Editing 2C-B

{{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.

{{TOC limit|3}}

==Use==
===Recreational===
[[File:4-bromo-2,5-dimethoxyphenethylamine.jpg|1000mg of 2C-B|thumb|right]]

2C-B became briefly popular in the United States as substitute for the street drug [[MDMA|ecstasy]] (MDMA) when the latter became illegal in 1985.<ref name=Colombia>{{cite news | vauthors = Pachico E |title=2CB Now Drug of Choice for Colombia Elite|url=http://www.insightcrime.org/news-analysis/2c-b-now-drug-of-choice-for-colombia-elite|access-date=11 February 2013|newspaper=InSight Crime|date=1 November 2012}}</ref> Many 2C-B users are young adults who attend [[rave]]s.<ref name="DEA - Evaluation Section" /> Although 2C-B is still used in the rave subculture (commonly mistaken for and/or sold as ecstasy), more knowledgeable use has become more widespread in the 2000s.<ref name="Gahlinger book">{{cite book| vauthors = Gahlinger P |title=Illegal Drugs: A Complete Guide to Their History, Chemistry, Use and Abuse|year=2004|publisher=Penguin|isbn=9780452285057|pages=343–344|url=https://books.google.com/books?id=kPszgXPVQAsC&pg=PT463}}</ref>

===Entheogenic===
There are claims that 2C-B was used as [[entheogen]] by the [[Sangoma]], [[Nyanga people|Nyanga]], and [[Xhosa people#Folklore and religion|Amagqirha]] people in place of their traditional plants; they refer to the chemical as ''Ubulawu Nomathotholo'', which roughly translates to "''Medicine of the Singing Ancestors''".<ref>{{cite web |date=2008-03-27 |title=2CB chosen over traditional entheogen's by South African healers. |url=http://www.tacethno.com/info/2cb/2cbhistory.html#South%20Africa |access-date=May 15, 2012 |publisher=Tacethno.com}}</ref><ref>[http://www.erowid.org/chemicals/2cb/2cb_article1.shtml The Nexus Factor - An Introduction to 2C-B] Erowid</ref><ref>[http://www.erowid.org/chemicals/show_image.php?i=2cb/ubulawu_pack.jpg Ubulawu Nomathotholo Pack] Photo by Erowid. © 2002 Erowid.org</ref>

===Dosage===
In Shulgin's book ''[[PiHKAL]]'', the oral dosage range is listed as 12 to 24{{nbsp}}mg.<ref name="PiHKAL">{{Cite book |url=https://www.worldcat.org/oclc/25627628 |title=Pihkal : a chemical love story |vauthors=Shulgin AT |date=1991 |publisher=Transform Press |others=Ann Shulgin |isbn=0-9630096-0-5 |location=Berkeley, CA |oclc=25627628}}</ref> The common oral recreational dose per [[Erowid]] is around 15 to 25{{nbsp}}mg.<ref name="urlErowid 2C-B Vault : Dose/Dosage">{{cite web |title=Erowid 2C-B Vault : Dose/Dosage |url=http://www.erowid.org/chemicals/2cb/2cb_dose.shtml}}</ref> Shulgin and others describe 2C-B as having a steep [[dose–response curve]], such that a small increase in dose can result in an unexpectedly large increase in effects.<ref name="PiHKAL" /><ref name="PalamarAcosta2020" />

{| class="wikitable"
|+ 2C-B dosage{{Citation needed|date=May 2025}}
|-
! |
! width="100px" | Oral
! width="120px" | Insufflated
|-
| [[Effective dose (pharmacology)|ED<sub>50</sub>]] || 10&nbsp;mg || 4–6&nbsp;mg
|-
| Moderate || 15–25&nbsp;mg || 5–9&nbsp;mg
|-
| Strong || 26–35&nbsp;mg || 10–20&nbsp;mg
|-
| Extremely Intense || >35&nbsp;mg || >20&nbsp;mg
|-
| Duration || 4–8 hours || 2–4 hours
|}

When sold as "Ecstasy", tablets containing 2C-B often contain about 5&nbsp;mg of the drug, an amount which produces stimulatory effects that mimic the effects of MDMA; in contrast, tablets marketed as 2C-B have larger quantities of the drug (10–20&nbsp;mg) which cause [[hallucinogen]]ic effects.<ref name="Netherlands 2c-b emergence">{{cite journal |vauthors=de Boer D, Gijzels MJ, Bosman IJ, Maes RA |year=1999 |title=More data about the new psychoactive drug 2C-B |journal=Journal of Analytical Toxicology |volume=23 |issue=3 |pages=227–8 |doi=10.1093/jat/23.3.227 |pmid=10369336 |doi-access=free}}</ref>

===Duration===
When [[Oral administration|orally]] consumed, 2C-B has a much longer delay before the onset of effects than when it is insufflated. Oral ingestion generally takes roughly 45–75 minutes for the effects to be felt, plateau lasts 2–4 hours, and coming down lasts 1–2 hours. [[Rectal administration]] onset varies from 5 to 20 minutes. Insufflated onset takes 1–10 minutes for effects to be felt. The duration can last from 4 to 12 hours depending on route of administration, dose, and other factors.<ref name="erowid effects"/>

With insufflation, the effects are more abrupt and intense but have a significantly shorter duration, while oral usage results in a milder, longer experience. When insufflated, the onset happens very rapidly, usually reaching the peak at about 20–40 minutes and plateauing for 2–3 hours. 2C-B is also considered one of the most painful drugs to insufflate, with users reporting intense nasal burning.<ref name="erowid basics"/> The sudden intensity of the experience combined with the pain can often start the experience with a negative imprint and nausea is also increased with insufflation, compounding the issue.

==Effects==
[[Image:2cb pill.jpg|thumb|right|2C-B pill with [[heart (symbol)|heart]] logo]]

Little academic research has been conducted on the effects of 2C-B in humans. The information available is largely [[Anecdotal evidence|anecdotal]] and limited. Effects are often described as being more easily managed than other psychedelics;<ref name="erowid basics">{{cite web | url = http://www.erowid.org/chemicals/2cb/2cb_basics.shtml | title = Erowid 2C-B Vault: Basics | access-date = 2013-09-25 | date = 2011-02-20 | publisher = [[Erowid]]}}</ref><ref name="PalamarAcosta2020">{{cite journal | vauthors = Palamar JJ, Acosta P | title = A qualitative descriptive analysis of effects of psychedelic phenethylamines and tryptamines | journal = Human Psychopharmacology | volume = 35 | issue = 1 | pages = e2719 | date = January 2020 | pmid = 31909513 | pmc = 6995261 | doi = 10.1002/hup.2719 }}</ref> it is often compared to a mixture of a [[serotonergic psychedelic]] and [[MDMA]].<ref name="Spain study">{{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=1026–35 |doi=10.1177/0269881111431752 |pmid=22234927 |s2cid=35535891}}</ref> At 5–10&nbsp;mg, experiments with young chickens have shown it to produce effects similar to a low dosage of [[amphetamine]]s.<ref>{{cite journal | vauthors = Bronson ME, Jiang W, DeRuiter J, Clark CR | title = A behavioral comparison of Nexus, cathinone, BDB, and MDA | journal = Pharmacology, Biochemistry, and Behavior | volume = 51 | issue = 2–3 | pages = 473–475 | year = 1995 | pmid = 7667371 | doi = 10.1016/0091-3057(95)00013-M | s2cid = 32246652 }}</ref>

