4-Bromomethcathinone

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,[1][2] but acts more like an antidepressant than a stimulant.[3] Some 4-halogenated cathinones seem to share the selective serotonergic neurotoxicity of their corresponding amphetamine analogues.[4]

4-Bromomethcathinone
Legal status
Legal status
  • BR: Class F2 (Prohibited psychotropics)
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class B
Identifiers
  • 1-(4-bromophenyl)-2-(methylamino)propan-1-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC10H12BrNO
Molar mass242.116 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • CC(C(=O)C1=CC=C(C=C1)Br)NC
  • InChI=1S/C10H12BrNO/c1-7(12-2)10(13)8-3-5-9(11)6-4-8/h3-7,12H,1-2H3 ☒N
  • Key:OOJXMFNDUXHDOV-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

As of October 2015, 4-BMC is a controlled substance in China.[5] 4-Bromomethcathinone is considered a Schedule 1 substance in Virginia.[6]

See also

References
  1. Foley KF, Cozzi NV (1999). "Bromine substitution at the ring 3- or 4-position of methcathinone enhances potency at serotonin uptake transporters". Society for Neuroscience Abstracts. 25 (1–2): 1701. 678.17. Archived from the original on 2013-09-07. Retrieved 2013-07-28.
  2. Foley KF, Cozzi NV (June 2002). "Inhibition of transport function and desipramine binding at the human noradrenaline transporter by N-ethylmaleimide and protection by substrate analogs". Naunyn-Schmiedeberg's Archives of Pharmacology. 365 (6): 457–461. doi:10.1007/s00210-002-0532-3. PMID 12070759. S2CID 3244808.
  3. Foley KF, Cozzi NV (2003). "Novel aminopropiophenones as potential antidepressants" (PDF). Drug Development Research. 60 (4): 252–260. doi:10.1002/ddr.10297. S2CID 84128787. Archived from the original (PDF) on 2016-03-06. Retrieved 2015-09-09.
  4. Wojcieszak J, Kuczyńska K, Zawilska JB (August 2020). "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". Neurotoxicity Research. 38 (2): 536–551. doi:10.1007/s12640-020-00227-8. PMC 7334283. PMID 32506339.
  5. "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
  6. "18VAC110-20-322. Placement of Chemicals in Schedule I." Commonwealth of Virginia. 2 December 2015. Retrieved 11 March 2016.
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