25E-NBOMe
{{Short description|Chemical compound}}
{{Drugbox
| image = 2C-E-NBOMe 2DACS.svg
| width = 200px
| tradename =
| legal_BR = F2
| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-07-25}}
| legal_DE = NpSG
| legal_UK = Class A
| CAS_number = 1354632-14-6
| PubChem = 118796522
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 52085495
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 02HX6G35T3
| synonyms = 2C-E-NBOMe; NBOMe-2C-E
| IUPAC_name = 2-(4-ethyl-2,5-dimethoxyphenyl)-N-(2-methoxybenzyl)ethanamine
| C=20 | H=27 | N=1 | O=3
| SMILES = COC(C=CC=C1)=C1CNCCC2=C(OC)C=C(CC)C(OC)=C2
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C20H27NO3/c1-5-15-12-20(24-4)16(13-19(15)23-3)10-11-21-14-17-8-6-7-9-18(17)22-2/h6-9,12-13,21H,5,10-11,14H2,1-4H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = PXDVGFGXPVCNAB-UHFFFAOYSA-N
}}
25E-NBOMe, also known as 2C-E-NBOMe or NBOMe-2C-E, is a derivative of the phenethylamine 2C-E. It acts in a similar manner to related compounds such as 25I-NBOMe, which are potent agonists at the 5-HT2A receptor.{{cite journal | vauthors = Hansen M, Phonekeo K, Paine JS, Leth-Petersen S, Begtrup M, Bräuner-Osborne H, Kristensen JL | title = Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists | journal = ACS Chemical Neuroscience | volume = 5 | issue = 3 | pages = 243–249 | date = March 2014 | pmid = 24397362 | pmc = 3963123 | doi = 10.1021/cn400216u }}{{cite thesis | vauthors = Hansen M | title = Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain. | degree = Ph.D. | publisher = University of Copenhagen | date = 2010-12-16 | doi = 10.13140/RG.2.2.33671.14245}} 25E-NBOMe has been sold as a drug and produces similar effects in humans to related compounds such as 25I-NBOMe and 25C-NBOMe.
Interactions
{{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}
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}}
Pharmacology
25E-NBOMe acts as an agonist of the serotonin 5-HT2 receptors.{{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 }} In accordance with its psychedelic effects in humans, it produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.
25E-NBOMe has shown reinforcing effects in rodents.{{cite journal | vauthors = Kim YJ, Kook WA, Ma SX, Lee BR, Ko YH, Kim SK, Lee Y, Lee JG, Lee S, Kim KM, Lee SY, Jang CG | title = The novel psychoactive substance 25E-NBOMe induces reward-related behaviors via dopamine D1 receptor signaling in male rodents | journal = Arch Pharm Res | volume = 47 | issue = 4 | pages = 360–376 | date = April 2024 | pmid = 38551761 | doi = 10.1007/s12272-024-01491-4 | url = }} This included conditioned place preference (CPP) and self-administration. The reinforcing effects of 25E-NBOMe were mediated by increased dopaminergic signaling in the nucleus accumbens. Blockade of the dopamine D1 receptor could attenuate the CPP induced by 25E-NBOMe.
Society and culture
=Legal status=
==Sweden==
Sweden's public health agency classified 25E-NBOMe as a narcotic substance, on January 18, 2019.{{cite web | url=https://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2019/januari/sexton-nya-amnen-klassas-som-narkotika-eller-halsofarlig-vara/ | title=Sexton nya ämnen klassas som narkotika eller hälsofarlig vara | publisher=Folkhälsomyndigheten | language=sv | date=18 January 2019 | access-date=11 November 2019 | archive-date=3 June 2021 | archive-url=https://web.archive.org/web/20210603114630/https://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2019/januari/sexton-nya-amnen-klassas-som-narkotika-eller-halsofarlig-vara/ | url-status=dead }}
==United Kingdom==
{{N-benzylphenethylamine-Legality-United Kingdom}}
See also
Notes
{{Notelist}}
References
{{Reflist}}
External links
- [https://isomerdesign.com/pihkal/explore/5543 25E-NBOMe - Isomer Design]
{{Psychedelics}}
{{Serotonin receptor modulators}}
{{Phenethylamines}}
{{Hallucinogen-stub}}