The anecdotal effects of 2C-B that have been reported by users on online discussion forums include:<ref name="erowid effects">{{cite web | url = http://www.erowid.org/chemicals/2cb/2cb_effects.shtml | title = Erowid 2C-B Vault: Effects | access-date = 2013-09-25 | publisher = [[Erowid]]}}</ref><ref name="Drugscope">{{cite web | url = http://www.drugscope.org.uk/resources/drugsearch/drugsearchpages | title = Drugscope: 2C-B | access-date = 2013-09-25 | date = Jan 2004 | publisher = [[Drugscope]] | archive-url = https://web.archive.org/web/20130928055351/http://www.drugscope.org.uk/resources/drugsearch/drugsearchpages | archive-date = 2013-09-28 | url-status = dead }}</ref><ref name="dancesafe">{{cite web | url = http://www.dancesafe.org/drug-information/2c-b | title = 2C-B - Dancesafe.org | access-date = 2013-09-25 | publisher = [[Dancesafe]]}}</ref>

* At low doses, the experience may shift in intensity from engaging to mild/undetectable. Experienced users report the ability to take control of the effects and switch from engaged to sober at will.
* The hallucinations have a tendency to decrease and then increase in intensity, giving the users a sense of "waves" or even glowing. These are popularly described as "[[cliché]]d '70s visuals" or objects taking on "water color"-like textures.
* While the effects of the drug often render users unable to concentrate deeply on anything in particular, some can become engrossed in an activity such as watching a movie or playing a video game, thus distracting themselves from the visual and auditory effects of the drug.
* Excessive giggling or smiling is common, as is a tendency for deeper "belly laughs".
* Some users say that the effects are more intense when listening to music and report that they can [[Synesthesia|see sounds]] and noises.
* Some users experience a decrease in [[visual acuity]], although others report sharper vision.
* Through increased awareness of one's body, attention may be brought to perceived "imperfections" or internal body processes.{{break|2}}''The following effects are highly dose-dependent.''
* Open eye visuals (OEVs), such as cartoon-like distortions and red or green halos around objects. [[Closed-eye visualization|Closed eye visuals]] (CEVs) are more common than OEVs.
* Affects and alters ability to communicate, engage in deep thought, or maintain attention span.
* Some users report experiencing frightening or fearful effects during the experience. Users describe feeling frigid or cold on reaching a plateau, while others feel wrapped in comfortable blankets/ultimate pleasure.
* Coordination may be affected; some users lose balance or have perceptual distinction problems.
* Onset time of 2C-B is highly dose dependent, but usually from 45 to 75 minutes. Taken on a full stomach, the onset time is increased to two hours or more.
* Before it was scheduled, 2C-B was sold in small doses as an aphrodisiac {{crossreference|(see: {{slink||History}})}}. Some users report [[aphrodisiac]] effects at lower doses.<ref name="PiHKAL" /><ref name="Drugscope"/>{{break|2}}

Clinical studies in humans suggest that 2C-B is a psychedelic with some possible entactogen-like effects.<ref name="GonzálezTorrensFarré2015" /><ref name="PapaseitFarréPérez-Mañá2018" /><ref name="MallaroniMasonReckweg2023">{{cite journal | vauthors = Mallaroni P, Mason NL, Reckweg JT, Paci R, Ritscher S, Toennes SW, Theunissen EL, Kuypers KP, Ramaekers JG | title = Assessment of the Acute Effects of 2C-B vs. Psilocybin on Subjective Experience, Mood, and Cognition | journal = Clin Pharmacol Ther | volume = 114 | issue = 2 | pages = 423–433 | date = August 2023 | pmid = 37253161 | doi = 10.1002/cpt.2958 | url = }}</ref> Specific effects have included slight hallucinogenic states, perceptual changes, ego dissolution, time dilation, euphoria, feelings of well-being, reduced anger, increased reactivity to negative emotional stimuli, decreased ability to recognize expressions of happiness, augmented emotionality in speech, and mild sympathomimetic effects such as pressor effects, among others.<ref name="GonzálezTorrensFarré2015" /><ref name="PapaseitFarréPérez-Mañá2018" /><ref name="MallaroniMasonReckweg2023" />

==Side effects==
* Some users report mild "jitters" (body tremors), shuddering breath, and/or mild muscle spasms after insufflating 2C-B. Whether or not these effects are enjoyable depends on the user;
* Mild to intense diarrhea, gas, nausea, and general gastrointestinal discomfort;
* Severe headaches after coming down from large doses have been reported. However, many users report a lack of "comedown" or "crash", instead noting a gradual return to sobriety;
* At doses over 30–40&nbsp;mg the user may experience frightening [[hallucination]]s, as well as [[tachycardia]], [[hypertension]], and [[hyperthermia]];<ref name="CarmoHengstlerdeBoer2005">{{cite journal | vauthors = Carmo H, Hengstler JG, de Boer D, Ringel M, Remião F, Carvalho F, Fernandes E, dos Reys LA, Oesch F, de Lourdes Bastos M | title = Metabolic pathways of 4-bromo-2,5-dimethoxyphenethylamine (2C-B): analysis of phase I metabolism with hepatocytes of six species including human | journal = Toxicology | volume = 206 | issue = 1 | pages = 75–89 | date = January 2005 | pmid = 15590110 | doi = 10.1016/j.tox.2004.07.004 | bibcode = 2005Toxgy.206...75C | url = https://www.erowid.org/references/refs_view.php?A=ShowDocPartFrame&C=ref&ID=7928&DocPartID=7021 | url-access = subscription }}</ref>
* 2C-B HCl is very painful to insufflate. Anecdotal evidence suggests that 2C-B HBr, the [[hydrobromide]] salt with greater water solubility, is less irritating to the mucous membranes lining the nose but slightly less potent when compared dose-for-dose with the HCl salt;<ref>{{cite web|url=https://erowid.org/chemicals/2cb/2cb_faq.shtml|title=Erowid 2C-B Vault : FAQ v1.0 |website=erowid.org}}</ref>
* Rectal administration of a water-based solution of 2C-B is known to be less painful than insufflation and much more potent than oral administration.

