2C-B

{{Short description|Psychedelic drug}} {{Distinguish|Tusi (drug)|text=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 | image_class = skin-invert-image | width = 225px | caption = Molecular structure of 2C-B | image2 = 4-bromo-2,5-dimethoxyphenethylamine (2C-B).png | image_class2 = bg-transparent | width2 = 200px

| bioavailability = Low<ref name="Mallaroni_2023" /> | protein_bound = Unknown<ref name="DrugBank">{{cite web | title = 4-Bromo-2,5-dimethoxyphenethylamine: Uses, Interactions, Mechanism of Action | date = 31 July 2007 | website = DrugBank | url = https://go.drugbank.com/drugs/DB01537 | access-date = 7 January 2026 }}</ref> | metabolism = Liver (MAO and CYP450)<ref name="Inan_2020" /><ref name="Nugteren-van_Lonkhuyzen_2015" /> | 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="Cole_2002" /><ref name="HolzeArikciThomann2025" /> | onset = Oral: 0.5–1.2 hours (range 0.3–1.5 hours)<ref name="HolzeArikciThomann2025" /><ref name="Caudevilla-Galligo_2012" /><ref name="Cole_2002" /><ref name="Spoelder_2019" /> | elimination_half-life = 1.2–2.5 hours<ref name="HolzeArikciThomann2025" /><ref name="Papaseit_2018">{{cite journal | vauthors = Papaseit E, Farré M, Pérez-Mañá C, Torrens M, Ventura M, Pujadas M, de la Torre R, González D | date = 2018 | title = Acute Pharmacological Effects of 2C-B in Humans: An Observational Study | journal = Frontiers in Pharmacology | volume = 9 | article-number = 206 | doi = 10.3389/fphar.2018.00206 | doi-access = free | pmc = 5859368 | pmid = 29593537 }}</ref><ref name="Mallaroni_2023" /><ref name="Thomann_2025">{{cite journal | vauthors = Thomann J, Rudin D, Kraus S, Arikci D, Holze F, Liechti ME, Luethi D | title = Liquid chromatography-tandem mass spectrometry-based pharmacokinetic and metabolic analysis of 4-bromo-2,5-dimethoxyphenethylamine and its metabolites in human plasma | journal = Drug Metabolism and Disposition | volume = 53 | issue = 6 | date = June 2025 | pmid = 40408905 | doi = 10.1016/j.dmd.2025.100086 | doi-access = free | article-number = 100086 }}</ref> | duration_of_action = Oral: 3–5 hours (range 2–8 hours)<ref name="PiHKAL" /><ref name="HolzeArikciThomann2025" /><ref name="Mallaroni_2023" /><ref name="Mallaroni_2022" /><ref name="Inan_2020">{{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 = Therapeutic Drug Monitoring | volume = 42 | issue = 2 | pages = 271–281 | date = April 2020 | pmid = 32022784 | doi = 10.1097/FTD.0000000000000725 | url = https://pure.amsterdamumc.nl/en/publications/8e964705-c9e9-49ae-85a5-a71877384f15 }}</ref><ref name="Cole_2002" /><ref name="Nugteren-van_Lonkhuyzen_2015" /> | excretion = Urine<ref name="Cole_2002" /><ref name="Nugteren-van_Lonkhuyzen_2015" />

