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BOH-2C-B

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Chemical compound

Pharmaceutical compound
BOH-2C-B
Clinical data
Other namesBOH-2C-B-; BOHB; β-Hydroxy-4-bromo-2,5-dimethoxyphenethylamine; β-Hydroxy-2C-B; β-OH-2C-B
Routes of
administration 		Oral [1]
Drug class Serotonin 5-HT2 receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
Legal status
Legal status
Pharmacokinetic data
Onset of action Unknown[1]
Duration of action Unknown[1]
Identifiers
  • 2-Amino-1-(4-bromo-2,5-dimethoxyphenyl)ethan-1-ol
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C10H14BrNO3
Molar mass 276.130g·mol−1
3D model (JSmol)
  • NCC(c1cc(OC)c(cc1OC)Br)O
  • InChI=1S/C10H14BrNO3/c1-14-9-4-7(11)10(15-2)3-6(9)8(13)5-12/h3-4,8,13H,5,12H2,1-2H3
  • Key:PCSKDXWCLQXURQ-UHFFFAOYSA-N

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.[2] It is the β-hydroxy derivative of 2C-B.[2] The drug has been encountered as a novel designer drug.[3] [4]

Use and effects

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BOH-2C-B was not included or mentioned in Alexander Shulgin's book PiHKAL (Phenethylamines I Have Known and Loved).[5] Subsequently, Daniel Trachsel listed BOHB's dose as 30mg or more orally in his book Phenethylamine: von der Struktur zur Funktion (Phenethylamines: From Structure to Function).[1]

Interactions

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Pharmacology

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Pharmacodynamics

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BOH-2C-B acts as a serotonin 5-HT2A receptor agonist.[2] [4] [6]

Chemistry

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BOH-2C-B is a substituted phenethylamine.[2] It features methoxy substituents at the 2- and 5-position of the ring, as well as a bromine at the 4-position.[2] 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.[2]

Analogues

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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.[5]

History

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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.[2] It was encountered as a novel designer drug in 2019.[3] [4] However, it is said to have been on the market since 2015.[4]

Society and culture

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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

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References

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  1. 1 2 3 4 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. p. 833. ISBN 978-3-03788-700-4. OCLC 858805226. Archived from the original on 21 August 2025.
  2. 1 2 3 4 5 6 7 Glennon RA, Bondarev ML, Khorana N, Young R, May JA, Hellberg MR, et al. (November 2004). "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. doi:10.1021/jm040082s. PMID 15537358.
  3. 1 2 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"
  4. 1 2 3 4 "BOHB (beta-Hydroxy-2C-B, BOH-2C-B)". АИПСИН (in Russian). Retrieved 30 October 2025.
  5. 1 2 Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
  6. ↑ Stalberga D, Kronstrand R, Schranz B, van Zijl N, Karlman S, Aref S, et al. (July 2026). "Comprehensive in vitro profiling of traditional and emerging stimulants at monoamine transporters and the 5-HT2A receptor". Br J Pharmacol. doi:10.1111/bph.70587. PMID 42449077.
  7. ↑ "Controlled Drugs and Substances Act". Department of Justice Canada. 5 December 2025. Retrieved 20 January 2026.
  8. ↑ "NpSG Neue-psychoaktive-Stoffe-Gesetz" [New Psychoactive Substances Act (NpSG)]. Bundesrecht - tagaktuell konsolidiert - alle Fassungen seit 2006 [Federal law - consolidated daily - all versions since 2006] (in German). Retrieved 2024年02月19日.
  9. ↑ Ministerie van Binnenlandse Zaken en Koninkrijksrelaties (Ministry of the Interior and Kingdom Relations). "Opiumwet" [Opium Act]. wetten.overheid.nl (in Dutch). Retrieved 2024年02月19日.
  10. ↑ "Psychoactive Substances Act 2016". U.K. Home Office. 28 January 2016. Retrieved 8 September 2016.
  11. ↑ "21 U.S. Code § 813 - Treatment of controlled substance analogues". LII / Legal Information Institute. Retrieved 2024年02月19日.
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