Severe adverse reactions are rare, but use of 2C-B was linked to significant brain injury in one case report; the alleged "2C-B" was never actually discovered by testing so the only evidence suggesting 2C-B was the cause was the victim's own words, without taking into consideration that adulteration and impurities are very common in illicit drugs.<ref name="pmid20445431">{{cite journal |vauthors=Ambrose JB, Bennett HD, Lee HS, Josephson SA |date=May 2010 |title=Cerebral vasculopathy after 4-bromo-2,5-dimethoxyphenethylamine ingestion |journal=The Neurologist |volume=16 |issue=3 |pages=199–202 |doi=10.1097/NRL.0b013e3181a3cb53 |pmid=20445431 |s2cid=35035721}}</ref> There is a [[case report]] of acquired [[synesthesia]] following a single very high dose of 2C-B.<ref name="YanakievaLukeJansari2019">{{cite journal | vauthors = Yanakieva S, Luke DP, Jansari A, Terhune DB | title = Acquired synaesthesia following 2C-B use | journal = Psychopharmacology (Berl) | volume = 236 | issue = 7 | pages = 2287–2289 | date = July 2019 | pmid = 31025060 | doi = 10.1007/s00213-019-05242-y | url = }}</ref> There is also a case report of persistent [[psychosis]] following a single dose of 2C-B.<ref name="HuangBai2011">{{cite journal | vauthors = Huang HH, Bai YM | title = Persistent psychosis after ingestion of a single tablet of '2C-B' | journal = Prog Neuropsychopharmacol Biol Psychiatry | volume = 35 | issue = 1 | pages = 293–294 | date = January 2011 | pmid = 21036198 | doi = 10.1016/j.pnpbp.2010.10.018 | url = }}</ref>

==Overdose==
The [[Lethal dose|lethal dosage]] is unknown. It was reported in ''[[PiHKAL]]'', by [[Alexander Shulgin]], that a psychologist had accidentally taken a 100&nbsp;mg dose orally without apparent harm.<ref name="PiHKAL" />

==Interactions==
{{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}

2C-B is [[drug metabolism|metabolized]] by the [[monoamine oxidase]] (MAO) [[enzyme]]s [[MAO-A]] and [[MAO-B]].<ref name="DeanStellpflugBurnett2013">{{cite journal | vauthors = Dean BV, Stellpflug SJ, Burnett AM, Engebretsen KM | title = 2C or not 2C: phenethylamine designer drug review | journal = J Med Toxicol | volume = 9 | issue = 2 | pages = 172–178 | date = June 2013 | pmid = 23494844 | pmc = 3657019 | doi = 10.1007/s13181-013-0295-x | url = }}</ref><ref name="TheobaldMaurer2007">{{cite journal | vauthors = Theobald DS, Maurer HH | title = Identification of monoamine oxidase and cytochrome P450 isoenzymes involved in the deamination of phenethylamine-derived designer drugs (2C-series) | journal = Biochem Pharmacol | volume = 73 | issue = 2 | pages = 287–297 | date = January 2007 | pmid = 17067556 | doi = 10.1016/j.bcp.2006.09.022 | url = }}</ref> [[Monoamine oxidase inhibitor]]s (MAOIs) such as [[phenelzine]], [[tranylcypromine]], [[moclobemide]], and [[selegiline]] may potentiate the effects of 2C-B.<ref name="DeanStellpflugBurnett2013" /><ref name="TheobaldMaurer2007" /><ref name="HalmanKongSarris2024">{{Cite journal |vauthors=Halman A, Kong G, Sarris J, Perkins D |date=January 2024 |title=Drug-drug interactions involving classic psychedelics: A systematic review |journal=J Psychopharmacol |volume=38 |issue=1 |pages=3–18 |doi=10.1177/02698811231211219 |pmc=10851641 |pmid=37982394}}</ref> This may result in [[overdose]] and serious [[toxicity]].<ref name="HalmanKongSarris2024" /><ref name="DeanStellpflugBurnett2013" /> 2C-B may also have interactions with other medications and drugs.<ref name="InanBruntContrucci2020" />

