5-Bromo-DMT

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). It is the 5-bromo derivative of DMT. 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. It has been encountered as a novel designer drug.

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. Subsequently, the drug has been reported by others to have a dose of 20 to 50mg smoked and a duration of 15minutes to 1.5hours. It is minimally active or inactive orally. It was described as producing mild psychedelic effects, such as visuals, pronounced tactile effects, and euphoria. 5-Bromo-DMT was said to be similar to low-dose DMT, but also distinct from it. A 50mg dose was said to be near the limit of what can be physically inhaled. However, it was thought that greater exposure to the drug nonetheless might be able to produce stronger effects. These findings were reported in a Shulgin- or TiHKAL-like style via credible anonymous personal communication with Hamilton Morris and Jason Wallach.

Interactions

Pharmacology Pharmacodynamics 5-Bromo-DMT is a partial agonist of the serotonin 5-HT2A receptor, with an affinity (Ki) of 138nM, an of 77.7 to 3,090nM, and an of 34 to 100%. It also shows affinity for the serotonin 5-HT1A, 5-HT2B, and 5-HT2C receptors and for the serotonin transporter (SERT) (Ki = 16.9nM, 403nM, 193nM, and 971nM, respectively). The drug is a weak serotonin 5-HT1A receptor full agonist ( = 1,810nM; = 94%) and a very weak serotonin reuptake inhibitor ( = 8,055nM).

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. As such, 5-bromo-DMT would be expected to be non-hallucinogenic in humans. In addition, 5-bromo-DMT antagonized the head-twitch response induced by 5-fluoro-DMT. On the other hand, 5-bromo-DMT produced antidepressant-like effects, hypolocomotion or sedative-like effects, and hypothermia in rodents. Moreover, 5-bromo-DMT has been found to produce psychoplastogenic effects.

Chemistry Synthesis The chemical synthesis of 5-bromo-DMT has been described.

Analogues Analogues of 5-bromo-DMT include 5,6-dibromo-DMT, 4-bromo-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. 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." 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". 5-Bromo-DMT was described as a novel designer drug by 2020.

Society and culture Legal status Canada 5-Bromo-DMT is not a controlled substance in Canada as of 2025.

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

United States 5-Bromo-DMT is not an explicitly controlled substance in the United States. However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.

5-Bromo-DMT

Bron en licentie