25-NB

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The NBOMe drugs are highly potent and selective agonists of the serotonin 5-HT₂ receptors, including of the 5-HT_2A, 5-HT_2B, and 5-HT_2C receptors.{{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 = 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 = http://edoc.unibas.ch/56163/1/20170921163006_59c3cceeb8e5d.pdf}}{{cite journal | vauthors = Wallach J, Cao AB, Calkins MM, Heim AJ, Lanham JK, Bonniwell EM, Hennessey JJ, Bock HA, Anderson EI, Sherwood AM, Morris H, de Klein R, Klein AK, Cuccurazzu B, Gamrat J, Fannana T, Zauhar R, Halberstadt AL, McCorvy JD | title = Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential | journal = Nat Commun | volume = 14 | issue = 1 | pages = 8221 | date = December 2023 | pmid = 38102107 | pmc = 10724237 | doi = 10.1038/s41467-023-44016-1 | url = https://bitnest.netfirms.com/external/10.1038/s41467-023-44016-1}} However, they are much less potent and efficacious at the serotonin 5-HT_2B receptor compared to the serotonin 5-HT_2A and 5-HT_2C receptors. The drugs are highly selective for the serotonin 5-HT₂ receptors over other serotonin receptors and over a variety of other biological targets. They are likewise inactive as monoamine reuptake inhibitors and releasing agents. Many of the NBOMe drugs are partial agonists of the rat and mouse trace amine-associated receptor 1 (TAAR1), but they are inactive as agonists of 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 = }}

In accordance with their psychedelic effects, NBOMe drugs induce the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.{{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 = Toxicol Rep | volume = 14 | issue = | pages = 101890 | date = June 2025 | pmid = 39867514 | doi = 10.1016/j.toxrep.2025.101890 | url = | pmc = 11762925 | bibcode = 2025ToxR...1401890G }} They have also been found to produce hyperlocomotion at low doses and hypolocomotion at high doses in rodents.

Unlike most other serotonergic psychedelics, the NBOMe drugs 25B-NBOMe and 25N-NBOMe have been found to produce reinforcing effects in rodents, and hence may have misuse potential.{{cite journal | vauthors = Custodio RJ, Sayson LV, Botanas CJ, Abiero A, You KY, Kim M, Lee HJ, Yoo SY, Lee KW, Lee YS, Seo JW, Ryu IS, Kim HJ, Cheong JH | title = 25B-NBOMe, a novel N-2-methoxybenzyl-phenethylamine (NBOMe) derivative, may induce rewarding and reinforcing effects via a dopaminergic mechanism: Evidence of abuse potential | journal = Addict Biol | volume = 25 | issue = 6 | pages = e12850 | date = November 2020 | pmid = 31749223 | doi = 10.1111/adb.12850 | url = }}{{cite journal | vauthors = Seo JY, Hur KH, Ko YH, Kim K, Lee BR, Kim YJ, Kim SK, Kim SE, Lee YS, Kim HC, Lee SY, Jang CG | title = A novel designer drug, 25N-NBOMe, exhibits abuse potential via the dopaminergic system in rodents | journal = Brain Res Bull | volume = 152 | issue = | pages = 19–26 | date = October 2019 | pmid = 31279579 | doi = 10.1016/j.brainresbull.2019.07.002 | url = }} Relatedly, 25B-NBOMe robustly increased dopamine levels in the nucleus accumbens similarly to methamphetamine. The reinforcing effects of 25B-NBOMe were not blocked by serotonin 5-HT_2A receptor antagonism, and it is unclear how they are produced. However, some NBOMe drugs, such as 25N-NBOMe, have been found to increase phosphorylation of the dopamine transporter (DAT) in the striatum similarly to methamphetamine in rodents.{{cite journal | vauthors = Kim YJ, Ma SX, Hur KH, Lee Y, Ko YH, Lee BR, Kim SK, Sung SJ, Kim KM, Kim HC, Lee SY, Jang CG | title = New designer phenethylamines 2C-C and 2C-P have abuse potential and induce neurotoxicity in rodents | journal = Arch Toxicol | volume = 95 | issue = 4 | pages = 1413–1429 | date = April 2021 | pmid = 33515270 | doi = 10.1007/s00204-021-02980-x | bibcode = 2021ArTox..95.1413K | url = | quote = 25N-NBOMe and other 2C drug derivatives similarly increased p-DAT levels in the NAc and striatum of mice (Seo et al. 2019). [...] increased p-DAT levels lead to an increase in dopamine release, which contribute to elevated dopamine levels. }} DAT phosphorylation is associated with dopamine reverse transport and efflux, which in turn increases extracellular dopamine levels.

