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βOH-2C-B

Skeletal formula of βOH-2C-B
Clinical data
Routes of administration	Oral
Legal status
Legal status	DE: NpSG (Industrial and scientific use only) UK: Under Psychoactive Substances Act Illegal in Netherlands
Identifiers
IUPAC name 2-Amino-1-(4-bromo-2,5-dimethoxyphenyl)ethan-1-ol
CAS Number	677277-62-2
PubChem CID	11370394
ChemSpider	9545311
UNII	W6KJ195I24
ChEMBL	ChEMBL191050
CompTox Dashboard (EPA)	DTXSID101342414
Chemical and physical data
Formula	C10H14BrNO3
Molar mass	276.127 g/mol (freebase) 310.572 g/mol (HCl salt) g·mol
3D model (JSmol)	Interactive image
SMILES NCC(c1cc(OC)c(cc1OC)Br)O
InChI 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

βOH-2C-B (also known as beta-hydroxy-4-bromo-2,5-dimethoxyphenylamine or beta-hydroxy 2C-B), is a psychedelic phenethylamine of the 2C family. It is the beta (β) hydroxy structural analogue of 2C-B and is considered a novel psychoactive substance.

History

βOH-2C-B is a relatively obscure substance. It appears in a 2004 study on β-oxygenated 5-HT2A serotonin receptor agonists, although it is not mentioned by name. It has occasionally been sold online as research chemical since it began to appear on the grey market in 2020.

Chemistry

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

Pharmacology and toxicity

Very little is known about the pharmacology and toxicity of βOH-2C-B. Its LD₅₀ and toxicity profile have yet to be established.

There are some anecdotal reports of users experiencing headaches or migraines as the drug wears off, which could indicate a toxicity of some kind.

Legal status

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

• Germany: βOH-2C-B is controlled under the New Psychoactive Substances Act (NpSG) as of November 26, 2016. Possession is illegal but not penalized.
• Netherlands:: βOH-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.
• United Kingdom: βOH-2C-B is illegal to produce, supply or import under the Psychoactive Substance Act as of May 26, 2016.
• United States: βOH-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.

See also

• 2C-B
• βk-2C-B
• β-Methyl-2C-B
• BOHD (psychedelic)
• Psychedelic
• Substituted phenethylamines

References

1. 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. "BOH-2C-B (also βOH-2C-B; β-OH-2C-B; β-Hydroxy-2C-B) : Erowid Exp: Main Index". www.erowid.org. Retrieved 2024-02-19.
3. "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.
4. 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.
5. "Psychoactive Substances Act 2016". U.K. Home Office. 28 January 2016. Retrieved 8 September 2016.
6. "21 U.S. Code § 813 - Treatment of controlled substance analogues". LII / Legal Information Institute. Retrieved 2024-02-19.

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• Designer drugs
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• Methoxy compounds
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