Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 25I-NBOH: Difference between pages

{{Short description|Chemical compound}}

| Verifiedfields = changed

| verifiedrevid = 477215972

| IUPAC_name = 2-((2-(4-Iodo-2,5-dimethoxyphenyl)ethylamino)methyl)phenol

| image = 2C-I-NBOH-skeletal.svg

| legal_BR = F2

| legal_BR_comment = <ref>{{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}}</ref>

| legal_DE = NpSG

| legal_UK = Class A

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

| CAS_number = 919797-20-9

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

| UNII = W9G4BGW8K4

'''25I-NBOH''' ('''NBOH-2CI''', '''Cimbi-27''', '''2-C-I-NBOH''') is a derivative of the [[phenethylamine]]-derived hallucinogen [[2C-I]] that was discovered in 2006 by a team at [[Purdue University]].

==Pharmacology==

25I-NBOH acts as a potent [[agonist]] of the [[5HT2A receptor|5HT_2A receptor]],<ref>{{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 = 681–93 | date = April 2011 | pmid = 21174090 | doi = 10.1007/s00259-010-1686-8 | s2cid = 12467684 }}</ref><ref name="pmid21088982">{{cite journal | vauthors = Silva ME, Heim R, Strasser A, Elz S, Dove S | title = Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor | journal = Journal of Computer-Aided Molecular Design | volume = 25 | issue = 1 | pages = 51–66 | date = January 2011 | pmid = 21088982 | doi = 10.1007/s10822-010-9400-2 | citeseerx = 10.1.1.688.2670 | bibcode = 2011JCAMD..25...51S | s2cid = 3103050 }}</ref> with a [[Dissociation constant|K_i]] of 0.061&nbsp;nM at the human 5HT_2A receptor, similar to the better-known compound [[25I-NBOMe]], making it some twelve times the potency of 2C-I itself.

Although ''[[in vitro]]'' tests show this compound acts as an [[agonist]], animal studies to confirm these findings have not been reported. While the ''N''-benzyl derivatives of 2C-I had significantly increased binding to [[5HT2A receptor|5HT_2A]] receptor fragments, compared to 2C-I, the ''N''-benzyl derivatives of [[2,5-Dimethoxy-4-iodoamphetamine|DOI]] were less active compared to DOI.<ref>{{cite journal | vauthors = Braden MR, Parrish JC, Naylor JC, Nichols DE | s2cid = 15840304 | 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 = 1956–64 | date = December 2006 | pmid = 17000863 | doi = 10.1124/mol.106.028720 }}</ref>

25I-NBOH is notable as one of the most selective agonist ligands for the 5-HT_2A receptor with an EC₅₀ value of 0.074&nbsp;nM with more than 400 times selectivity over the 5-HT_2C receptor.<ref>{{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 = 243–9 | date = March 2014 | pmid = 24397362 | pmc = 3963123 | doi = 10.1021/cn400216u }}</ref>

==Analytical chemistry==

25I-NBOH is a labile molecule which fragments into 2C-I when analyzed by routine [[gas chromatography]] (GC) methods.<ref>{{cite journal | vauthors = Arantes LC, Júnior EF, de Souza LF, Cardoso AC, Alcântara TL, Lião LM, Machado Y, Lordeiro RA, Neto JC, Andrade AF | display-authors = 6 | title = 2A receptor agonist identified in blotter paper seizures in Brazil | journal = Forensic Toxicology | volume = 35 | issue = 2 | pages = 408–414 | year = 2017 | pmid = 28706567 | pmc = 5486617 | doi = 10.1007/s11419-017-0357-x }}</ref> A specific method for reliable identification of 25I-NBOH using [[GC/MS]] has been reported, allowing forensic forces worldwide to correctly identify this compound.<ref>{{cite journal | vauthors = Neto JC, Andrade AF, Lordeiro RA, Machado Y, Elie M, Júnior EF, Arantes LC | title = Preventing misidentification of 25I-NBOH as 2C-I on routine GC–MS analyses| journal = Forensic Toxicology| volume = 35| issue = 2| pages = 415–420| year = 2017 | doi = 10.1007/s11419-017-0362-0 | s2cid = 32432586| url = http://eprints.lincoln.ac.uk/26957/7/25i-nboh%20aceito.pdf}}</ref>

==Legality==

===Sweden===

[[Riksdag|The Riksdag]] added 25I-NBOH to {{ill|Narcotic Drugs Punishments Act|sv|Narkotikastrafflagen}} under Swedish schedule I (''"substances, plant materials and fungi which normally do not have medical use"'') as of August 18, 2015, published by [[Medical Products Agency (Sweden)|Medical Products Agency]] MPA) in regulation ''HSLF-FS 2015:12'' listed as "25I-NBOH" and "2-([2-(4-jodo-2,5-dimetoxifenyl)etylamino]metyl)fenol".<ref>{{cite web | url = https://lakemedelsverket.se/upload/lvfs/HSLF_FS_2015_12.pdf | title = Gemensamma författningssamlingen avseende hälso- och sjukvård, socialtjänst, läkeme del, folkhälsa m.m. | work = Lakemedelsverket | access-date = 2017-04-21 | archive-url = https://web.archive.org/web/20171030210108/https://lakemedelsverket.se/upload/lvfs/HSLF_FS_2015_12.pdf | archive-date = 2017-10-30 | url-status = dead }}</ref>

===United Kingdom===

{{N-benzylphenethylamine-Legality-United Kingdom}}

==Analogues and derivatives==

{{2C-I analogues and derivatives}}

== References ==

{{Reflist}}

{{Hallucinogens}}

{{Serotonin receptor modulators}}

{{Phenethylamines}}

[[Category:25-NB (psychedelics)]]

[[Category:Designer drugs]]

[[Category:Iodobenzene derivatives]]

[[Category:Selective 5-HT2A receptor agonists]]