Similarly to other psychedelics like DOI and 2C-T-7, tolerance has been found to gradually develop to the head-twitch response induced by 25I-NBOMe with chronic administration in rodents.{{cite journal | vauthors = Herian M, Skawski M, Wojtas A, Sobocińska MK, Noworyta K, Gołembiowska K | title = Tolerance to neurochemical and behavioral effects of the hallucinogen 25I-NBOMe | journal = Psychopharmacology (Berl) | volume = 238 | issue = 8 | pages = 2349–2364 | date = August 2021 | pmid = 34032876 | pmc = 8292280 | doi = 10.1007/s00213-021-05860-5 | url = }}

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

NBOMe compounds are often associated with life-threatening toxicity and death.{{cite journal | journal = Clinical Toxicology | title = A cluster of 25B-NBOH poisonings following exposure to powder sold as lysergic acid diethylamide (LSD) | doi = 10.1080/15563650.2022.2053150 | vauthors = Sean I, Joe R, Jennifer S, and Shaun G |url=https://www.tandfonline.com/doi/abs/10.1080/15563650.2022.2053150 | pages = 966–969 | date = 28 March 2022 | volume = 60 | issue = 8 | pmid = 35343858| s2cid = 247764056 }}{{cite journal | journal = Biochemical Pharmacology | vauthors = Amy E, Katherine W, John R, Sonyoung K, Robert J, Aaron J | title = Neurochemical pharmacology of psychoactive substituted N-benzylphenethylamines: High potency agonists at 5-HT2A receptors | doi = 10.1016/j.bcp.2018.09.024 | pmid = 30261175 | pmc = 6298744 | volume = 158 | pages = 27–34 | date = December 2018}} Studies on NBOMe family of compounds demonstrated that the substance exhibit neurotoxic and cardiotoxic activity.{{cite journal | journal = Frontiers in Neuroscience | vauthors = Jolanta Z, Monika K, and Piotr A | doi = 10.3389/fnins.2020.00078 | date = 26 February 2020 | volume = 14 | pmid = 32174803 | title = NBOMes–Highly Potent and Toxic Alternatives of LSD | page = 78 | pmc = 7054380 | doi-access = free | quote = Recently, a new class of psychedelic compounds named NBOMe (or 25X-NBOMe) has appeared on the illegal drug market. NBOMes are analogs of the 2C family of phenethylamine drugs, originally synthesized by Alexander Shulgin, that contain a N-(2-methoxy)benzyl substituent. The most frequently reported drugs from this group are 25I-NBOMe, 25B-NBOMe, and 25C-NBOMe. NBOMe compounds are ultrapotent and highly efficacious agonists of serotonin 5-HT2A and 5-HT2C receptors (Ki values in low nanomolar range) with more than 1000-fold selectivity for 5-HT2A compared with 5-HT1A. They display higher affinity for 5-HT2A receptors than their 2C counterparts and have markedly lower affinity, potency, and efficacy at the 5-HT2B receptor compared to 5-HT2A or 5-HT2C. }} Reports of autonomic dysfunction remains prevalent with NBOMe compounds, with most individuals experiencing sympathomimetic toxicity such as vasoconstriction, hypertension and tachycardia in addition to hallucinations.{{cite journal | vauthors = Tirri M, Bilel S, Arfè R, Corli G, Marchetti B, Bernardi T, Boccuto F, Serpelloni G, Botrè F, De-Giorgio F, Golembiowska K, Marti M | title = Effect of -NBOMe Compounds on Sensorimotor, Motor, and Prepulse Inhibition Responses in Mice in Comparison With the 2C Analogs and Lysergic Acid Diethylamide: From Preclinical Evidence to Forensic Implication in Driving Under the Influence of Drugs | journal = Front Psychiatry | volume = 13 | issue = | pages = 875722 | date = 2022 | pmid = 35530025 | pmc = 9069068 | doi = 10.3389/fpsyt.2022.875722 | doi-access = free | url = }}{{cite journal | title = Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs) | journal = Neuropharmacology | doi = 10.1016/j.neuropharm.2015.08.034 | pmid = 26318099 | vauthors = Anna R, Dino L, Julia R, Daniele B, Marius H, Matthias L | pages = 546–553 | date = December 2015 |url=https://www.sciencedirect.com/science/article/abs/pii/S0028390815300794 | volume = 99 | s2cid = 10382311 | issn = 1873-7064}}{{cite journal | journal = Clinical Toxicology | title = Prevalence of use and acute toxicity associated with the use of NBOMe drugs | vauthors = David W, Roumen S, Andrew C, Paul D |url=https://www.tandfonline.com/doi/abs/10.3109/15563650.2015.1004179 | doi = 10.3109/15563650.2015.1004179 | date = 6 February 2015 | pages = 85–92 | volume = 53 | issue = 2 | pmid = 25658166| s2cid = 25752763 }} Other symptoms of toxidrome include agitation or aggression, seizure, hyperthermia, diaphoresis, hypertonia, rhabdomyolysis, and death.{{Cite journal | vauthors = Lipow M, Kaleem SZ, Espiridion E | date = 30 March 2022 | 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 }} Researchers report that NBOMe intoxication frequently display signs of serotonin syndrome.{{Cite journal | vauthors = Humston C, Miketic R, Moon K, Ma P, Tobias J |date=2017-06-05 |title=Toxic Leukoencephalopathy in a Teenager Caused by the Recreational Ingestion of 25I-NBOMe: A Case Report and Review of Literature |url=https://www.journalmc.org/index.php/JMC/article/view/2811 |journal=Journal of Medical Cases |volume=8 |issue=6 |pages=174–179 |doi=10.14740/jmc2811w |issn=1923-4163|doi-access=free }} The likelihood of seizure is higher in NBOMes compared to other psychedelics.

