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Exploring N-(2-Fluorobenzyl)-4-iodo-2,5-dimethoxyphenethylamine. To explore a different substance…

Names

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

IUPAC names

N-[(2-Fluorophenyl)methyl]-2-(4-iodo-2,5-dimethoxyphenyl)ethan-1-amine
N-(2-Fluorobenzyl)-2-(4-iodo-2,5-dimethoxyphenyl)ethan-1-amine

ID 5398 · Formula C₁₇H₁₉FINO₂ · Molecular weight 415.241

InChI 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

InChI Key LPBKNBHMWRBPHT-UHFFFAOYSA-N This stereoisomer Any stereoisomer

SMILES COc1cc(I)c(cc1CCNCc1ccccc1F)OC

ChemSpider 24751866
PubChem 57469209
Wikidata Q4632131
Wikipedia 25I-NBF
Wikipedia, see also 25-NB
Project Response 25I-NBF (1386-15)
Project Response 25I-NBF (1376-16)
bluelight.org The Big & Dandy 25I-NBF Thread

Phenethylamine: Von der Strucktur zur Funktion 25I-NBF: 8.5 (329) 837, 838, 839

Braden, MR. Towards a biophysical understanding of hallucinogen action Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8.4 MB. #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-HT_2A agonist PET tracers Eur. J. Nucl. Med. Mol. Imaging, 1 Apr 2011, 38 (4), 681–693. 752 kB. https://doi.org/10.1007/s00259-010-1686-8 #Cimbi-21 LC

Braden, MR; Parrish, JC; Naylor, JC; Nichols, DE. Molecular interaction of serotonin 5-HT_2A 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. https://doi.org/10.1124/mol.106.028720 #25I-NBF

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. #2.3 NMR

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

Leth-Petersen, S; Bundgaard, C; Hansen, M; Carnerup, MA; Kehler, J; Kristensen, JL. Correlating the metabolic stability of psychedelic 5-HT_2A agonists with anecdotal reports of human oral bioavailability Neurochem. Res., 12 Feb 2014, 39 (10), 2018-2023. 625 kB. https://doi.org/10.1007/s11064-014-1253-y #1c

McGonigal, MK; Wilhide, JA; Smith, PB; Elliott, NM; Dorman, FL. Analysis of synthetic phenethylamine street drugs using direct sample analysis coupled to accurate mass time of flight mass spectrometry Forensic Sci. Int., 1 Jun 2017, 275, 83–89. 2.3 MB. https://doi.org/10.1016/j.forsciint.2017.02.025 #25I-NBF MS

EMCDDA. New drugs in Europe, 2015, European Monitoring Centre for Drugs and Drug Addiction, Lisbon, 1 May 2016. 1.0 MB. #16

Hansen, M; Phonekeo, K; Paine, JS; Leth-Petersen, S; Begtrup, M; Bräuner-Osborne, H; Kristensen, JL. Synthesis and structure–activity relationships of N-benzyl phenethylamines as 5-HT_2A/2C agonists ACS Chem. Neurosci., 19 Mar 2014, 5 (3), 243-249. 21.5 MB. https://doi.org/10.1021/cn400216u #1c NMR

Nichols, DE. Chemistry and structure–activity relationships of psychedelics In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 1-43. 2.6 MB. https://doi.org/10.1007/7854_2017_475 #Table 3: 2-F

Nichols, DE. Structure-activity relationships of serotonin 5-HT_2A agonists WIREs Membr. Transp. Signal, 1 Sep 2012, 1 (5), 559-579. 573 kB. https://doi.org/10.1002/wmts.42

Lum, BJ; Brophy, JJ; Hibbert, DB. Identification of 4-substituted 2-(4-x-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine (25X-NBOMe) and analogues by gas chromatography–mass spectrometry analysis of heptafluorobutyric anhydride (HFBA) derivatives Aust. J. Forensic Sci., 2 Jan 2016, 48 (1), 59–73. 5.5 MB. https://doi.org/10.1080/00450618.2015.1026274 #25I-NBF GC,MS

Poklis, JL; Raso, SA; Alford, KN; Poklis, A; Peace, MR. Analysis of 25I-NBOMe, 25B-NBOMe, 25C-NBOMe and other dimethoxyphenyl-N-[(2-methoxyphenyl)methyl]ethanamine derivatives on blotter paper J. Anal. Toxicol., 1 Oct 2015, 39 (8), 617–623. 495 kB. https://doi.org/10.1093/jat/bkv073 #25I-NBF LC,MS

Ettrup, A. Serotonin receptor studies in the pig brain: Pharmacological intervention and positron emission tomography tracer development Ph. D. Thesis, University of Copenhagen, 15 Nov 2010. 5.0 MB. #Cimbi-21 NMR

Edmunds, R; Donovan, R; Reynolds, D. The analysis of illicit 25X-NBOMe seizures in Western Australia Drug Test. Anal., 1 Apr 2018, 10 (4), 786-790. 507 kB. https://doi.org/10.1002/dta.2260 LC

25I-NB4F · 25I-NBpF · N-(4-Fluorobenzyl)-4-iodo-2,5-dimethoxyphenethylamine

7 Dec 2019 · · Isomer Design