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[1]
Drug classSerotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Identifiers
  • 2-(2,6-dibromo-3,4,5-trimethoxyphenyl)ethanamine
PubChem CID
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.[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]

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

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

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]

See also

References

  1. ^ a b c d e f g h "2,6-BM (Dibromomescaline)". АИПСИН (in Russian). 1 May 1998. Retrieved 25 November 2025.
  2. ^ a b c d e f g h i j 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. ^ a b c d e f 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. ^ a b c d 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.
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