View source for Chemistry:25I-NBOMe

{{Short description|Synthetic hallucinogen}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477216002
| IUPAC_name = 2-(4-iodo-2,5-dimethoxyphenyl)-''N''-[(2-methoxyphenyl)methyl]ethanamine
| image = 2C-I-NBOMe-skeletal.svg
| image2 = 25I-NBOMe-spacefill.png

<!--Clinical data-->
| tradename =
| pregnancy_category =
| routes_of_administration = [[Medicine:Buccal administration|Buccal]] ([[Medicine:Sublabial administration|sublabial]]), [[Medicine:Sublingual administration|sublingual]], [[Medicine:Insufflation|insufflated]], [[Biology:Inhalation|inhalation]], intravenous, intramuscular, rectal
| legal_BR = F2
| legal_UK = Class A
| legal_UK_comment = <ref name="Misuse of Drugs Act order 2014">{{cite web | url = http://www.legislation.gov.uk/ukdsi/2014/9780111110904 | title = The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014 | author = UK Home Office | date = 2014 | publisher = UK Government}}</ref>
| legal_US = Schedule I
| legal_DE = Anlage I
| legal_EU = Controlled<!-- per source; not a predefined status -->
| legal_CA = Schedule III
| legal_CA_comment = <ref name="Regulations Amending the Food and Drug Regulations (Part J - 2C-phenethylamines)">{{cite web | url=http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php | title=Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)| date=4 May 2016| publisher=Canada Gazette }}</ref>
| legal_UN = P I 
| legal_UN_comment = <ref>{{Cite web |title=Substance Details 25I-NBOMe |url=https://www.unodc.org/LSS/Substance/Details/5ef39f1f-aa5b-42c3-9f07-0b3f1f4b2c92 |access-date=2024-01-23}}</ref>

<!--Pharmacokinetic data-->
| bioavailability =
| metabolism =
| elimination_half-life =
| excretion =

<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 919797-19-6
| CAS_number2 = 1043868-97-8
| index2_label = [[Chemistry:Hydrochloride|hydrochloride]]
| ATC_prefix = none
| PubChem = 10251906
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 8427392
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = 547KGL06IP
| UNII2 = 0V30416N51
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1908863
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = C22774

<!--Chemical data-->
| C=18 | H=22 | I=1 | N=1 | O=3
| SMILES = COC1=CC=CC=C1CNCCC2=CC(=C(C=C2OC)I)OC
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ZFUOLNAKPBFDIJ-UHFFFAOYSA-N
}}

'''25I-NBOMe''' ('''2C-I-NBOMe''', '''Cimbi-5''', '''Smiles''' and also shortened to "'''25I'''") is a novel synthetic psychoactive substance with strong [[Unsolved:Hallucinogen|hallucinogen]]ic properties, synthesized in 2003 for research purposes. Since 2010, it has circulated in the recreational drug scene, often misrepresented as [[Chemistry:LSD|LSD]]. The recreational usage of 25I is associated with severe intoxication and deaths in humans.<ref>{{Cite journal | vauthors = Papoutsis I, Nikolaou P, Stefanidou M, Spiliopoulou C, Athanaselis S |date=2015-01-01 |title=25B-NBOMe and its precursor 2C-B: modern trends and hidden dangers |url=https://doi.org/10.1007/s11419-014-0242-9 |journal=Forensic Toxicology |language=en |volume=33 |issue=1 |pages=1–11 |doi=10.1007/s11419-014-0242-9 |s2cid=10469635 |issn=1860-8973}}</ref>

25I was synthesized for biochemistry research to map the brain's usage of the [[Biology:5-HT2A receptor|type 2A]] [[Chemistry:Serotonin receptor|serotonin receptor]]. A derivative of the [[Chemistry:Substituted phenethylamine|substituted phenethylamine]] [[Chemistry:2C-I|2C-I]] family, it is the most well-known member of the 25-NB family. It was discovered in 2003 by chemist Ralf Heim at the Free University of Berlin, who published his findings in his PhD dissertation.<ref name="ralfheim">{{cite web | vauthors = Heim R |title=Synthese und Pharmakologie potenter 5-HT<sub>2A</sub>-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts. |url=http://www.diss.fu-berlin.de/diss/receive/FUDISS_thesis_000000001221 |publisher=diss.fu-berlin.de |date=25 March 2003|language=German |access-date=2013-05-10}}</ref> The compound was subsequently investigated by a team at [[Organization:Purdue University|Purdue University]] led by David Nichols.<ref>{{cite journal | url=https://docs.lib.purdue.edu/dissertations/AAI3287241/ | title=Towards a biophysical understanding of hallucinogen action | publisher=Purdue University | journal=Dissertation | date=2007 | vauthors = Braden MR | pages=1–176 | name-list-style = vanc }}</ref>