| 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 }}  '''2C-B''', also known as '''4-bromo-2,5-dimethoxyphenethylamine''' or by names such as '''Nexus''' or '''Erox''', is a psychedelic drug of the phenethylamine and 2C families.<ref name="Cole_2002">{{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 = Science & Justice | volume = 42 | issue = 4 | pages = 223–224 | date = 2002 | pmid = 12632938 | doi = 10.1016/S1355-0306(02)71832-7 | url = https://figshare.com/articles/journal_contribution/23783454 | quote = 2C-B gained popularity during the mid 1980s as a replacement of choice for LSD and psilocybin [4]. It is encountered by the forensic scientist in powdered and tablet forms. It may be consumed orally, in tablets which typically contain 5 mg, in doses of between 10 and 50 mg. A light dose is considered to be 5–15 mg, a strong dose 20–50 mg [5]. Following an onset period of 20–90 minutes, the effects may last for two to five hours and after-effects may last between two and four hours. It may also be insufflated in powdered form, the doses for this route of administration being approximately one third of the oral dose. }}</ref><ref name="Nugteren-van_Lonkhuyzen_2015">{{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 and Alcohol Dependence | volume = 157 | pages = 18–27 | date = December 2015 | pmid = 26530501 | doi = 10.1016/j.drugalcdep.2015.10.011 | quote = Nasal insufflation is rarely practiced, but it produces more rapid and intense effects than oral exposure (Caudevilla-Gálligo et al., 2012; Dean et al., 2013). [...] 2CB was first synthesized in the 1970s for psychotherapeutic use (Shulgin and Carter, 1975; Shulgin and Shulgin, 1991), but was abandoned due to significant gastrointestinal effects and the lack of empathogenic effects (Dean et al., 2013). [...] }}</ref><ref name="Wills_2012" /><ref name="Anilanmert_2018">{{cite book | vauthors = Anilanmert B, Yonar FÇ, Özdemir AA | date = 31 January 2018 | chapter = 2C Derivatives of Phenylethylamines and Their Analysis | title = Chromatographic Techniques in the Forensic Analysis of Designer Drugs | publisher = CRC Press | pages = 277–304 | isbn = 978-1-315-31317-7 | doi = 10.1201/9781315313177-15 | publication-place = Boca Raton (FL) | series = Chromatographic science series }}</ref> The drug is used as a recreational drug and is usually taken orally.<ref name="PiHKAL" /> 2C-B produces hallucinogenic, mild stimulant, and mild entactogenic-like effects.<ref name="PiHKAL" /><ref name="Wills_2012" /><ref name="Nugteren-van_Lonkhuyzen_2015" /><ref name="Luethi_2020">{{cite journal | vauthors = Luethi D, Liechti ME | title = Designer drugs: mechanism of action and adverse effects | journal = Archives of Toxicology | volume = 94 | issue = 4 | pages = 1085–1133 | date = April 2020 | pmid = 32249347 | pmc = 7225206 | doi = 10.1007/s00204-020-02693-7 | quote = In one of the few clinical studies of a designer drug, 4-bromo-2,5-dimethoxyphenylethylamine (2C-B) was shown to induce euphoria, well-being, and changes in perception, and to have mild stimulant properties (González et al. 2015). 2C-B may thus be classified as a psychedelic with entactogenic properties, an effect profile that is similar to various other phenethylamine psychedelics (Shulgin and Shulgin 1995). | bibcode = 2020ArTox..94.1085L }}</ref><ref name="Gonzalez_2015">{{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 | date = 2015-10-12 | pmid = 26543863 | pmc = 4620274 | doi = 10.1155/2015/643878 | doi-access = free | article-number = 643878 }}</ref><ref name="Oeri_2021">{{cite journal | vauthors = Oeri HE | title = Beyond ecstasy: Alternative entactogens to 3,4-methylenedioxymethamphetamine with potential applications in psychotherapy | journal = Journal of Psychopharmacology | volume = 35 | issue = 5 | pages = 512–536 | date = May 2021 | pmid = 32909493 | pmc = 8155739 | doi = 10.1177/0269881120920420 | quote = While an argument can be made that compounds like 4-bromo-2,5-dimethoxyphenethylamine (2CB) or N,N-diisopropyl-5-methoxytryptamine (5-MeO-DiPT) are also entactogenic, and they have been described as such in the past (González et al., 2015; Palamar and Acosta, 2020; Schifano et al., 2019), they were also excluded due to their high affinity as agonists at post-synaptic 5-HT2 and 5-HT1A receptors (Fantegrossi et al., 2006; Nugteren-van Lonkhuyzen et al., 2015; Taylor et al., 1986; Villalobos et al., 2004), which would indicate that their effects also include a marked psychedelic component. }}</ref><ref name="Shulgin_1975" /> Its hallucinogenic effects at typical doses are milder than those of other psychedelics like LSD or psilocybin.<ref name="Nugteren-van_Lonkhuyzen_2015" /><ref name="Caudevilla-Galligo_2012" /><ref name="Palamar_2020" /><ref name="Mallaroni_2023" /><ref name="Shulgin_1975" />

The drug acts as a potent partial agonist of the serotonin 5-HT2 receptors, including of the serotonin 5-HT2A receptor.<ref name="Wallach_2023" /><ref name="Rickli_2015" /><ref name="Ray_2010" /> It produces psychedelic-like effects in animals.<ref name="Wallach_2023" /> Numerous analogues and derivatives of 2C-B are known, such as DOB, 2C-B-FLY, and 25B-NBOMe among others.<ref name="PiHKAL" /><ref name="Shulgin_2011" /><ref name="Trachsel_2013" /><ref name="Duan_2024" />