==Pharmacology==
===Pharmacodynamics===
{| class="wikitable floatright" style="font-size:small;"
|+ {{Nowrap|2C-B activities}}
|-
! [[Biological target|Target]] !! [[Affinity (pharmacology)|Affinity]] (K<sub>i</sub>, nM)
|-
| [[5-HT1A receptor|5-HT<sub>1A</sub>]] || 130–311
|-
| [[5-HT1B receptor|5-HT<sub>1B</sub>]] || 104
|-
| [[5-HT1D receptor|5-HT<sub>1D</sub>]] || 26
|-
| [[5-HT1E receptor|5-HT<sub>1E</sub>]] || 120
|-
| [[5-HT1F receptor|5-HT<sub>1F</sub>]] || {{Abbr|ND|No data}}
|-
| [[5-HT2A receptor|5-HT<sub>2A</sub>]] || 0.66–32 (K<sub>i</sub>)<br />1.20–689 ({{Abbrlink|EC<sub>50</sub>|half-maximal effective concentration}})<br />4–101% ({{Abbrlink|E<sub>max</sub>|maximal efficacy}})
|-
| [[5-HT2B receptor|5-HT<sub>2B</sub>]] || 13.5–97 (K<sub>i</sub>)<br />12.6–130 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})<br />52–97% ({{Abbr|E<sub>max</sub>|maximal efficacy}})
|-
| [[5-HT2C receptor|5-HT<sub>2C</sub>]] || 32–90 (K<sub>i</sub>)<br />0.03–493 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})<br />50–116% ({{Abbr|E<sub>max</sub>|maximal efficacy}})
|-
| [[5-HT3 receptor|5-HT<sub>3</sub>]] || >10,000
|-
| [[5-HT4 receptor|5-HT<sub>4</sub>]] || {{Abbr|ND|No data}}
|-
| [[5-HT5A receptor|5-HT<sub>5A</sub>]] || >10,000
|-
| [[5-HT6 receptor|5-HT<sub>6</sub>]] || 320
|-
| [[5-HT7 receptor|5-HT<sub>7</sub>]] || 210
|-
| [[Alpha-1A adrenergic receptor|α<sub>1A</sub>]] || >10,000
|-
| [[Alpha-1B adrenergic receptor|α<sub>1B</sub>]] || >10,000
|-
| [[Alpha-1D adrenergic receptor|α<sub>1D</sub>]] || {{Abbr|ND|No data}}
|-
| [[Alpha-2A adrenergic receptor|α<sub>2A</sub>]] || 309–320
|-
| [[Alpha-2B adrenergic receptor|α<sub>2B</sub>]] || >10,000
|-
| [[Alpha-2C adrenergic receptor|α<sub>2C</sub>]] || 103
|-
| [[Beta-1 adrenergic receptor|β<sub>1</sub>]] || >10,000
|-
| [[Beta-2 adrenergic receptor|β<sub>2</sub>]] || >10,000
|-
| [[Beta-3 adrenergic receptor|β<sub>3</sub>]] || {{Abbr|ND|No data}}
|-
| [[D1 receptor|D<sub>1</sub>]] || 12,000
|-
| [[D2 receptor|D<sub>2</sub>]] || 2,200–25,200
|-
| [[D3 receptor|D<sub>3</sub>]] || 7,116–10,000
|-
| [[D4 receptor|D<sub>4</sub>]] || >10,000
|-
| [[D5 receptor|D<sub>5</sub>]] || >10,000
|-
| [[H1 receptor|H<sub>1</sub>]]–[[H4 receptor|H<sub>4</sub>]] || >10,000
|-
| [[Muscarinic acetylcholine M1 receptor|M<sub>1</sub>]]–[[M2 receptor|M<sub>2</sub>]] || >10,000
|-
| [[Muscarinic acetylcholine M3 receptor|M<sub>3</sub>]] || 822
|-
| [[M4 receptor|M<sub>4</sub>]]–[[M5 receptor|M<sub>5</sub>]] || >10,000
|-
| [[I1 receptor|I<sub>1</sub>]] || 2,155
|-
| [[Sigma-1 receptor|σ<sub>1</sub>]] || >10,000
|-
| [[Sigma-2 receptor|σ<sub>2</sub>]] || >10,000
|-
| {{Abbrlink|TAAR1|Trace amine-associated receptor 1}} || 90–3,000 (K<sub>i</sub>) (rodent)<br />3,300–7,190 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}}) (human)
|-
| {{Abbrlink|SERT|Serotonin transporter}} || 9,700–13,300 (K<sub>i</sub>)<br />18,000–312,900 ({{Abbrlink|IC<sub>50</sub>|half-maximal inhibitory concentration}})
|-
| {{Abbrlink|NET|Norepinephrine transporter}} || 27,400–31,000 (K<sub>i</sub>)<br />44,000–122,000 ({{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}})
|-
| {{Abbrlink|DAT|Dopamine transporter}} || 6,500–>30,000 (K<sub>i</sub>)<br />132,000–231,000 ({{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}})
|-
| {{Abbrlink|MAO-A|Monoamine oxidase A}} || 125,000 ({{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}})
|-
| {{Abbrlink|MAO-B|Monoamine oxidase B}} || 58,000 ({{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}})
|- class="sortbottom"
| colspan="2" style="width: 1px; background-color:#eaecf0; text-align: center;" | '''Notes:''' The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. '''Refs:''' <ref name="PDSPKiDatabase">{{cite web | title=PDSP Database | website=UNC | url=https://pdspdb.unc.edu/databases/pdsp.php?testDDRadio=testDDRadio&testLigandDD=13930&kiAllRadio=all&doQuery=Submit+Query | language=zu | access-date=3 December 2024}}</ref><ref name="BindingDB">{{cite web | last=Liu | first=Tiqing | title=BindingDB BDBM50005267 2,5-dimethoxy-4-bromophenethylamine::2-(4-Bromo-2,5-dimethoxy-phenyl)-ethylamine::2-(4-bromo-2,5-dimethoxyphenyl)ethylamine::CHEMBL292821::US20240166618, Compound 88 | website=BindingDB | url=https://www.bindingdb.org/rwd/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50005267 | access-date=3 December 2024}}</ref><ref name="Ray2010">{{cite journal | vauthors = Ray TS | title = Psychedelics and the human receptorome | journal = PLOS ONE | volume = 5 | issue = 2 | pages = e9019 | date = February 2010 | pmid = 20126400 | pmc = 2814854 | doi = 10.1371/journal.pone.0009019 | doi-access = free | bibcode = 2010PLoSO...5.9019R | url = }}</ref><ref name="RickliLuethiReinisch2015">{{cite journal | vauthors = Rickli A, Luethi D, Reinisch J, Buchy D, Hoener MC, Liechti ME | title = Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs) | journal = Neuropharmacology | volume = 99 | issue = | pages = 546–553 | date = December 2015 | pmid = 26318099 | doi = 10.1016/j.neuropharm.2015.08.034 | url = http://edoc.unibas.ch/56163/1/20170921163006_59c3cceeb8e5d.pdf}}</ref><ref name="Nugteren-vanLonkhuyzenvanRielBrunt2015" /><ref name="WallachCaoCalkins2023">{{cite journal | vauthors = Wallach J, Cao AB, Calkins MM, Heim AJ, Lanham JK, Bonniwell EM, Hennessey JJ, Bock HA, Anderson EI, Sherwood AM, Morris H, de Klein R, Klein AK, Cuccurazzu B, Gamrat J, Fannana T, Zauhar R, Halberstadt AL, McCorvy JD | title = Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential | journal = Nat Commun | volume = 14 | issue = 1 | pages = 8221 | date = December 2023 | pmid = 38102107 | pmc = 10724237 | doi = 10.1038/s41467-023-44016-1 | url = https://bitnest.netfirms.com/external/10.1038/s41467-023-44016-1}}</ref><br /><ref name="Marcher-RørstedHalberstadtKlein2020">{{cite journal | vauthors = Marcher-Rørsted E, Halberstadt AL, Klein AK, Chatha M, Jademyr S, Jensen AA, Kristensen JL | title = Investigation of the 2,5-Dimethoxy Motif in Phenethylamine Serotonin 2A Receptor Agonists | journal = ACS Chem Neurosci | volume = 11 | issue = 9 | pages = 1238–1244 | date = May 2020 | pmid = 32212672 | doi = 10.1021/acschemneuro.0c00129 | url = }}</ref><ref name="LuethiTrachselHoener2018">{{cite journal | vauthors = Luethi D, Trachsel D, Hoener MC, Liechti ME | title = Monoamine receptor interaction profiles of 4-thio-substituted phenethylamines (2C-T drugs) | journal = Neuropharmacology | volume = 134 | issue = Pt A | pages = 141–148 | date = May 2018 | pmid = 28720478 | doi = 10.1016/j.neuropharm.2017.07.012 | url = https://edoc.unibas.ch/57358/1/20170920150712_59c2680084ec5.pdf}}</ref><ref name="RudinLuethiHoener2022">{{cite journal | vauthors = Rudin D, Luethi D, Hoener MC, Liechti ME | title=Structure-activity Relation of Halogenated 2,5-Dimethoxyamphetamines Compared to their α‑Desmethyl (2C) Analogues | journal=The FASEB Journal | volume=36 | issue=S1 | date=2022 | issn=0892-6638 | doi=10.1096/fasebj.2022.36.S1.R2121 | doi-access=free | url=https://www.researchgate.net/publication/360423277_Structure-activity_relation_of_halogenated_25-dimethoxyamphetamines_compared_to_their_a-desmethyl_2C_analogues}}</ref><ref name="PottieCannaertStove2020" /><ref name="Acuña-CastilloVillalobosMoya2002">{{cite journal | vauthors = Acuña-Castillo C, Villalobos C, Moya PR, Sáez P, Cassels BK, Huidobro-Toro JP | title = Differences in potency and efficacy of a series of phenylisopropylamine/phenylethylamine pairs at 5-HT(2A) and 5-HT(2C) receptors | journal = Br J Pharmacol | volume = 136 | issue = 4 | pages = 510–519 | date = June 2002 | pmid = 12055129 | pmc = 1573376 | doi = 10.1038/sj.bjp.0704747 | url = }}</ref><ref name="FlanaganBillacLandry2021">{{cite journal | vauthors = Flanagan TW, Billac GB, Landry AN, Sebastian MN, Cormier SA, Nichols CD | title = Structure-Activity Relationship Analysis of Psychedelics in a Rat Model of Asthma Reveals the Anti-Inflammatory Pharmacophore | journal = ACS Pharmacol Transl Sci | volume = 4 | issue = 2 | pages = 488–502 | date = April 2021 | pmid = 33860179 | pmc = 8033619 | doi = 10.1021/acsptsci.0c00063 | url = }}</ref><ref name="WagmannBrandtStratford2019">{{cite journal | vauthors = Wagmann L, Brandt SD, Stratford A, Maurer HH, Meyer MR | title = Interactions of phenethylamine-derived psychoactive substances of the 2C-series with human monoamine oxidases | journal = Drug Test Anal | volume = 11 | issue = 2 | pages = 318–324 | date = February 2019 | pmid = 30188017 | doi = 10.1002/dta.2494 | url = }}</ref><ref name="ZwartsenVerbovenvanKleef2017">{{cite journal | vauthors = Zwartsen A, Verboven AH, van Kleef RG, Wijnolts FM, Westerink RH, Hondebrink L | title = Measuring inhibition of monoamine reuptake transporters by new psychoactive substances (NPS) in real-time using a high-throughput, fluorescence-based assay | journal = Toxicol In Vitro | volume = 45 | issue = Pt 1 | pages = 60–71 | date = December 2017 | pmid = 28506818 | doi = 10.1016/j.tiv.2017.05.010 | url = }}</ref><ref name="SimmlerBuchyChaboz2016">{{cite journal | vauthors = Simmler LD, Buchy D, Chaboz S, Hoener MC, Liechti ME | title = In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1 | journal = J Pharmacol Exp Ther | volume = 357 | issue = 1 | pages = 134–144 | date = April 2016 | pmid = 26791601 | doi = 10.1124/jpet.115.229765 | url = https://web.archive.org/web/20250509235235/https://d1wqtxts1xzle7.cloudfront.net/74120533/eae6c6e62565b82d46b4d111bbea0f77b9c2-libre.pdf?1635931703=&response-content-disposition=inline%3B+filename%3DIn_Vitro_Characterization_of_Psychoactiv.pdf&Expires=1746838268&Signature=Sy4fJ90yUhxs68314NxYsW5PAaNrBGePRu35WRR4PIF-3YC7Z~sLdnCn5wfqqbLg9bDEGdt~oW55ugMP3D3jgA0BoRI~~GOb0NQOwrtfUEQK1PQs1uuN9qg5Y1ct8z5NsABm44RgtukkwRMdU6fO7OlfIsQ68hOiFk129Ll7UYqldxD2f1xhE2fTTfsxSpb8cMCJzHn7-ItqLdwnAUPFK7WggDIjmY1kCnaHLwIxMwdJCAq8L6DYzSTg7pZkbR8qlou~GXbTPQt~gYpyZTJp5hgW-7V6K5wLlQ7Z2xE7B0f9wEfuc1W1QNafg125Tr-vvAe4LEGKXV58bnn1bpfWKw__&Key-Pair-Id=APKAJLOHF5GGSLRBV4ZA}}</ref>
|}

