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'''5-Bromo-DMT''' ('''5-bromo-N,N-dimethyltryptamine''') is a [[bromide|brominated]] [[indole]] [[alkaloid]] found in certain marine [[invertebrate]]s. It is the 5-[[bromo]] [[analog (chemistry)|analogue]] of [[dimethyltryptamine|DMT]], a [[hallucinogen]] found in many plants and animals.<ref>{{cite journal | author = Djura, Peter et al. | year = 1980 | title = Some Metabolites of the Marine Sponges ''Smenospongia aurea'' and ''Smenospongia'' (= ''Polyfibrospongia'') ''echina'' | journal = Journal of Organic Chemistry | volume = 45 | issue = 8 | pages = 1435–1441 | doi = 10.1021/jo01296a019}}</ref> 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.<ref>{{cite journal | author = Kochanowska AJ, Rao KV, Childress S, El-Alfy A, Matsumoto RR, Kelly M, Stewart GS, Sufka KJ, Hamann MT | title = Secondary metabolites from three Florida sponges with antidepressant activity | journal = Journal of Natural Products | volume = 71 | issue = 2 | pages = 186–9 | year = 2008 | month = February | pmid = 18217716 | doi = 10.1021/np070371u | url = }}</ref>
'''5-Bromo-DMT''' ('''5-bromo-N,N-dimethyltryptamine''') is a [[bromide|brominated]] [[indole]] [[alkaloid]] found in certain marine [[invertebrate]]s. It is the 5-[[bromo]] [[analog (chemistry)|analogue]] of [[dimethyltryptamine|DMT]], a [[hallucinogen]] found in many plants and animals.<ref>{{cite journal | author = Djura, Peter et al. | year = 1980 | title = Some Metabolites of the Marine Sponges ''Smenospongia aurea'' and ''Smenospongia'' (= ''Polyfibrospongia'') ''echina'' | journal = Journal of Organic Chemistry | volume = 45 | issue = 8 | pages = 1435–1441 | doi = 10.1021/jo01296a019}}</ref> 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.<ref>{{cite journal | author = Kochanowska AJ, Rao KV, Childress S, El-Alfy A, Matsumoto RR, Kelly M, Stewart GS, Sufka KJ, Hamann MT | title = Secondary metabolites from three Florida sponges with antidepressant activity | journal = Journal of Natural Products | volume = 71 | issue = 2 | pages = 186–9 | year = 2008 | month = February | pmid = 18217716 | doi = 10.1021/np070371u | url = }}</ref>


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.<ref name=hamilton>{{cite web|url=http://www.vice.com/read/sea-dmt-000481-v20n3?Contentpage=-1 |title=SEA DMT: God Molecule or Barnacle Repellant |last=Morris|first=H.|last=Wallach|first=J. |publisher=Vice Magazine |date= March 2013 |accessdate=2013-03-27}}</ref>
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.<ref name=hamilton>{{cite web|url=http://www.vice.com/read/sea-dmt-000481-v20n3?Contentpage=-1 |title=SEA DMT: God Molecule or Barnacle Repellant |last=Morris H. Wallach J. |publisher=Vice Magazine |date= March 2013 |accessdate=2013-03-27}}</ref>


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. <ref>Kochanowska et al. 2008</ref>
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. <ref>Kochanowska et al. 2008</ref>

Revision as of 15:13, 27 March 2013

5-Bromo-DMT
Names
IUPAC name
[2-(5-bromo-1H-indol-3-yl)ethyl]dimethylamine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • 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 checkY
    Key: ATEYZYQLBQUZJE-UHFFFAOYSA-N checkY
  • 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,5-6H2,1-2H3
    Key: ATEYZYQLBQUZJE-UHFFFAOYAL
  • CN(C)CCC1=CNC2=C1C=C(Br)C=C2
  • CN(C)CCc2cnc1ccc(Br)cc12
Properties
C12H15N2Br
Melting point 98-99 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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.[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 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. [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. {{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. ^ 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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