2C-B was developed by Alexander Shulgin in 1974<ref name="Poulie_2020" /><ref name="Dean_2013" /><ref name="Wills_2012" /> and was described by him in the scientific literature in 1975.<ref name="Passie_2018">{{cite book | vauthors = Passie T, Brandt SD | title = New Psychoactive Substances | chapter = Self-Experiments with Psychoactive Substances: A Historical Perspective | volume = 252 | pages = 69–110 | date = 2018 | pmid = 30478735 | doi = 10.1007/164_2018_177 | isbn = 978-3-030-10560-0 | series = Handbook of Experimental Pharmacology | quote = Noteworthy is Shulgin's first synthesis, SE, and description of the subjective effects of 2C-B (Shulgin 1975). }}</ref><ref name="Shulgin_1975" /> The drug also emerged as a novel recreational designer drug and MDMA (ecstasy) substitute in the mid-1980s.<ref name="Dean_2013" /><ref name="Wills_2012" /><ref name="Anilanmert_2018" /><ref name="Johnson_2018" /> Subsequently, it became a controlled substance in the United States in the mid-1990s.<ref name="Dean_2013" /><ref name="Wills_2012" /><ref name="Anilanmert_2018" /> 2C-B was one of the first 2C psychedelics to be described.<ref name="Dean_2013" /><ref name="Wills_2012" /><ref name="Shulgin_1975" /> It is the most popular and well-known of the 2C psychedelics and is one of the most widely used designer drugs.<ref name="Wills_2012" /><ref name="Anilanmert_2018" /><ref name="Palamar_2020" /><ref name="Gonzalez_2015" /><ref name="Mallaroni_2022" />

