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BOH-2C-B

From Wikipedia, the free encyclopedia
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 classSerotonin5-HT2 receptoragonist;Serotonin 5-HT2A receptor agonist;Serotonergic psychedelic;Hallucinogen
Legal status
Legal status
Pharmacokinetic data
Onset of actionUnknown[1]
Duration of actionUnknown[1]
Identifiers
  • 2-Amino-1-(4-bromo-2,5-dimethoxyphenyl)ethan-1-ol
CAS Number
PubChemCID
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, orBOHB, also known as4-bromo-2,5-dimethoxy-β-hydroxyphenethylamine or asβ-hydroxy-2C-B, is apsychedelic drug of thephenethylamine,2C, andBOx families.[2] It is the β-hydroxyderivative of2C-B.[2] The drug has been encountered as a noveldesigner drug.[3][4]

Use and effects

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

Interactions

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

Pharmacology

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Pharmacodynamics

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BOH-2C-B acts as aserotonin5-HT2A receptoragonist.[2][4][6]

Chemistry

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BOH-2C-B is asubstituted phenethylamine.[2] It featuresmethoxy 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 include2C-B,BOB (β-methoxy-2C-B),βk-2C-B (β-keto-2C-B),β-methyl-2C-B,BOHD (β-hydroxy-2C-D), andBOD (β-methoxy-2C-D), among others.[5]

History

[edit]

BOH-2C-B was first described in a 2004 study byRichard Glennon and colleagues on β-oxygenated 5-HT2A serotonin receptor agonists, although it is not mentioned by name.[2] It was encountered as a noveldesigner 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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Legal status

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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.[7]
  • 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.[8]
  • United Kingdom: BOH-2C-B is illegal to produce, supply or import under the Psychoactive Substance Act as of May 26, 2016.[9]
  • 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.[10]

See also

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References

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  1. ^abcdTrachsel 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 fromthe original on 21 August 2025.
  2. ^abcdefgGlennon 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. ^abhttps://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. ^abcd"BOHB (beta-Hydroxy-2C-B, BOH-2C-B)".АИПСИН (in Russian). Retrieved30 October 2025.
  5. ^abShulgin 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., ... & Gréen, H. (2025). Comprehensive in vitro profiling of traditional and emerging stimulants at monoamine transporters and the 5HT2A receptor.https://doi.org/10.22541/au.176253891.19158813/v1
  7. ^"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). Retrieved2024-02-19.
  8. ^Ministerie van Binnenlandse Zaken en Koninkrijksrelaties (Ministry of the Interior and Kingdom Relations)."Opiumwet" [Opium Act].wetten.overheid.nl (in Dutch). Retrieved2024-02-19.
  9. ^"Psychoactive Substances Act 2016". U.K. Home Office. 28 January 2016. Retrieved8 September 2016.
  10. ^"21 U.S. Code § 813 - Treatment of controlled substance analogues".LII / Legal Information Institute. Retrieved2024-02-19.

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