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5-Bromo-DMT

January 06, 2023

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
Legal status
Legal status
Identifiers
  • [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
FormulaC12H15BrN2
Molar mass267.170 g·mol−1
3D model (JSmol)
  • Interactive image
  • BrC2=CC=C1[NH]C=C(C1=C2)CCN(C)C
  • 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 has a pEC50 value of 5.51 for the 5-HT2A 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]

Related compounds

References

  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. PMC 3111189. 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-HT2A-Rezeptoren: Synthese und In-vitro-Pharmakologie (Ph.D. thesis) (in German). Universität Regensburg. Retrieved 21 October 2015.
  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. PMC 4918908. PMID 18217716.
  7. ^ Morris H, Wallach J (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.
 

This drug article relating to the nervous system is a stub. You can help Wikipedia by expanding it.

January 06, 2023
bromo, bromo, dimethyltryptamine, psychedelic, brominated, indole, alkaloid, found, sponges, smenospongia, aurea, smenospongia, echina, well, verongula, rigida, 00142, weight, alongside, dibromo, weight, seven, other, alkaloids, bromo, derivative, psychedelic,. 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 DMTLegal statusLegal statusUK Class A Illegal in SingaporeIdentifiersIUPAC name 2 5 Bromo 1H indol 3 yl ethyl dimethylamineCAS Number17274 65 6PubChem CID360252ChemSpider319812UNII2F81I6UW8CCompTox Dashboard EPA DTXSID90326928Chemical and physical dataFormulaC 12H 15Br N 2Molar mass267 170 g mol 13D model JSmol Interactive imageSMILES BrC2 CC C1 NH C C C1 C2 CCN C CInChI 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 N5 Bromo DMT has a pEC50 value of 5 51 for the 5 HT2A 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 Edit5 Bromo DMT is specifically listed as a controlled drug in Singapore 8 Related compounds Edit5 Chloro aMT 5 Fluoro AMT 5 Fluoro DMT Convolutindole A Desformylflustrabromine PlakohypaphorineReferences Edit 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 Quevrain E Roue 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 PMC 3111189 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 fur 5 HT7 und 5 HT2A Rezeptoren Synthese und In vitro Pharmakologie Ph D thesis in German Universitat Regensburg Retrieved 21 October 2015 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 PMC 4918908 PMID 18217716 Morris H Wallach J 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 This drug article relating to the nervous system is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title 5 Bromo DMT amp oldid 1088483688, wikipedia, wiki, book, books, library,

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