==Use and effects== In his book ''PiHKAL'' (''Phenethylamines I Have Known and Loved'') and other publications, Alexander Shulgin lists 2C-B's dose range as 12 to 24{{nbsp}}mg orally and its duration as 4 to 8{{nbsp}}hours.<ref name="PiHKAL">{{CitePiHKAL }} https://www.erowid.org/library/books_online/pihkal/pihkal020.shtml</ref><ref name="Jacob_1994">{{cite book | vauthors = Jacob P, Shulgin AT | date = 1994 | veditors = Lin GC, Glennon RA | chapter = Structure-Activity Relationships of the Classic Hallucinogens and Their Analogs | title = Hallucinogens: An Update | publisher = National Institute on Drug Abuse | volume = 146 | pages = 74–91 | pmid = 8742795 | url = https://archives.nida.nih.gov/sites/default/files/monograph146.pdf | archive-date = 13 July 2025 | archive-url = https://web.archive.org/web/20250713011914/https://bibliography.maps.org/resources/download/11534 | series = National Institute on Drug Abuse Research Monograph Series | chapter-url = https://bibliography.maps.org/resources/download/11534 }}</ref><ref name="Shulgin_2003">{{cite book | vauthors = Shulgin AT | year = 2003 | veditors = Laing RR | chapter = Basic Pharmacology and Effects | title = Hallucinogens: A Forensic Drug Handbook | publisher = Elsevier Science | pages = 67–137 | isbn = 978-0-12-433951-4 | url = https://books.google.com/books?id=l1DrqgobbcwC | archive-date = 13 July 2025 | archive-url = https://web.archive.org/web/20250713013624/https://bibliography.maps.org/resources/download/12634 | series = Forensic Drug Handbook Series | chapter-url = https://bibliography.maps.org/resources/download/12634 }}</ref> However, in an earlier report, he described an effective dose range of 8 to 10{{nbsp}}mg orally and a duration of 6 to 8{{nbsp}}hours.<ref name="Shulgin_1975" /><ref name="Caudevilla-Galligo_2012" /> Threshold effects occur at a dose of 4{{nbsp}}mg orally.<ref name="Shulgin_1975" /><ref name="Shulgin_1978">{{cite book | vauthors = Shulgin AT | date = 1978 | veditors = Iversen LL, Iversen SD, Snyder SH | chapter = Psychotomimetic Drugs: Structure-Activity Relationships | title = Stimulants | publisher = Springer US | pages = 243–333 | isbn = 978-1-4757-0512-6 | doi = 10.1007/978-1-4757-0510-2_6 | publication-place = Boston, MA | chapter-url = https://bitnest.netfirms.com/external/10.1007/978-1-4757-0510-2_6 }}</ref> A wider recreational dose range of 2 to 55{{nbsp}}mg or more orally has been described as well, with a typical dose estimate of about 20{{nbsp}}mg.<ref name="Luethi_2018">{{cite journal | vauthors = Luethi D, Liechti ME | title = Monoamine Transporter and Receptor Interaction Profiles in Vitro Predict Reported Human Doses of Novel Psychoactive Stimulants and Psychedelics | journal = The International Journal of Neuropsychopharmacology | volume = 21 | issue = 10 | pages = 926–931 | date = October 2018 | pmid = 29850881 | pmc = 6165951 | doi = 10.1093/ijnp/pyy047 }}</ref><ref name="Halberstadt_2020">{{cite journal | vauthors = Halberstadt AL, Chatha M, Klein AK, Wallach J, Brandt SD | title = Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species | journal = Neuropharmacology | volume = 167 | date = May 2020 | pmid = 31917152 | pmc = 9191653 | doi = 10.1016/j.neuropharm.2019.107933 | article-number = 107933 }}</ref><ref name="Cole_2002" /><ref name="Caudevilla-Galligo_2012" /><ref name="Gonzalez_2015" /><ref name="Mallaroni_2023" /><ref name="Mallaroni_2022" /> A low dose has been said to be 5 to 15{{nbsp}}mg, a moderate dose 10 to 25{{nbsp}}mg, and a high or strong dose 20 to 50{{nbsp}}mg.<ref name="Cole_2002" /><ref name="Papaseit_2018" /><ref name="Nugteren-van_Lonkhuyzen_2015" /> Most people use doses of 20{{nbsp}}mg or lower.<ref name="Caudevilla-Galligo_2012" /> 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="Palamar_2020" /><ref name="Shulgin_1978" /> Over the 12 to 24{{nbsp}}mg dose range, every 2{{nbsp}}mg increment can result in a profound increase or change in effects.<ref name="PiHKAL" /> Higher doses are said to lead to more intense but not longer-lasting effects.<ref name="Shulgin_1978" /> The drug's onset is about 0.5 to 1.2{{nbsp}}hours, with a range of 0.3 to 1.5{{nbsp}}hours, and its time to peak effects is about 2.5{{nbsp}}hours on average.<ref name="HolzeArikciThomann2025" /><ref name="Caudevilla-Galligo_2012" /><ref name="Cole_2002" /><ref name="Spoelder_2019" /> Effects on average last about 3.1 to 4.9{{nbsp}}hours on average and are shorter than those of psilocybin.<ref name="HolzeArikciThomann2025" /><ref name="Caudevilla-Galligo_2012" /><ref name="Papaseit_2018" /><ref name="Mallaroni_2023" /> In addition to oral administration, 2C-B may be insufflated less commonly, with doses being approximately one-third of those of the oral route or in the range of 10 to 30{{nbsp}}mg and with this route producing more rapid and intense effects.<ref name="Cole_2002" /><ref name="Caudevilla-Galligo_2012" /><ref name="Nugteren-van_Lonkhuyzen_2015" /><ref name="Mallaroni_2022" />

