6-Bromo-MDMA

Last updated
6-Bromo-MDMA
6-Br-MDMA.svg
Clinical data
Other names6-Br-MDMA; 6Br-MDMA; 6-Bromo-3,4-methylenedioxy-N-methylamphetamine; 2-Br-4,5-MDMA
Drug class Psychoactive drug; Serotonin reuptake inhibitor
ATC code
  • None
Identifiers
  • 1-(6-bromo-1,3-benzodioxol-5-yl)-N-methylpropan-2-amine
CAS Number
PubChem CID
UNII
Chemical and physical data
Formula C11H14BrNO2
Molar mass 272.142 g·mol−1
3D model (JSmol)
  • CC(CC1=CC2=C(C=C1Br)OCO2)NC
  • InChI=1S/C11H14BrNO2/c1-7(13-2)3-8-4-10-11(5-9(8)12)15-6-14-10/h4-5,7,13H,3,6H2,1-2H3
  • Key:ZIBHSZQEEWBQLW-UHFFFAOYSA-N

6-Bromo-MDMA, also known as 6-bromo-3,4-methylenedioxy-N-methylamphetamine or as 2-bromo-4,5-methylenedioxymethamphetamine (2-Br-4,5-MDMA), is a psychoactive drug of the phenethylamine, amphetamine, and MDxx families related to MDMA. [1] [2] [3] It does not appear to be a serotonin releasing agent like MDMA, but instead to be a serotonin reuptake inhibitor like citalopram, and with much greater serotonin transporter (SERT) affinity than MDMA. [1] Relatedly, 6-bromo-MDMA lacked key MDMA-like behavioral effects in rodents, including hyperlocomotion, enhanced active avoidance conditioning, and increased social interaction. [1] The drug was encountered as a novel designer drug in Europe in 2014. [2] [3]

Contents

See also

References

  1. 1 2 3 Sáez-Briones P, Castro-Castillo V, Díaz-Véliz G, Valladares L, Barra R, Hernández A, Cassels BK (2019). "Aromatic Bromination Abolishes the Psychomotor Features and Pro-social Responses of MDMA ("Ecstasy") in Rats and Preserves Affinity for the Serotonin Transporter (SERT)". Front Pharmacol. 10: 157. doi:10.3389/fphar.2019.00157. PMC   6403168 . PMID   30873030.{{cite journal}}: CS1 maint: unflagged free DOI (link)
  2. 1 2 "EMCDDA-Europol 2014 Annual Report on the implementation of Council Decision 2005/387/JHA". www.euda.europa.eu. 2 July 2024. Retrieved 29 October 2025.
  3. 1 2 Liu C, Jia W, Qian Z, Li T, Hua Z (February 2017). "Identification of five substituted phenethylamine derivatives 5-MAPDB, 5-AEDB, MDMA methylene homolog, 6-Br-MDMA, and 5-APB-NBOMe". Drug Test Anal. 9 (2): 199–207. doi:10.1002/dta.1955. PMID   26856255.
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