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

Martins, D; Barratt, MJ; Pires, CV; Carvalho, H; Ventura, M; Fornís, I; Valente, H. The detection and prevention of unintentional consumption of DOx and 25x-NBOMe at Portugal’s Boom Festival. Hum. Psychopharmacol. Clin. Exp., 1 May 2017, n/a-n/a. 400 kB. http://dx.doi.org/10.1002/hup.2608

Leth-Petersen, S; Bundgaard, C; Hansen, M; Carnerup, MA; Kehler, J; Kristensen, JL. Correlating the metabolic stability of psychedelic 5-HT2A agonists with anecdotal reports of human oral bioavailability. Neurochem. Res., 12 Feb 2014, 39 (10), 2018-2023. 625 kB. http://dx.doi.org/10.1007/s11064-014-1253-y

Nichols, DE; Sassano, MF; Halberstadt, AL; Klein, LM; Brandt, SD; Elliott, SP; Fiedler, WJ. N-Benzyl-5-methoxytryptamines as potent serotonin 5-HT2 receptor family agonists and comparison with a series of phenethylamine analogues. ACS Chem. Neurosci., 15 Jul 2015, 6 (7), 1165-1175. 406 kB. http://dx.doi.org/10.1021/cn500292d

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. 2.2 MB. http://dx.doi.org/10.1002/rcm.7134

Chapman, SJ; Avanes, AA. PeakAL: Protons I Have Known and Loved — Fifty Shades of Grey-Market Spectra. BLOTTER, 1 Aug 2015, 1 (1). 2.6 MB. http://dx.doi.org/10.16889/isomerdesign-1 Open access DOI

Chapman, SJ; Avanes, AA. PeakAL: Protons I Have Known and Loved — Fifty Shades of Grey-Market Spectra. Supplementary Data. BLOTTER, 1 Aug 2015, 1 (1). 11.9 MB. http://dx.doi.org/10.16889/isomerdesign-1-supp Open access DOI

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. 8.1 MB.

Prabhakaran, J; Underwood, MD; Kumar, JSD; Simpson, NR; Kassir, SA; Bakalian, MJ; Mann, JJ; Arango, V. Synthesis and in vitro evaluation of [18F]FECIMBI-36: A potential agonist PET ligand for 5-HT2A/2C receptors. Bioorg. Med. Chem. Lett., 15 Sep 2015, 25 (18), 3933–3936. 603 kB. http://dx.doi.org/10.1016/j.bmcl.2015.07.034

Kaizaki-Mitsumoto, A; Noguchi, N; Yamaguchi, S; Odanaka, Y; Matsubayashi, S; Kumamoto, H; Fukuhara, K; Funada, M; Wada, K; Numazawa, S. Three 25-NBOMe-type drugs, three other phenethylamine-type drugs (25I-NBMD, RH34, and escaline), eight cathinone derivatives, and a phencyclidine analog MMXE, newly identified in ingredients of drug products before they were sold on the drug market. Forensic Toxicol., 1 Jan 2016, 34 (1), 108-114. 854 kB. http://dx.doi.org/10.1007/s11419-015-0293-6

Nielsen, LM; Holm, NB; Leth-Petersen, S; Kristensen, JL; Olsen, L; Linnet, K. Characterization of the hepatic cytochrome P450 enzymes involved in the metabolism of 25I-NBOMe and 25I-NBOH. Drug Test. Analysis, 1 Jan 2016, n/a-n/a. 553 kB. http://dx.doi.org/10.1002/dta.2031

Halberstadt, AL. Pharmacology and Toxicology of N-Benzylphenethylamine (“NBOMe”) Hallucinogens. In Current Topics in Behavioral Neurosciences; , 2016; pp 1–29. 826 kB. http://dx.doi.org/10.1007/7854_2016_64

Halberstadt, AL; Geyer, MA. Effects of the hallucinogen 2,5-dimethoxy-4-iodophenethylamine (2C-I) and superpotent N-benzyl derivatives on the head twitch response. Neuropharmacology, 1 Feb 2014, 77, 200–207. 1.4 MB. http://dx.doi.org/10.1016/j.neuropharm.2013.08.025

Wohlfarth, A; Roman, M; Andersson, M; Kugelberg, FC; Diao, X; Carlier, J; Eriksson, C; Wu, X; Konradsson, P; Josefsson, M; Huestis, MA; Kronstrand, R. 25C-NBOMe and 25I-NBOMe metabolite studies in human hepatocytes, in vivo mouse and human urine with high-resolution mass spectrometry. Drug Test. Analysis, 1 Jan 2016, n/a-n/a. 837 kB. http://dx.doi.org/10.1002/dta.2044

Hyperlab. Hyperlab new compounds. 29 Sep 2014. 232 kB. Note: Contains links to hyperlab.info that require elevated access/karma to follow.

Edmunds, R; Donovan, R; Reynolds, D. The analysis of illicit 25X-NBOMe seizures in Western Australia. Drug Test. Analysis, 20 Aug 2017, n/a-n/a. 481 kB. http://dx.doi.org/10.1002/dta.2260

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. 500 kB.

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

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

Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8.4 MB.

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

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.

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. JW, Personal communication of unpublished research. 1 Dec 2011.

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. http://dx.doi.org/10.1124/mol.106.028720

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. http://dx.doi.org/10.1007/s10822-010-9400-2

Silva, ME. Theoretical study of the interaction of agonists with the 5-HT2A receptor. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 26 Aug 2008. 5.9 MB.

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. 7.9 MB.

Parrish, JC. Toward a molecular understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2006. 5.5 MB.

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

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

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. 4.6 MB.

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
21 October 2017 · Creative Commons BY-NC-SA ·