:2C-B

File:4-bromo-2,5-dimethoxyphenethylamine.jpg

2C-B became briefly popular in the United States as substitute for the street drug ecstasy (MDMA) when the latter became illegal in 1985.{{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}} Many 2C-B users are young adults who attend raves. 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.{{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}}

There are claims that 2C-B was used as entheogen by the Sangoma, Nyanga, and 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".{{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}}[http://www.erowid.org/chemicals/2cb/2cb_article1.shtml The Nexus Factor - An Introduction to 2C-B] Erowid[http://www.erowid.org/chemicals/show_image.php?i=2cb/ubulawu_pack.jpg Ubulawu Nomathotholo Pack] Photo by Erowid. © 2002 Erowid.org

In Shulgin's book PiHKAL, the oral dosage range is listed as 12 to 24{{nbsp}}mg.{{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}} The common oral recreational dose per Erowid is around 15 to 25{{nbsp}}mg.{{cite web |title=Erowid 2C-B Vault : Dose/Dosage |url=http://www.erowid.org/chemicals/2cb/2cb_dose.shtml}} 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.

When sold as "Ecstasy", tablets containing 2C-B often contain about 5 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 mg) which cause hallucinogenic effects.{{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}}

When 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.

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. 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.

Image:2cb pill.jpg logo]]

Little academic research has been conducted on the effects of 2C-B in humans. The information available is largely anecdotal and limited. Effects are often described as being more easily managed than other psychedelics;{{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}}{{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 }} it is often compared to a mixture of a serotonergic psychedelic and MDMA.{{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}} At 5–10 mg, experiments with young chickens have shown it to produce effects similar to a low dosage of amphetamines.{{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 }}

The anecdotal effects of 2C-B that have been reported by users on online discussion forums include:{{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}}{{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 }}{{cite web | url = http://www.dancesafe.org/drug-information/2c-b | title = 2C-B - Dancesafe.org | access-date = 2013-09-25 | publisher = Dancesafe}}

• 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 "clichéd '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 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 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.{{break|2}}

Clinical studies in humans suggest that 2C-B is a psychedelic with some possible entactogen-like effects.{{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 = }} 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.

• 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 mg the user may experience frightening hallucinations, as well as tachycardia, hypertension, and hyperthermia;{{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 }}
• 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;{{cite web|url=https://erowid.org/chemicals/2cb/2cb_faq.shtml|title=Erowid 2C-B Vault : FAQ v1.0 |website=erowid.org}}
• 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.{{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}} There is a case report of acquired synesthesia following a single very high dose of 2C-B.{{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 = }} There is also a case report of persistent psychosis following a single dose of 2C-B.{{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 = }}

The lethal dosage is unknown. It was reported in PiHKAL, by Alexander Shulgin, that a psychologist had accidentally taken a 100 mg dose orally without apparent harm.

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

2C-B is metabolized by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B.{{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 = }}{{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 = }} Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C-B.{{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}} This may result in overdose and serious toxicity. 2C-B may also have interactions with other medications and drugs.

Unlike most psychedelics, 2C-B has been shown to be a low efficacy human serotonin 5-HT_2A and 5-HT_2C receptor partial agonist.{{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 }} This suggests that activation of the 5-HT_2A-coupled phospholipase D pathway or functional antagonism of 5-HT_2A may also play a role. The rank order of 5-HT_2A receptor antagonist potency for this family of drugs in Xenopus is 2C-I > 2C-B > 2C-D > 2C-H.{{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}}

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 agents of serotonin, norepinephrine, or dopamine ({{Abbrlink|EC₅₀|half-maximal effective concentration}} = >100,000{{nbsp}}nM or "inactive").{{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 = }}{{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 = }} Likewise, these other 2C derivatives showed little activity as serotonin 5-HT_1A receptor agonists ({{Abbr|EC₅₀|half-maximal effective concentration}} = >3,000{{nbsp}}nM).

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}}

With 30{{nbsp}}mg 2C-B by oral administration, its peak concentrations (mean ± SD) were 5.4 ± 1.7{{nbsp}}ng/mL and its time to peak concentrations were 2.3 ± 1.0{{nbsp}}hours.

2C-B has been shown to be metabolized by liver hepatocytes, resulting in deamination and demethylation that produces several products. 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. Deamination of 2C-B is mediated by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B.

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.

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.

The elimination half-life of 2C-B in humans is 1.2 to 2.5{{nbsp}}hours.

{{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_2A receptor. The N-benzyl derivative however was found to have higher binding affinity than 2C-B itself, with N-(4-bromobenzyl)-2CB binding even more tightly.{{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 }} 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,{{cite thesis |url=http://www.diss.fu-berlin.de/diss/receive/FUDISS_thesis_000000001221 | vauthors = Heim R |title=Synthese und Pharmakologie potenter 5-HT_2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur: Entwicklung eines neuen Struktur-Wirkungskonzepts |trans-title=Synthesis and pharmacology of potent 5-HT_2A 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}} and 25B-NBOH. βk-2C-B shows dramatically reduced potency and efficacy as a serotonin 5-HT_2A receptor agonist compared to 2C-B.{{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 }}

ASR-2001 (2CB-5PrO) is another notable analogue of 2C-B which is under development for treatment of psychiatric disorders.{{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}}{{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}}{{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 = }}

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

2C-B was 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 empathogenic effects. 2C-B was first sold commercially as a purported aphrodisiac under the trade name "Erox", which was manufactured by the German pharmaceutical company Drittewelle.{{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}} For several years, it was available as tablets in Dutch smart shops under the name "Nexus" and "B-Dub".{{citation needed|date=June 2020}}

Street purity of 2C-B, when tested, has been found to be relatively high.{{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}} 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". 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.

In 2011, street prices in the United States ranged between $10 and $30 per tablet when purchased in small quantities. 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).{{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}}

The UN Commission on Narcotic Drugs added 2C-B to Schedule II of the Convention on Psychotropic Substances in March 2001.{{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 }}

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

2C-B is controlled under the List 1, as well as similar substances like 2C-I or 2C-T-2.{{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}}

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 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.Poisons Standard October 2015 https://www.comlaw.gov.au/Details/F2015L01534

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

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

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".{{cite web |url=http://isomerdesign.com/Cdsa/schedule.php?schedule=3§ion=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§ion=ALL&structure=C |url-status=dead }}

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.{{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 }}

In August 2007, 2C-B, along with many other psychologically active substances,{{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.}} was added to Ley 20.000, known as the {{ill|Ley de Drogas|es|Ley de drogas (Chile)}}.

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

In Denmark, 2C-B is listed as a category B drug.{{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}}

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

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

2C-B is schedule I (tabella I).{{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 }}

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

In Luxembourg, 2C-B is a prohibited substance since 2001.[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].

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.

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

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

Banned as a narcotic drug with a criminal penalty for possession of at least 10 mg.{{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}}

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

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{{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 }} that made it illegal to sell or possess. Then it became schedule I as of June 1, 2002, published in LVFS 2002:4{{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 }} but mislabeled "2-CB" in the document. However, this was corrected in a new document, LVFS 2009:22{{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 }} effective December 9, 2009.

In Switzerland, 2C-B is listed in Anhang D of the DetMV and is illegal to possess.{{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}}

All drugs in the 2C family are Class A under the 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.{{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}}

In the United States, 2C-B is classified as a Schedule I controlled substance. This became permanent law on June 2, 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}} following a proposal by the Drug Enforcement Administration in December 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}}

{{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