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BOH-2C-B

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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
Drug classSerotonin 5-HT2 receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
Legal status
Legal status
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
FormulaC10H14BrNO3
Molar mass276.130 g·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, also known as BOHB, β-hydroxy-2C-B, or β-hydroxy-4-bromo-2,5-dimethoxyphenethylamine, 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]

Interactions

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

Pharmacology

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Pharmacodynamics

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

Chemistry

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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

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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.

History

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BOH-2C-B was first described in a 2004 study by Richard Glennon and colleagues on β-oxygenated 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

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

  • Germany: BOH-2C-B is controlled under the New Psychoactive Substances Act (NpSG) as of November 26, 2016. Possession is illegal but not penalized.[4]
  • 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.[5]
  • United Kingdom: BOH-2C-B is illegal to produce, supply or import under the Psychoactive Substance Act as of May 26, 2016.[6]
  • 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.[7]

See also

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References

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  1. ^ a b c d e f g 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.
  2. ^ a b 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. ^ a b c d "BOHB (beta-Hydroxy-2C-B, BOH-2C-B)". АИПСИН (in Russian). Retrieved 30 October 2025.
  4. ^ "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 2024-02-19.
  5. ^ Ministerie van Binnenlandse Zaken en Koninkrijksrelaties (Ministry of the Interior and Kingdom Relations). "Opiumwet" [Opium Act]. wetten.overheid.nl (in Dutch). Retrieved 2024-02-19.
  6. ^ "Psychoactive Substances Act 2016". U.K. Home Office. 28 January 2016. Retrieved 8 September 2016.
  7. ^ "21 U.S. Code § 813 - Treatment of controlled substance analogues". LII / Legal Information Institute. Retrieved 2024-02-19.
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