NBOMe and NBOHs are regularly sold as LSD in blotter papers,{{cite journal | journal = Journal of Analytical Toxicology | doi = 10.1093/jat/bkv073 | pmc = 4570937 | pmid = 26378135 | title = Analysis of 25I-NBOMe, 25B-NBOMe, 25C-NBOMe and Other Dimethoxyphenyl-N-[(2-Methoxyphenyl) Methyl]Ethanamine Derivatives on Blotter Paper | vauthors = Justin P, Stephen R, Kylin A, Alphonse P, Michelle P | year = 2015 | volume = 39 | issue = 8 | pages = 617–623}} which have a bitter taste and different safety profiles. Despite high potency, recreational doses of LSD have only produced low incidents of acute toxicity. Fatalities involved in NBOMe intoxication suggest that a significant number of individuals ingested the substance which they believed was LSD,{{cite journal | journal = Frontiers in Pharmacology | date = 12 December 2019 | doi = 10.3389/fphar.2019.01406 | vauthors = Cristina M, Matteo M, Nicholas P, Maria C, Micaela T, Raffaella A, Maria L | title = Neurochemical and Behavioral Profiling in Male and Female Rats of the Psychedelic Agent 25I-NBOMe | volume = 10 | page = 1406 | pmid = 31915427 | pmc = 6921684 | doi-access = free }} and researchers report that "users familiar with LSD may have a false sense of security when ingesting NBOMe inadvertently". While most fatalities are due to the physical effects of the drug, there have also been reports of death due to self-harm and suicide under the influence of the substance.{{cite journal | vauthors = Morini L, Bernini M, Vezzoli S, Restori M, Moretti M, Crenna S, Papa P, Locatelli C, Osculati AM, Vignali C, Groppi A | title = Death after 25C-NBOMe and 25H-NBOMe consumption | journal = Forensic Science International | volume = 279 | pages = e1–e6 | date = October 2017 | pmid = 28893436 | doi = 10.1016/j.forsciint.2017.08.028 |url=https://www.sciencedirect.com/science/article/abs/pii/S0379073817303377}}{{cite journal | vauthors = Byard RW, Cox M, Stockham P | title = Blunt Craniofacial Trauma as a Manifestation of Excited Delirium Caused by New Psychoactive Substances | journal = Journal of Forensic Sciences | volume = 61 | issue = 6 | pages = 1546–1548 | date = November 2016 | pmid = 27723094 | doi = 10.1111/1556-4029.13212 | s2cid = 4734566 |url=https://onlinelibrary.wiley.com/doi/abs/10.1111/1556-4029.13212}}

Given limited documentation of NBOMe consumption, the long-term effects of the substance remain unknown. NBOMe compounds are not active orally,{{efn|The potency of N-benzylphenethylamines via buccal, sublingual, or nasal absorption is 50- to 100-fold greater (by weight) than oral route compared to the parent 2C-x compounds.