5-Bromo-DMT

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5-Bromo-DMT
IUPAC name

[2-(5-bromo-1H-indol-3-yl)ethyl]dimethylamine

Identifiers
CAS number 17274-65-6 N
PubChem 360252
ChemSpider 319812 YesY
ChEMBL CHEMBL403031 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C12H15N2Br
Melting point 98-99 °C
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

5-Bromo-DMT (5-bromo-N,N-dimethyltryptamine) is a brominated indole alkaloid found in certain marine invertebrates. It is the 5-bromo analogue of DMT, a psychedelic found in many plants and animals.[1] Other naturally occurring 5-substituted analogues of DMT include bufotenin and 5-MeO-DMT, both of which, like DMT, are psychoactive and found in plants and animals. Animal studies on 5-bromo-DMT showed it to produce effects suggestive of sedative and antidepressant activity.[2]

Anecdotal reports published by Hamilton Morris indicate that 5-Bromo-DMT freebase is psychoactive in humans when smoked at doses between 20 and 50 milligrams.[3]

This compound is soluble in ethanol and methanol. It has been found in Verongula rigida (0.00142% dry wt.) along with 5,6-diBr-DMT (0.35% dry wt.) and seven other alkaloids. 5-Br-DMT caused significant reduction of locomotor activity in the rodent FST model (suggested to indicate a potential sedative action). It did not show any antidepressant activity in either test. [4]

References

  1. ↑ Djura, Peter et al. (1980). "Some Metabolites of the Marine Sponges Smenospongia aurea and Smenospongia (= Polyfibrospongia) echina". Journal of Organic Chemistry 45 (8): 1435–1441. doi:10.1021/jo01296a019. 
  2. ↑ Kochanowska AJ, Rao KV, Childress S, El-Alfy A, Matsumoto RR, Kelly M, Stewart GS, Sufka KJ, Hamann MT (February 2008). "Secondary metabolites from three Florida sponges with antidepressant activity". Journal of Natural Products 71 (2): 186–9. doi:10.1021/np070371u. PMID 18217716. 
  3. ↑ Morris H. Wallach J. (March 2013). "SEA DMT: God Molecule or Barnacle Repellant". Vice Magazine. Retrieved 2013-03-27. 
  4. ↑ Kochanowska et al. 2008



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