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Names

25N-NBOMe
N-(2-Methoxybenzyl)-4-nitro-2,5-dimethoxyphenethylamine
2C-N-NBOMe

IUPAC names

2-(2,5-Dimethoxy-4-nitrophenyl)-N-[(2-methoxyphenyl)methyl]ethan-1-amine
2-(2,5-Dimethoxy-4-nitrophenyl)-N-(2-methoxybenzyl)ethan-1-amine

ID 2422 · Formula C₁₈H₂₂N₂O₅ · Molecular weight 346.378

InChI InChI=1S/C18H22N2O5/c1-23-16-7-5-4-6-14(16)12-19-9-8-13-10-18(25-3)15(20(21)22)11-17(13)24-2/h4-7,10-11,19H,8-9,12H2,1-3H3

InChI Key TXCKTIBHURMASQ-UHFFFAOYSA-N This stereoisomer Any stereoisomer

SMILES COc1cc(N(=O)=O)c(cc1CCNCc1ccccc1OC)OC

ChemSpider 52085577
PubChem 118536028
Wikidata Q16154831
Wikipedia 25N-NBOMe
Wikipedia, see also 25-NB
PsychonautWiki 25N-NBOMe
Project Response 25N-NBOMe (1621-16)
swgdrug.org 25N-NBOMe
bluelight.org The Big & Dandy 25N-NBOMe Thread

Anon. JW, Personal communication of unpublished research 1 Dec 2011.

Casale, JF; Hays, PA. Characterization of eleven 2,5-dimethoxy-N-(2-methoxybenzyl)phenethylamine (NBOMe) derivatives and differentiation from their 3- and 4-methoxybenzyl analogues—Part I Microgram J., 1 Jan 2012, 9 (2), 84–109. 4.6 MB. #19: 25N-NB2OMe GC,MS,IR

Uchiyama, N; Shimokawa, Y; Matsuda, S; Kawamura, M; Kikura-Hanajiri, R; Goda, Y. Two new synthetic cannabinoids, AM-2201 benzimidazole analog (FUBIMINA) and (4-methylpiperazin-1-yl)(1-pentyl-1H-indol-3-yl)methanone (MEPIRAPIM), and three phenethylamine derivatives, 25H-NBOMe 3,4,5-trimethoxybenzyl analog, 25B-NBOMe, and 2C-N-NBOMe, identified in illegal products Forensic Toxicol., 26 Nov 2013, 21 (1), 105-115. 827 kB. https://doi.org/10.1007/s11419-013-0217-2 #4 GC,LC,MS,NMR,UV

Hays, PA; Casale, JF. Characterization of eleven 2,5-dimethoxy-N-(2-methoxybenzyl)phenethylamine (NBOMe) derivatives and differentiation from their 3-and 4-methoxybenzyl analogues - Part II Microgram J., 1 Jan 2014, 11 (1–4), 3–22. 8.1 MB. #19: 25N-NB2OMe NMR

Hyperlab. Hyperlab new compounds 29 Sep 2014. 232 kB. Note: Contains links to hyperlab.info that require elevated access/karma to follow.

EMCDDA. New drugs in Europe, 2012, European Monitoring Centre for Drugs and Drug Addiction, Lisbon, 1 May 2013. 773 kB. #71

Rickli, A; Luethi, D; Reinisch, J; Buchy, D; Hoener, MC; Liechti, ME. Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs) Neuropharmacology, 1 Dec 2015, 99, 546–553. 625 kB. https://doi.org/10.1016/j.neuropharm.2015.08.034 #25N-NBOMe

King, LA. New phenethylamines in Europe Drug Test. Anal., 1 Jul 2014, 6 (7-8), 808-818. 472 kB. https://doi.org/10.1002/dta.1570

Seo, H; Kim, IS; Kim, Y; Yoo, HH; Hong, J. Metabolic profile determination of 25N-NBOMe in human liver microsomes by liquid chromatography-quadrupole time-of-flight mass spectrometry Int. J. Legal Med., 9 Aug 2018, 133 (3), 833-841. 2.0 MB. https://doi.org/10.1007/s00414-018-1904-7 #25N-NBOMe

Lum, BJ; Brophy, JJ; Hibbert, DB. Identification of 4-substituted 2-(4-x-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine (25X-NBOMe) and analogues by gas chromatography–mass spectrometry analysis of heptafluorobutyric anhydride (HFBA) derivatives Aust. J. Forensic Sci., 2 Jan 2016, 48 (1), 59–73. 5.5 MB. https://doi.org/10.1080/00450618.2015.1026274 #25N-NBOMe GC,MS

