βOH-2C-B

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;
PubChem CID	11370394;
ChemSpider	9545311;
UNII	W6KJ195I24;
ChEMBL	ChEMBL191050;
Chemical and physical data
Formula	C10H14BrNO3
Molar mass	276.127 g/mol (freebase); 310.572 g/mol (HCl salt) g·mol−1
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[edit]

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.^[1] It has occasionally been sold online as research chemical since it began to appear on the grey market in 2020.

Chemistry[edit]

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[edit]

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.^[2]^{[unreliable source?]}

Legal status[edit]

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.^[3]
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.^[4]
United Kingdom: βOH-2C-B is illegal to produce, supply or import under the Psychoactive Substance Act as of May 26, 2016.^[5]
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.^[6]

References[edit]

^ Glennon, Richard A.; Bondarev, Mikhail L.; Khorana, Nantaka; Young, Richard; May, Jesse A.; Hellberg, Mark R.; McLaughlin, Marsha A.; Sharif, Najam A. (2004-11-01). "β-Oxygenated Analogues of the 5-HT 2A Serotonin Receptor Agonist 1-(4-Bromo-2,5-dimethoxyphenyl)-2-aminopropane". Journal of Medicinal Chemistry. 47 (24): 6034–6041. doi:10.1021/jm040082s. ISSN 0022-2623. PMID 15537358.
^ "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.
^ "NpSG Neue-psychoaktive-Stoffe-Gesetz". www.buzer.de. Retrieved 2024-02-19.
^ Koninkrijksrelaties, Ministerie van Binnenlandse Zaken en. "Opiumwet". wetten.overheid.nl (in Dutch). Retrieved 2024-02-19.
^ "Psychoactive Substances Act 2016". U.K. Home Office. 28 January 2016. Retrieved 8 September 2016.
^ "21 U.S. Code § 813 - Treatment of controlled substance analogues". LII / Legal Information Institute. Retrieved 2024-02-19.

[1] Glennon, Richard A.; Bondarev, Mikhail L.; Khorana, Nantaka; Young, Richard; May, Jesse A.; Hellberg, Mark R.; McLaughlin, Marsha A.; Sharif, Najam A. (2004-11-01). "β-Oxygenated Analogues of the 5-HT 2A Serotonin Receptor Agonist 1-(4-Bromo-2,5-dimethoxyphenyl)-2-aminopropane". Journal of Medicinal Chemistry. 47 (24): 6034–6041. doi:10.1021/jm040082s. ISSN 0022-2623. 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". www.buzer.de. Retrieved 2024-02-19.

[4] Koninkrijksrelaties, Ministerie van Binnenlandse Zaken en. "Opiumwet". 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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v t e Phenethylamines
Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-TFE 2C-TFM 2C-YN 2C-V Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants: Phenylethanolamine Hordenine Phenethylamine Phenpromethamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
Amphetamines	Psychedelics: 3C-AL 3C-BZ 3C-E 3C-MAL 3C-P Aleph Beatrice Bromo-DragonFLY D-Deprenyl DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA-2 Psi-DOM TMA TeMA ZDCM-04 Stimulants: 2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L-Norpseudoephedrine N,alpha-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens: 4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others: 3,4-DCA Amiflamine DiFMDA Selegiline (also D-Deprenyl)
Phentermines	Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH Others: Cericlamine
Cathinones	Stimulants: 3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB N-Ethylhexedrone N-Ethylpentedrone Pentedrone Pentylone Radafaxine Entactogens: 3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone
Phenylisobutylamines	Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants: α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D-DOPA (Dextrodopa) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L-DOPA (Levodopa) L-DOPS (Droxidopa) L-Phenylalanine L-Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin (Levonordefrin) Norepinephrine Norfenefrine (m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine
Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol (Levosalbutamol) Solriamfetol Theodrenaline Thiamphenicol UWA-101 Venlafaxine

History[edit]

Chemistry[edit]

Pharmacology and toxicity[edit]

Legal status[edit]

See also[edit]

References[edit]