:25I-NBF

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 451565266

| IUPAC_name = 2-(4-iodo-2,5-dimethoxyphenyl)-N-[(2-fluorophenyl)methyl]ethan-1-amine

| image = 25i-NBF.svg

| width = 200

| tradename =

| pregnancy_category =

| routes_of_administration =

| legal_BR = F2

| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-07-25}}

| legal_DE = NpSG

| legal_UK = Class A

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 919797-21-0

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = MR8FRH5W3C

| CAS_supplemental =

| ATC_prefix = none

| PubChem = 57469209

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 24751866

| C=17 | H=19 | F=1 | I=1 | N=1 | O=2

| smiles = COc1cc(I)c(OC)cc1CCNCc2ccccc2F

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = LPBKNBHMWRBPHT-UHFFFAOYSA-N

}}

25I-NBF (2C-I-NBF, NBF-2C-I, Cimbi-21) is a derivative of the phenethylamine hallucinogen 2C-I, which acts as a highly potent partial agonist for the human 5-HT_2A receptor,{{cite journal | vauthors = Braden MR, Parrish JC, Naylor JC, Nichols DE | title = Molecular interaction of serotonin 5-HT2A receptor residues Phe339(6.51) and Phe340(6.52) with superpotent N-benzyl phenethylamine agonists | journal = Molecular Pharmacology | volume = 70 | issue = 6 | pages = 1956–1964 | date = December 2006 | pmid = 17000863 | doi = 10.1124/mol.106.028720 | s2cid = 15840304 }}{{cite thesis | first = Michael Robert | last = Braden | name-list-style = vanc | degree = Ph.D. | title = Towards a biophysical understanding of hallucinogen action. | publisher = Purdue University | date = 2007 | id = {{ProQuest|304838368}} }}{{cite journal | vauthors = Hansen M, Phonekeo K, Paine JS, Leth-Petersen S, Begtrup M, Bräuner-Osborne H, Kristensen JL | title = Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists | journal = ACS Chemical Neuroscience | volume = 5 | issue = 3 | pages = 243–249 | date = March 2014 | pmid = 24397362 | pmc = 3963123 | doi = 10.1021/cn400216u }} with bias towards the β-arrestin 2 coupled signalling pathway.{{cite journal | vauthors = Pottie E, Dedecker P, Stove CP | title = Identification of psychedelic new psychoactive substances (NPS) showing biased agonism at the 5-HT_2AR through simultaneous use of β-arrestin 2 and miniGα_q bioassays | journal = Biochemical Pharmacology | volume = 182 | pages = 114251 | date = December 2020 | pmid = 32998000 | doi = 10.1016/j.bcp.2020.114251 | s2cid = 222150466 | url = https://biblio.ugent.be/publication/8687066 | hdl = 1854/LU-8687066 | hdl-access = free | access-date = 2024-05-27 | archive-date = 2024-01-08 | archive-url = https://web.archive.org/web/20240108072825/https://biblio.ugent.be/publication/8687066 | url-status = live }} It has been studied in its ¹¹C radiolabelled form as a potential ligand for mapping the distribution of 5-HT_2A receptors in the brain, using positron emission tomography (PET).{{cite thesis | vauthors = Hansen M | title = Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain. | degree = Ph.D. | publisher = University of Copenhagen | date = 2010-12-16 | doi = 10.13140/RG.2.2.33671.14245}}{{cite journal | vauthors = Ettrup A, Hansen M, Santini MA, Paine J, Gillings N, Palner M, Lehel S, Herth MM, Madsen J, Kristensen J, Begtrup M, Knudsen GM | display-authors = 6 | title = Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT (2A) agonist PET tracers | journal = European Journal of Nuclear Medicine and Molecular Imaging | volume = 38 | issue = 4 | pages = 681–693 | date = April 2011 | pmid = 21174090 | doi = 10.1007/s00259-010-1686-8 | s2cid = 12467684 }}