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Names

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

IUPAC name

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

ID 5379 · Formula C₁₇H₂₀INO₃ · Molecular weight 413.25

InChI 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

InChI Key FEUZHYRXGQTBRO-UHFFFAOYSA-N This stereoisomer Any stereoisomer

SMILES COc1cc(I)c(cc1CCNCc1ccccc1O)OC

ChemSpider 8177342
PubChem 10001761
Wikidata Q4632139
Wikipedia 25I-NBOH
Wikipedia, see also 25-NB
Blotter 25I-NBOH
PsychonautWiki 25I-NBOH
Project Response 25I-NBOH (1383-15)
bluelight.org The Big & Dandy 25I-NBOH Thread

Phenethylamine: Von der Strucktur zur Funktion 25I-NBOH: 8.5 (334) 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-NBOH

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-27 LC

Heim, R. Synthesis and pharmacology of potent 5-HT_2A receptor agonists with N-2-methoxybenzyl partial structure SC. D. Thesis, Freie Universität, Berlin, 1 Jan 2004. 3.9 MB. #235 In German. MS,NMR,IR

Blaazer, AR; Smid, P; Kruse, CG. Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT_2A receptors ChemMedChem, 15 Sep 2008, 3 (9), 1299–1309. 461 kB. https://doi.org/10.1002/cmdc.200800133 #33

Silva, ME; Heim, R; Strasser, A; Elz, S; Dove, S. Theoretical studies on the interaction of partial agonists with the 5-HT_2A receptor J. Comput. Aided Mol. Des., 1 Jan 2011, 25 (1), 51–66. 834 kB. https://doi.org/10.1007/s10822-010-9400-2 #26

Silva, ME. Theoretical study of the interaction of agonists with the 5-HT_2A receptor Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 26 Aug 2008. 5.9 MB. #235

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. #2.2 NMR

Heim, R; Elz, S. Novel extremely potent partial 5-HT_2A-receptor agonists: Successful application of a new structure-activity concept Arch. Pharm. Pharm. Med. Chem., , 333 (Suppl. 1), 18. 566 kB. #2 Poster abstract

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. https://doi.org/10.16889/isomerdesign-1 #B4 NMR

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. https://doi.org/10.16889/isomerdesign-1-supp #B4 NMR

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. Anal., 1 May 2017, 9 (5), 671-679. 553 kB. https://doi.org/10.1002/dta.2031 MS

Halberstadt, AL. Pharmacology and Toxicology of N-Benzylphenethylamine (“NBOMe”) Hallucinogens In Neuropharmacology of New Psychoactive Substances (NPS): The Science Behind the Headlines; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 18 Jan 2017; pp 283-311. 826 kB. https://doi.org/10.1007/7854_2016_64

EMCDDA. New drugs in Europe, 2016, European Monitoring Centre for Drugs and Drug Addiction, Lisbon, 1 May 2017. 489 kB. #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 #1b 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-OH

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

Arantes, LC; Júnior, EF; Figueiredo de Souza, L; Cardoso, AC; Alcântara, TLF; Lião, LM; Machado, Y; Lordeiro, RA; Neto, JC; Andrade, AFB. 25I-NBOH: A new potent serotonin 5-HT_2A receptor agonist identified in blotter paper seizures in Brazil Forensic Toxicol., 1 Jul 2017, 35 (2), 408–414. 1.3 MB. https://doi.org/10.1007/s11419-017-0357-x #25I-NBOH GC,MS,NMR,IR

Neto, JC; Andrade, AFB; Lordeiro, RA; Machado, Y; Elie, M; Júnior, EF; Arantes, LC. Preventing misidentification of 25I-NBOH as 2C-I on routine GC–MS analyses Forensic Toxicol., 1 Jul 2017, 35 (2), 415–420. 1.3 MB. https://doi.org/10.1007/s11419-017-0362-0 #25I-NBOH

Pertz, HH; Heim, R; Elz, S. N-Benzylated phenylethanamines are highly potent partial agonists at 5-HT_2A receptors Arch. Pharm. Pharm. Med. Chem., , 333 (Suppl. 2), 30. 583 kB. #3b-OH Poster abstract

Eshleman, AJ; Wolfrum, KM; Reed, JF; Kim, SO; Johnson, RA; Janowsky, A. Neurochemical pharmacology of psychoactive substituted N-benzylphenethylamines: High potency agonists at 5-HT_2A receptors Biochem. Pharmacol., 1 Dec 2018, 158 27–34. 790 kB. https://doi.org/10.1016/j.bcp.2018.09.024 #25I-NBOH

Halberstadt, AL; Chatha, M; Klein, AK; Wallach, J; Brandt, SD. Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species Neuropharmacology, 1 May 2020, 167, 107933. 2.4 MB. https://doi.org/10.1016/j.neuropharm.2019.107933 #25I-NBOH

Pottie, E; Cannaert, A; Stove, CP. In vitro structure–activity relationship determination of 30 psychedelic new psychoactive substances by means of β-arrestin 2 recruitment to the serotonin 2A receptor Arch. Toxicol., 1 Oct 2020, 94 (10), 3449–3460. 919 kB. https://doi.org/10.1007/s00204-020-02836-w #25I-NBOH

Clancy, L; Philp, M; Shimmon, R; Fu, S. Development and validation of a color spot test method for the presumptive detection of 25-NBOMe compounds Drug Test. Anal., 19 Aug 2020, 13 (5), 929-943. 11.3 MB. https://doi.org/10.1002/dta.2905 #25I-NBOH spot

Cumming, P; Scheidegger, M; Dornbierer, D; Palner, M; Quednow, BB; Martin-Soelch, C. Molecular and functional imaging studies of psychedelic drug action in animals and humans Molecules, 1 Jan 2021, 26 (9), 2451. 3.5 MB. https://doi.org/10.3390/molecules26092451 #32

de Oliveira Magalhães, L; Arantes, LC; Braga, JWB. Identification of NBOMe and NBOH in blotter papers using a handheld NIR spectrometer and chemometric methods Microchem. J., 1 Jan 2019, 144, 151–158. 2.7 MB. https://doi.org/10.1016/j.microc.2018.08.051 #25I-NBOH

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-NBOH

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-27 NMR

Duan, W; Cao, D; Wang, S; Cheng, J. Serotonin 2A receptor (5-HT_2AR) agonists: Psychedelics and non-hallucinogenic analogues as emerging antidepressants Chem. Rev., 10 Jan 2024, 124 (1), 124–163. 12.6 MB. https://doi.org/10.1021/acs.chemrev.3c00375 #145

2-DM-25I-NBOMe · N-(2-Methoxybenzyl)-2-hydroxy-4-iodo-5-methoxyphenethylamine

7 Dec 2019 · · Isomer Design