{{cite journal | journal = Neurochemical Research | date = 14 February 2014 | vauthors = Sabastian LP, Christoffer B, Martin H, Martin AC, Jan K, Jesper LK | title = Correlating the Metabolic Stability of Psychedelic 5-HT2A Agonists with Anecdotal Reports of Human Oral Bioavailability | volume = 39 | issue = 10 |url=https://link.springer.com/article/10.1007/s11064-014-1253-y | pages = 2018–2023 | doi = 10.1007/s11064-014-1253-y | pmid = 24519542| s2cid = 254857910 }} Researchers hypothesize the low oral metabolic stability of N-benzylphenethylamines is likely causing the low bioavailability on the oral route, although the metabolic profile of this compounds remains unpredictable; therefore researchers state that the fatalities linked to these substances may partly be explained by differences in the metabolism between individuals.}} and are usually taken sublingually.{{cite book | title = Neuropharmacology of New Psychoactive Substances | vauthors = Adam H | doi = 10.1007/7854_2016_64 | date = 18 January 2017 | isbn = 978-3-319-52444-3 | publisher = Springer |chapter-url=https://link.springer.com/chapter/10.1007/7854_2016_64 | chapter = Pharmacology and Toxicology of N-Benzylphenethylamine ("NBOMe") Hallucinogens | series = Current Topics in Behavioral Neurosciences | volume = 32 | pages = 283–311 | pmid = 28097528}}{{rp|3}} When NBOMes are administered sublingually, numbness of the tongue and mouth followed by a metallic chemical taste was observed, and researchers describe this physical side effect as one of the main discriminants between NBOMe compounds and LSD.{{cite journal | vauthors = Boris D, Cristian C, Marcelo K, Edwar F, Bruce KC | journal = Journal of Chromatographic Science | volume = 54 | issue = 7 | date = August 2016 | pages = 1153–1158 | title = Analysis of 25 C NBOMe in Seized Blotters by HPTLC and GC–MS | pmc = 4941995 | pmid = 27406128 | doi = 10.1093/chromsci/bmw095 |url=https://academic.oup.com/chromsci/article/54/7/1153/2754859}}{{cite journal | pmid = 25105138 | pmc = 4106087 | doi = 10.1155/2014/734749 | title = 25C-NBOMe: preliminary data on pharmacology, psychoactive effects, and toxicity of a new potent and dangerous hallucinogenic drug | journal = BioMed Research International | date = 3 July 2014 | vauthors = Francesco SB, Ornella C, Gabriella A, Giuseppe V, Rita S, Flaminia BP, Eduardo C, Pierluigi S, Giovanni M, Guiseppe B, Fabrizio S | volume = 2014 | page = 734749 | doi-access = free }}{{cite book | title = Novel Psychoactive Substances: Classification, Pharmacology and Toxicology | chapter = Pharmacology and toxicology of N-Benzyl-phenylethylamines (25X-NBOMe) hallucinogens | vauthors = Adam JP, Simon HT, Simon LH | doi = 10.1016/B978-0-12-818788-3.00008-5 | isbn = 978-0-12-818788-3 | pages = 279–300 | edition = 2 | publisher = Academic Press | date = September 2021 | s2cid = 240583877 |chapter-url=https://www.sciencedirect.com/science/article/abs/pii/B9780128187883000085}}