The [[Physics:Isotopes of carbon#Carbon-11|carbon-11]] labelled version of 25I-NBOMe, [<sup>11</sup>C]Cimbi-5, was synthesized and validated as a [[Biology:Radioactive tracer|radiotracer]] for [[Physics:Positron emission tomography|positron emission tomography]] (PET) in Copenhagen.<ref name="11C-CIMBI-5">{{cite journal | vauthors = Ettrup A, Palner M, Gillings N, Santini MA, Hansen M, Kornum BR, Rasmussen LK, Någren K, Madsen J, Begtrup M, Knudsen GM | display-authors = 6 | title = Radiosynthesis and evaluation of 11C-CIMBI-5 as a 5-HT2A receptor agonist radioligand for PET | journal = Journal of Nuclear Medicine | volume = 51 | issue = 11 | pages = 1763–1770 | date = November 2010 | pmid = 20956470 | doi = 10.2967/jnumed.109.074021 | doi-access = free }}</ref><ref>{{cite journal | title=Design and synthesis of selective serotonin receptor agonists for positron emission tomography imaging of the brain | publisher=Det Farmaceutiske Fakultet, København | journal=Ph.D. Thesis | date=16 December 2010 | vauthors = Hansen M |citeseerx = 10.1.1.690.4529}}</ref> Being the first [[Biology:5-HT2A receptor|5-HT<sub>2A</sub>]] receptor full agonist PET radioligand, [<sup>11</sup>C]CIMBI-5 shows promise as a more functional marker of these receptors, particularly in their high affinity states.<ref name="11C-CIMBI-5"/>

Street and media nicknames for this drug are: "N-Bomb", "Solaris", "Smiles", and "Wizard", although the drug is frequently fraudulently sold as [[Chemistry:Lysergic acid diethylamide|LSD]].<ref>{{cite web | url=https://www.erowid.org/chemicals/2ci_nbome/ |title=Erowid 25I-NBOMe Vault}}</ref><ref>{{cite web | url=https://www.sciencedaily.com/releases/2015/04/150409162230.htm | title=Poison center warns against designer drug 'N-bomb' | publisher=ScienceDaily | date=9 April 2015 | author=Vanderbilt University Medical Center}}</ref><ref name="mackin2012">Mackin, Teresa (October 9, 2012). [http://www.wishtv.com/dpp/news/indiana/dangerous-synthetic-drug-smiles-making-its-way-across-the-country Dangerous synthetic drug making its way across the country.] {{webarchive |url=https://web.archive.org/web/20121031163611/http://www.wishtv.com/dpp/news/indiana/dangerous-synthetic-drug-smiles-making-its-way-across-the-country |date=October 31, 2012 }} WISH-TV</ref>

Due to its physical effects and risk of overdose, there have been multiple deaths attributed to the drug. Its long term toxicity is unknown due to lack of existing research.

==Recreational use==
Although 25I-NBOMe was discovered in 2003, it did not emerge as a common recreational drug until 2010, when it was first sold by vendors specializing in the supply of [[Chemistry:Designer drug|designer drug]]s.<ref>{{cite web | vauthors = Morgans J | title=Everything We Know About NBOMe and Why it's Killing People | website=Vice | date=2017-02-08 | url=https://www.vice.com/en_nz/article/4x7jen/nbome-in-australia-everything-we-know-about-what-it-is-and-why-its-killing-people | access-date=2019-07-23}}</ref> In a slang context, the name of the compound is often shortened to "25I" or is simply called "N-Bomb"( Enbalm?).<ref name="NY Daily news"/> According to a 2014 survey, 25I-NBOMe was the most frequently used of the NBOMe series.<ref name="Lawn 2014">{{cite journal | vauthors = Lawn W, Barratt M, Williams M, Horne A, Winstock A | title = The NBOMe hallucinogenic drug series: Patterns of use, characteristics of users and self-reported effects in a large international sample | journal = Journal of Psychopharmacology | volume = 28 | issue = 8 | pages = 780–788 | date = August 2014 | pmid = 24569095 | doi = 10.1177/0269881114523866 | s2cid = 35219099 | url = https://researchrepository.rmit.edu.au/view/delivery/61RMIT_INST/12247449250001341/13257311840001341 }}</ref> By 2013, case reports of 25I-NBOMe intoxication, with and without analytic confirmation of the drug in the body, were becoming increasingly common in the medical literature.<ref name="Clinical Toxicology Cases" />

