5-Bromo-DMT

5-Bromo-DMT
Legal status
Legal status
Identifiers
  • [2-(5-Bromo-1H-indol-3-yl)ethyl]dimethylamine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H15BrN2
Molar mass267.170 g·mol−1
3D model (JSmol)
  • BrC2=CC=C1[NH]C=C(C1=C2)CCN(C)C
  • InChI=1S/C12H15BrN2/c1-15(2)6-5-9-8-14-12-4-3-10(13)7-11(9)12/h3-4,7-8,14H,5-6H2,1-2H3
  • Key:ATEYZYQLBQUZJE-UHFFFAOYSA-N

5-Bromo-DMT (5-bromo-N,N-dimethyltryptamine) is a psychedelic brominated indole alkaloid found in the sponges Smenospongia aurea and Smenospongia echina, as well as in Verongula rigida (0.00142% dry weight) alongside 5,6-dibromo-DMT (0.35% dry weight) and seven other alkaloids. It is the 5-bromo derivative of DMT, a psychedelic found in many plants and animals.

5-Bromo-DMT is an agonist of the serotonin 5-HT2A receptor, with an EC50Tooltip half-maximal effective concentration of 3,090 nM.

Animal studies on 5-Bromo-DMT showed that it produces effects suggestive of sedative and antidepressant activity and caused significant reduction of locomotor activity in the rodent FST model. In contrast to 5-fluoro-DMT and 5-chloro-DMT, 5-bromo-DMT failed to produce the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.

5-Bromo-DMT was reported to be psychoactive in humans at doses of 20 to 50 mg via vaporization with mild psychedelic-like effects.