Editing 2C-B (section)

{{Short description|Psychoactive drug}}
{{Distinguish|Tusi (drug)|text=[[Tusi (drug)|tusi]], a recreational drug in pink-dyed powder form that contains a mixture of different drugs}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Infobox drug
| image = 2C-B.svg
| width = 200px
| caption = 2C-B structure
| image2 = 4-bromo-2,5-dimethoxyphenethylamine (2C-B).png
| image_class = skin-invert-image
| caption2 = 3D representation of a 2C-B molecule

<!-- Clinical data -->
| pronounce = 
| tradename = 
| Drugs.com = 
| MedlinePlus = 
| licence_EU = 
| licence_US = 
| pregnancy_AU = <!-- A/B1/B2/B3/C/D/X -->
| pregnancy_AU_comment = 
| pregnancy_US = <!-- A/B/C/D/X/N -->
| pregnancy_category = 
| routes_of_administration = [[Oral administration|By mouth]], [[insufflation (medicine)|insufflation]], [[rectal administration|rectal]]
| class = [[Serotonergic psychedelic]]; [[Hallucinogen]]; [[Serotonin]] [[5-HT2A receptor|5-HT<sub>2A</sub> receptor]] [[agonist]]
| ATC_prefix = None
| ATC_suffix = 

<!-- Legal status -->
| legal_AU = Schedule 9
| legal_AU_comment = 
| legal_BR = F2
| legal_BR_comment = 
| legal_CA = Schedule III
| legal_DE = Anlage I
| legal_NZ = <!-- Class A, B, C -->
| legal_UK = Class A
| legal_US = Schedule I
| legal_UN = P II
| legal_status = <!-- Free text -->

<!-- Pharmacokinetic data -->
| bioavailability = 
| protein_bound = 
| metabolism = [[Liver]] ([[monoamine oxidase|MAO]] and [[cytochrome P450|CYP450]])<ref name="InanBruntContrucci2020" /><ref name="Nugteren-vanLonkhuyzenvanRielBrunt2015" />
| metabolites = {{Abbr|BDMPE|4-bromo-5-hydroxy-2-methoxyphenethylamine}}, {{Abbr|BDMPAA|4-bromo-2,5-dimethoxyphenylacetic acid}}, {{Abbr|BDMBA|4-bromo-2,5-dimethoxybenzoic acid}}, and others<ref name="ColeLeaOxley2002" />
| onset = [[Oral administration|Oral]]: 20–90 min<ref name="ColeLeaOxley2002" />
| elimination_half-life = 1.2–2.5 hours<ref name="PapaseitFarréPérez-Mañá2018">{{cite journal | vauthors = Papaseit E, Farré M, Pérez-Mañá C, Torrens M, Ventura M, Pujadas M, de la Torre R, González D | title = Acute Pharmacological Effects of 2C-B in Humans: An Observational Study | language = en | journal = Frontiers in Pharmacology | volume = 9 | pages = 206 | date = 2018 | pmid = 29593537 | pmc = 5859368 | doi = 10.3389/fphar.2018.00206 | doi-access = free }}</ref><ref name="ThomannRudinKraus2025">{{cite journal | vauthors = Thomann J, Rudin D, Kraus S, Arikci D, Holze F, Liechti ME, Luethi D | title=LC–MS/MS-based pharmacokinetic and metabolic analysis of 4-bromo-2,5-dimethoxyphenethylamine (2C-B) and its metabolites in human plasma | journal=Drug Metabolism and Disposition | date=2025 | doi=10.1016/j.dmd.2025.100086 | doi-access=free | page=100086}}</ref>
| duration_of_action = Oral: 2–8 hours<ref name="InanBruntContrucci2020">{{cite journal | vauthors = Inan F, Brunt TM, Contrucci RR, Hondebrink L, Franssen EJ | title = Novel Phenethylamines and Their Potential Interactions With Prescription Drugs: A Systematic Critical Review | journal = Ther Drug Monit | volume = 42 | issue = 2 | pages = 271–281 | date = April 2020 | pmid = 32022784 | doi = 10.1097/FTD.0000000000000725 | url = }}</ref><ref name="ColeLeaOxley2002" /><ref name="Nugteren-vanLonkhuyzenvanRielBrunt2015" />
| excretion = [[Urine]]<ref name="ColeLeaOxley2002" /><ref name="Nugteren-vanLonkhuyzenvanRielBrunt2015" />

