5-Bromo-DMT

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5-Bromo-DMT
5-Bromo-DMT.svg
Names
IUPAC name
[2-(5-Bromo-1H-indol-3-yl)ethyl]dimethylamine
Identifiers
17274-65-6 N
ChEMBL ChEMBL403031 YesY
ChemSpider 319812 YesY
Jmol-3D images Image
Image
PubChem 360252
Properties
C12H15BrN2
Molar mass 267.17 g·mol−1
Melting point 98 to 99 °C (208 to 210 °F; 371 to 372 K) [citation needed]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N verify (what isYesY/N?)
Infobox references

5-Bromo-DMT (5-bromo-N,N-dimethyltryptamine) is a brominated indole alkaloid found in certain[specify] marine invertebrates. It is the 5-bromo derivative of DMT, a psychedelic found in many plants and animals.[1] Animal studies on 5-bromo-DMT showed that it produces effects suggestive of sedative and antidepressant activity.[2]

This compound is soluble in ethanol and methanol.[citation needed] 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.[citation needed] 5-Br-DMT caused significant reduction of locomotor activity in the rodent FST model (suggested to indicate a potential sedative action).[citation needed] It did not show any antidepressant activity in either test.[2]

The synthesis and description on the subjective effects of 5-Br-DMT ingestion in humans has been reported. Melting point of the freebase from hexanes is reported to be 99-102.3°C The compound was reported to be psychoactive at 20-50 mg via vaporization with mild psychedelic-like activity. This is the first report of human ingestion.[3]

References[edit]

  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. ^ a b 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. SEA DMT GOD MOLECULE OR BARNACLE REPELLENT? VICE. 2013. http://www.vice.com/read/sea-dmt-000481-v20n3