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5-Bromo-DMT

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5-Bromo-DMT
Names
IUPAC name dimethylamine
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • 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,5-6H2,1-2H3Key: ATEYZYQLBQUZJE-UHFFFAOYSA-N
  • InChI=1/C12H15BrN2/c1-15(2)6-5-9-8-14-12-4-3-10(13)7-11(9)12/h3-4,7-8,14H,5-6H2,1-2H3Key: ATEYZYQLBQUZJE-UHFFFAOYAL
SMILES
  • CN(C)CCC1=CNC2=C1C=C(Br)C=C2
  • CN(C)CCc2cnc1ccc(Br)cc12
Properties
Chemical formula C12H15N2Br
Melting point 98-99 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkverify (what is  ?) Infobox references
Chemical compound

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 hallucinogen found in many plants and animals. 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.

This compound is soluble in ethanol and methanol. It is found in Verongula rigida (0.00142% dry wt.) and also 5,6-diBr-DMT (0.35% dry wt.) was found as well as 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.

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. {{cite journal}}: Explicit use of et al. in: |author= (help)
  2. Kochanowska AJ, Rao KV, Childress S, El-Alfy A, Matsumoto RR, Kelly M, Stewart GS, Sufka KJ, Hamann MT (2008). "Secondary metabolites from three Florida sponges with antidepressant activity". Journal of Natural Products. 71 (2): 186–9. doi:10.1021/np070371u. PMID 18217716. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  3. Kochanowska et al. 2008


Tryptamines
Tryptamines
N-Acetyltryptamines
α-Alkyltryptamines
Triptans
Cyclized tryptamines
Isotryptamines
Related compounds


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