<!-- Identifiers -->
| CAS_number = 66142-81-2
| PubChem = 98527
| KEGG = C22775
| ChEBI = 189669
| ChEMBL = 292821
| ChemSpiderID = 88978
| DrugBank = DB01537
| UNII = V77772N32H
| synonyms = 4-Bromo-2,5-dimethoxyphenethylamine; 2,5-Dimethoxy-4-bromophenethylamine; Nexus; Venus; Bromo; Bees; Erox; Synergy; Performax; Toonies<ref name="Nugteren-vanLonkhuyzenvanRielBrunt2015" />

<!-- Chemical data -->
| IUPAC_name = 2-(4-Bromo-2,5-dimethoxyphenyl)ethanamine
| C = 10 | H = 14 | Br = 1 | N = 1 | O = 2
| SMILES = COc1cc(CCN)c(OC)cc1Br
| StdInChI = 1S/C10H14BrNO2/c1-13-9-6-8(11)10(14-2)5-7(9)3-4-12/h5-6H,3-4,12H2,1-2H3
| StdInChIKey = YMHOBZXQZVXHBM-UHFFFAOYSA-N
}}
<!-- Definition and uses -->
'''2C-B''', also known as '''4-bromo-2,5-dimethoxyphenethylamine''' or by the [[slang]] name '''Nexus''', is a [[synthetic compound|synthetic]] [[psychedelic drug]] of the [[2C (psychedelics)|2C family]], mainly used as a [[recreational drug]].<ref name="ColeLeaOxley2002">{{cite journal | vauthors = Cole MD, Lea C, Oxley N | title = 4-Bromo-2,5-dimethoxyphenethylamine (2C-B): a review of the public domain literature | journal = Sci Justice | volume = 42 | issue = 4 | pages = 223–224 | date = 2002 | pmid = 12632938 | doi = 10.1016/S1355-0306(02)71832-7 | url = }}</ref><ref name="Nugteren-vanLonkhuyzenvanRielBrunt2015">{{cite journal | vauthors = Nugteren-van Lonkhuyzen JJ, van Riel AJ, Brunt TM, Hondebrink L | title = Pharmacokinetics, pharmacodynamics and toxicology of new psychoactive substances (NPS): 2C-B, 4-fluoroamphetamine and benzofurans | journal = Drug Alcohol Depend | volume = 157 | issue = | pages = 18–27 | date = December 2015 | pmid = 26530501 | doi = 10.1016/j.drugalcdep.2015.10.011 | url = }}</ref><ref>{{cite journal |vauthors=Caudevilla-Gálligo F, Riba J, Ventura M, González D, Farré M, Barbanoj MJ, Bouso JC |date=July 2012 |title=4-Bromo-2,5-dimethoxyphenethylamine (2C-B): presence in the recreational drug market in Spain, pattern of use and subjective effects |journal=Journal of Psychopharmacology |volume=26 |issue=7 |pages=1026–1035 |doi=10.1177/0269881111431752 |pmid=22234927 |s2cid=35535891}}</ref> It was first synthesized by [[Alexander Shulgin]] in 1974 for use in [[psychotherapy]].

To date, there is limited scientific information regarding the drug's [[pharmacokinetics]] and pharmacological effects in humans. The existing studies primarily classify 2C-B as a [[stimulant]] and [[hallucinogen]], and less commonly an [[entactogen]].<ref name="GonzálezTorrensFarré2015">{{cite journal | vauthors = González D, Torrens M, Farré M | title = Acute Effects of the Novel Psychoactive Drug 2C-B on Emotions | journal = BioMed Research International | volume = 2015 | pages = 643878 | date = 2015-10-12 | pmid = 26543863 | doi = 10.1155/2015/643878 | pmc = 4620274 | doi-access = free }}</ref>

2C-B is also known by a number of slang names and appears on the illicit market in multiple forms:<ref name="DEA - Evaluation Section">{{cite web |date=February 1, 2011 |title=2C-B Street Names |url=https://www.deadiversion.usdoj.gov/drug_chem_info/bromo_dmp.pdf |url-status=dead |archive-url=https://web.archive.org/web/20121016220942/http://www.deadiversion.usdoj.gov/drugs_concern/bromo_dmp/bromo_dmp.pdf |archive-date=October 16, 2012 |access-date=2012-09-28}}</ref><ref>{{cite book |title=Fentanyl, Inc. |vauthors=Westhoff B |publisher=Atlantic Monthly Press |year=2019 |isbn=978-1-0941-6390-1 |location=New York |page=62 |oclc=1136538402}}</ref> as a powder, in [[Capsule (pharmacy)|capsules]] or [[Tablet (pharmacy)|pills]]. For recreational use, the substance is generally consumed orally or nasally.

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