Unlike most [[psychedelic]]s, 2C-B has been shown to be a low [[Efficacy (pharmacology)|efficacy]] human [[serotonin]] [[5-HT2A receptor|5-HT<sub>2A</sub>]] and [[5-HT2C receptor|5-HT<sub>2C</sub>]] receptor [[partial agonist]].<ref name="MoyaBergGutiérrez-Hernandez2007">{{cite journal | vauthors = Moya PR, Berg KA, Gutiérrez-Hernandez MA, Sáez-Briones P, Reyes-Parada M, Cassels BK, Clarke WP | title = Functional selectivity of hallucinogenic phenethylamine and phenylisopropylamine derivatives at human 5-hydroxytryptamine (5-HT)2A and 5-HT2C receptors | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 321 | issue = 3 | pages = 1054–61 | date = June 2007 | pmid = 17337633 | doi = 10.1124/jpet.106.117507 | citeseerx = 10.1.1.690.3752 | s2cid = 11651502 }}</ref> This suggests that activation of the 5-HT<sub>2A</sub>-coupled [[phospholipase D]] pathway<ref name="MoyaBergGutiérrez-Hernandez2007" /> or functional antagonism of 5-HT<sub>2A</sub> may also play a role. The rank order of 5-HT<sub>2A</sub> receptor antagonist potency for this family of drugs in ''[[Xenopus]]'' is [[2C-I]] > 2C-B > [[2C-D]] > [[2C-H]].<ref name="WPCleanerAuto1">{{cite journal |vauthors=Villalobos CA, Bull P, Sáez P, Cassels BK, Huidobro-Toro JP |date=April 2004 |title=4-Bromo-2,5-dimethoxyphenethylamine (2C-B) and structurally related phenylethylamines are potent 4-HT2A receptor antagonists in Xenopus laevis oocytes |journal=British Journal of Pharmacology |volume=141 |issue=7 |pages=1167–74 |doi=10.1038/sj.bjp.0705722 |pmc=1574890 |pmid=15006903}}</ref>

Although 2C-B itself was not evaluated, other closely related members of the 2C series, including [[2C-C]], [[2C-D]], [[2C-E]], [[2C-I]], and [[2C-T-2]], all showed no activity as [[monoamine releasing agent]]s of [[serotonin]], [[norepinephrine]], or [[dopamine]] ({{Abbrlink|EC<sub>50</sub>|half-maximal effective concentration}} = >100,000{{nbsp}}nM or "inactive").<ref name="NagaiNonakaSatohHishashiKamimura2007">{{cite journal | vauthors = Nagai F, Nonaka R, Satoh Hisashi Kamimura K | title = The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain | journal = Eur J Pharmacol | volume = 559 | issue = 2–3 | pages = 132–137 | date = March 2007 | pmid = 17223101 | doi = 10.1016/j.ejphar.2006.11.075 | url = }}</ref><ref name="EshlemanForsterWolfrum2014">{{cite journal | vauthors = Eshleman AJ, Forster MJ, Wolfrum KM, Johnson RA, Janowsky A, Gatch MB | title = Behavioral and neurochemical pharmacology of six psychoactive substituted phenethylamines: mouse locomotion, rat drug discrimination and in vitro receptor and transporter binding and function | journal = Psychopharmacology (Berl) | volume = 231 | issue = 5 | pages = 875–888 | date = March 2014 | pmid = 24142203 | pmc = 3945162 | doi = 10.1007/s00213-013-3303-6 | url = }}</ref> Likewise, these other 2C derivatives showed little activity as serotonin 5-HT<sub>1A</sub> receptor agonists ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}} = >3,000{{nbsp}}nM).<ref name="EshlemanForsterWolfrum2014" />

The September 1998 issue of ''[[Journal of Analytical Toxicology]]'' reported that very little data exists about the pharmacological properties, [[metabolism]], and [[toxicity]] of 2C-B.{{Citation needed|date=May 2025}}

===Pharmacokinetics===
With 30{{nbsp}}mg 2C-B by [[oral administration]], its [[Cmax (pharmacology)|peak]] concentrations (mean ± SD) were 5.4 ± 1.7{{nbsp}}ng/mL and its [[Tmax (pharmacology)|time to peak]] concentrations were 2.3 ± 1.0{{nbsp}}hours.<ref name="ThomannRudinKraus2025" />

2C-B has been shown to be [[drug metabolism|metabolized]] by [[liver]] [[hepatocytes]], resulting in [[deamination]] and [[demethylation]] that produces several [[metabolite|product]]s. [[Oxidative deamination]] results in the 2-(4-bromo-2,5-dimethoxyphenyl)ethanol (BDMPE) and 4-bromo-2,5-dimethoxyphenylacetic acid (BDMPAA) metabolites. Additionally, 4-bromo-2,5-dimethoxybenzoic acid (BDMBA) can be produced by [[oxidative deamination]]. Further metabolism of BDMPE and BDMPAA may occur by demethylation. Alternatively, the later metabolites can be generated by demethylation of 2C-B followed by oxidative deamination.<ref name="CarmoHengstlerdeBoer2005" /> Deamination of 2C-B is mediated by the [[monoamine oxidase]] (MAO) [[enzyme]]s [[MAO-A]] and [[MAO-B]].<ref name="DeanStellpflugBurnett2013" /><ref name="TheobaldMaurer2007" /><ref name="ThomannRudinKraus2025" />

