25D-NBOMe

{{Short description|Chemical compound}}

{{Drugbox

| IUPAC_name = 2-(2,5-dimethoxy-4-methylphenyl)-N-(2-methoxybenzyl)ethanamine

| image = 25D-NBOMe2DACS.svg

| width = 240

| 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

| legal_status = Illegal in China and Sweden

| CAS_number = 1354632-02-2

| PubChem = 118536027

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 48059920

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 7RET11HE13

| synonyms = NBOMe-2C-D

| C=19 | H=25 | N=1 | O=3

| SMILES = COC1=C(C=C(C(=C1)C)OC)CCNCC2=C(C=CC=C2)OC

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C19H25NO3/c1-14-11-19(23-4)15(12-18(14)22-3)9-10-20-13-16-7-5-6-8-17(16)21-2/h5-8,11-12,20H,9-10,13H2,1-4H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = UTVHBNXCFSATDB-UHFFFAOYSA-N

}}

25D-NBOMe, also known as NBOMe-2C-D, is a derivative of the phenethylamine derived hallucinogen 2C-D. It acts in a similar manner to related compounds such as 25I-NBOMe, which is a potent agonist at the 5-HT_2A 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 = 243–9 | 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}} 25D-NBOMe has been sold as a street drug since 2010 and produces similar effects in humans to related compounds such as 25I-NBOMe and 25C-NBOMe.{{cite journal |vauthors=Casale JF, Hays PA |title=Characterization of Eleven 2,5-Dimethoxy-N-(2-methoxybenzyl)phenethylamine (NBOMe) Derivatives and Differentiation from their 3- and 4-Methoxybenzyl Analogues - Part I |journal=Microgram Journal |year=2012 |volume=9 |issue=2 |pages=84–109 |url=https://www.dea.gov/pr/microgram-journals/2012/mj9_84-109.pdf |access-date=14 January 2014 |archive-date=13 May 2017 |archive-url=https://web.archive.org/web/20170513130505/https://www.dea.gov/pr/microgram-journals/2012/mj9_84-109.pdf |url-status=dead }} It was banned as a Temporary Class Drug in the UK on 10 June 2013 after concerns about its recreational use.{{cite web | url = https://www.gov.uk/government/publications/temporary-class-drug-order-report-on-benzofury-and-nbome-compounds | title = Temporary class drug order report on 5-6APB and NBOMe compounds | access-date = 2013-07-10 | date = 4 Jun 2013 | publisher = UK Home Office}}