25I-NBOMe is widely rumored to be orally inactive; however, apparent overdoses have occurred via oral administration. Common routes of administration include [[Medicine:Sublingual administration|sublingual]], [[Medicine:Buccal administration|buccal]], and intranasal.<ref name="Lawn 2014" /> For sublingual and buccal administration, 25I-NBOMe is often applied to sheets of blotter paper of which small portions (''tabs'') are held in the mouth to allow absorption through the oral mucosa.<ref>{{cite journal | vauthors = Poklis JL, Raso SA, Alford KN, Poklis A, Peace MR | title = Analysis of 25I-NBOMe, 25B-NBOMe, 25C-NBOMe and Other Dimethoxyphenyl-N-[(2-Methoxyphenyl) Methyl]Ethanamine Derivatives on Blotter Paper | journal = Journal of Analytical Toxicology | volume = 39 | issue = 8 | pages = 617–623 | date = October 2015 | pmid = 26378135 | pmc = 4570937 | doi = 10.1093/jat/bkv073 }}</ref><ref name="ACMD Report" /> There are reports of intravenous injection of 25I-NBOMe solution and smoking the drug in powdered form.<ref name="British Case Reports">{{cite journal | vauthors = Hill SL, Doris T, Gurung S, Katebe S, Lomas A, Dunn M, Blain P, Thomas SH | display-authors = 6 | title = Severe clinical toxicity associated with analytically confirmed recreational use of 25I-NBOMe: case series | journal = Clinical Toxicology | volume = 51 | issue = 6 | pages = 487–492 | date = July 2013 | pmid = 23731373 | doi = 10.3109/15563650.2013.802795 | s2cid = 41259282 }}</ref><ref name="erowid effects" />

Due to its potency and much lower cost than so-called classical or traditional psychedelics, 25I-NBOMe blotters are frequently misrepresented as, or mistaken for, [[Chemistry:Lysergic acid diethylamide|LSD]] blotters.<ref name="Erowid Main">{{cite web |title=25I-NBOMe |url=https://www.erowid.org/chemicals/2ci_nbome/2ci_nbome.shtml |publisher=Erowid}}</ref> Even small quantities of 25I-NBOMe can produce a large number of blotters. Vendors would import 25I-NBOMe in bulk (e.g., 1&nbsp;kg containers) and resell individual doses for a considerable profit.<ref name="ACMD Report" />

==Dosage==
25I-NBOMe is potent, being active in sub-milligram doses. A common dose of the hydrochloride salt is 600–1,200&nbsp;[[Microgram|μg]]. The UK Advisory Council on the Misuse of Drugs states that a common dose is between 50 and 100&nbsp;μg,<ref name="ACMD Report">{{cite web | url=https://www.gov.uk/government/publications/temporary-class-drug-order-report-on-benzofury-and-nbome-compounds | title=Temporary class drug order on benzofury and NBOMe compounds | publisher=Gov.Uk | work=Advisory Council on the Misuse of Drugs | date=4 June 2013 | vauthors = Iversen L }}</ref> although other sources indicate that these figures are incorrect; [[Organization:Erowid|Erowid]] tentatively suggests that the threshold dosage for humans is 50–250&nbsp;μg, with a light dose between 200–600&nbsp;μg, a common dose at 500–800&nbsp;μg, and a strong dose at 700–1500&nbsp;μg.<ref name="erowid-dose">{{Cite web |url=https://www.erowid.org/chemicals/2ci_nbome/2ci_nbome_dose.shtml |title=2C-I-NBOMe (25I) Dose |publisher=Erowid}}</ref>

At this level of potency, it is not possible to accurately measure a single dose of 25I-NBOMe powder without an [[Engineering:Analytical balance|analytical balance]], and attempting to do so may put the user at significant risk of overdose.<ref name="ACMD Report" /> There is a high risk of overdose due to the small margin between a high-dose and an over-dose, which is not a risk with the similar drug [[Chemistry:Lysergic acid diethylamide|LSD]]. One study has shown that 25I-NBOMe blotters have 'hotspots' of the drug and the dosage is not evenly applied over the surface of the paper, which could lead to overdose.<ref>{{cite journal | vauthors = Lützen E, Holtkamp M, Stamme I, Schmid R, Sperling M, Pütz M, Karst U | title = Multimodal imaging of hallucinogens 25C- and 25I-NBOMe on blotter papers | journal = Drug Testing and Analysis | volume = 12 | issue = 4 | pages = 465–471 | date = April 2020 | pmid = 31846172 | doi = 10.1002/dta.2751 | s2cid = 209388281 | doi-access = free }}</ref>