There is species differentiation in the metabolism of 2C-B. Mice hepatocytes produce 4-bromo-2,5-dimethoxyphenol (BDMP), a previously unknown metabolite. Meanwhile, human, monkey, and rabbit hepatocytes produce 2-(4-bromo-2-hydroxy-5-methoxyphenyl)-ethanol (B-2-HMPE), but dog, rat, and mouse hepatocytes do not.<ref name="CarmoHengstlerdeBoer2005" />

2C-B's metabolites BDMPAA and 4-bromo-2-hydroxy-5-methoxyphenylacetic acid (B-2-HMPAA) in humans occur at peak concentrations 280-fold and 17-fold higher than those of 2C-B with [[oral administration]] of 2C-B, respectively.<ref name="ThomannRudinKraus2025" />

The [[elimination half-life]] of 2C-B in humans is 1.2 to 2.5{{nbsp}}hours.<ref name="PapaseitFarréPérez-Mañá2018" /><ref name="ThomannRudinKraus2025" />

==Chemistry==
===Analogues and derivatives===
{{2C-B analogues and derivatives}}

A variety of N-substituted derivatives of 2C-B have been tested, including N-methyl-2CB, N,N-dimethyl-2CB, N-ethyl-2CB and N-benzyl-2CB. Most simple [[alkyl]] derivatives were considerably less potent than 2C-B, with N-ethyl-2CB for instance having a 40 times lower affinity for the 5-HT<sub>2A</sub> receptor. The N-[[Benzyl group|benzyl]] derivative however was found to have higher [[binding affinity]] than 2C-B itself, with N-(4-bromobenzyl)-2CB binding even more tightly.<ref name="pmid8027974">{{cite journal | vauthors = Glennon RA, Dukat M, el-Bermawy M, Law H, De los Angeles J, Teitler M, King A, Herrick-Davis K | title = Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines | journal = Journal of Medicinal Chemistry | volume = 37 | issue = 13 | pages = 1929–35 | date = June 1994 | pmid = 8027974 | doi = 10.1021/jm00039a004 }}</ref> This initial research did not include functional assays of activity, but later led to the development of potent substituted N-benzyl derivatives such as [[25B-NBOMe]],<ref>{{cite thesis |url=http://www.diss.fu-berlin.de/diss/receive/FUDISS_thesis_000000001221 | vauthors = Heim R |title=Synthese und Pharmakologie potenter 5-HT<sub>2A</sub>-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur: Entwicklung eines neuen Struktur-Wirkungskonzepts |trans-title=Synthesis and pharmacology of potent 5-HT<sub>2A</sub> receptor agonists which have a partial N-2-methoxybenzyl structure: Development of a new structure-activity concept |language=de |publisher=[[Free University of Berlin]] |date=March 19, 2004 |access-date=August 1, 2014}}</ref> and [[25B-NBOH]]. [[βk-2C-B]] shows dramatically reduced [[potency (pharmacology)|potency]] and [[intrinsic activity|efficacy]] as a serotonin [[5-HT2A receptor|5-HT<sub>2A</sub> receptor]] agonist compared to 2C-B.<ref name="PottieCannaertStove2020">{{cite journal | vauthors = Pottie E, Cannaert A, Stove CP | title = In vitro structure-activity relationship determination of 30 psychedelic new psychoactive substances by means of β-arrestin 2 recruitment to the serotonin 2A receptor | journal = Arch Toxicol | volume = 94 | issue = 10 | pages = 3449–3460 | date = October 2020 | pmid = 32627074 | doi = 10.1007/s00204-020-02836-w | bibcode = 2020ArTox..94.3449P | url = | hdl = 1854/LU-8687071 | hdl-access = free }}</ref>

[[ASR-2001]] (2CB-5PrO) is another notable analogue of 2C-B which is under development for treatment of [[psychiatric disorder]]s.<ref name="Busby2023">{{cite web | last=Busby | first=Mattha | title=The Heirs to a Vault of Novel Psychedelics Take a Trip Into the Unknown | website=DoubleBlind Mag | date=2 November 2023 | url=https://doubleblindmag.com/sasha-shulgin-legacy/ | access-date=19 April 2025}}</ref><ref name="Busby2025">{{cite web | last=Busby | first=Mattha | title=What Happens When You Inherit 500 Psychedelic Compounds? | website=DoubleBlind Mag | date=30 March 2025 | url=https://doubleblindmag.com/what-happens-when-you-inherit-500-psychedelic-compounds/ | access-date=19 April 2025}}</ref><ref name="Kargbo2025">{{cite journal | vauthors = Kargbo RB | title = Innovative Approaches in Psychedelics, AI, and Communication: A Multi-Domain Perspective | journal = ACS Med Chem Lett | volume = 16 | issue = 4 | pages = 514–516 | date = April 2025 | pmid = 40236531 | doi = 10.1021/acsmedchemlett.5c00114 | url = }}</ref>

===Reagent results===
Exposing compounds to the reagents gives a colour change which is indicative of the compound under test.

{| class="wikitable"
! [[Marquis reagent|Marquis]]
! [[Mecke reagent|Mecke]]
! [[Mandelin reagent|Mandelin]]
! [[Liebermann reagent|Liebermann]]
! [[Froehde reagent|Froehde]]
! [[Robadope reagent|Robadope]]
|-
| Yellow to green
| Yellow to olive brownish
| green
| Yellow to black
| Yellow to green
| Slow pink
|-
! [[Ehrlich's reagent|Ehrlich]]
! Hofmann
! [[Simon's reagent|Simon's]]
! [[Cobalt(II) thiocyanate|Scott]]
! colspan="2" |[[Folin's reagent|Folin]]
|-
| No reaction
| No reaction
| No reaction
| No reaction
| colspan="2" |(Light) purple
|}

==History==
2C-B was [[chemical synthesis|synthesized]] from [[2,5-dimethoxybenzaldehyde]] by American chemist [[Alexander Shulgin]] in 1974. It first saw use among the psychiatric community as an aid during therapy, but was abandoned due to [[gastrointestinal]] effects and the lack of [[empathogen]]ic effects.<ref name="Nugteren-vanLonkhuyzenvanRielBrunt2015" /> 2C-B was first sold commercially as a purported [[aphrodisiac]]<ref name="Reappears"/> under the trade name "Erox", which was manufactured by the German pharmaceutical company Drittewelle.<ref name="dritte pack">{{cite web|title=Drittewelle 2C-B Packaging|url=https://www.erowid.org/chemicals/show_image.php?i=2cb/2cb_pack2.jpg|publisher=Erowid.org|access-date=25 September 2013|year=2002}}</ref> For several years, it was available as tablets in Dutch [[smart shop]]s under the name "Nexus" and "B-Dub".{{citation needed|date=June 2020}}

