2,6-Dibromomescaline

2,6-Dibromomescaline
Clinical data
Other names2,6-DBM; 2,6-BM; DBM; DBR-M; DBr-M; Dibromomescaline; 2,6-Dibromo-3,4,5-trimethoxyphenethylamine
Routes of
administration		Oral
Drug classSerotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Identifiers
  • 2-(2,6-dibromo-3,4,5-trimethoxyphenyl)ethanamine
PubChem CID
ChemSpider
Chemical and physical data
FormulaC11H15Br2NO3
Molar mass369.053 g·mol−1
3D model (JSmol)
  • COC1=C(C(=C(C(=C1OC)Br)CCN)Br)OC
  • InChI=1S/C11H15Br2NO3/c1-15-9-7(12)6(4-5-14)8(13)10(16-2)11(9)17-3/h4-5,14H2,1-3H3
  • Key:SDKSMIRGLNJZJW-UHFFFAOYSA-N

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. It is the 2,6-dibromo derivative of mescaline and the 6-bromo derivative of 2-bromomescaline. The drug was first described in the scientific literature by Arthur Heffter in 1901 and is said to have been on the recreational market since at least the 1990s.

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. It is said to have doses of up to 50 mg orally.

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). These affinities were 135-fold, 31-fold, and 35-fold higher than those of mescaline, respectively. It was 3.4-fold more potent than mescaline in substituting for LSD in rodent drug discrimination tests.

Chemistry

Synthesis

The chemical synthesis of 2,6-dibromomescaline has been described.

Analogues

Analogues of 2,6-dibromomescaline include 2,6-dichloromescaline, 2,6-dimethylmescaline, 2-bromomescaline, 2-chloromescaline, 2-iodomescaline, and 2-methylmescaline, among others.

History

2,6-Dibromomescaline was first described in the scientific literature by Arthur Heffter in 1901. 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. 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. 2,6-Dibromomescaline is said to have been on the recreational market since at least the 1990s.

Society and culture

Canada

2,6-Dibromomescaline is not a controlled substance in Canada as of 2025.

See also

References

  1. 1 2 3 4 5 6 7 8 "2,6-BM (Dibromomescaline)". АИПСИН (in Russian). 1 May 1998. Retrieved 25 November 2025.
  2. 1 2 3 4 5 6 7 8 9 10 Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. pp. 934–936, 944. ISBN 978-3-03788-700-4. OCLC 858805226. Archived from the original on 21 August 2025.
  3. 1 2 3 4 5 6 Parker M (1998). Studies of perceptiotropic phenethylamines: Determinants of affinity for the 5-HT2A receptor (PhD. Thesis). Purdue University. Archived from the original on 2012-04-25. Retrieved 2011-12-16.
  4. ↑ Shulgin A, Manning T, Daley P (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. ISBN 978-0-9630096-3-0.
  5. 1 2 3 4 Heffter A (1901). "Ueber Cacteenalkaloide. (IV. Mittheilung)" [On cactus alkaloids. (IV. Communication)]. Berichte der deutschen chemischen Gesellschaft [Reports of the German Chemical Society] (in German). 34: 3004–3015.
  6. ↑ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.