Grafinger, KE; Stahl, K; Wilke, A; König, S; Weinmann, W. In vitro phase I metabolism of three phenethylamines 25D-NBOMe, 25E-NBOMe and 25N-NBOMe using microsomal and microbial models Drug Test. Anal., 1 Oct 2018, 10 (10), 1607–1626. 3.8 MB. https://doi.org/10.1002/dta.2446 #25N-NBOMe

Adamowicz, P; Zuba, D. Discrimination among designer drug isomers by chromatographic and spectrometric methods In Chromatographic Techniques in the Forensic Analysis of Designer Drugs; Kowalska, T; Sajewicz, M; Sherma, J, Eds., CRC Press, Taylor & Francis Group, 1 Jan 2018; pp 211–232. 1.1 MB. LC,MS,IR,UV

Luethi, D; Liechti, ME. Monoamine transporter and receptor interaction profiles in vitro predict reported human doses of novel psychoactive stimulants and psychedelics Int. J. Neuropsychoph., 1 Oct 2018, 21 (10), 926–931. 254 kB. https://doi.org/10.1093/ijnp/pyy047 #S2 Phenethylamines 25N-NBOMe

Eshleman, AJ; Wolfrum, KM; Reed, JF; Kim, SO; Johnson, RA; Janowsky, A. Neurochemical pharmacology of psychoactive substituted N-benzylphenethylamines: High potency agonists at 5-HT_2A receptors Biochem. Pharmacol., 1 Dec 2018, 158 27–34. 790 kB. https://doi.org/10.1016/j.bcp.2018.09.024 #25N-NBOMe

Bork, W; Dahlenburg, R; Gimbel, M; Jacobsen-Bauer, A; Zörntlein, S. Herleitung Von Grenzwerten Der „nicht Geringen Menge“ Im Sinne Des Btmg Toxichem Krimtech, 1 Jan 2019, 86 (1), 5–91. 4.4 MB. #HP-022

Clancy, L; Philp, M; Shimmon, R; Fu, S. Development and validation of a color spot test method for the presumptive detection of 25-NBOMe compounds Drug Test. Anal., 19 Aug 2020, 13 (5), 929-943. 11.3 MB. https://doi.org/10.1002/dta.2905 #25N-NBOMe spot

Åstrand, A; Guerrieri, D; Vikingsson, S; Kronstrand, R; Green, H. In vitro characterization of new psychoactive substances at the μ-opioid, CB1, 5HT_1A, and 5-HT2_A receptors—On-target receptor potency and efficacy, and off-target effects Forensic Sci. Int., 1 Dec 2020, 317, 110553. 1.7 MB. https://doi.org/10.1016/j.forsciint.2020.110553 #25N-NBOMe

Wallach, J; McCorvy, J; Halberstadt, A. Selective, partial, and arrestin-biased 5-HT_2A agonists with utility in various disorders Patent WO 2022/241006 A1, 17 Nov 2022. 11.7 MB. #4

Martins, D; Gil-Martins, E; Cagide, F; Da Fonseca, C; Benfeito, S; Fernandes, C; Chavarria, D; Remião, F; Silva, R; Borges, F. Unraveling the in vitro toxicity profile of psychedelic 2C phenethylamines and their N-benzylphenethylamine (NBOMe) analogues Pharmaceuticals, 15 Aug 2023, 16 (8), 1158. 6.0 MB. https://doi.org/10.3390/ph16081158 #25N-NBOMe MS,NMR

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. Identification of 5-HT_2A receptor signaling pathways responsible for psychedelic potential bioRxiv, 31 Jul 2023, 2023.07.29.551106. 9.8 MB. https://doi.org/10.1101/2023.07.29.551106 #25N-NBOMe (4) LC,MS,NMR

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. Identification of 5-HT_2A receptor signaling pathways associated with psychedelic potential Nat. Commun., 15 Dec 2023, 14 (1), 8221. 14.9 MB. https://doi.org/10.1038/s41467-023-44016-1 #4 MS,NMR

Duan, W; Cao, D; Wang, S; Cheng, J. Serotonin 2A receptor (5-HT_2AR) agonists: Psychedelics and non-hallucinogenic analogues as emerging antidepressants Chem. Rev., 10 Jan 2024, 124 (1), 124–163. 12.6 MB. https://doi.org/10.1021/acs.chemrev.3c00375 #113

25N-NB3OMe · N-(3-Methoxybenzyl)-4-nitro-2,5-dimethoxyphenethylamine

25N-NB4OMe · N-(4-Methoxybenzyl)-4-nitro-2,5-dimethoxyphenethylamine

25N-NBOH3Me · N-(2-Hydroxy-3-methylbenzyl)-4-nitro-2,5-dimethoxyphenethylamine

7 Dec 2019 · · Isomer Design