==Effects==
25I-NBOMe effects usually last 6–10 hours if taken sublingually, or buccally (between gum and cheek).<ref name="erowid effects" />{{medical citation needed | date = June 2023}} When it is insufflated (snorted), effects usually last 4–6 hours.<ref name= "erowid effects">{{Cite web |url=https://www.erowid.org/chemicals/2ci_nbome/2ci_nbome_effects.shtml |title=2C-I-NBOMe (25I) Effects |publisher=Erowid}}</ref>{{medical citation needed | date = June 2023}}

25I-NBOMe has similar effects to LSD, though users report more negative effects while under the influence and more risk of harm following use as compared to the classical psychedelics.<ref name="Lawn 2014" />

Case reports of seven British males who presented to an emergency room following analytically confirmed 25I-NBOMe intoxication suggest the following potential adverse effects: "[[Medicine:Tachycardia|tachycardia]] (n = 7), [[Medicine:Hypertension|hypertension]] (4), agitation (6), [[Philosophy:Aggression|aggression]], visual and [[Unsolved:Auditory hallucination|auditory]] hallucinations (6), seizures (3), hyperpyrexia (3), [[Medicine:Clonus|clonus]] (2), elevated [[Biology:White blood cell|white blood cell]] count (2), elevated [[Biology:Creatine kinase|creatine kinase]] (7), metabolic acidosis (3), and [[Medicine:Acute kidney injury|acute kidney injury]] (1)."<ref name="British Case Reports" />

25I-NBOMe can be consumed in liquid, powder or paper form and can be snorted, injected, mixed with food, or smoked, but sublingual administration is most common.<ref>{{Cite web| vauthors = Areas-Holmblad L |date=2016-12-11|title=Using 'n-bomb' can kill you ~ Drug Addiction Now|url=https://www.drugaddictionnow.com/2016/12/11/using-n-bomb-can-kill-you/|access-date=2020-09-04|website=Addiction Now {{!}} Substance Abuse, Drug Addiction and Recovery News Source|language=en-US}}</ref>

==Toxicity and harm potential==
{{Excerpt | 25-NB | Toxicity and harm potential}}
===Neurotoxic and cardiotoxic actions===
{{Excerpt | 25-NB | Neurotoxic and cardiotoxic actions}}
===Emergency treatment===
{{Excerpt | 25-NB | Emergency treatment}}

== Attributed deaths ==
Reports of deaths and significant injuries have been attributed to the use of 25I-NBOMe, prompting some governments to control its possession, production, and sale. The website [[Organization:Erowid|Erowid]] states that 25I-NBOMe is extremely potent and should not be snorted, and that the drug "appears to have led to several deaths in the past year."<ref name="Erowid Main" /> Several non-fatal overdoses requiring prolonged hospitalization have also been reported.<ref name="ACMD Report" /><ref name="Clinical Toxicology Cases" /><ref name="British Case Reports" />