Many of the NBOMe compounds have high potency agonist activity at additional 5-HT receptors and prolonged activation of 5-HT_2B can cause cardiac valvulopathy in high doses and chronic use. 5-HT_2B receptors have been strongly implicated in causing drug-induced valvular heart disease.{{cite journal | vauthors = Rothman RB, Baumann MH, Savage JE, Rauser L, McBride A, Hufeisen SJ, Roth BL|author7-link=Bryan Roth | title = Evidence for possible involvement of 5-HT(2B) receptors in the cardiac valvulopathy associated with fenfluramine and other serotonergic medications | journal = Circulation | volume = 102 | issue = 23 | pages = 2836–41 | date = Dec 2000 | pmid = 11104741 | doi = 10.1161/01.CIR.102.23.2836 | doi-access = free }}{{cite journal | vauthors = Fitzgerald LW, Burn TC, Brown BS, Patterson JP, Corjay MH, Valentine PA, Sun JH, Link JR, Abbaszade I, Hollis JM, Largent BL, Hartig PR, Hollis GF, Meunier PC, Robichaud AJ, Robertson DW | title = Possible role of valvular serotonin 5-HT(2B) receptors in the cardiopathy associated with fenfluramine |url=https://pubmed.ncbi.nlm.nih.gov/10617681/ | journal = Molecular Pharmacology | volume = 57 | issue = 1 | pages = 75–81 | date = Jan 2000 | doi = 10.1016/S0026-895X(24)26444-0 | pmid = 10617681 }}{{cite journal | vauthors = Roth BL | title = Drugs and valvular heart disease | journal = The New England Journal of Medicine | volume = 356 | issue = 1 | pages = 6–9 | date = Jan 2007 | pmid = 17202450 | doi = 10.1056/NEJMp068265 |url=https://www.nejm.org/doi/full/10.1056/NEJMp068265}} The high affinity of NBOMe compounds for adrenergic α₁ receptor has been reported to contribute to the stimulant-type cardiovascular effects.

In vitro studies, 25C-NBOMe has been shown to exhibit cytotoxicity on neuronal cell lines SH-SY5Y, PC12, and SN471, and the compound was more potent than methamphetamine at reducing the visibility of the respective cells; the neurotoxicity of the compound involves activation of MAPK/ERK cascade and inhibition of Akt/PKB signaling pathway. 25C-NBOMe, including the other derivative 25D-NBOMe, reduced the visibility of cardiomyocytes H9c2 cells, and both substances downregulated expression level of p21 (CDC24/RAC)-activated kinase 1 (PAK1), an enzyme with documented cardiac protective effects.

