25I-NBOMe

Although 25I-NBOMe was first described by 2000, it did not emerge as a common recreational drug until 2010, when it was first sold by vendors specializing in the supply of designer drugs.{{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/article/nbome-in-australia-everything-we-know-about-what-it-is-and-why-its-killing-people/ | access-date=2019-07-23 | archive-date=2019-07-24 | archive-url=https://web.archive.org/web/20190724033545/https://www.vice.com/en_nz/article/4x7jen/nbome-in-australia-everything-we-know-about-what-it-is-and-why-its-killing-people | url-status=live }} In a slang context, the name of the compound is often shortened to "25I" or is simply called "N-Bomb". According to a 2014 survey, 25I-NBOMe was the most frequently used of the NBOMe series.{{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 | hdl = 1959.4/unsworks_73366 | hdl-access = free }} 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.

25I-NBOMe is widely rumored to be orally inactive; however, apparent overdoses have occurred via oral administration. Common routes of administration include sublingual, buccal, and intranasal. 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.{{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 }} There are reports of intravenous injection of 25I-NBOMe solution and smoking the drug in powdered form.{{cite journal | vauthors = Hill SL, Doris T, Gurung S, Katebe S, Lomas A, Dunn M, Blain P, Thomas SH | 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 }}

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 LSD blotters.{{cite web |title=25I-NBOMe |url=https://www.erowid.org/chemicals/2ci_nbome/2ci_nbome.shtml |publisher=Erowid}} Even small quantities of 25I-NBOMe can produce a large number of blotters. Vendors would import 25I-NBOMe in bulk (e.g., 1 kg containers) and resell individual doses for a considerable profit.

25I-NBOMe is potent, being active in sub-milligram doses. A common dose of the hydrochloride salt is 600–1,200 μg. The UK Advisory Council on the Misuse of Drugs states that a common dose is between 50 and 100 μg,{{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 | access-date=28 June 2016 | archive-date=24 August 2017 | archive-url=https://web.archive.org/web/20170824221356/https://www.gov.uk/government/publications/temporary-class-drug-order-report-on-benzofury-and-nbome-compounds | url-status=live }} although other sources indicate that these figures are incorrect; Erowid tentatively suggests that the threshold dosage for humans is 50–250 μg, with a light dose between 200–600 μg, a common dose at 500–800 μg, and a strong dose at 700–1500 μg.{{Cite web |url=https://www.erowid.org/chemicals/2ci_nbome/2ci_nbome_dose.shtml |title=2C-I-NBOMe (25I) Dose |publisher=Erowid |access-date=2016-06-28 |archive-date=2016-06-30 |archive-url=https://web.archive.org/web/20160630093827/https://www.erowid.org/chemicals/2ci_nbome/2ci_nbome_dose.shtml |url-status=live }}

At this level of potency, it is not possible to accurately measure a single dose of 25I-NBOMe powder without an analytical balance, and attempting to do so may put the user at significant risk of overdose. 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 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.{{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 }}

25I-NBOMe effects usually last 6–10 hours if taken sublingually, or buccally (between gum and cheek). When it is insufflated (snorted), effects usually last 4–6 hours.{{Cite web |url=https://www.erowid.org/chemicals/2ci_nbome/2ci_nbome_effects.shtml |title=2C-I-NBOMe (25I) Effects |publisher=Erowid |access-date=2016-06-28 |archive-date=2016-06-30 |archive-url=https://web.archive.org/web/20160630093825/https://www.erowid.org/chemicals/2ci_nbome/2ci_nbome_effects.shtml |url-status=live }}

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.

Case reports of seven British males who presented to an emergency room following analytically confirmed 25I-NBOMe intoxication suggest the following potential adverse effects: "tachycardia (n = 7), hypertension (4), agitation (6), aggression, visual and auditory hallucinations (6), seizures (3), hyperpyrexia (3), clonus (2), elevated white blood cell count (2), elevated creatine kinase (7), metabolic acidosis (3), and acute kidney injury (1)."

