5-Bromo-DMT

Last updated

5-Bromo-DMT
5-Bromo-DMT.svg
Clinical data
Other names5-Br-DMT; 5-Bromo-N,N-dimethyltryptamine; Sea DMT; Spongebob DMT
Routes of
administration 		Smoking [1]
Drug class Serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Duration of action 15 minutes–1.5 hours [1]
Identifiers
  • [2-(5-Bromo-1H-indol-3-yl)ethyl]dimethylamine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C12H15BrN2
Molar mass 267.170 g·mol−1
3D model (JSmol)
  • 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, or 5-Br-DMT, also known as 5-bromo-N,N-dimethyltryptamine or by informal names like sea DMT or SpongeBob DMT, is a psychedelic drug and brominated indole alkaloid of the tryptamine family related to dimethyltryptamine (DMT). [1] [2] [3] It is the 5-bromo derivative of DMT. [1] The drug is naturally occurring 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] [4] [5] [6] [7] It has been encountered as a novel designer drug. [8]

Contents

Use and effects

5-Bromo-DMT was only briefly mentioned in Alexander Shulgin's book TiHKAL (Tryptamines I Have Known and Loved) and its properties and effects were not described. [9] Subsequently, the drug has been reported by others to have a dose of 20 to 50 mg smoked and a duration of 15 minutes to 1.5 hours. [1] It is minimally active or inactive orally. [1] It was described as producing mild psychedelic effects, such as visuals, pronounced tactile effects, and euphoria. [1] 5-Bromo-DMT was said to be similar to low-dose DMT, but also distinct from it. [1] A 50 mg dose was said to be near the limit of what can be physically inhaled. [1] However, it was thought that greater exposure to the drug nonetheless might be able to produce stronger effects. [1] These findings were reported in a Shulgin- or TiHKAL-like style via credible anonymous personal communication with Hamilton Morris and Jason Wallach. [1]

Interactions

Pharmacology

Pharmacodynamics

5-Bromo-DMT is a partial agonist of the serotonin 5-HT2A receptor, with an affinity (Ki) of 138 nM, an EC50 Tooltip half-maximal effective concentration of 77.7 to 3,090 nM, and an Emax Tooltip maximal efficacy of 34 to 100%. [2] [3] [10] It also shows affinity for the serotonin 5-HT1A, 5-HT2B, and 5-HT2C receptors and for the serotonin transporter (SERT) (Ki = 16.9 nM, 403 nM, 193 nM, and 971 nM, respectively). [3] The drug is a weak serotonin 5-HT1A receptor full agonist (EC50 = 1,810 nM; Emax = 94%) and a very weak serotonin reuptake inhibitor (IC50 Tooltip half-maximal inhibitory concentration = 8,055 nM). [3]

In contrast to 5-fluoro-DMT and 5-chloro-DMT, 5-bromo-DMT failed to significantly produce the head-twitch response, a behavioral proxy of psychedelic effects, in rodents. [2] [3] [11] [12] As such, 5-bromo-DMT would be expected to be non-hallucinogenic in humans. [2] In addition, 5-bromo-DMT antagonized the head-twitch response induced by 5-fluoro-DMT. [3] On the other hand, 5-bromo-DMT produced antidepressant-like effects, hypolocomotion or sedative-like effects, and hypothermia in rodents. [3] [2] [1] [13] Moreover, 5-bromo-DMT has been found to produce psychoplastogenic effects. [3]

Chemistry

Synthesis

The chemical synthesis of 5-bromo-DMT has been described. [1]

Analogues

Analogues of 5-bromo-DMT include 5,6-dibromo-DMT, 5-fluoro-DMT, 5-chloro-DMT, bretisilocin (5-fluoro-MET), 5-fluoro-DET, 5-fluoro-AMT, 5-chloro-AMT, BK-5Br-NM-AMT, 5-nitro-DMT, convolutindole A, desformylflustrabromine, and plakohypaphorine, among others.