Preliminary studies on 25C-NBOMe have shown that the substance is toxic to development, heart health, and brain health in zebrafish, rats, and Artemia salina, a common organism for studying potential drug effects on humans, but more research is needed on the topic, the dosages, and if the toxicology results apply to humans. Researchers of the study also recommended further investigation of the drug's potential in damaging pregnant women and their fetus due to the substance's damaging effects to development.{{cite journal | vauthors = Xu P, Qiu Q, Li H, Yan S, Yang M, Naman CB, Wang Y, Zhou W, Shen H, Cui W | title = 25C-NBOMe, a Novel Designer Psychedelic, Induces Neurotoxicity 50 Times More Potent Than Methamphetamine In Vitro | journal = Neurotoxicity Research | volume = 35 | issue = 4 | pages = 993–998 | date = 26 February 2019 | pmid = 30806983 | doi = 10.1007/s12640-019-0012-x |url=https://link.springer.com/article/10.1007/s12640-019-0012-x | s2cid = 255763701}}{{cite journal | vauthors = Álvarez-Alarcón N, Osorio-Méndez JJ, Ayala-Fajardo A, Garzón-Méndez WF, Garavito-Aguilar ZV | title = Zebrafish and Artemia salina in vivo evaluation of the recreational 25C-NBOMe drug demonstrates its high toxicity | journal = Toxicology Reports | volume = 8 | pages = 315–323 | year = 2021 | issn = 2214-7500 | pmid = 33598409 | pmc = 7868744 | doi = 10.1016/j.toxrep.2021.01.010 | bibcode = 2021ToxR....8..315A }}

At present, there are no specific antidotes for NBOMes, and all acute intoxication is managed by symptomatic treatments, such as administration of benzodiazepines, antipsychotic drugs, and antiarrhythmic agents, such as beta blockers; some emergency interventions are intended to specifically treat rhabdomyolysis, which may lead to critical complications such as metabolic acidosis and acute kidney injury.

The 25-NB compounds are mostly N-benzylphenethylamines, though in some cases the phenyl ring of the N-benzyl group is replaced by other heterocycles such as thiophene, pyridine, furan, tetrahydrofuran, benzodioxole or naphthalene, among others.{{cite journal | url=https://docs.lib.purdue.edu/dissertations/AAI3287241/ | title=Towards a biophysical understanding of hallucinogen action | pages=1–176 | journal=Dissertation | date=2007 | author=Michael Robert Braden}}{{Cite journal |doi = 10.1002/wmts.42|title = Structure-activity relationships of serotonin 5-HT2A agonists|year = 2012| vauthors = Nichols DE |journal = Wiley Interdisciplinary Reviews: Membrane Transport and Signaling|volume = 1|issue = 5|pages = 559–579|doi-access = free}}

Generally speaking, they have methoxy groups at the 2 and 5 positions of the phenyl ring, a substitution such as a halogen or alkyl group at the 4 position of the phenyl ring, and a methoxy or other substitution (e.g., hydroxyl, fluoro) at the 2 position of the N-benzyl ring. More rarely, other substitution patterns may be present {{cite journal | vauthors = Leth-Petersen S, Petersen IN, Jensen AA, Bundgaard C, Bæk M, Kehler J, Kristensen JL | title = 5-HT_2A/5-HT_2C Receptor Pharmacology and Intrinsic Clearance of N-Benzylphenethylamines Modified at the Primary Site of Metabolism | journal = ACS Chemical Neuroscience | volume = 7 | issue = 11 | pages = 1614–1619 | date = November 2016 | pmid = 27564969 | doi = 10.1021/acschemneuro.6b00265 }}{{cite journal | vauthors = Prabhakaran J, Solingapuram Sai KK, Zanderigo F, Rubin-Falcone H, Jorgensen MJ, Kaplan JR, Tooke KI, Mintz A, Mann JJ, Kumar JS | title = In vivo evaluation of [¹⁸F]FECIMBI-36, an agonist 5-HT_2A/2C receptor PET radioligand in nonhuman primate | journal = Bioorganic & Medicinal Chemistry Letters | volume = 27 | issue = 1 | pages = 21–23 | date = January 2017 | pmid = 27889455 | pmc = 5348621 | doi = 10.1016/j.bmcl.2016.11.043 }} (see e.g. NBOMe-mescaline, 25G-NBOMe, 2CBFly-NBOMe, 25C-NB3OMe). They differ from the 2C series by the presence of the N-benzyl moiety.

