Chemistry:BOH-2C-B

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BOH-2C-B, or BOHB, also known as 4-bromo-2,5-dimethoxy-β-hydroxyphenethylamine or as β-hydroxy-2C-B, is a psychedelic drug of the phenethylamine, 2C, and BOx families.[1] It is the β-hydroxy derivative of 2C-B.[1] The drug has been encountered as a novel designer drug.[2][3]

Use and effects

BOH-2C-B was not included or mentioned in Alexander Shulgin's book PiHKAL (Phenethylamines I Have Known and Loved).[4] Subsequently, Daniel Trachsel listed BOHB's dose as 30 mg or more orally in his book Phenethylamine: von der Struktur zur Funktion (Phenethylamines: From Structure to Function).[5]

Interactions

Pharmacology

Pharmacodynamics

BOH-2C-B acts as a serotonin 5-HT2A receptor agonist.[1][3][6]

Chemistry

BOH-2C-B is a substituted phenethylamine.[1] It features methoxy substituents at the 2- and 5-position of the ring, as well as a bromine at the 4-position.[1] A hydroxy group is present at the beta (β) position from the functional amine group connected to the alpha (α) carbon, giving rise to its name.[1]

Analogues

Analogues of BOH-2C-B include 2C-B, BOB (β-methoxy-2C-B), βk-2C-B (β-keto-2C-B), β-methyl-2C-B, BOHD (β-hydroxy-2C-D), and BOD (β-methoxy-2C-D), among others.[4]

History

BOH-2C-B was first described in a 2004 study by Richard Glennon and colleagues on the optimization of phenethylamine 5-HT2A serotonin receptor agonists, although it is not mentioned by name.[1] It was encountered as a novel designer drug in 2019.[2][3] However, it is said to have been on the market since 2015.[3]

Society and culture

BOH-2C-B is a controlled substance in the following countries:

  • Canada: BOH-2C-B is a controlled substance under phenethylamine blanket-ban language.[7]
  • Germany: BOH-2C-B is controlled under the New Psychoactive Substances Act (NpSG) as of November 26, 2016. Possession is illegal but not penalized.[8]
  • Netherlands:: BOH-2C-B is not specifically scheduled in the NL but may be considered a ring-derived analogue of 2-phenethylamine which would make it illegal under updates made to the Dutch Opium Act in February 2024.[9]
  • United Kingdom: BOH-2C-B is illegal to produce, supply or import under the Psychoactive Substance Act as of May 26, 2016.[10]
  • United States: BOH-2C-B is unscheduled in the U.S., but may be considered an analogue of 2C-B under the Federal Analogue Act, and thus a Schedule I drug.[11]

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 "Beta-oxygenated analogues of the 5-HT2A serotonin receptor agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane". Journal of Medicinal Chemistry 47 (24): 6034–6041. November 2004. doi:10.1021/jm040082s. PMID 15537358. 
  2. ↑ 2.0 2.1 https://isomerdesign.com/bitnest/external/EMCDDA/1-June-2020 "As of 16 June 2020, a total of 14 new psychoactive substances have been formally notified by the Member States so far this year. These comprise: • Arylalkylamines: 2 (BOH-PHP, BOH-2C-B)" [...] "14.BOH-2C-B (2-amino-1-(4-bromo-2,5-dimethoxyphenyl)ethanol) — arylalkylamine, customs seizure, Sweden, 9 April 2020 (also seized by Danish customs on 6 December 2019). Notified: 9 June 2020. EU-EWS-RCS-FN-2020-0014"
  3. ↑ 3.0 3.1 3.2 3.3 "BOHB (beta-Hydroxy-2C-B, BOH-2C-B)" (in ru). https://aipsin.com/newsubstance/458/. 
  4. ↑ 4.0 4.1 Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. http://www.erowid.org/library/books_online/pihkal/pihkal.shtml. 
  5. ↑ (in de) Phenethylamine: von der Struktur zur Funktion. Nachtschatten-Science (1 ed.). Solothurn: Nachtschatten-Verlag. 2013. pp. 833. ISBN 978-3-03788-700-4. OCLC 858805226. https://books.google.com/books?id=-Us1kgEACAAJ. 
  6. ↑ "Comprehensive in vitro profiling of traditional and emerging stimulants at monoamine transporters and the 5-HT2A receptor". Br J Pharmacol. July 2026. doi:10.1111/bph.70587. PMID 42449077. 
  7. ↑ "Controlled Drugs and Substances Act". 5 December 2025. https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 
  8. ↑ "NpSG Neue-psychoaktive-Stoffe-Gesetz" (in de). Bundesrecht - tagaktuell konsolidiert - alle Fassungen seit 2006. https://www.buzer.de/gesetz/12250/index.htm. 
  9. ↑ "Opiumwet" (in nl). https://wetten.overheid.nl/BWBR0001941/2021-10-28. 
  10. ↑ "Psychoactive Substances Act 2016". U.K. Home Office. 28 January 2016. http://www.legislation.gov.uk/ukpga/2016/2. 
  11. ↑ "21 U.S. Code § 813 - Treatment of controlled substance analogues" (in en). https://www.law.cornell.edu/uscode/text/21/813. 



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