History

5-Bromo-DMT was briefly mentioned by Alexander Shulgin in his 1991 book TiHKAL (Tryptamines I Have Known and Loved), but he did not synthesize or test it. [1] [9] Hamilton Morris and Jason Wallach reported the properties and hallucinogenic effects of 5-bromo-DMT in humans in 2013 via publication of credible personal communication with an anonymous "Dr. Osculum". [1] 5-Bromo-DMT was described as a novel designer drug by 2020. [8]

Society and culture

5-Bromo-DMT is specifically listed as a controlled drug in Singapore. [14]

See also

References

  1. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 Morris H, Wallach J (26 March 2013). "Sea DMT: God Molecule or Barnacle Repellent?". Vice. Archived from the original on 26 March 2013. Retrieved 21 October 2015.
  2. 1 2 3 4 5 Duan W, Cao D, Wang S, Cheng J (January 2024). "Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants". Chem Rev. 124 (1): 124–163. doi:10.1021/acs.chemrev.3c00375. PMID   38033123. Halogen substitution on position 5 was also studied. For example, 5-Br-DMT (32) is a weak h5-HT2AR agonist (pEC50 = 5.51) and failed to induce HTRs in rats even at a high dose of 50 mg/kg, but it produced antidepressant activity in mice and chicks.144 These results indicate that compound 5-Br-DMT is a weak but nonhallucinogenic h5-HT2AR agonist. Compounds 5-F-DMT (33) and 5-Cl-DMT (34), however, produced robust HTRs at 0.5 mg/kg and 5.0 mg/kg, respectively.105
  3. 1 2 3 4 5 6 7 8 Puigseslloses P, Nadal-Gratacós N, Fumàs B, Modenutti CP, Pottie E, Ortigosa JR, et al. (October 2025). "Neuropharmacology of halogenated DMT analogs: psychoplastogenic and antidepressant properties of 5-Br-DMT, a psychedelic derivative with low hallucinogenic potential". Mol Psychiatry. doi: 10.1038/s41380-025-03308-2 . PMID   41120735.
  4. ↑ 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
  5. ↑ 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.
  6. ↑ 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. Bibcode:2002JNAtP..65..476H. doi:10.1021/np010471e. PMID   11975483.
  7. ↑ 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.
  8. 1 2 "5-Br-DMT (5-Bromo-DMT)". АИПСИН (in Russian). Retrieved 29 October 2025.
  9. 1 2 Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN   0-9630096-9-9. OCLC   38503252. https://www.erowid.org/library/books_online/tihkal/tihkal06.shtml "Two additional ring-substituted derivatives of DMT come from the marine world. 5-Bromo-DMT and 5,6-dibromo-DMT are found in the sponges Smenospongia auria and S. echina resp. I have no idea if they are active by smoking (the 5-Br-DMT just might be) but they are quantitatively reduced to DMT by stirring under hydrogen in methanol, in the presence of palladium on charcoal. A very closely related sponge, Polyfibrospongia maynardii, contains the very closely related 5,6-dibromotryptamine and the corresponding monomethyl NMT. I had the fantasy of trying to scotch the rumor I'm about to start, that all the hippies of the San Francisco Bay Area were heading to the Caribbean with packets of Zig-Zag papers, to hit the sponge trade with a psychedelic fervor. This is not true. I refuse to take credit for this myth."
  10. ↑ 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.
  11. ↑ Fumàs B, Nadal-Gratacós N, Pablo-Quesada A, Berzosa X, Camarasa J, Pubill D, et al. (2024). "5-halo-substituted DMT derivatives. Hallucinogenic response and early gene expression in mice". Neuroscience Applied. 3 104390. doi: 10.1016/j.nsa.2024.104390 .
  12. ↑ Dong C, Ly C, Dunlap LE, Vargas MV, Sun J, Hwang IW, et al. (May 2021). "Psychedelic-inspired drug discovery using an engineered biosensor". Cell. 184 (10): 2779–2792.e18. doi:10.1016/j.cell.2021.03.043. PMC   8122087 . PMID   33915107. We next screened a small library consisting of thirty-four compounds with unknown hallucinogenic potentials (Figure 4E). By assessing ligand scores, we predicted that the smaller 5-FDMT and 5-Cl-DMT would be hallucinogenic, while the larger 5-Br-DMT would not (Figures 4E and 5A). To confirm this prediction in vivo, we performed a three-point dose-response study measuring HTR (Figure 5B). As expected, both 5-F-DMT and 5-Cl-DMT produced robust HTRs, while 5-Br-DMT failed to induce HTRs at any dose (Figure 5B). Interestingly, the effects of the compounds on locomotion and the HTR were not correlated (Figure 5C). The 5-halo-DMT series really highlights the power of psychLight for detecting profound functional differences between compounds that share a high degree of structural similarity.
  13. ↑ 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): 186–189. Bibcode:2008JNAtP..71..186K. doi:10.1021/np070371u. PMC   4918908 . PMID   18217716.
  14. ↑ "Misuse of Drugs Act - Singapore Statutes Online". sso.agc.gov.sg.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.