==Society and culture==
===Illicit forms===
Street purity of 2C-B, when tested, has been found to be relatively high.<ref name="Review of public domain">{{cite journal |vauthors=Cole MD, Lea C, Oxley N |date=October 2002 |title=4-Bromo-2,5-dimethoxyphenethylamine (2C-B): a review of the public domain literature |url=http://lib.mdpu.org.ua/load/Chemistry/Organic%20chemistry/Organic%20syntheses/English%20edition/2c-b.review |journal=Science & Justice |volume=42 |issue=4 |pages=223–4 |doi=10.1016/S1355-0306(02)71832-7 |pmid=12632938|url-access=subscription }}{{Dead link|date=September 2018|bot=InternetArchiveBot|fix-attempted=yes}}</ref> Researchers in Spain found that 2C-B samples in the country doubled between 2006 and 2009, switched from primarily powder form to tablets, and exhibited "low falsification rates".<ref name="Spain study" /> An analysis of street samples in the Netherlands found impurities "in small percentages"; only one of the impurities, the N-acetyl derivative of 2C-B, could be identified, and comprised 1.3% of the sample. The authors suggested that this compound was a by-product of 2C-B synthesis.<ref name="Netherlands 2c-b emergence" />

In 2011, street prices in the United States ranged between $10 and $30 per tablet when purchased in small quantities.<ref name="DEA - Evaluation Section" /> Larger retail purchases cost between $200 and $500 per gram. Wholesale purchases of 2C-B would lower the price ($100 to $300 per gram in 2001, $30 to $100 on the [[darknet]] in 2020).<ref name="Reappears">{{cite web|title=2C-B (Nexus) Reappears on the Club Drug Scene|url=https://www.justice.gov/archive/ndic/pubs0/665/665p.pdf|work=National Drug Intelligence Center|publisher=Department of Justice|access-date=11 February 2013 |date=May 2001}}</ref>

===Legal status===
====United Nations====
The [[United Nations|UN]] [[Commission on Narcotic Drugs]] added 2C-B to Schedule II of the [[Convention on Psychotropic Substances]] in March 2001.<ref>{{cite web|url=http://www.incb.org/pdf/e/list/green.pdf |title=List of psychotropic substances under international control | work = Green List | edition = 23rd | date = August 2003 | publisher = International Narcotics Control Board |archive-url=https://web.archive.org/web/20070302130637/http://www.incb.org/pdf/e/list/green.pdf |archive-date=2 March 2007 |url-status=dead }}</ref>

2C-B is a scheduled drug in most jurisdictions.<ref>{{cite web| url=http://www.erowid.org/chemicals/2cb/2cb_law.shtml |title=Erowid 2C-B page}}</ref> The following is a partial list of territories where the substance has been scheduled.

====Argentina====
2C-B is controlled under the List 1, as well as similar substances like [[2C-I]] or [[2C-T-2]].<ref>{{cite web|url=http://www.cicad.oas.org/fortalecimiento_institucional/legislations/PDF/AR/decreto_299.pdf|title=Last Argentina Controlled Drugs List |access-date=May 15, 2012}}</ref>

====Australia====
2C-B is controlled in [[Australia]] and on the list of substances subject to import and export controls (Appendix B). It was placed on Schedule One of the Drugs Misuse and Trafficking Act when it first came to notice in 1994, when in a showcase legal battle chemist R. Simpson was charged with manufacturing the substance in Sydney. Alexander Shulgin came to Australia to testify on behalf of the defense, to no avail.

2C-B is not specifically listed in the Australia [[Standard for the Uniform Scheduling of Medicines and Poisons|Poisons Standard]] (October 2015), however similar drugs such as [[2C-T-2]] and [[2C-I]] are making 2C-B fall under the Australian analogue act.<ref name="Poisons Standard">Poisons Standard October 2015 https://www.comlaw.gov.au/Details/F2015L01534</ref>

====Belgium====
In [[Belgium]], 2C-B is a controlled substance making production, distribution, and possession illegal.

====Brazil====
In [[Brazil]], 2C-B is a controlled substance making production, distribution, and possession illegal.

====Canada====
In [[Canada]], 2C-B is classified under [[Controlled Drugs and Substances Act]] as Schedule III as "4-bromo-2,5-dimethoxybenzeneethanamine and any salt, isomer or salt of isomer thereof".<ref>{{cite web |url=http://isomerdesign.com/Cdsa/schedule.php?schedule=3&section=ALL&structure=C |title=CDSA Schedule II |access-date=2008-06-13 |archive-date=2020-07-25 |archive-url=https://web.archive.org/web/20200725132820/http://isomerdesign.com/Cdsa/schedule.php?schedule=3&section=ALL&structure=C |url-status=dead }}</ref>

2C-B has been rescheduled (Schedule III), in a new amendment, taking effect on October 31, 2016. This is to include the other 2C-x analogues.<ref>{{cite web|url=http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php|work = Canada Gazette | title = Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)| publisher =Government of Canada, Public Works and Government Services Canada, Public Services and Procurement Canada, Integrated Services Branch, Canada |date = 2016-05-04 }}</ref>

====Chile====
In August 2007, 2C-B, along with many other psychologically active substances,<ref>{{cite web|url=http://www.ispch.cl/sites/default/files/5_agencia_reguladora/decreto_867_07.pdf|title=APRUEBA REGLAMENTO DE LA LEY Nº 20.000 QUE SANCIONA EL TRÁFICO ILÍCITO DE ESTUPEFACIENTES Y SUSTANCIAS SICOTRÓPICAS Y SUSTITUYE LA LEY Nº 19.366.}}</ref> was added to Ley 20.000, known as the {{ill|Ley de Drogas|es|Ley de drogas (Chile)}}.

====Czech Republic====
Possession of more than 200&nbsp;mg of 2C-B is punishable with a two years jail sentence.<ref>{{cite web|url=https://www.erowid.org/psychoactives//law/countries/law_czech.shtml|title=Erowid Psychoactive Vaults : Drug Laws : Czech Republic|website=erowid.org}}</ref> Smaller amount is punishable by a fine. The 200&nbsp;mg threshold is merely a guideline which the court can reconsider depending on circumstances.

====Denmark====
In [[Denmark]], 2C-B is listed as a category B drug.<ref name="danish order on drugs">{{cite web | url = https://www.retsinformation.dk/Forms/R0710.aspx?id=137169 | title = Bekendtgørelse om euforiserende stoffer | access-date = 2013-10-01 | date = 2008-07-01 | language = da}}</ref>

====Estonia====
In [[Estonia]], 2C-B is classified as Schedule I.

====Germany====
In [[Germany]], 2C-B is controlled in the [[Betäubungsmittelgesetz]] (BtMG) Anlage I as "Bromdimethoxyphenethylamin" (BDMPEA).

====Italy====
2C-B is schedule I (tabella I).<ref>{{cite web|url=http://www.salute.gov.it/medicinaliSostanze/paginaInternaMedicinaliSostanze.jsp?id=7&menu=strumenti |title=Italy Drug Schedule (Tabella I) |url-status=dead |archive-url=https://web.archive.org/web/20110627153948/http://www.salute.gov.it/medicinaliSostanze/paginaInternaMedicinaliSostanze.jsp?id=7&menu=strumenti |archive-date=2011-06-27 }}</ref>

====Japan====
In [[Japan]], 2C-B was scheduled in 1998. It was previously marketed as "Performax".