As of August 2015, 25I-NBOMe has reportedly led to at least 19 overdose deaths in the United States.<ref name="NY Daily news">{{cite news| vauthors = Hastings D |title=New drug N-bomb hits the street, terrifying parents, troubling cops|url=http://www.nydailynews.com/news/national/new-synthetic-hallucinogen-n-bomb-killing-users-cops-article-1.1336327|access-date=7 May 2013|newspaper=New York Daily News|date=May 6, 2013}}</ref><ref name="DEA 2013">{{cite web | url=https://www.dea.gov/divisions/hq/2013/hq111513.shtml | title=Three More Synthetic Drugs Become Illegal for at Least Two Years | publisher=United States Drug Enforcement Administration (DEA) | date=15 November 2013}}</ref> In June 2012, two teens in Grand Forks, North Dakota and East Grand Forks, Minnesota fatally overdosed on a substance that was allegedly 25I-NBOMe, resulting in lengthy sentences for two of the parties involved and a Federal indictment against the Texas-based online vendor.<ref>{{cite web | url=http://www.houstonpress.com/news/breaking-bad-digital-drug-sales-analog-drug-deaths-6600085 | title=Breaking Bad: Digital Drug Sales, Analog Drug Deaths | publisher=Houston Press | date=13 March 2013 | vauthors = Malisow C }}</ref> A 21-year-old man from Little Rock, Arkansas died in October 2012 after taking a liquid drop of the drug nasally at a music festival. He was reported to have consumed caffeinated alcoholic beverages for "several hours" beforehand. It is unclear what other drugs he may have consumed, as autopsies generally do not test for the presence of research chemicals.<ref>{{cite web | url=http://www.nola.com/crime/index.ssf/2012/11/21-year-old_dies_after_one_dro.html | title=21-year-old dies after one drop of new synthetic drug at Voodoo Fest | publisher=NOLA.com | date=1 November 2012 | vauthors = Martin N }}</ref> In January 2013, an 18-year-old in Scottsdale, Arizona, died after consuming 25I-NBOMe sold as LSD; a toxicology screening found no other drugs in the person's system. The drug is the suspected cause of death in another Scottsdale, Arizona, incident in April 2013.<ref name="ACMD Report" /> It is also cited in the death of a 21-year-old woman in August 2013<ref>{{cite web | url=http://www.hibbingmn.com/news/local/fatal-overdose-case-continues/article_9f8ddd1e-c2e7-11e4-a5d4-1b3a0556b8e7.html | title=Fatal overdose case continues | publisher=Hibbing Daily Tribune | date=5 March 2015}}</ref> and the death of a 17-year-old in Minnesota in January 2014,<ref>{{cite web | url=http://www.startribune.com/after-friend-s-od-death-teens-get-a-reprieve/301502311/ | title=After friend's OD death, teens get a reprieve | publisher=Star Tribune | date=28 April 2015 | vauthors = Giles K }}</ref> as well as the death of a 15-year old in Washington in September 2014.<ref>{{cite journal | vauthors = Lowe LM, Peterson BL, Couper FJ | title = A Case Review of the First Analytically Confirmed 25I-NBOMe-Related Death in Washington State | journal = Journal of Analytical Toxicology | volume = 39 | issue = 8 | pages = 668–671 | date = October 2015 | pmid = 26378143 | doi = 10.1093/jat/bkv092 | doi-access = free }}</ref> In October 2015, a 20-year-old UCSB student from Isla Vista, California died of "acute hallucinogenic polysubstance intoxication" with an additional significant cause of death being "sharp force trauma of the upper extremity", according to a statement from Santa Barbara County Sheriff's office; the autopsy determined Sanchez was under the influence of two hallucinogenic drugs at the time of his death: ketamine and 25I-NBOMe. The noted sharp force trauma refers to a deep cut on Sanchez's right forearm, which was caused when he punched and broke a large residential window while suffering hallucinations.<ref>{{cite web | url = https://dailynexus.com/2015-11-16/autopsy-results-released-in-death-of-ucsb-student/ | title = Autopsy Results Released in Death of UCSB Student | vauthors = Nicholas BB | date = 16 November 2015 | publisher = Daily Nexus | url-status = live | archive-url = https://web.archive.org/web/20230323201110/https://dailynexus.com/2015-11-16/autopsy-results-released-in-death-of-ucsb-student/ | archive-date = 23 March 2023}}</ref>

25I-NBOMe has been implicated in multiple deaths in Australia. In March 2012, a man in Australia died from injuries sustained by running into trees and power poles while intoxicated by 25I-NBOMe.<ref name="Crashing into poles">{{cite news | url=https://www.news.com.au/tablet/new-hallucinogenic-drug-25b-nbome-and-25i-nbome-led-to-south-australian-mans-bizarre-death/news-story/4152ed55c8105a07b513718fd13694e4 | title=New hallucinogenic drug 25B-NBOMe and 25I-NBOMe led to South Australian man's bizarre death | date=12 September 2012 | vauthors = Rice S | newspaper=News.com.au | location=Australia}}</ref> A Sydney teenager jumped off a balcony to his death on June 5, 2013, while on 25I-NBOMe.<ref>{{Cite web | vauthors = Davies N, Ralston L | date=2013-06-07 |title='He wanted to fly': father says son made a fatal mistake |url=https://www.smh.com.au/national/nsw/he-wanted-to-fly-father-says-son-made-a-fatal-mistake-20130607-2nu3i.html |access-date=2022-06-22 |website=The Sydney Morning Herald |language=en}}</ref>

25I-NBOMe has been linked to a major case on January 20, 2016, in Cork, Republic of Ireland, which left six teenagers hospitalized, one of whom later died. At least one of the teenagers suffered a [[Medicine:Cardiac arrest|cardiac arrest]], according to reports, along with extreme internal bleeding.<ref name="Ireland injuries">{{cite news | url=http://www.independent.ie/irish-news/powerful-nbomb-drug-responsible-for-spate-of-deaths-internationally-responsible-for-hospitalisation-of-six-in-cork-34384507.html | title=Powerful N-Bomb drug - responsible for spate of deaths internationally - responsible for hospitalisation of six in Cork | date=21 January 2016 | vauthors = Feehan C | newspaper=Irish Independent}}</ref>