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.{{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|archive-date=2020-09-13|archive-url=https://web.archive.org/web/20200913183353/https://www.drugaddictionnow.com/2016/12/11/using-n-bomb-can-kill-you/|url-status=live}}

{{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}

2C drugs like 2C-I are metabolized by the monoamine oxidase (MAO) enzymes, including both MAO-A and MAO-B.{{cite journal | vauthors = Dean BV, Stellpflug SJ, Burnett AM, Engebretsen KM | title = 2C or not 2C: phenethylamine designer drug review | journal = J Med Toxicol | volume = 9 | issue = 2 | pages = 172–178 | date = June 2013 | pmid = 23494844 | pmc = 3657019 | doi = 10.1007/s13181-013-0295-x | url = }}{{cite journal | vauthors = Theobald DS, Maurer HH | title = Identification of monoamine oxidase and cytochrome P450 isoenzymes involved in the deamination of phenethylamine-derived designer drugs (2C-series) | journal = Biochem Pharmacol | volume = 73 | issue = 2 | pages = 287–297 | date = January 2007 | pmid = 17067556 | doi = 10.1016/j.bcp.2006.09.022 | url = }} As a result, 2C drugs may be potentiated by monoamine oxidase inhibitors (MAOIs), such as phenelzine, tranylcypromine, moclobemide, and selegiline.{{Cite journal |vauthors=Halman A, Kong G, Sarris J, Perkins D |date=January 2024 |title=Drug-drug interactions involving classic psychedelics: A systematic review |journal=J Psychopharmacol |volume=38 |issue=1 |pages=3–18 |doi=10.1177/02698811231211219 |pmc=10851641 |pmid=37982394}} This has the potential to lead to overdose and serious toxicity. In contrast to 2C drugs, 25I-NBOMe has been found not to be metabolized by MAO-A or MAO-B and instead only by cytochrome P450 enzymes. Other 25-NB drugs besides 25I-NBOMe were not assessed.

{{Excerpt | 25-NB | Toxicity and harm potential}}

{{Excerpt | 25-NB | Neurotoxic and cardiotoxic actions}}

{{Excerpt | 25-NB | Emergency treatment}}

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 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." Several non-fatal overdoses requiring prolonged hospitalization have also been reported.

As of August 2015, 25I-NBOMe has reportedly led to at least 19 overdose deaths in the United States.{{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|archive-date=10 May 2013|archive-url=https://web.archive.org/web/20130510103039/http://www.nydailynews.com/news/national/new-synthetic-hallucinogen-n-bomb-killing-users-cops-article-1.1336327|url-status=live}}{{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 | access-date=28 June 2016 | archive-date=15 August 2016 | archive-url=https://web.archive.org/web/20160815162920/https://www.dea.gov/divisions/hq/2013/hq111513.shtml | url-status=live }} 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.{{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 | access-date=28 June 2016 | archive-date=10 August 2016 | archive-url=https://web.archive.org/web/20160810010003/http://www.houstonpress.com/news/breaking-bad-digital-drug-sales-analog-drug-deaths-6600085 | url-status=live }} 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.{{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 | access-date=2 November 2012 | archive-date=3 November 2012 | archive-url=https://web.archive.org/web/20121103092517/http://www.nola.com/crime/index.ssf/2012/11/21-year-old_dies_after_one_dro.html | url-status=live }} 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. It is also cited in the death of a 21-year-old woman in August 2013{{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}} and the death of a 17-year-old in Minnesota in January 2014,{{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 | access-date=28 June 2016 | archive-date=11 June 2016 | archive-url=https://web.archive.org/web/20160611223052/http://www.startribune.com/after-friend-s-od-death-teens-get-a-reprieve/301502311/ | url-status=live }} as well as the death of a 15-year old in Washington in September 2014.{{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 }} 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.{{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}}