==== Luxembourg ====
In [[Luxembourg]], 2C-B is a prohibited substance since 2001.<ref>[http://legilux.public.lu/eli/etat/leg/rgd/2001/12/14/n10/jo Règlement grand-ducal du 14 décembre 2001 modifiant l'annexe du règlement grand-ducal modifié du 4 mars 1974 concernant certaines substances toxiques].</ref>

====Netherlands====
In the [[Netherlands]], 2C-B was scheduled on July 9, 1997.

In the Netherlands, 2C-B became a list I substance of the [[Opium Law]] despite no health incidents occurring. Following the ban, other phenethylamines were sold in place of 2C-B until the Netherlands became the first country in the world to ban [[2C-I]], [[2C-T-2]] and [[2C-T-7]] alongside 2C-B.

====Norway====
In [[Norway]], 2C-B was classified as Schedule II on March 22, 2004, listed as 4-bromo-2,5-dimethoxyphenethylamine.<ref>{{cite web |url=http://www.lovdata.no/for/sf/ho/xo-19780630-0008.html |title=Norway Drug Schedule}}</ref>

====Poland====
2C-B is schedule I (I-P group) in [[Poland]].

====Russia====
Banned as a narcotic drug with a criminal penalty for possession of at least 10&nbsp;mg.<ref>{{cite web|url=http://base.garant.ru/70237124/|title=Постановление Правительства РФ от 01.10.2012 N 1002 "Об утверждении значительного, крупного и особо крупного размеров наркотических средств и психотропных веществ, а также значительного, крупного и особо крупного размеров для растений, содержащих наркотические средства или психотропные вещества, либо их частей, содержащих наркотические средства или психотропные вещества, для целей статей 228, 228.1, 229 и 229.1 Уголовного кодекса Российской Федерации" (с изменениями и дополнениями) |website=base.garant.ru}}</ref>

====Spain====
In [[Spain]], 2C-B was added to Category 2 prohibited substances in 2002.

====Sweden====
2C-B is currently classified as Schedule I in [[Sweden]].

2C-B was first classified as "health hazard" under the act Lagen om förbud mot vissa hälsofarliga varor (Act on the Prohibition of Certain Goods Dangerous to Health) as of April 1, 1999, under SFS 1999:58<ref name='Sweden 1999:58'>{{cite web | url = http://www.notisum.se/rnp/sls/fakta/a9990058.HTM | title = Förordning (1999:58) om förbud mot vissa hälsofarliga varo | access-date = 2013-10-01 | date = 1999-02-25 | language = sv | archive-date = 2013-10-04 | archive-url = https://web.archive.org/web/20131004215233/http://www.notisum.se/rnp/sls/fakta/a9990058.HTM | url-status = dead }}</ref> that made it illegal to sell or possess. Then it became schedule I as of June 1, 2002, published in LVFS 2002:4<ref>{{cite web | url = http://www.lakemedelsverket.se/upload/lvfs/LVFS_2002-4.pdf | title = Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 1997:12) om förteckningar över narkotika: LVFS 2002:4 | language = sv | access-date = 2013-09-14 | archive-url = https://web.archive.org/web/20131004213216/http://www.lakemedelsverket.se/upload/lvfs/LVFS_2002-4.pdf | archive-date = 2013-10-04 | url-status = dead }}</ref> but mislabeled "2-CB" in the document. However, this was corrected in a new document, LVFS 2009:22<ref>{{cite web | url = http://www.lakemedelsverket.se/upload/lvfs/LVFS_2009-22.pdf | title = Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 1997:12) om förteckningar över narkotika: LVFS 2009:22 | language = sv | access-date = 2013-09-14 | archive-url = https://web.archive.org/web/20180916034638/https://lakemedelsverket.se/upload/lvfs/LVFS_2009-22.pdf | archive-date = 2018-09-16 | url-status = dead }}</ref> effective December 9, 2009.

====Switzerland====
In [[Switzerland]], 2C-B is listed in Anhang D of the DetMV and is illegal to possess.<ref>{{cite web|url = http://www.swissmedic.ch/produktbereiche/00447/00536/index.html?lang=en&download=NHzLpZeg7t,lnp6I0NTU042l2Z6ln1ad1IZn4Z2qZpnO2Yuq2Z6gpJCDdn12hGym162epYbg2c_JjKbNoKSn6A--&.pdf|title = Verzeichnis aller betäubungsmittelhaltigen Stoffe|access-date = 2013-11-30|website = Swissmedic|publisher = Swiss Agency for Therapeutic Products|language = de|date = 2011-08-18|page = 2|trans-title = Directory of all narcotics-containing substances|archive-url = https://web.archive.org/web/20120315071907/http://www.swissmedic.ch/produktbereiche/00447/00536/index.html?lang=en|archive-date = 2012-03-15|url-status = dead}}</ref>

====United Kingdom====
All drugs in the 2C family are Class A under the [[Drugs controlled by the UK Misuse of Drugs Act|Misuse of Drugs Act]] which means they are illegal to produce, supply or possess. Possession carries a maximum sentence of seven years imprisonment while supply is punishable by life imprisonment and an unlimited fine.<ref name="talk_to_frank_law_uk">{{Cite web |title=2C family {{!}} FRANK |url=https://www.talktofrank.com/drug/2c#the-law |archive-url=https://web.archive.org/web/20241007052545/https://www.talktofrank.com/drug/2c#the-law |archive-date=2024-10-07 |access-date=2024-11-12 |website=www.talktofrank.com |language=en-GB}}</ref>

====United States====
In the United States, 2C-B is classified as a [[Controlled Substances Act#Schedule I|Schedule I]] controlled substance. This became permanent law on June 2, 1995,<ref name="fed_reg_1995">{{Cite web |date=1994-06-02 |title=Federal Register, Volume 60 Issue 106 (Friday, June 2, 1995) |url=https://www.govinfo.gov/content/pkg/FR-1995-06-02/html/95-13454.htm |archive-url=https://web.archive.org/web/20231104010125/https://www.govinfo.gov/content/pkg/FR-1995-06-02/html/95-13454.htm |archive-date=2023-11-04 |access-date=2024-11-12 |website=[[GovInfo]]}}</ref> following a proposal by the [[Drug Enforcement Administration]] in December 1994.<ref name="fed_reg_1994">{{Cite web |date=1994-12-20 |title=Federal Register, Volume 59 Issue 243 (Tuesday, December 20, 1994) |url=https://www.govinfo.gov/content/pkg/FR-1994-12-20/html/94-31162.htm |archive-url=https://web.archive.org/web/20240520001044/https://www.govinfo.gov/content/pkg/FR-1994-12-20/html/94-31162.htm |archive-date=2024-05-20 |access-date=2024-11-12 |website=GovInfo}}</ref>

==References==
{{Reflist}}

{{Psychedelics}}
{{Entactogens}}
{{Serotonin receptor modulators}}
{{Phenethylamines}}

{{DEFAULTSORT:2c-B}}

[[Category:5-HT2A agonists]]
[[Category:5-HT2B agonists]]
[[Category:5-HT2C agonists]]
[[Category:2C (psychedelics)]]
[[Category:Alexander Shulgin]]
[[Category:Bromobenzene derivatives]]
[[Category:Entactogens]]
[[Category:Entheogens]]
[[Category:O-methylated phenols]]