5-Bromo-DMT

5-Bromo-DMT
Legal status
Legal status	UK:Class A; Illegal in Singapore;
Identifiers
	IUPAC name [2-(5-Bromo-1H-indol-3-yl)ethyl]dimethylamine;
CAS Number	17274-65-6;
PubChemCID	360252;
ChemSpider	319812;
UNII	2F81I6UW8C;
CompTox Dashboard(EPA)	DTXSID90326928;
Chemical and physical data
Formula	C12H15BrN2
Molar mass	267.170g·mol−1
3D model (JSmol)	Interactive image;
	SMILES BrC2=CC=C1[NH]C=C(C1=C2)CCN(C)C;
	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,5-6H2,1-2H3; Key:ATEYZYQLBQUZJE-UHFFFAOYSA-N;

5-Bromo-DMT(5-bromo-N,N-dimethyltryptamine) is a psychedelicbrominated indole alkaloidfound in thespongesSmenospongia aureaandSmenospongia echina,as well as inVerongula rigida(0.00142% dry weight) alongside5,6-Dibromo-DMT(0.35% dry weight) and seven other alkaloids.^[1]^[2]^[3]^[4]It is the 5-bromo derivativeofDMT,a psychedelic found in many plants and animals.

5-Bromo-DMT has a pEC50 value of 5.51 for the5-HT_2Areceptor.^[5]

Animal studies on 5-Bromo-DMT showed that it produces effects suggestive ofsedativeandantidepressantactivity and caused significant reduction of locomotor activity in the rodent FST model.^[6]

5-Bromo-DMT was reported to be psychoactive at 20–50 mg via vaporization with mild psychedelic-like activity.^[7]

Legality

5-Bromo-DMT is specifically listed as a controlled drug in Singapore.^[8]

Related compounds

References

^US 2012029010,Hamann MT, Kochanowska AJ, El-Alfy A, Matsumoto RR, Boujos A, "Method to use compositions having antidepressant anxiolytic and other neurological activity and compositions of matter", published 2 February 2012
^Longeon A, Copp BR, Quévrain E, Roué M, Kientz B, Cresteil T, et al. (May 2011)."Bioactive indole derivatives from the South Pacific marine sponges Rhopaloeides odorabile and Hyrtios sp".Marine Drugs.9(5): 879–88.doi:10.3390/md9050879.PMC3111189.PMID 21673896.
^Hu JF, Schetz JA, Kelly M, Peng JN, Ang KK, Flotow H, et al. (April 2002). "New antiinfective and human 5-HT2 receptor binding natural and semisynthetic compounds from the Jamaican sponge Smenospongia aurea".Journal of Natural Products.65(4): 476–80.doi:10.1021/np010471e.PMID 11975483.
^Djura P, Stierle DB, Sullivan B, Faulkner DJ, Arnold EV, Clardy J (April 1980). "Some metabolites of the marine sponges Smenospongia aurea and Smenospongia (.ident.Polyfibrospongia) echina".Journal of Organic Chemistry.45(8): 1435–1441.doi:10.1021/jo01296a019.
^Matzdorf T (10 March 2015).5-Carboxamidotryptamin-Derivate als Liganden für 5-HT₇- und 5-HT_2A-Rezeptoren: Synthese und In-vitro-Pharmakologie(Ph.D. thesis) (in German). Universität Regensburg.Retrieved21 October2015.
^Kochanowska AJ, Rao KV, Childress S, El-Alfy A, Matsumoto RR, Kelly M, et al. (February 2008)."Secondary metabolites from three Florida sponges with antidepressant activity".Journal of Natural Products.71(2): 186–9.doi:10.1021/np070371u.PMC4918908.PMID 18217716.
^Morris H, Wallach J (26 March 2013)."Sea DMT: God Molecule or Barnacle Repellent?".Vice.Retrieved21 October2015.
^"Misuse of Drugs Act - Singapore Statutes Online".sso.agc.gov.sg.

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[1] US 2012029010,Hamann MT, Kochanowska AJ, El-Alfy A, Matsumoto RR, Boujos A, "Method to use compositions having antidepressant anxiolytic and other neurological activity and compositions of matter", published 2 February 2012

[2] Longeon A, Copp BR, Quévrain E, Roué M, Kientz B, Cresteil T, et al. (May 2011)."Bioactive indole derivatives from the South Pacific marine sponges Rhopaloeides odorabile and Hyrtios sp".Marine Drugs.9(5): 879–88.doi:10.3390/md9050879.PMC3111189.PMID 21673896.

[3] Hu JF, Schetz JA, Kelly M, Peng JN, Ang KK, Flotow H, et al. (April 2002). "New antiinfective and human 5-HT2 receptor binding natural and semisynthetic compounds from the Jamaican sponge Smenospongia aurea".Journal of Natural Products.65(4): 476–80.doi:10.1021/np010471e.PMID 11975483.

[4] Djura P, Stierle DB, Sullivan B, Faulkner DJ, Arnold EV, Clardy J (April 1980). "Some metabolites of the marine sponges Smenospongia aurea and Smenospongia (.ident.Polyfibrospongia) echina".Journal of Organic Chemistry.45(8): 1435–1441.doi:10.1021/jo01296a019.

[5] Matzdorf T (10 March 2015).5-Carboxamidotryptamin-Derivate als Liganden für 5-HT₇- und 5-HT_2A-Rezeptoren: Synthese und In-vitro-Pharmakologie(Ph.D. thesis) (in German). Universität Regensburg.Retrieved21 October2015.

[6] Kochanowska AJ, Rao KV, Childress S, El-Alfy A, Matsumoto RR, Kelly M, et al. (February 2008)."Secondary metabolites from three Florida sponges with antidepressant activity".Journal of Natural Products.71(2): 186–9.doi:10.1021/np070371u.PMC4918908.PMID 18217716.

[7] Morris H, Wallach J (26 March 2013)."Sea DMT: God Molecule or Barnacle Repellent?".Vice.Retrieved21 October2015.

[8] "Misuse of Drugs Act - Singapore Statutes Online".sso.agc.gov.sg.

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