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4-Bromo-DMT

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4-Bromo-DMT
Clinical data
Other names4-Br-DMT; 4-Bromo-N,N-dimethyltryptamine; 4-Bromo-N,N-DMT
Drug classSerotonin receptor modulator; Serotonin releasing agent; Psychoactive drug
ATC code
  • None
Identifiers
  • 2-(4-bromo-1H-indol-3-yl)-N,N-dimethylethanamine
PubChem CID
ChemSpider
Chemical and physical data
FormulaC12H15BrN2
Molar mass267.170 g·mol−1
3D model (JSmol)
  • CN(C)CCC1=CNC2=C1C(=CC=C2)Br
  • InChI=1S/C12H15BrN2/c1-15(2)7-6-9-8-14-11-5-3-4-10(13)12(9)11/h3-5,8,14H,6-7H2,1-2H3
  • Key:HBSUMCTTXGWDDS-UHFFFAOYSA-N

4-Bromo-DMT, or 4-Br-DMT, also known as 4-bromo-N,N-dimethyltryptamine, is a non-selective serotonin receptor modulator and serotonin releasing agent of the tryptamine family related to serotonergic psychedelics like psilocin (4-HO-DMT) and 5-bromo-DMT.[1][2]

Pharmacology

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Pharmacodynamics

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4-Bromo-DMT shows high affinity for a variety of serotonin receptors, including the serotonin 5-HT1A, 5-HT2A, 5-HT2B, 5-HT2C, 5-HT6, and 5-HT7 receptors (Ki = 3.5–82 nM).[1][2] The drug shows higher affinity for almost all of these receptors than psilocin or dimethyltryptamine (DMT).[1] Its potential agonistic and antagonistic activities at serotonin receptors including the serotonin 5-HT2A receptor were not assessed.[1] In addition to interacting with serotonin receptors, 4-bromo-DMT is a potent serotonin reuptake inhibitor (IC50Tooltip half-maximal inhibitory concentration = 167 nM) as well as a partial serotonin releasing agent in rat brain synaptosomes (EC50Tooltip half-maximal effective concentration = 132 nM; EmaxTooltip half-maximal effective concentration = 45%).[1] It showed little or no activity in terms of inhibition of dopamine and norepinephrine reuptake.[1]

Unlike psilocin and DMT, 4-bromo-DMT fails to induce the head-twitch response, a behavioral proxy of psychedelic effects, in rodents, suggesting that 4-bromo-DMT would not produce hallucinogenic effects in humans.[1] The serotonin 5-HT1A receptor antagonist WAY-100635 and the serotonin 5-HT2C receptor antagonist SB-242084 did not unmask latent head-twitch response activity with 4-bromo-DMT.[1] Although it did not produce psychedelic-like activity in rodents, 4-bromo-DMT produced hypolocomotion and hypothermia at high doses in rodents similarly to psilocin and DMT.[1] In contrast to psilocin and DMT however, 4-bromo-DMT produced seizures and death at the highest assessed dose in rodents.[1]

Chemistry

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The chemical synthesis of 4-bromo-DMT has been described.[1][2] It is not a controlled substance and is considered useful as a precursor in 4-substituted tryptamine synthesis.[1][3]

History

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4-Bromo-DMT was first described in the scientific literature by Jeremy Rolquin at Virginia Commonwealth University by 2022.[2] Subsequently, it was described in greater detail by Grant C. Glatfelter and colleagues by 2026.[1] The drug was encountered as a novel designer drug in Canada in 2022.[3]

See also

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References

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  1. 1 2 3 4 5 6 7 8 9 10 11 12 13 Bray E, Glatfelter GC, Maitland AD, Gonzalez NR, Walther D, Yacoub J, et al. (July 2026). "Synthesis and Biological Evaluation of 4-Bromo-N,N-dimethyltryptamine (4-Br-DMT): A Synthetic Building Block for Future Analog Development". ACS Omega. 11 (26): 39102–39113. doi:10.1021/acsomega.6c02996. PMC 13347390. PMID 42428867.
  2. 1 2 3 4 Rolquin J (2022). Examining Ayahuasca Constituents at 5-HT2A Receptors in Search of Antidepressant Action (Thesis). VCU Theses and Dissertations. doi:10.25772/0HV0-SN48.
  3. 1 2 Gilbert ML, Boileau-Falardeau M, Maurice-Gelinas C, Chiasson JF, Pitre J, Archambault B, et al. (2023). At-a-Glance: New Psychoactive Substances in Canada - 2022 (Report). Health Canada, Drug Analysis Service; Public Health Agency of Canada.
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