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.{{cite news |date=12 September 2012 |title=New hallucinogenic drugs lead to Aussie man's death after running repeatedly into trees |url=https://www.tntmagazine.com/archive/new-hallucinogenic-drugs-lead-to-aussie-mans-death-after-running-repeatedly-into-trees/ |url-status=live |archive-url=https://web.archive.org/web/20221208064232/https://www.tntmagazine.com/archive/new-hallucinogenic-drugs-lead-to-aussie-mans-death-after-running-repeatedly-into-trees/ |archive-date=8 December 2022 |access-date=23 August 2024 |newspaper=TNT Magazine |location=United Kingdom |vauthors= }} A Sydney teenager jumped off a balcony to his death on June 5, 2013, while on 25I-NBOMe.{{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 |archive-date=2022-06-22 |archive-url=https://web.archive.org/web/20220622125305/https://www.smh.com.au/national/nsw/he-wanted-to-fly-father-says-son-made-a-fatal-mistake-20130607-2nu3i.html |url-status=live }}

25I-NBOMe has been linked to a major case on January 20, 2016, in Cork, Ireland, which left six teenagers hospitalized, one of whom later died. At least one of the teenagers suffered a cardiac arrest, according to reports, along with extreme internal bleeding.{{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 | access-date=22 January 2016 | archive-date=12 April 2019 | archive-url=https://web.archive.org/web/20190412203933/https://www.independent.ie/irish-news/powerful-nbomb-drug-responsible-for-spate-of-deaths-internationally-responsible-for-hospitalisation-of-six-in-cork-34384507.html | url-status=live }}

At least one suicide, and two attempted suicides leading to hospitalisation, have occurred while under the effects of 25I-NBOMe.{{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 |access-date=2022-06-21 |archive-date=2023-02-01 |archive-url=https://web.archive.org/web/20230201142446/https://scholarcommons.towerhealth.org/t-med/vol1/iss1/3/ |url-status=live }}

25I-NBOMe acts as a highly potent full agonist for the human 5-HT_2A receptor,{{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 | 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 }}{{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 }} with a affinity (K_i) of 0.044 nM, making it some 16-fold higher affinity than 2C-I at this receptor. 25I-NBOMe induces a head-twitch response in mice which is blocked completely by a selective 5-HT_2A antagonist, suggesting its psychedelic effects are mediated by 5-HT_2A. This study suggested that 25I-NBOMe is approximately 14-fold more potent than 2C-I in-vivo.{{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 | quote = For example, the 5-HT2A affinity of 25I-NBOMe (Ki= 0.044 nM) is more than an order of magnitude greater than that of 2C-I (Ki= 0.73 nM). 25I-NBOMe is a potent and highly efficacious 5-HT2A agonist that is selective for 5-HT2 sites (Braden et al., 2006; Nichols et al., 2008; Ettrup et al., 2010, 2011). }} 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 DOI were inactive.{{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 }} 25B-NBOMe is a low-potency weak partial agonist of the rat and mouse trace amine-associated receptor 1 (TAAR1) but is inactive at the human TAAR1.{{cite journal | vauthors = Simmler LD, Buchy D, Chaboz S, Hoener MC, Liechti ME | title = In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1 | journal = J Pharmacol Exp Ther | volume = 357 | issue = 1 | pages = 134–144 | date = April 2016 | pmid = 26791601 | doi = 10.1124/jpet.115.229765 | url = https://d1wqtxts1xzle7.cloudfront.net/74120533/eae6c6e62565b82d46b4d111bbea0f77b9c2-libre.pdf?1635931703=&response-content-disposition=inline%3B+filename%3DIn_Vitro_Characterization_of_Psychoactiv.pdf&Expires=1746838268&Signature=Sy4fJ90yUhxs68314NxYsW5PAaNrBGePRu35WRR4PIF-3YC7Z~sLdnCn5wfqqbLg9bDEGdt~oW55ugMP3D3jgA0BoRI~~GOb0NQOwrtfUEQK1PQs1uuN9qg5Y1ct8z5NsABm44RgtukkwRMdU6fO7OlfIsQ68hOiFk129Ll7UYqldxD2f1xhE2fTTfsxSpb8cMCJzHn7-ItqLdwnAUPFK7WggDIjmY1kCnaHLwIxMwdJCAq8L6DYzSTg7pZkbR8qlou~GXbTPQt~gYpyZTJp5hgW-7V6K5wLlQ7Z2xE7B0f9wEfuc1W1QNafg125Tr-vvAe4LEGKXV58bnn1bpfWKw__&Key-Pair-Id=APKAJLOHF5GGSLRBV4ZA | archive-url = https://web.archive.org/web/20250509235235/https://d1wqtxts1xzle7.cloudfront.net/74120533/eae6c6e62565b82d46b4d111bbea0f77b9c2-libre.pdf?1635931703=&response-content-disposition=inline%3B+filename%3DIn_Vitro_Characterization_of_Psychoactiv.pdf&Expires=1746838268&Signature=Sy4fJ90yUhxs68314NxYsW5PAaNrBGePRu35WRR4PIF-3YC7Z~sLdnCn5wfqqbLg9bDEGdt~oW55ugMP3D3jgA0BoRI~~GOb0NQOwrtfUEQK1PQs1uuN9qg5Y1ct8z5NsABm44RgtukkwRMdU6fO7OlfIsQ68hOiFk129Ll7UYqldxD2f1xhE2fTTfsxSpb8cMCJzHn7-ItqLdwnAUPFK7WggDIjmY1kCnaHLwIxMwdJCAq8L6DYzSTg7pZkbR8qlou~GXbTPQt~gYpyZTJp5hgW-7V6K5wLlQ7Z2xE7B0f9wEfuc1W1QNafg125Tr-vvAe4LEGKXV58bnn1bpfWKw__&Key-Pair-Id=APKAJLOHF5GGSLRBV4ZA | url-status = dead | archive-date = 2025-05-09 }}

