2OMe · 25C-NBOMe
25E-NBOMe
25T4-NBOMe
25EF-NBOMe
25TFM-NBOMe
25IP-NBOMe
25CN-NBOMe
25F-NBOMe
25N-NBOMe
245-NBOMe
25P-NBOMe
25T-NBOMe
25T2-NBOMe
25T7-NBOMe
IBOX
738
25I-NBMeOH
DOI-NBOH
25I-NB3OMe
25I-NB4OMe
2C-I
25I-NBOH
25I-NNap
INBMDO · 25I-NBMD
25I-NMeFur
25I-NMeThiop
25I-NMePyr
25I-NBCN
25I-NBAm
25I-NMeInd
25I-NNap2
25I-NBMeOH
25I-NDHF
25I-N2Nap3OH
25I-N1Nap2OH
25I-NBOH45MD
25I-N2Nap1OH
25I-NB34MD
25I-NBpTFM
25I-NBTFM
25I-NBF
25I-NB4F · 25I-NBpF
25I-NB
N4MT3M-2C-I
N3MT2M-2C-I
25I-NEPOMe
25I-NB3OMe
25I-NB4OMe
25I-NB4B
25I-NB3B
25I-NBBr · 25I-NB2B
DOI-NBOMe
DMPEA-NBOMe · 25H-NBOMe
25B-NB2OMe · 25B-NBOMe
25D-NBOMe
25C-NB2OMe · 25C-NBOMe
25E-NBOMe
25T4-NBOMe
25EF-NBOMe
25TFM-NBOMe
25IP-NBOMe
25CN-NBOMe
25F-NBOMe
25N-NBOMe
245-NBOMe
25P-NBOMe
25T-NBOMe
25T2-NBOMe
25T7-NBOMe
IBOX
738
25I-NBMeOH
DOI-NBOH
25I-NB3OMe
25I-NB4OMe
8 December 2016 · Creative Commons BY-NC-SA ·