25H-NBOMe
{{Short description|Chemical compound}}
{{cs1 config|name-list-style=vanc}}
{{Infobox drug
| verifiedrevid =
| image = 25H-NBOMe.svg
| width = 200px
| tradename =
| pregnancy_category =
| routes_of_administration =
| ATC_prefix = None
| 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
| legal_status =
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 919797-16-3
| CAS_supplemental =
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = RN5ZVN74Y9
| PubChem = 39424372
| DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 25511924
| synonyms = 2C-H-NBOMe; NBOMe-2C-H; DMPEA-NBOMe; N-(2-Methoxybenzyl)-2,5-dimethoxyphenethylamine; 2,5-Dimethoxy-N-(2-methoxybenzyl)phenethylamine
| IUPAC_name = 2-(2,5-Dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine
| C=18 | H=23 | N=1 | O=3
| SMILES = COC1=CC(=C(C=C1)OC)CCNCC2=CC=CC=C2OC
| StdInChI = 1S/C18H23NO3/c1-20-16-8-9-18(22-3)14(12-16)10-11-19-13-15-6-4-5-7-17(15)21-2/h4-9,12,19H,10-11,13H2,1-3H3
| StdInChIKey = RMLXCDMTGWSEOU-UHFFFAOYSA-N
}}
25H-NBOMe, also known as NBOMe-2C-H, is a derivative of the phenethylamine hallucinogen 2C-H, which acts as a highly potent full agonist for the human 5-HT2A receptor.{{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}}
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
25H-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.{{cite journal | vauthors = Ferri BG, de Novais CO, Bonani RS, de Barros WA, de Fátima Â, Vilela FC, Giusti-Paiva A | title = Psychoactive substances 25H-NBOMe and 25H-NBOH induce antidepressant-like behavior in male rats | journal = Eur J Pharmacol | volume = 955 | issue = | pages = 175926 | date = September 2023 | pmid = 37479015 | doi = 10.1016/j.ejphar.2023.175926 | url = | doi-access = free }} The drug has also been found to produce antidepressant-like effects in rodents.
25H-NBOMe has shown reinforcing effects in rodents.{{cite journal | vauthors = Jo C, Joo H, Youn DH, Kim JM, Hong YK, Lim NY, Kim KS, Park SJ, Choi SO | title = Rewarding and Reinforcing Effects of 25H-NBOMe in Rodents | journal = Brain Sci | volume = 12 | issue = 11 | date = November 2022 | page = 1490 | pmid = 36358416 | doi = 10.3390/brainsci12111490 | doi-access = free | url = | pmc = 9688077 }} This included conditioned place preference (CPP) and self-administration.
Society and culture
=Legal status=
==Sweden==
The Riksdag added 25H-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 25H-NBOMe, and 2-(2,5-dimetoxifenyl)-N-(2-metoxibensyl)etanamin.{{cite web|title=Läkemedelsverkets föreskrifter - LVFS och HSLF-FS;Läkemedelsverket/Swedish Medical Products Agency|url=https://lakemedelsverket.se/upload/lvfs/LVFS_2013-15.pdf|url-status=live|archive-url=https://web.archive.org/web/20130928024035/http://www.lakemedelsverket.se/upload/lvfs/LVFS_2013-15.pdf |archive-date=2013-09-28 }}
==United Kingdom==
{{N-benzylphenethylamine-Legality-United Kingdom}}
See also
Notes
{{Notelist}}
References
{{Reflist}}
External links
- [https://isomerdesign.com/pihkal/explore/5386 25H-NBOMe - Isomer Design]
{{Psychedelics}}
{{Serotonin receptor modulators}}
{{Phenethylamines}}