The affinities and potencies of 25I-NBOMe at the serotonin 5-HT₂ receptors have varied in different studies.{{cite journal | vauthors = Eshleman AJ, Wolfrum KM, Reed JF, Kim SO, Johnson RA, Janowsky A | title = Neurochemical pharmacology of psychoactive substituted N-benzylphenethylamines: High potency agonists at 5-HT2A receptors | journal = Biochem Pharmacol | volume = 158 | issue = | pages = 27–34 | date = December 2018 | pmid = 30261175 | pmc = 6298744 | doi = 10.1016/j.bcp.2018.09.024 | url = }}{{cite journal | vauthors = Wojtas A, Gołembiowska K | title = Molecular and Medical Aspects of Psychedelics | journal = Int J Mol Sci | volume = 25 | issue = 1 | date = December 2023 | page = 241 | pmid = 38203411 | pmc = 10778977 | doi = 10.3390/ijms25010241 | doi-access = free | url = }}{{cite journal | vauthors = Rickli A, Luethi D, Reinisch J, Buchy D, Hoener MC, Liechti ME | title = Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs) | journal = Neuropharmacology | volume = 99 | issue = | pages = 546–553 | date = December 2015 | pmid = 26318099 | doi = 10.1016/j.neuropharm.2015.08.034 | url = https://psilosybiini.info/paperit/Receptor%20interaction%20profiles%20of%20novel%20N-2-methoxybenzyl%20(NBOMe)%20derivatives%20of%202,5-dimethoxy-substituted%20phenethylamines%20(2C%20drugs)%20(Rickli%20et%20al.,%202015).pdf}}{{cite journal | vauthors = Elmore JS, Decker AM, Sulima A, Rice KC, Partilla JS, Blough BE, Baumann MH | title = Comparative neuropharmacology of N-(2-methoxybenzyl)-2,5-dimethoxyphenethylamine (NBOMe) hallucinogens and their 2C counterparts in male rats | journal = Neuropharmacology | volume = 142 | issue = | pages = 240–250 | date = November 2018 | pmid = 29501528 | pmc = 6119551 | doi = 10.1016/j.neuropharm.2018.02.033 | url = }} Its affinities (K_i) have ranged from 0.044 to 0.6{{nbsp}}nM for the serotonin 5-HT_2A receptor, 1.91 to 130{{nbsp}}nM for the serotonin 5-HT_2B receptor, and 1.03 to 4.6{{nbsp}}nM for the serotonin 5-HT_2C receptor. Conversely, its potencies ({{Abbrlink|EC₅₀|half-maximal effective concentration}}) have ranged from 0.76 to 240{{nbsp}}nM at the serotonin 5-HT_2A receptor, 111 to 130{{nbsp}}nM at the serotonin 5-HT_2B receptor, and 2.38 to 88.9{{nbsp}}nM at the serotonin 5-HT_2C receptor.