The effects of 2C-B were reported by Shulgin to include sensory enhancement, brightened colors, visual richness, mental imagery, psychedelic visuals including kaleidoscopic and organic forms, sound distortion, increased appreciation of art and music, passivity, relaxation, emotional changes, euphoria, increased body awareness, tactile enhancement, feeling like waves of energy are flowing through oneself, feeling like one's body is flooded with orgasms, and sexual enhancement.<ref name="PiHKAL" /><ref name="Shulgin_1975" /><ref name="Shulgin_1986">{{cite journal | vauthors = Shulgin AT, Shulgin LA, Jacob P | title = A protocol for the evaluation of new psychoactive drugs in man | journal = Methods and Findings in Experimental and Clinical Pharmacology | volume = 8 | issue = 5 | pages = 313–320 | date = May 1986 | pmid = 3724306 | url = https://bibliography.maps.org/resources/download/10894 | quote = Somatic sensitizer: In addition to an extensive visual syndrome, the phenethylamine 2-CB (4-bromo-2,5-dimethoxyphenethylamine) (13) produces an intense awareness of physical responses to stimuli: olfactory, auditory, gustatory and sexual. | archive-url = https://web.archive.org/web/20250712234439/https://bibliography.maps.org/resources/download/10894 | archive-date = 2025-07-12 }}</ref><ref name="Shulgin2003b">{{cite web | title = Ask Dr. Alexander "Sasha" Shulgin Online | date = 7 February 2003 | website = keeping freedom in mind - | url = https://www.cognitiveliberty.org/ccle1/shulgin/adsarchive/2cb.htm | quote = Dear Dr. Shulgin: What is 2C-B? What are its effects? --Brian [...] And what is its action? It is, in my opinion, one of the most graceful, erotic, sensual, introspective compounds I have ever invented. For most people, it is a short-lived and comfortable psychedelic, with neither toxic side-effects nor next-day hang-over. Its effects are felt very much in the body, as well as in the mind, and thus it has found clinical use as a follow-up to MDMA. Once the MDMA has shown you where your problems are, the 2C-B opens up the emotional, intuitive and archetypal area of your psyche to help you solve them. It was probably one of my favorite drugs, back in those yesteryear days when one could explore one's consciousness with legal immunity. }}</ref> He has succinctly described 2C-B as having "a luxury of sensory enhancement (visual, sexual, gustatory) with a minimum of introspective demands".<ref name="Shulgin_1983">{{cite book | vauthors = Shulgin AT | date = 1983 | veditors = Grinspoon L, Bakalar JB | chapter = Twenty Years On an Ever-Changing Quest | title = Psychedelic Reflections | publisher = Human Sciences Press | pages = 205–212 | isbn = 978-0-89885-129-8 | url = https://books.google.com/books?id=USkQAQAAIAAJ | archive-date = 6 July 2025 | archive-url = https://web.archive.org/web/20250706234524/https://bibliography.maps.org/resources/download/9049 | location = New York | oclc = 9195516 | chapter-url = https://bibliography.maps.org/resources/download/9049 }}</ref> The drug was one of his favorite psychedelics<ref name="Shulgin2003b" /> and one of his "magical half-dozen" most important psychedelic phenethylamines.<ref name="PiHKAL" /> At doses of 8 to 10{{nbsp}}mg, 2C-B was described as consistently producing substantial sensory enhancement, but as not "superimposing hallucinogenesis" or as having "no hallucinogenic effects", with the state being described as quite distinct from that usually associated with psychedelics.<ref name="Shulgin_1975" /><ref name="Caudevilla-Galligo_2012" /> It was also said to lack the lassitude that can be associated with psilocybin.<ref name="Shulgin_1975" />

In published reports by other authors, 2C-B has been claimed to produce effects including visual, auditory, and tactile perceptual changes, closed-eye imagery, LSD-like visuals such as colors and geometric shapes, time dilation, MDMA-like stimulant and entactogenic effects, such as being more in touch with emotions, as well as feelings of love, enhanced sociability, and empathy, feelings of peace and well-being, euphoria, a "body high", increased sensitivity to touch, touch feeling pleasurable, and being erotic.<ref name="Palamar_2020" /><ref name="Mallaroni_2022" /><ref name="Sexton_2019" /><ref name="Caudevilla-Galligo_2012" /> The presence of entactogenic effects with 2C-B is said to be unique among most psychedelics, along with certain other atypical psychedelics like 5-MeO-DiPT and 5-MeO-MiPT.<ref name="Luethi_2020" /><ref name="Oeri_2021" /><ref name="Gonzalez_2015" /><ref name="Palamar_2020" /> 2C-B's effects are often described as being milder and more easily managed than other psychedelics.<ref name="Palamar_2020">{{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 | date = January 2020 | pmid = 31909513 | pmc = 6995261 | doi = 10.1002/hup.2719 | article-number = e2719 }}</ref><ref name="Mallaroni_2022">{{cite journal | vauthors = Mallaroni P, Mason NL, Vinckenbosch FR, Ramaekers JG | title = The use patterns of novel psychedelics: experiential fingerprints of substituted phenethylamines, tryptamines and lysergamides | journal = Psychopharmacology | volume = 239 | issue = 6 | pages = 1783–1796 | date = June 2022 | pmid = 35487983 | pmc = 9166850 | doi = 10.1007/s00213-022-06142-4 | quote = Entheogenic features such as oceanic boundlessness and dread of ego dissolution were rated significantly less for 2C-B than for 4-AcO-DMT and 1P-LSD. Characterised as an entactogen with psychedelic-like effects, observational studies have demonstrated 2C-B only produces mild psychedelic effects. As with other entactogens such as 2C-E, 4-FA and MDMA, its effects are limited to perceptual alterations and pseudohallucinations (Papaseit et al. 2018; Kuypers et al. 2019; Papaseit et al. 2020; Studerus et al. 2021). These descriptions may be exemplified by the absence of dose-dependent effects, endorsement of euphoria as a motivation by 49% of users and its reiterated use at music events (Palamar et al. 2016a, b). Consequently, that what distinguishes certain phenethylamines from tryptamines and lysergamides may not be a question of experience quality, but rather depth. }}</ref><ref name="Caudevilla-Galligo_2012" /><ref name="Nugteren-van_Lonkhuyzen_2015" /> For example, it is said to be less incapacitating or impairing, "non-ego-threatening", not "mentally challenging" or confusing, not leading to an "extreme headspace", and leaving the mind "very clear".<ref name="Palamar_2020" /><ref name="Caudevilla-Galligo_2012" /> In addition, it is said to produce changes in thought and time perception less frequently.<ref name="Caudevilla-Galligo_2012" /> Due to its potential for relatively light effects, the drug has been referred to as the "Diet Coke of psychedelics" or as a "beginner psychedelic".<ref name="Palamar_2020" /> Nonetheless, it has been described as quite visual, with the potential for all of the visuals of LSD but without the head space that LSD and psilocybin produce.<ref name="Palamar_2020" /> However, the visuals are dose-dependent, being mild at lower doses and being more substantial and LSD-like at higher doses.<ref name="Palamar_2020" /> 2C-B is often compared to a mixture of LSD and MDMA or a "candyflip".<ref name="Palamar_2020" /><ref name="Caudevilla-Galligo_2012" /> However, it is described as a "clear-headed candyflip", with entactogenic-like effects, LSD-like effects such as visuals, but a very clear head space.<ref name="Palamar_2020" /> In addition, it is said to not have the same kind of forceful positive mood push that MDMA has, and to be a little more unpredictable and capable of causing bad trips or negative head spaces.<ref name="Palamar_2020" /> 2C-B is said to be more of a "party drug", to be more recreational drug, and to have less likelihood of challenging, emotional-breakthrough, or mystical-type experiences, relative to psychedelics like psilocybin and LSD.<ref name="Sexton_2019" /><ref name="Caudevilla-Galligo_2012" />

