4-Bromomethcathinone

4-Bromomethcathinone

Legal status
Legal status	BR: Class F2 (Prohibited psychotropics) DE: NpSG (Industrial and scientific use only) UK: Class B
Identifiers
IUPAC name 1-(4-bromophenyl)-2-(methylamino)propan-1-one
CAS Number	486459-03-4^Y
PubChem CID	10421832
ChemSpider	8597261^N
UNII	9GU9FVS6HH
CompTox Dashboard (EPA)	DTXSID401014169
Chemical and physical data
Formula	C10H12BrNO
Molar mass	242.116 g·mol^−1
3D model (JSmol)	Interactive image
Chirality	Racemic mixture
SMILES CC(C(=O)C1=CC=C(C=C1)Br)NC
InChI 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
^NY (what is this?)  (verify)

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] Halogenated cathinones, including 4-BMC, possess neurotoxic and cytotoxic properties.^[4]

Legal status

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

• 4B-MAR
• 4-Chloromethcathinone
• 4-Ethylmethcathinone

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.