Rarely an alpha-methyl group is present making them N-benzyl amphetamines rather than N-benzyl phenethylamines, but this greatly reduces potency and activity. However in some cases where a side chain methyl group is cyclised back to the ring (e.g. in 2CBCB-NBOMe) or links the two alpha positions (e.g. in DMBMPP), this can improve selectivity for the 5-HT_2A receptor subtype.{{cite journal | vauthors = Juncosa JI, Hansen M, Bonner LA, Cueva JP, Maglathlin R, McCorvy JD, Marona-Lewicka D, Lill MA, Nichols DE | title = Extensive rigid analogue design maps the binding conformation of potent N-benzylphenethylamine 5-HT2A serotonin receptor agonist ligands | journal = ACS Chemical Neuroscience | volume = 4 | issue = 1 | pages = 96–109 | date = January 2013 | pmid = 23336049 | pmc = 3547484 | doi = 10.1021/cn3000668 }}

File:2C-I-NBOMe-skeletal.svg, the most well-known 25-NB derivative]]

This list includes notable compounds representative of most of the structural variations that have been explored in this series, but is by no means exhaustive. Many derivatives invented for scientific study into the structure-activity relationships of 5-HT₂ receptor agonists have never appeared as designer drugs, while conversely some derivatives that have appeared as designer drugs are structurally novel and of unknown pharmacological activity (e.g. C30-NBOMe, 5-APB-NBOMe).

{{Sticky}}

Similar compounds with related structures are also known including;

{{Sticky}}

A large number of substances in the 25-NB class are Class A drugs in the United Kingdom as a result of the N-benzylphenethylamine catch-all clause in the Misuse of Drugs Act 1971{{cite web|title=The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014|url=http://www.legislation.gov.uk/uksi/2014/1106/made|website=www.legislation.gov.uk|language=en}} or are otherwise covered by the Psychoactive Substances Act 2016.{{cite web|title=Psychoactive Substances Act 2016|url=http://www.legislation.gov.uk/ukpga/2016/2/contents/enacted|website=www.legislation.gov.uk|language=en}}

• Substituted methoxyphenethylamine
• 4-Substituted 2,5-dimethoxyphenethylamines (2Cs)
• 4-Substituted 2,5-dimethoxyamphetamines (DOx)
• 4-Substituted 2,5-dimethoxy-α-ethylphenethylamines (4Cs)
• List of miscellaneous 5-HT_2A receptor agonists

{{Notelist}}

{{Reflist}}

• [https://psychonautwiki.org/wiki/25x-NBOMe 25x-NBOMe - PsychonautWiki]
• [https://www.erowid.org/chemicals/nbome/ NBOMe Series - Erowid]
• [https://tripsitter.com/nbome/ What Are N-Bombs? (25-I-NBOMe) — Avoid This Psychedelic - Tripsitter]
• [https://www.youtube.com/watch?v=NzpqJgwuQuA VICE In-house Chemist Hamilton Morris on the Dangers of the NBOMe Hallucinogen - VICE - YouTube]

{{Psychedelics}}

{{Serotonin receptor modulators}}

{{TAAR modulators}}

{{Phenethylamines}}

{{Chemical classes of psychoactive drugs}}

Category:5-HT2A agonists

Category:5-HT2B agonists

Category:5-HT2C agonists

Category:Chemical classes of psychoactive drugs

Category:Secondary amines

Category:TAAR1 agonists