Formal clinical studies have found that 2C-B produces a mixture of psychedelic, some possible entactogen-like, and some stimulant effects.<ref name="Gonzalez_2015" /><ref name="Papaseit_2018" /><ref name="Mallaroni_2023">{{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 = Clinical Pharmacology and Therapeutics | volume = 114 | issue = 2 | pages = 423–433 | date = August 2023 | pmid = 37253161 | doi = 10.1002/cpt.2958 }}</ref><ref>{{cite journal | vauthors = Arikci D, Borgulya J, Straumann I, Vizeli P, Luethi D, Thomann J, Rudin D, Vukalovic I, Eckert A, Liechti ME, Holze F | date = April 2026 | title = Acute dose-dependent effects of 4-bromo-2,5-dimethoxyphenethylamine (2C-B) compared with 3,4-methylenedioxymethamphetamine (MDMA) and psilocybin in a double-blind, placebo-controlled study in healthy participants | journal = Neuropsychopharmacology | pages = 1–8 | doi = 10.1038/s41386-026-02428-9 | pmid = 42049943 }}</ref> Specific effects in these studies have included slight hallucinogenic states, perceptual changes, ego dissolution, time dilation, increased creativity, stimulation, vigor, happiness or elation, euphoria, feelings of well-being, reduced anger, enhanced sociability and friendliness, increased reactivity to negative emotional stimuli, decreased ability to recognize expressions of happiness, augmented emotionality in speech, tenseness, confusion, and mild sympathomimetic effects such as pressor effects, among others.<ref name="Gonzalez_2015" /><ref name="Papaseit_2018" /><ref name="Mallaroni_2023" /> Findings on the entactogen-like effects of 2C-B have been mixed, with some studies reporting that it produces such effects<ref name="Caudevilla-Galligo_2012" /><ref name="Gonzalez_2015" /> but other studies finding no such effects similarly to psilocybin.<ref name="Mallaroni_2023" /> However, in other research, both psilocybin and MDMA have been found to increase emotional empathy.<ref name="Mallaroni_2023" /> Compared to psilocybin in a double-blind, placebo-controlled clinical trial, 2C-B produced fewer negative mood effects, greater positive mood effects, less intense hallucinogenic effects including overall altered consciousness, oceanic boundlessness, ego dissolution, experiential depth, and time dilation, and less cognitive impairment.<ref name="Mallaroni_2023" /> Conversely, their effects in terms of visual changes and enhanced body perception were equivalent.<ref name="Mallaroni_2023" /> Besides having more positively valenced mood effects than psilocybin, 2C-B produced MDMA-like positive mood effects with little in the way of negative mood effects.<ref name="Mallaroni_2023" /> It was concluded that in line with anecdotal reports, 2C-B is non-ego-threatening, lacks the more serious head space of other psychedelics, and has a greater emphasis on visual and tactile changes.<ref name="Mallaroni_2023" /> It was also remarked that 2C-B may be a more optimal psychedelic for people afraid of the psychedelic experience or at greater risk for negative experiences such as due to high neuroticism, with this applicable for instance in the context of psychedelic-assisted psychotherapy.<ref name="Mallaroni_2023" />

