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;
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−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

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

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

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.^[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

^ 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.
^ "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" [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.
^ 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.
^ "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 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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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

Chemistry

Pharmacology and toxicity

Legal status

See also

References