At least one suicide, and two attempted suicides leading to hospitalisation, have occurred while under the effects of 25I-NBOMe.<ref name="Lipow_2022">{{Cite journal | vauthors = Lipow M, Kaleem SZ, Espiridion E |date=2022-03-30 |title=NBOMe Toxicity and Fatalities: A Review of the Literature |url=https://scholarcommons.towerhealth.org/t-med/vol1/iss1/3 |journal=Transformative Medicine |volume=1 |issue=1 |pages=12–18 |doi=10.54299/tmed/msot8578 |s2cid=247888583 |issn=2831-8978|doi-access=free }}</ref>

==Pharmacology==
{| class="wikitable sortable" style="text-align: right; float: right; margin-left: 2em;"
|+ 25I-NBOMe<ref name="pmid21174090"/><ref name="pmid18468904"/>
|-
! scope="col" | Receptor || ''K''<sub>d</sub> (nM) || class="unsortable" | ±
|-
! scope="row" | 5-HT<sub>2A</sub>
| 0.044
|-
! scope="row" | 5-HT<sub>2B</sub>
| 231 || 73
|-
! scope="row" | 5-HT<sub>2C</sub>
| 2
|-
! scope="row" | 5-HT<sub>6</sub>
| 73 || 12
|-
! scope="row" | μ-opioid
| 82 || 14
|-
! scope="row" | [[Biology:Κ-opioid receptor|κ-opioid]]
| 288 || 50
|-
! scope="row" | H<sub>1</sub>
| 189 || 35
|}

25I-NBOMe acts as a highly [[Chemistry:Potency (pharmacology)|potent]] full [[Biology:Agonist|agonist]] for the [[Biology:Human|human]] [[Biology:5-HT2A receptor|5-HT<sub>2A</sub>]] [[Biology:Receptor (biochemistry)|receptor]],<ref name="pmid21174090">{{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 }}
</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 | s2cid = 3103050 | citeseerx = 10.1.1.688.2670 | bibcode = 2011JCAMD..25...51S }}</ref> with a [[Chemistry:Dissociation constant|dissociation constant]] (''K''<sub>d</sub>) of 0.044&nbsp;nM, making it some sixteen times the potency of [[Chemistry:2C-I|2C-I]] itself at this receptor. A radiolabelled form of 25I-NBOMe can be used for mapping the distribution of 5-HT<sub>2A</sub> receptors in the brain.<ref name="pmid18468904">{{cite journal | vauthors = Nichols DE, Frescas SP, Chemel BR, Rehder KS, Zhong D, Lewin AH | title = High specific activity tritium-labeled N-(2-methoxybenzyl)-2,5-dimethoxy-4-iodophenethylamine (INBMeO): a high-affinity 5-HT2A receptor-selective agonist radioligand | journal = Bioorganic & Medicinal Chemistry | volume = 16 | issue = 11 | pages = 6116–6123 | date = June 2008 | pmid = 18468904 | pmc = 2719953 | doi = 10.1016/j.bmc.2008.04.050 }}</ref>

25I-NBOMe induces a [[Medicine:Head-twitch response|head-twitch response]] in mice which is blocked completely by a selective 5-HT<sub>2A</sub> antagonist, suggesting its psychedelic effects are mediated by 5-HT<sub>2A</sub>. This study suggested that 25I-NBOMe is approximately 14-fold more potent than 2C-I ''in-vivo''.<ref name="pmid=24012658">{{cite journal | vauthors = Halberstadt AL, Geyer MA | title = Effects of the hallucinogen 2,5-dimethoxy-4-iodophenethylamine (2C-I) and superpotent N-benzyl derivatives on the head twitch response | journal = Neuropharmacology | volume = 77 | pages = 200–207 | date = February 2014 | pmid = 24012658 | pmc = 3866097 | doi = 10.1016/j.neuropharm.2013.08.025 }}</ref>

While ''in-vitro'' studies showed that ''N''-benzyl derivatives of 2C-I were significantly increased in potency compared to 2C-I, the ''N''-benzyl derivatives of the related compound [[Chemistry:2,5-Dimethoxy-4-iodoamphetamine|DOI]] were inactive.<ref>{{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 }}</ref>

25I-NBOMe also has weaker interactions with multiple other receptors.  ''K''<sub>d</sub> values for interaction with the following targets were greater than 500&nbsp;nM: 5-HT<sub>1A</sub>, [[Biology:Dopamine receptor D3|D<sub>3</sub>]], H<sub>2</sub>, 5-HT<sub>1D</sub>, [[Biology:Alpha-1 adrenergic receptor|α<sub>1A</sub> adrenergic]], [[Biology:Δ-opioid receptor|δ opioid]], [[Biology:Serotonin transporter|serotonin uptake transporter]], 5-HT<sub>5A</sub>, 5-HT<sub>1B</sub>, [[Biology:Dopamine receptor D2|D<sub>2</sub>]], 5-HT<sub>7</sub>, [[Biology:Dopamine receptor D1|D<sub>1</sub>]], 5-HT<sub>3</sub>, 5-HT<sub>1E</sub>, [[Biology:Dopamine receptor D5|D<sub>5</sub>]], [[Biology:Muscarinic acetylcholine receptor|muscarinic M<sub>1</sub>-M<sub>5</sub>]], [[Biology:Histamine H3 receptor|H<sub>3</sub>]], and the [[Biology:Dopamine transporter|dopamine uptake transporter]].<ref name="pmid18468904"/>