In a dose-ranging clinical study of 2C-B employing a subjective visual analogue scale (VAS), maximal "any drug effects" were 27, 56, and 72 at doses of 10, 20, and 30{{nbsp}}mg orally, respectively.<ref name="HolzeArikciThomann2025" /> At these same respective doses, maximal "good drug effects" were 29, 60, and 68, while maximal "bad drug effects" were 2.0, 7.4, and 9.8.<ref name="HolzeArikciThomann2025" /> "Bad drug effects" were generally mild at low doses, but became more pronounced at higher doses, which is similar to the case of other psychedelics like LSD and psilocybin.<ref name="HolzeArikciThomann2025" />

2C-B tablets often contain a dose of 5 or 10{{nbsp}}mg of the drug.<ref name="Cole_2002" /><ref name="Papaseit_2018" /> Low doses of 2C-B like 5 to 10{{nbsp}}mg orally are said to produce stimulation, entactogen-like effects, and perceptual enhancement, while higher doses like 10 to 20{{nbsp}}mg orally are said to produce psychedelic and hallucinogenic effects.<ref name="Spoelder_2019" /><ref name="de_Boer_1999">{{cite journal | vauthors = de Boer D, Gijzels MJ, Bosman IJ, Maes RA | title = More data about the new psychoactive drug 2C-B | journal = Journal of Analytical Toxicology | volume = 23 | issue = 3 | pages = 227–228 | year = 1999 | pmid = 10369336 | doi = 10.1093/jat/23.3.227 | quote = The amount of 2C-B found in Ecstasy tablets is in the range of required dosages, 5–10 mg for stimulating effects and 10–20 mg for hallucinogenic effects. | doi-access = free }}</ref><ref name="Wills_2012" /><ref name="Nugteren-van_Lonkhuyzen_2015" /> 2C-B is frequently used at low doses as a substitute for MDMA.<ref name="Sexton_2019">{{cite journal | vauthors = Sexton JD, Nichols CD, Hendricks PS | date = 2019 | title = Population Survey Data Informing the Therapeutic Potential of Classic and Novel Phenethylamine, Tryptamine, and Lysergamide Psychedelics | journal = Frontiers in Psychiatry | volume = 10 | article-number = 896 | doi = 10.3389/fpsyt.2019.00896 | doi-access = free | pmc = 7026018 | pmid = 32116806 | quote = In support of this view, 2C-B, the most commonly reported novel phenethylamine, is often substituted for MDMA among electronic music party goers secondary to its purported psychostimulant properties (15, 20, 65). Indeed, novel phenethylamines are often described in terms of psychostimulant effects (20, 29), whereas challenging, emotional breakthrough, and mystical-type experiences appear to underlie the therapeutic outcomes of the classic tryptamine psychedelic psilocybin (16, 66, 67). [...] As noted above, the novel phenethylamine 2C-B may have a reputation as a "party drug, " and thus the associations reported here may reflect the influence of recreational use motives. }}</ref> It is often used by people who go to electronic music festivals, also known as raves.<ref name="Sexton_2019" /><ref name="Mallaroni_2022" /> The drug is also frequently used at clubs and parties, at home, or in nature.<ref name="Caudevilla-Galligo_2012" /> 2C-B is often combined with other drugs, such as MDMA, alcohol, and cannabis.<ref name="Caudevilla-Galligo_2012" /> Besides recreational use, 2C-B has been used in psychedelic-assisted psychotherapy at doses of 15 to 30{{nbsp}}mg orally.<ref name="Sessa_2016">{{cite journal | vauthors = Sessa B, Fischer FM | title = Underground MDMA-, LSD- and 2-CB-assisted individual and group psychotherapy in Zurich: Outcomes, implications and commentary | journal = Drug Science, Policy and Law | volume = 2 | date = 2016 | doi = 10.1177/2050324515578080 | issn = 2050-3245 | url = https://journals.sagepub.com/doi/10.1177/2050324515578080 | access-date = 20 November 2025 | article-number = 2050324515578080 }}</ref>