25I-NBOMe also has weaker interactions with multiple other receptors. K_d values for interaction with the following targets were greater than 500 nM: 5-HT_1A, D₃, H₂, 5-HT_1D, α_1A adrenergic, δ opioid, serotonin uptake transporter, 5-HT_5A, 5-HT_1B, D₂, 5-HT₇, D₁, 5-HT₃, 5-HT_1E, D₅, muscarinic M₁-M₅, H₃, and the dopamine uptake transporter. 25I-NBOMe is inactive as a monoamine reuptake inhibitor and releasing agent. However, 25I-NBOMe has been found to increase dopamine release from mouse striatal synaptosomes similarly to methamphetamine in vitro.{{cite journal | vauthors = Gil-Martins E, Barbosa DJ, Borges F, Remião F, Silva R | title=Toxicodynamic insights of 2C and NBOMe drugs – Is there abuse potential? | journal=Toxicology Reports | volume=14 | date=2025 | doi=10.1016/j.toxrep.2025.101890 | doi-access=free | page=101890| pmid=39867514 | pmc=11762925 | bibcode=2025ToxR...1401890G }}{{cite journal | vauthors = Jeon SY, Kim YH, Kim SJ, Suh SK, Cha HJ | title = Abuse potential of 2-(4-iodo-2, 5-dimethoxyphenyl)N-(2-methoxybenzyl)ethanamine (25INBOMe); in vivo and ex vivo approaches | journal = Neurochem Int | volume = 125 | issue = | pages = 74–81 | date = May 2019 | pmid = 30769030 | doi = 10.1016/j.neuint.2019.02.007 | url = }} Likewise, 25I-NBOMe has been found to increase dopamine levels in the nucleus accumbens in rodents in vivo.{{cite journal | vauthors = Bilel S, Miliano C, Corli G, Bassi M, Trusel M, Tonini R, De Luca MA, Marti M | title = Acute Effects of the Psychedelic Phenethylamine 25I-NBOMe in C57BL/6J Male Mice | journal = Int J Mol Sci | volume = 26 | issue = 6 | date = March 2025 | page = 2815 | pmid = 40141457 | doi = 10.3390/ijms26062815 | doi-access = free | pmc = 11943083 | url = }}

A radiolabelled form of 25I-NBOMe can be used for mapping the distribution of 5-HT_2A receptors in the brain.

25I-NBOMe is metabolized by the cytochrome P450 enzymes CYP3A4 and CYP2D6.{{cite journal | vauthors = Nielsen LM, Holm NB, Leth-Petersen S, Kristensen JL, Olsen L, Linnet K | title = Characterization of the hepatic cytochrome P450 enzymes involved in the metabolism of 25I-NBOMe and 25I-NBOH | journal = Drug Test Anal | volume = 9 | issue = 5 | pages = 671–679 | date = May 2017 | pmid = 27400739 | doi = 10.1002/dta.2031 | url = }} It does not appear to be metabolized by the monoamine oxidase (MAO) enzymes MAO-A or MAO-B.

Like other 2C-X-NBOMe molecules, 25I-NBOMe is a derivative of the 2C family of phenethylamines described by chemist Alexander Shulgin in his book PiHKAL.{{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 }} Specifically, 25I-NBOMe is an N-benzyl derivative of the phenethylamine molecule 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.

{{2C-I analogues and derivatives}}

25I-NBOMe is usually synthesised from 2C-I and 2-methoxybenzaldehyde, via reductive alkylation. It can be done stepwise by first making the imine and then reducing the formed imine with sodium borohydride, or by direct reaction with sodium triacetoxyborohydride.