==Chemistry==
Like other 2C-''X''-NBOMe molecules, 25I-NBOMe is a derivative of the [[Chemistry:2C (psychedelics)|2C]] family of phenethylamines described by chemist Alexander Shulgin in his book [[Chemistry:PiHKAL|PiHKAL]].<ref name="ACMD Report" /><ref name="Clinical Toxicology Cases">{{cite journal | vauthors = Rose SR, Poklis JL, Poklis A | title = A case of 25I-NBOMe (25-I) intoxication: a new potent 5-HT2A agonist designer drug | journal = Clinical Toxicology | volume = 51 | issue = 3 | pages = 174–177 | date = March 2013 | pmid = 23473462 | pmc = 4002208 | doi = 10.3109/15563650.2013.772191 }}</ref> Specifically, 25I-NBOMe is an ''N''-benzyl derivative of the phenethylamine molecule [[Chemistry:2C-I|2C-I]], formed by adding a 2-methoxybenzyl (BnOMe) onto the nitrogen (N) of the phenethylamine backbone. This substitution significantly increases the potency of the molecule.<ref name="ACMD Report" />

===Analogues===
{{2C-I analogues and derivatives}}

===Synthesis===
25I-NBOMe is usually synthesised from 2C-I and 2-methoxybenzaldehyde, via reductive [[Chemistry:Alkylation|alkylation]]. It can be done stepwise by first making the [[Chemistry:Imine|imine]] and then [[Chemistry:Redox|reducing]] the formed imine with [[Chemistry:Sodium borohydride|sodium borohydride]], or by direct reaction with [[Chemistry:Sodium triacetoxyborohydride|sodium triacetoxyborohydride]].<ref name=ralfheim />

==Society and culture==

===Legal status===

====Australia====
25I-NBOMe was explicitly scheduled in Queensland drug law in April 2012, and in New South Wales in October 2013, as were some related compounds such as 25B-NBOMe. The Australian federal government has no specific legislation concerning any of the N-benzyl phenethylamines.<ref>{{cite web | url=https://www.legislation.gov.au/Details/F2015L01534/Html/Text#_Toc420496379 | title=Poisons Standard October 2015 | publisher=Australian Government | date=October 2015}}</ref>

====Canada====
As of October 31, 2016; 25I-NBOMe is a controlled substance (Schedule III) in Canada.<ref>{{cite web | url=http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php | title=Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)| date=4 May 2016| publisher=Canada Gazette }}</ref>

====China====
As of October 2015 25I-NBOMe is a controlled substance in China.<ref>{{cite web | url=http://www.sfda.gov.cn/WS01/CL0056/130753.html | title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | publisher=China Food and Drug Administration | date=27 September 2015 | language=Chinese | access-date=1 October 2015 | archive-url=https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html | archive-date=1 October 2015 | url-status=dead }}</ref>

====European Union====
In September 2014 the [[Social:European Union|European Union]] implemented a ban of 25I-NBOMe in all its member states.<ref>{{cite web | url=http://eur-lex.europa.eu/legal-content/EN/TXT/PDF/?uri=CELEX:32014D0688 | title=Council Implementing Decision (2014/688/EU) | publisher=Official Journal of the European Union | date=1 October 2014}}</ref>

====Israel====
Israel banned 25I-NBOMe in 2013.<ref name="Legal status erowid" />

====Russia====
Russia was the first country to pass specific regulations on the NBOMe series. All drugs in the NBOMe series, including 25I-NBOMe, became illegal in Russia in October 2011.<ref name="Legal status erowid">{{cite web |url=https://www.erowid.org/chemicals/2ci_nbome/2ci_nbome_law.shtml |title=2C-I-NBOMe Legal Status |publisher=Erowid}}</ref>

