2,6-Dibromomescaline
Pharmaceutical compound
From Wikipedia, the free encyclopedia
2,6-Dibromomescaline (2,6-DBM or 2,6-BM), or dibromomescaline (DBM), also known as 2,6-dibromo-3,4,5-trimethoxyphenethylamine, is a psychedelic drug of the scaline family related to mescaline.[2][3][4][1] It is the 2,6-dibromo derivative of mescaline and the 6-bromo derivative of 2-bromomescaline.[2][1] The drug was first described in the scientific literature by Arthur Heffter in 1901[2][3][5] and is said to have been on the recreational market since at least the 1990s.[1]
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| Other names | 2,6-DBM; 2,6-BM; DBM; DBR-M; DBr-M; Dibromomescaline; 2,6-Dibromo-3,4,5-trimethoxyphenethylamine |
| Routes of administration | Oral[1] |
| Drug class | Serotonin receptor modulator; Serotonergic psychedelic; Hallucinogen |
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| Formula | C11H15Br2NO3 |
| Molar mass | 369.053 g·mol−1 |
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Use and effects
2,6-Dibromomescaline is described as having pronounced psychoactive effects but also toxicity, with this toxicity limiting its popularity and adoption as a recreational drug.[1] It is said to have doses of up to 50 mg orally.[1]
Interactions
Pharmacology
Pharmacodynamics
2,6-Dibromomescaline shows affinity for serotonin receptors, including the serotonin 5-HT1A, 5-HT2A, and 5-HT2C receptors (Ki = 22 nM, 149 nM, and 221 nM, respectively).[2] These affinities were 135-fold, 31-fold, and 35-fold higher than those of mescaline, respectively.[2] It was 3.4-fold more potent than mescaline in substituting for LSD in rodent drug discrimination tests.[2][3]
Chemistry
Synthesis
The chemical synthesis of 2,6-dibromomescaline has been described.[3][5]
Analogues
Analogues of 2,6-dibromomescaline include 2,6-dichloromescaline, 2,6-dimethylmescaline, 2-bromomescaline, 2-chloromescaline, 2-iodomescaline, and 2-methylmescaline, among others.[2]
History
2,6-Dibromomescaline was first described in the scientific literature by Arthur Heffter in 1901.[2][3][5] It was among the first synthetic psychedelic drugs to be described, although Heffter did not report its properties or effects in humans and those were not described until much later.[2][5][1] Subsequently, the drug was studied and described in greater detail by Matthew Aaron Parker of the lab of David E. Nichols at Purdue University in 1998.[2][3] 2,6-Dibromomescaline is said to have been on the recreational market since at least the 1990s.[1]
Society and culture
Legal status
Canada
2,6-Dibromomescaline is not a controlled substance in Canada as of 2025.[6]