2C-B, the first major 2C drug and an analogue of mescaline, was first described by Alexander Shulgin in the 1970s. Richard Glennon and colleagues synthesized and described 25B-NB, the N-benzyl analogue of 2C-B and the first 25-NB drug to be developed, in 1994.{{cite book | vauthors = Halberstadt AL | date = 2017 | chapter = Pharmacology and Toxicology of N-Benzylphenethylamine (“NBOMe”) Hallucinogens | veditors = Baumann M, Glennon R, Wiley J | title = Neuropharmacology of New Psychoactive Substances (NPS). | series = Current Topics in Behavioral Neurosciences | volume = 32 | pages = 283–311 | publisher = Springer | location = Cham | doi = 10.1007/7854_2016_64 | pmid = 28097528 | isbn = 978-3-319-52444-3 }}{{cite journal | vauthors = Poulie CB, Jensen AA, Halberstadt AL, Kristensen JL | title = DARK Classics in Chemical Neuroscience: NBOMes | journal = ACS Chem Neurosci | volume = 11 | issue = 23 | pages = 3860–3869 | date = December 2020 | pmid = 31657895 | pmc = 9191638 | doi = 10.1021/acschemneuro.9b00528 | url = }}{{cite journal | vauthors = Glennon RA, Dukat M, el-Bermawy M, Law H, De los Angeles J, Teitler M, King A, Herrick-Davis K | title = Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines | journal = Journal of Medicinal Chemistry | volume = 37 | issue = 13 | pages = 1929–1935 | date = June 1994 | pmid = 8027974 | doi = 10.1021/jm00039a004 }} Subsequently, modification of 25B-NB led to the development of the more well-known 25-NB family drugs such as 25I-NBOMe.

25I-NBOMe was first described in the scientific literature, in the form of conference abstracts, by Ralf Heim and colleagues at the Free University of Berlin by 2000.{{cite journal | vauthors = Heim R, Elz S | title = 39. Novel Extremely Potent Partial 5-HT2A-Receptor Agonists: Successful Application of a New Structure-Activity Concept | date = March 2000 | journal = Arch. Pharm. Pharm. Med. Chem. | volume = 333 | issue = Suppl 1 | pages = 1–40 (18) | issn = 0365-6233 | url = https://scholar.google.com/scholar?cluster=5753981208249154444 | archive-url = https://web.archive.org/web/20250320195942/https://bitnest.netfirms.com/external/Arch.Pharm.Pharm.Med.Chem/333.S1.18 | archive-date = 20 March 2025 }}{{cite journal | vauthors = Pertz HH, Heim R, Elz S | title = B 1.11. N-Benzylated phenylethanamines are highly potent partial agonists at 5-HT2A receptors | date = 2000 | journal = Arch. Pharm. Pharm. Med. Chem | volume = 333 | issue = Suppl 2 | pages = 1–84 (30) | url = https://scholar.google.com/scholar?cluster=18169232060279208950 | archive-url = https://web.archive.org/web/20250320194355/https://bitnest.netfirms.com/external/Arch.Pharm.Pharm.Med.Chem/333.S2.30 | archive-date = 20 March 2025}}{{cite web |vauthors=Heim R |title=Synthese und Pharmakologie potenter 5-HT_2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts. | trans-title=Synthesis and pharmacology of potent 5-HT2A receptor agonists with an N-2-methoxybenzyl partial structure. Development of a new structure-activity concept. | 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 |archive-date=2012-04-16 |archive-url=https://web.archive.org/web/20120416040543/http://www.diss.fu-berlin.de/diss/receive/FUDISS_thesis_000000001221 |url-status=live }} Then, in 2003, Heim described 25I-NBOMe in his dissertation. Other NBOMe derivatives such as 25B-NBOMe and 2CBFly-NBOMe were also described in the same publications. 25I-NBOMe was further investigated by a team at Purdue University led by David Nichols in 2006 through 2008.{{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 = Mol Pharmacol | volume = 70 | issue = 6 | pages = 1956–1964 | date = December 2006 | pmid = 17000863 | doi = 10.1124/mol.106.028720 | url = }}{{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 | access-date=2016-07-19 | archive-date=2016-09-19 | archive-url=https://web.archive.org/web/20160919143709/http://docs.lib.purdue.edu/dissertations/AAI3287241/ | url-status=live }}{{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 = Bioorg Med Chem | volume = 16 | issue = 11 | pages = 6116–6123 | date = June 2008 | pmid = 18468904 | pmc = 2719953 | doi = 10.1016/j.bmc.2008.04.050 | url = | quote = Recently, we reported on a series of high affinity N-benzyl phenethylamine ligands for the 5-HT2A receptor.14 The most potent of the ones reported, N-(2- methoxybenzyl)-2,5-dimethoxy-4-iodophenethylamine (INBMeO, 1), had exceptionally high affinity for the 5-HT2A receptor, [...] 14. Braden MR, Parrish JC, Naylor JC, Nichols DE. Mol Pharmacol 2006;70:1956–1964. [PubMed: 17000863]}}