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

====United States====
On Nov 15, 2013, the DEA added 25I-NBOMe (and 25C-, and 25B-NBOMe) to Schedule I using their emergency scheduling powers, making those NBOMe compounds "temporarily" in Schedule I for 2 years.<ref name="DEA 2013"/> In November 2015, the temporary scheduling was extended for an additional year<ref name="pmid26567439">{{cite journal | author = Drug Enforcement Administration | title = Schedules of Controlled Substances: Extension of Temporary Placement of Three Synthetic Phenethylamines in Schedule I. Final order | journal = Federal Register | volume = 80 | issue = 219 | pages = 70657–70659 | date = November 2015 | pmid = 26567439 | url = https://www.gpo.gov/fdsys/pkg/FR-2015-11-13/pdf/2015-29028.pdf }}</ref> while permanent scheduling was arranged.<ref>{{cite web |url=https://www.deadiversion.usdoj.gov/fed_regs/rules/2016/fr0927_2.htm |title=Schedules of Controlled Substances: Placement of Three Synthetic Phenethylamines Into Schedule I |archive-url=https://web.archive.org/web/20170513140029/https://www.deadiversion.usdoj.gov/fed_regs/rules/2016/fr0927_2.htm |archive-date=May 13, 2017 |access-date=May 15, 2017}}</ref> 25I-NBOMe, 25B-NBOMe and 25C-NBOMe are currently Schedule 1 Substances according to 21 CFR 1308.11(d).<ref>{{cite web|url=https://www.ecfr.gov/cgi-bin/text-idx?SID=b632b274cf6322a0450af69d7c7a4f46&node=pt21.9.1308&rgn=div5#se21.9.1308_111|title=eCFR PART 1308—SCHEDULES OF CONTROLLED SUBSTANCES Schedule I.}}</ref>

====Romania====
In 2011, Romania banned all psychoactive substances.<ref>{{cite web | url=http://www.dreptonline.ro/legislatie/legea_194_2011_combaterea_operatiunilor_produse_susceptibile_efecte_psihoactive.php | title=Legea 194/2011 privind combaterea operatiunilor cu produse susceptibile de a avea efecte psihoactive, altele decat cele prevazute de acte normative in vigoare, republicata 2014 | publisher=Drept OnLine}}</ref>

====Serbia====
25I-NBOMe was put on the list of prohibited substances in March 2015.<ref>{{cite web | url=http://www.zdravlje.gov.rs/ | title=Министарство здравља Републикe Србије}}</ref>

====Sweden====
The Riksdag added 25I-NBOMe to Narcotic Drugs Punishments Act under ''Swedish schedule I'' (''"substances, plant materials and fungi which normally do not have medical use"'') as of August 1, 2013, published by [[Organization:Medical Products Agency (Sweden)|Medical Products Agency (MPA)]] in regulation ''LVFS 2013:15'' listed as '''25I-NBOMe''', and '''2-(4-jodo-2,5-dimetoxifenyl)-N-(2-metoxibensyl)etanamin'''.<ref>{{cite web | title = Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 2011:10) om förteckningar över narkotika | trans-title = Regulations amending the Medical Products Agency's regulations (LVFS 2011: 10) on lists of drugs | language = Swedish | date = 11 July 2013 | work = Läkemedelsverkets (The Medical Products Agency) | url = https://lakemedelsverket.se/upload/lvfs/LVFS_2013-15.pdf | archive-url = https://web.archive.org/web/20130928024035/https://lakemedelsverket.se/upload/lvfs/LVFS_2013-15.pdf | archive-date = 28 September 2013 }}</ref>

====Taiwan====
Following the European rule from 2014, 25I-NBOMe was put in class 4 of prohibited substances.<ref>{{cite web | url=http://www.fda.gov.tw/TC/index.aspx | title=衛生福利部食品藥物管理署| date=25 July 2016}}</ref>

====Brazil====
All drugs in the NBOMe family, including 25I-NBOMe, are illegal.


'''United Arab Emirates'''

The UAE has a zero-tolerance policy for recreational use of drugs. Federal Law No. 14 of 1995 criminalises production, import, export, transport, buying, selling, possessing, storing of narcotic and psychotropic substances (Including 25i-NBOMe) unless done so as part of supervised and regulated medical or scientific activities in accordance with the applicable laws. The UAE police has dedicated departments to deal with drugs' issues.<ref>{{Cite web |title=Drugs and controlled medicines {{!}} The Official Portal of the UAE Government |url=https://u.ae/en/information-and-services/health-and-fitness/drugs-and-controlled-medicines |access-date=2024-01-25 |website=u.ae |language=en}}</ref>





==Notes==
{{notelist}}

== References ==
{{Reflist|30em}}

{{Hallucinogens}}
{{Serotonin receptor modulators}}
{{Phenethylamines}}

[[Category:Iodoarenes]]
[[Category:Designer drugs]]
[[Category:5-HT2A agonists]]
[[Category:5-HT2C agonists]]

{{Sourceattribution|25I-NBOMe}}