2-OH-2C-B

vanc 6 2-OH-2C-B.svg skin-invert-image 225px Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist None 84705552 23254187 2-Hydroxy-2C-B; 2-O-Desmethyl-2C-B; 2-DM-2C-B; B-2-HMPEA; 2-Hydroxy-5-methoxy-4-bromophenethylamine; 4-Bromo-2-hydroxy-5-methoxyphenethylamine 2-(2-aminoethyl)-5-bromo-4-methoxyphenol 9 12 1 1 2 COC1=C(C=C(C(=C1)CCN)O)Br 1S/C9H12BrNO2/c1-13-9-4-6(2-3-11)8(12)5-7(9)10/h4-5,12H,2-3,11H2,1H3 LTIUWTXENMGCDK-UHFFFAOYSA-N 2-OH-2C-B, also known as 2-O-desmethyl-2C-B (2-DM-2C-B) or as 4-bromo-2-hydroxy-5-methoxyphenethylamine (B-2-HMPEA), is a serotonin receptor modulator of the phenethylamine family related to the 2C psychedelic 2C-B (2,5-dimethoxy-4-bromophenethylamine). McCorvy JD Mapping the binding site of the 5-HT2A receptor using mutagenesis and ligand libraries: Insights into the molecular actions of psychedelics 16 January 2013 Ph.D. Purdue University Purdue e-Pubs https://docs.lib.purdue.edu/dissertations/AAI3545320/ https://web.archive.org/web/20250515110801/https://docs.lib.purdue.edu/dissertations/AAI3545320/ 15 May 2025 27 May 2025 live It is the 2-O-demethylated analogue of 2C-B. The drug is a potent agonist of the serotonin 5-HT2A receptor, with an affinity (Ki) of 0.92nM, an EC50 half-maximal effective concentration of 4.3nM, and an Emax maximal efficacy of 93%. For comparison, 2C-B had an affinity (Ki) of 0.64nM, an EC50 half-maximal effective concentration of 3.3nM, and an Emax maximal efficacy of 76%. 2-OH-2C-B is a known metabolite of 2C-B in rodents and humans. Kanamori T, Tsujikawa K, Ohmae Y, Iwata Y, Inoue H, Inouye Y, Kishi T Excretory Profile of 4-Bromo-2,5-dimethoxyphenethylamine (2C-B) in Rat. Journal of Health Science 49 2 166–169 2003 10.1248/jhs.49.166 1344-9702 http://www.jstage.jst.go.jp/article/jhs/49/2/49_2_166/_article 2 February 2026 free Carmo H, de Boer D, Remião F, Carvalho F, dos Reys LA, de Lourdes Bastos M Metabolism of the designer drug 4-bromo-2,5-dimethoxyphenethylamine (2C-B) in mice, after acute administration Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences 811 2 143–152 November 2004 15522713 10.1016/j.jchromb.2004.08.026 Kanamori T, Tsujikawa K, Ohmae Y, Iwata YT, Inoue H, Kishi T, Nakahama T, Inouye Y A study of the metabolism of methamphetamine and 4-bromo-2,5-dimethoxyphenethylamine (2C-B) in isolated rat hepatocytes Forensic Science International 148 2–3 131–137 March 2005 15639607 10.1016/j.forsciint.2004.04.084 Carmo H, Hengstler JG, de Boer D, Ringel M, Remião F, Carvalho F, Fernandes E, dos Reys LA, Oesch F, de Lourdes Bastos M Metabolic pathways of 4-bromo-2,5-dimethoxyphenethylamine (2C-B): analysis of phase I metabolism with hepatocytes of six species including human Toxicology 206 1 75–89 January 2005 15590110 10.1016/j.tox.2004.07.004 Kanamori T, Kuwayama K, Tsujikawa K, Miyaguchi H, Togawa-Iwata Y, Inoue H A model system for prediction of the in vivo metabolism of designer drugs using three-dimensional culture of rat and human hepatocytes Forensic Toxicology 29 2 142–151 2011 10.1007/s11419-011-0116-3 1860-8965 http://link.springer.com/10.1007/s11419-011-0116-3 2 February 2026 subscription Kanamori T, Nagasawa K, Kuwayama K, Tsujikawa K, Iwata YT, Inoue H Analysis of 4-bromo-2,5-dimethoxyphenethylamine abuser's urine: identification and quantitation of urinary metabolites Journal of Forensic Sciences 58 1 279–287 January 2013 23066942 10.1111/j.1556-4029.2012.02289.x Thomann J, Rudin D, Kraus S, Arikci D, Holze F, Liechti ME, Luethi D Liquid chromatography-tandem mass spectrometry-based pharmacokinetic and metabolic analysis of 4-bromo-2,5-dimethoxyphenethylamine and its metabolites in human plasma Drug Metabolism and Disposition 53 6 100086 June 2025 40408905 10.1016/j.dmd.2025.100086 In addition to the primary metabolic pathway involving MAO and aldehyde-oxidizing enzymes, CYP2D6 rapidly degraded 2C-B, suggesting its role in this metabolic pathway. However, neither BDMPAA nor B-2-HMPAA was detected, and the identities of the resulting metabolites remain unknown. In rats, cytochrome P450 enzymes have been implicated in a major demethylation pathway that converts 2C-B into 4-bromo-2-hydroxy-5-methoxyphenethylamine or 4-bromo-5-hydroxy-2-methoxyphenethylamine, a process that may also occur to a lesser extent in humans (Carmo et al, 2005; Kanamori et al, 2013) free Meyer MR, Maurer HH Metabolism of designer drugs of abuse: an updated review Current Drug Metabolism 11 5 468–482 June 2010 20540700 10.2174/138920010791526042 Meyer MR, Maurer HH Drugs of Abuse (Including Designer Drugs) Metabolism of Drugs and Other Xenobiotics 429–463 18 April 2012 10.1002/9783527630905.ch16 Wiley 978-3-527-32903-8 https://onlinelibrary.wiley.com/doi/10.1002/9783527630905.ch16 2 February 2026 Papaseit E, Pérez-Mañá C, González D, Fonseca F, Torrens M, Farré M Clinical Effects of 2C-B Abuse Handbook of Novel Psychoactive Substances 291–303 10 October 2018 10.4324/9781315158082-16 Routledge New York, NY 978-1-315-15808-2 https://www.taylorfrancis.com/books/9781351655538/chapters/10.4324/9781315158082-16 2 February 2026 The predicted log P of 2-OH-2C-B is 1.5 4-Bromo-2-hydroxy-5-methoxyphenethylamine PubChem https://pubchem.ncbi.nlm.nih.gov/compound/84705552 2 February 2026 and of 2C-B is 2.1. 4-Bromo-2,5-Dimethoxyphenethylamine PubChem https://pubchem.ncbi.nlm.nih.gov/compound/98527 2 February 2026 The drug was first described in the scientific literature by 2003 and its pharmacology was described by 2013. See also 2C (psychedelics) 2-DM-DOM and 5-DM-DOM 5-DM-25B-NBOMe References External links 2-DM-2C-B - Isomer Design Category:5-HT2A agonists Category:Bromobenzene derivatives Category:Hydroxyarenes Category:Methoxyphenethylamines Category:O-methylated phenols Category:Psychedelic drug metabolites Category:Serotonin receptor modulators