The NBOMe drugs, primarily 25I-NBOMe, were encountered as novel recreational drugs by 2010, and by 2012 had eclipsed other psychedelics like LSD and psilocybin-containing mushrooms in popularity, at least for a time.{{cite journal | vauthors = Wood DM, Sedefov R, Cunningham A, Dargan PI | title = Prevalence of use and acute toxicity associated with the use of NBOMe drugs | journal = Clin Toxicol (Phila) | volume = 53 | issue = 2 | pages = 85–92 | date = February 2015 | pmid = 25658166 | doi = 10.3109/15563650.2015.1004179 | url = }}{{cite web | last=Morgans | first=Julian | title=NBOMe in Australia: Everything We Know About the Drug and Why it's Killing People | website=VICE | date=8 February 2017 | url=https://www.vice.com/en/article/nbome-in-australia-everything-we-know-about-what-it-is-and-why-its-killing-people/ | access-date=4 April 2025}}{{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 = J Psychopharmacol | volume = 28 | issue = 8 | pages = 780–788 | date = August 2014 | pmid = 24569095 | doi = 10.1177/0269881114523866 | hdl = 1959.4/unsworks_73366 | hdl-access = free }} 25I-NBOMe and other NBOMes became Schedule I controlled substances in the United States in 2013.

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.{{cite web | url=https://www.legislation.gov.au/Details/F2015L01534/Html/Text#_Toc420496379 | title=Poisons Standard October 2015 | publisher=Australian Government | date=October 2015 | access-date=2016-06-28 | archive-date=2016-06-02 | archive-url=https://web.archive.org/web/20160602092257/https://www.legislation.gov.au/Details/F2015L01534/Html/Text#_Toc420496379 | url-status=live }}

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

As of October 31, 2016; 25I-NBOMe is a controlled substance (Schedule III) in Canada.{{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 | access-date=2016-08-22 | archive-date=2016-08-31 | archive-url=https://web.archive.org/web/20160831014117/http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php | url-status=live }}

As of October 2015 25I-NBOMe is a controlled substance in China.{{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 }}

In September 2014 the European Union implemented a ban of 25I-NBOMe in all its member states.{{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 | access-date=28 June 2016 | archive-date=3 August 2017 | archive-url=https://web.archive.org/web/20170803014226/http://eur-lex.europa.eu/legal-content/EN/TXT/PDF/?uri=CELEX:32014D0688 | url-status=live }}

25I-NBOMe is scheduled in government decree on narcotic substances, preparations and plants as of 2022 and is hence illegal to possess or use.{{Cite web |url=https://finlex.fi/fi/lainsaadanto/2008/543 |title=Valtioneuvoston asetus huumausaineina pidettävistä aineista, valmisteista ja kasveista |id= 543/2008 |website =Finlex |language=fi |access-date=2024-05-01 |archive-date=2023-11-29 |archive-url=https://web.archive.org/web/20231129212645/https://www.finlex.fi/fi/laki/ajantasa/2008/20080543 |url-status=live }}

Israel banned 25I-NBOMe in 2013.

