4-Bromomethcathinone

{{Short description|Psychoactive drug and research chemical}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 462783233

| IUPAC_name = 1-(4-bromophenyl)-2-(methylamino)propan-1-one

| image = 4-bromomethcathinone.svg

| width = 250px

| chirality = Racemic mixture

| drug_name =

| tradename =

| legal_BR = F2

| legal_DE = NpSG

| legal_UK = Class B

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 486459-03-4

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

| UNII = 9GU9FVS6HH

| PubChem = 10421832

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 8597261

| smiles = CC(C(=O)C1=CC=C(C=C1)Br)NC

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C10H12BrNO/c1-7(12-2)10(13)8-3-5-9(11)6-4-8/h3-7,12H,1-2H3

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = OOJXMFNDUXHDOV-UHFFFAOYSA-N

| C=10 | H=12 | Br=1 | N=1 | O=1

}}

4-Bromomethcathinone (4-BMC, Brephedrone) is a psychoactive drug and research chemical of the phenethylamine, amphetamine, and cathinone chemical classes. It acts as a serotonin and norepinephrine reuptake inhibitor,{{ cite journal | vauthors = Foley KF, Cozzi NV | title = Bromine substitution at the ring 3- or 4-position of methcathinone enhances potency at serotonin uptake transporters | journal = Society for Neuroscience Abstracts | year = 1999 | volume = 25 | issue = 1–2 | pages = 1701 | id = 678.17 | url = http://www.neurophys.wisc.edu/~cozzi/sfnabs25.html | access-date = 2013-07-28 | archive-url = https://web.archive.org/web/20130907120810/http://www.neurophys.wisc.edu/~cozzi/sfnabs25.html | archive-date = 2013-09-07 | url-status = dead }}{{cite journal | vauthors = Foley KF, Cozzi NV | title = Inhibition of transport function and desipramine binding at the human noradrenaline transporter by N-ethylmaleimide and protection by substrate analogs | journal = Naunyn-Schmiedeberg's Archives of Pharmacology | volume = 365 | issue = 6 | pages = 457–461 | date = June 2002 | pmid = 12070759 | doi = 10.1007/s00210-002-0532-3 | s2cid = 3244808 }} but acts more like an antidepressant than a stimulant.{{cite journal | vauthors = Foley KF, Cozzi NV | title = Novel aminopropiophenones as potential antidepressants | journal = Drug Development Research | year = 2003 | volume = 60 | issue = 4 | pages = 252–260 | doi = 10.1002/ddr.10297 | s2cid = 84128787 | url = https://ewsd.wiv-isp.be/Publications%20on%20new%20psychoactive%20substances/Mephedrone/Foley2003_methcathinone-analogs.pdf | access-date = 2015-09-09 | archive-url = https://web.archive.org/web/20160306221301/https://ewsd.wiv-isp.be/Publications%20on%20new%20psychoactive%20substances/Mephedrone/Foley2003_methcathinone-analogs.pdf | archive-date = 2016-03-06 | url-status = dead }} Halogenated cathinones, including 4-BMC, possess neurotoxic and cytotoxic properties.{{cite journal | vauthors = Wojcieszak J, Kuczyńska K, Zawilska JB | title = Four Synthetic Cathinones: 3-Chloromethcathinone, 4-Chloromethcathinone, 4-Fluoro-α-Pyrrolidinopentiophenone, and 4-Methoxy-α-Pyrrolidinopentiophenone Produce Changes in the Spontaneous Locomotor Activity and Motor Performance in Mice with Varied Profiles | journal = Neurotoxicity Research | volume = 38 | issue = 2 | pages = 536–551 | date = August 2020 | pmid = 32506339 | pmc = 7334283 | doi = 10.1007/s12640-020-00227-8 }}