Chemistry:2,6-Dibromomescaline

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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.[1][2][3][4] It is the 2,6-dibromo derivative of mescaline and the 6-bromo derivative of 2-bromomescaline.[1][4] The drug was first described in the scientific literature by Arthur Heffter in 1901[1][2][5] and is said to have been on the recreational market since at least the 1990s.[4]

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.[4] It is said to have doses of up to 50 mg orally.[4]

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).[1] These affinities were 135-fold, 31-fold, and 35-fold higher than those of mescaline, respectively.[1] It was 3.4-fold more potent than mescaline in substituting for LSD in rodent drug discrimination tests.[1][2]

Chemistry

Synthesis

The chemical synthesis of 2,6-dibromomescaline has been described.[2][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.[1]

History

2,6-Dibromomescaline was first described in the scientific literature by Arthur Heffter in 1901.[1][2][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.[1][5][4] 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.[1][2] 2,6-Dibromomescaline is said to have been on the recreational market since at least the 1990s.[4]

Society and culture

Canada

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

See also

  • Scaline

References

  1. ↑ 1.00 1.01 1.02 1.03 1.04 1.05 1.06 1.07 1.08 1.09 (in de) Phenethylamine: von der Struktur zur Funktion. Nachtschatten-Science (1 ed.). Solothurn: Nachtschatten-Verlag. 2013. pp. 934–936, 944. ISBN 978-3-03788-700-4. OCLC 858805226. https://books.google.com/books?id=-Us1kgEACAAJ. 
  2. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 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.
  3. ↑ The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. 1. Berkeley: Transform Press. 2011. ISBN 978-0-9630096-3-0. 
  4. ↑ 4.0 4.1 4.2 4.3 4.4 4.5 4.6 "2,6-BM (Dibromomescaline)" (in ru). 1 May 1998. https://aipsin.com/newsubstance/112/. 
  5. ↑ 5.0 5.1 5.2 5.3 "Ueber Cacteenalkaloide. (IV. Mittheilung)." (in de). Berichte der deutschen chemischen Gesellschaft 34: 3004–3015. 1901. https://bibliography.maps.org/bibliography/default/resource/13624. 
  6. ↑ "Controlled Drugs and Substances Act". https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 



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