In 2011, Romania banned all psychoactive substances.{{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 | access-date=2014-02-11 | archive-date=2020-09-01 | archive-url=https://web.archive.org/web/20200901085649/http://www.dreptonline.ro/legislatie/legea_194_2011_combaterea_operatiunilor_produse_susceptibile_efecte_psihoactive.php | url-status=live }}

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.{{cite web |url=https://www.erowid.org/chemicals/2ci_nbome/2ci_nbome_law.shtml |title=2C-I-NBOMe Legal Status |publisher=Erowid |access-date=2016-06-28 |archive-date=2016-06-30 |archive-url=https://web.archive.org/web/20160630093827/https://www.erowid.org/chemicals/2ci_nbome/2ci_nbome_law.shtml |url-status=live }}

25I-NBOMe was put on the list of prohibited substances in March 2015.{{cite web | url=http://www.zdravlje.gov.rs/ | title=Министарство здравља Републикe Србије | access-date=2016-06-28 | archive-date=2017-12-28 | archive-url=https://web.archive.org/web/20171228150952/http://zdravlje.gov.rs/ | url-status=live }}

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 Medical Products Agency (MPA) in regulation LVFS 2013:15 listed as 25I-NBOMe, and 2-(4-jodo-2,5-dimetoxifenyl)-N-(2-metoxibensyl)etanamin.{{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 }}

Following the European rule from 2014, 25I-NBOMe was put in class 4 of prohibited substances.{{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| access-date=28 June 2016| archive-date=7 October 2014| archive-url=https://web.archive.org/web/20141007131306/http://www.fda.gov.tw/TC/index.aspx| url-status=live}}

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.{{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 |archive-date=2024-01-25 |archive-url=https://web.archive.org/web/20240125220747/https://u.ae/en/information-and-services/health-and-fitness/drugs-and-controlled-medicines |url-status=live }}

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

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. In November 2015, the temporary scheduling was extended for an additional year{{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 | access-date = 2016-06-28 | archive-date = 2016-05-14 | archive-url = https://web.archive.org/web/20160514210118/https://www.gpo.gov/fdsys/pkg/FR-2015-11-13/pdf/2015-29028.pdf | url-status = live }} while permanent scheduling was arranged.{{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}} 25I-NBOMe, 25B-NBOMe and 25C-NBOMe are currently Schedule 1 Substances according to 21 CFR 1308.11(d).{{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.|access-date=2017-05-11|archive-date=2020-09-13|archive-url=https://web.archive.org/web/20200913161156/https://www.ecfr.gov/cgi-bin/text-idx?SID=b632b274cf6322a0450af69d7c7a4f46&node=pt21.9.1308&rgn=div5#se21.9.1308_111|url-status=live}}

{{Notelist}}

{{Reflist}}

• [https://isomerdesign.com/pihkal/explore/5380 25I-NBOMe - Isomer Design]
• [https://psychonautwiki.org/wiki/25I-NBOMe 25I-NBOMe - PsychonautWiki]
• [https://www.erowid.org/chemicals/2ci_nbome/2ci_nbome.shtml 25I-NBOMe - Erowid]
• [https://www.bluelight.org/xf/threads/551797 The Big & Dandy 25I-NBOMe Thread - Bluelight]
• [https://tripsit.me/factsheets/25i-nbome 25I-NBOMe - TripSit.me]
• [https://tripsitter.com/nbome/ What Are N-Bombs? (25-I-NBOMe) — Avoid This Psychedelic - Tripsitter]
• [https://psychedelicspotlight.com/unmasking-fake-acid-the-dangers-of-25i-nbome-disguised-as-lsd/ Unmasking Fake Acid: The Dangers of 25I-NBOMe Disguised as LSD - Psychedelic Spotlight]

{{Psychedelics}}

{{Serotonin receptor modulators}}

{{TAAR modulators}}

{{Phenethylamines}}

Category:25-NB (psychedelics)

Category:5-HT2A agonists

Category:5-HT2B agonists

Category:5-HT2C agonists

Category:Designer drugs

Category:Iodobenzene derivatives

Category:2-Methoxyphenyl compounds

Category:Psychedelic phenethylamines

Category:TAAR1 agonists