2-Bromomescaline

{{Short description|Mescaline derivative drug}}

{{Hatnote|Not to be confused with 2C-B (sometimes also referred to as "bromomescaline")}}

{{cs1 config |name-list-style=vanc|display-authors=6}}

{{Infobox drug

| IUPAC_name = 2-(2-Bromo-3,4,5-trimethoxyphenyl)ethanamine

| image = 2-BRM_structure.png

| tradename =

| legal_status =

| routes_of_administration =

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 37015-19-3

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

| UNII = A9M89XG7QW

| ATC_prefix = none

| PubChem = 16637783

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

| ChemSpiderID = 17574207

| C=11 | H=16 | Br=1 | N=1 | O=3

| smiles = COC1=C(C(=C(C(=C1)CCN)Br)OC)OC

| StdInChI = 1S/C11H16BrNO3/c1-14-8-6-7(4-5-13)9(12)11(16-3)10(8)15-2/h6H,4-5,13H2,1-3H3

| StdInChIKey = UXQBKANLBLUVMK-UHFFFAOYSA-N

}}

2-Bromomescaline (2-Br-M) is a derivative of the phenethylamine hallucinogen mescaline which has an unusual 2-bromo substitution.{{cite book | vauthors = Shulgin A, Manning T, Daley PF | title = The Shulgin Index. Volume 1. Psychedelic Phenethylamines and Related Compounds | pages = 280–281, 355 | publisher = Transform Press | date = 2011 | isbn = 978-0-9630096-3-0}}{{cite journal| vauthors = Pecherer B, Sunbury RC, Brossi A |title=A novel synthesis of aromatic methoxy and methylenedioxy substituted 2,3,4,5-tetrahydro-1H3-benzazepines|journal=Journal of Heterocyclic Chemistry|date=June 1972|volume=9|issue=3|pages=609–616|doi=10.1002/jhet.5570090322}} It is an agonist for serotonin receptors, with a binding affinity of 215 nM at 5-HT_1A, 513 nM at 5-HT_2A and 379 nM at 5-HT_2C, so while it is around ten times more tightly binding than mescaline at 5-HT_1A and 5-HT_2A receptors, it is over twenty times more potent at 5-HT_2C.{{Cite book | vauthors = Trachsel D, Lehmann D, Enzensperger C | title = Phenethylamine Von der Struktur zur Funktion | pages = 908–910 | publisher = Nachtschatten Verlag AG | date = 2013 | isbn = 978-3-03788-700-4}} It has been reported as a designer drug, first identified in Austria in January 2023.{{cite web | url = https://www.euda.europa.eu/sites/default/files/pdf/31883_en.pdf?606797 | title = New psychoactive substances - the current situation in Europe | work = European Drug Report | publisher = European Union Drugs Agency (EUDA) | date = 2024 }}