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;
PubChem CID	360252;
ChemSpider	319812;
UNII	2F81I6UW8C;
CompTox Dashboard (EPA)	DTXSID90326928 ;
Chemical and physical data
Formula	C12H15BrN2
Molar mass	267.170 g·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 psychedelic brominated indole alkaloid found in the sponges Smenospongia aurea and Smenospongia echina, as well as in Verongula rigida (0.00142% dry weight) alongside 5,6-Dibromo-DMT (0.35% dry weight) and seven other alkaloids.[1][2][3][4] It is the 5-bromo derivative of DMT, a psychedelic found in many plants and animals.

5-Bromo-DMT has a pEC50 value of 5.51 for the 5-HT_2A receptor.[5]

Animal studies on 5-Bromo-DMT showed that it produces effects suggestive of sedative and antidepressant activity 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] It is also banned under analogue provisions in a number of other jurisdictions.

Related compounds

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References

Mark T. Hamann; Anna J. Kochanowska; Abir El-Alfy; Rae R. Matsumoto; Angelo Boujos (2 February 2012). "Patent US 20120029010 - Method to use compositions having antidepressant anxiolytic and other neurological activity and compositions of matter". Retrieved 21 October 2015.
Arlette Longeon; Brent R. Copp; Elodie Quévrain; Mélanie Roué; Betty Kientz; Thierry Cresteil; Sylvain Petek; Cécile Debitus; Marie-Lise Bourguet-Kondracki (May 2011). "Bioactive Indole Derivatives from the South Pacific Marine Sponges Rhopaloeides odorabile and Hyrtios sp". Marine Drugs. 9 (5): 879–888. doi:10.3390/md9050879. PMC 3111189. PMID 21673896.
Jin-Feng Hu; John A. Schetz; Michelle Kelly; Jiang-Nan Peng; Kenny K. H. Ang; Horst Flotow; Chung Yan Leong; Siew Bee Ng; Antony D. Buss; Scott P. Wilkins; Mark T. Hamann (March 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): 476–480. doi:10.1021/np010471e. PMID 11975483.
Peter Djura; Donald B. Stierle; Brian Sullivan; D. John Faulkner; Edward V. Arnold; Jon Clardy (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.
Thorsten Matzdorf (10 March 2015). "5-Carboxamidotryptamin-Derivate als Liganden für 5-HT₇- und 5-HT_2A-Rezeptoren: Synthese und In-vitro-Pharmakologie" (in German). Universität Regensburg. Retrieved 21 October 2015.
Anna J. Kochanowska; Karumanchi V. Rao; Suzanne Childress; Abir El-Alfy; Rae R. Matsumoto; Michelle Kelly; Gina S. Stewart; Kenneth J. Sufka; Mark T. Hamann (January 2008). "Secondary Metabolites from Three Florida Sponges with Antidepressant Activity". Journal of Natural Products. 71 (2): 186–189. doi:10.1021/np070371u. PMC 4918908. PMID 18217716.
Hamilton Morris; Jason Wallach (26 March 2013). "Sea DMT: God Molecule or Barnacle Repellent?". Vice. Retrieved 21 October 2015.
"Misuse of Drugs Act - Singapore Statutes Online". sso.agc.gov.sg.

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[1] Mark T. Hamann; Anna J. Kochanowska; Abir El-Alfy; Rae R. Matsumoto; Angelo Boujos (2 February 2012). "Patent US 20120029010 - Method to use compositions having antidepressant anxiolytic and other neurological activity and compositions of matter". Retrieved 21 October 2015.

[2] Arlette Longeon; Brent R. Copp; Elodie Quévrain; Mélanie Roué; Betty Kientz; Thierry Cresteil; Sylvain Petek; Cécile Debitus; Marie-Lise Bourguet-Kondracki (May 2011). "Bioactive Indole Derivatives from the South Pacific Marine Sponges Rhopaloeides odorabile and Hyrtios sp". Marine Drugs. 9 (5): 879–888. doi:10.3390/md9050879. PMC 3111189. PMID 21673896.

[3] Jin-Feng Hu; John A. Schetz; Michelle Kelly; Jiang-Nan Peng; Kenny K. H. Ang; Horst Flotow; Chung Yan Leong; Siew Bee Ng; Antony D. Buss; Scott P. Wilkins; Mark T. Hamann (March 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): 476–480. doi:10.1021/np010471e. PMID 11975483.

[4] Peter Djura; Donald B. Stierle; Brian Sullivan; D. John Faulkner; Edward V. Arnold; Jon Clardy (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] Thorsten Matzdorf (10 March 2015). "5-Carboxamidotryptamin-Derivate als Liganden für 5-HT₇- und 5-HT_2A-Rezeptoren: Synthese und In-vitro-Pharmakologie" (in German). Universität Regensburg. Retrieved 21 October 2015.

[6] Anna J. Kochanowska; Karumanchi V. Rao; Suzanne Childress; Abir El-Alfy; Rae R. Matsumoto; Michelle Kelly; Gina S. Stewart; Kenneth J. Sufka; Mark T. Hamann (January 2008). "Secondary Metabolites from Three Florida Sponges with Antidepressant Activity". Journal of Natural Products. 71 (2): 186–189. doi:10.1021/np070371u. PMC 4918908. PMID 18217716.

[7] Hamilton Morris; Jason Wallach (26 March 2013). "Sea DMT: God Molecule or Barnacle Repellent?". Vice. Retrieved 21 October 2015.

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