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| Other names | 5-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 |
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| Duration of action | 15 minutes–1.5 hours[1] |
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| Chemical and physical data | |
| Formula | C12H15BrN2 |
| Molar mass | 267.170 g·mol−1 |
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5-Bromo-DMT, or5-Br-DMT, also known as5-bromo-N,N-dimethyltryptamine or by informal names likesea DMT orSpongeBob DMT, is apsychedelic drug andbrominatedindolealkaloid of thetryptamine family related todimethyltryptamine (DMT).[1][2][3] It is the 5-bromoderivative of DMT.[1] The drug isnaturally occurring in thespongesSmenospongia aurea andSmenospongia echina, as well as inVerongula rigida (0.00142% dry weight) alongside5,6-dibromo-DMT (0.35% dry weight) and seven other alkaloids.[1][4][5][6][7] It has been encountered as a noveldesigner drug.[8][9]
5-Bromo-DMT was only briefly mentioned inAlexander Shulgin's bookTiHKAL (Tryptamines I Have Known and Loved) and its properties and effects were not described.[10] Subsequently, the drug has been reported by others to have a dose of 20 to 50 mgsmoked and aduration of 15 minutes to 1.5 hours.[1][8] It is minimally active or inactiveorally.[1] It was described as producing mildpsychedelic effects, such asvisuals, pronouncedtactile effects, andeuphoria.[1][8] 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- orTiHKAL-like style via credible anonymous personal communication withHamilton Morris andJason Wallach.[1]
5-Bromo-DMT is apartial agonist of theserotonin5-HT2A receptor, with anaffinity (Ki) of 138 nM, anEC50Tooltip half-maximal effective concentration of 77.7 to 3,090 nM, and anEmaxTooltip maximal efficacy of 34 to 100%.[2][3][11] It also shows affinity for the serotonin5-HT1A,5-HT2B, and5-HT2C receptors and for theserotonin 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 weakserotonin reuptake inhibitor (IC50Tooltip half-maximal inhibitory concentration = 8,055 nM).[3]
In contrast to5-fluoro-DMT and5-chloro-DMT, 5-bromo-DMT failed to significantly produce thehead-twitch response, a behavioral proxy of psychedelic effects, in rodents.[2][3][12][13] 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 by5-fluoro-DMT.[3] On the other hand, 5-bromo-DMT producedantidepressant-like effects,hypolocomotion orsedative-like effects, andhypothermia in rodents.[3][2][1][14] Moreover, 5-bromo-DMT has been found to producepsychoplastogenic effects.[3]
Thechemical synthesis of 5-bromo-DMT has been described.[1]
Analogues of 5-bromo-DMT include5,6-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, andplakohypaphorine, among others.
5-Bromo-DMT was briefly mentioned byAlexander Shulgin in his 1991 bookTiHKAL (Tryptamines I Have Known and Loved), but he did notsynthesize or test it.[1][10]Hamilton Morris andJason 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 noveldesigner drug by 2020.[8][9]
5-Bromo-DMT is not acontrolled substance inCanada as of 2025.[15]
5-Bromo-DMT is specifically listed as a controlled drug inSingapore.[16]
5-Bromo-DMT is not an explicitlycontrolled substance in theUnited States.[17] However, it could be considered acontrolled substance under theFederal Analogue Act if intended for human consumption.
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
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.