==Contraindications== {{See also|Psilocybin#Contraindications}}

==Side effects== The adverse effects of 2C-B have been studied.<ref name="Caudevilla-Galligo_2012" /><ref name="Gonzalez_2015" /><ref name="Papaseit_2018" /><ref name="Mallaroni_2023" /> They have been reported to include difficulty focusing gaze, trembling, sweating, nausea, abdominal pain, tachycardia, jaw clenching, difficulty breathing, coughing, diarrhea, dizziness, muscle or joint pain, tenseness, confusion, psychomotor slowing, and spatial memory impairment, among others.<ref name="Caudevilla-Galligo_2012" /><ref name="Papaseit_2018" /><ref name="Mallaroni_2023" /> Autonomic or sympathomimetic side effects include slightly increased heart rate and blood pressure and are lower than the increases with amphetamines and MDMA but similar to those with psilocybin.<ref name="Gonzalez_2015" /><ref name="Papaseit_2018" /><ref name="Mallaroni_2023" /> It produces a slight increase in cortisol levels that is also much lower than the marked increases observed with other psychedelics and MDMA.<ref name="Papaseit_2018" /> Hyperthermia has been reported at high doses.<ref name="Papaseit_2018" /> Residual side effects of 2C-B have been reported to include insomnia, flashbacks, anxiety, coughing, difficulty concentrating, and depression or sadness, among others.<ref name="Caudevilla-Galligo_2012" />

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="Ambrose_2010">{{cite journal | vauthors = Ambrose JB, Bennett HD, Lee HS, Josephson SA | title = Cerebral vasculopathy after 4-bromo-2,5-dimethoxyphenethylamine ingestion | journal = The Neurologist | volume = 16 | issue = 3 | pages = 199–202 | date = May 2010 | pmid = 20445431 | doi = 10.1097/NRL.0b013e3181a3cb53 | s2cid = 35035721 }}</ref> In a later case report of unknown dose, 2C-B caused serotonin syndrome, seizures, severe brain edema, and severe and long-lasting neurological impairment.<ref name="Spoelder_2019">{{cite journal | vauthors = Spoelder AS, Louwerens JK, Krens SD, Jager N, LeCouffe NE, de Ruijter W, Brunt TM | title = Unexpected Serotonin Syndrome, Epileptic Seizures, and Cerebral Edema Following 2,5-dimethoxy-4-bromophenethylamine Ingestion | journal = Journal of Forensic Sciences | volume = 64 | issue = 6 | pages = 1950–1952 | date = November 2019 | pmid = 31643086 | pmc = 6900031 | doi = 10.1111/1556-4029.14214 | quote = In low doses, it produces enhanced sensory sensitivity and has stimulating effects similar to those of 3,4-methylenedioxymethamphetamine (MDMA) or "ecstasy." In higher doses, the psychedelic and hallucinogenic effects predominate. [...] After oral ingestion of 10–30 mg 2C-B, the onset of the effect is seen within 30–75 min and generally lasts 4–8 h (6,9). 2C-B displays a dose-response curve with lower doses resulting in stimulating effects with increased visual, auditory and tactile sensations, whereas in higher doses, the hallucinogenic effects prevail (1,10). }}</ref> There is a case report of acquired synesthesia following a single very high dose of 2C-B.<ref name="Yanakieva_2019">{{cite journal | vauthors = Yanakieva S, Luke DP, Jansari A, Terhune DB | title = Acquired synaesthesia following 2C-B use | journal = Psychopharmacology | volume = 236 | issue = 7 | pages = 2287–2289 | date = July 2019 | pmid = 31025060 | doi = 10.1007/s00213-019-05242-y }}</ref> There is also a case report of persistent psychosis following a single dose of 2C-B.<ref name="Huang_2011">{{cite journal | vauthors = Huang HH, Bai YM | title = Persistent psychosis after ingestion of a single tablet of '2C-B' | journal = Progress in Neuro-Psychopharmacology & Biological Psychiatry | volume = 35 | issue = 1 | pages = 293–294 | date = January 2011 | pmid = 21036198 | doi = 10.1016/j.pnpbp.2010.10.018 }}</ref>

===Tolerance=== Tolerance is said to build to the effects of 2C-B analogously to the case of other psychedelics.<ref name="Nolan2019">{{cite web | vauthors = Nolan J | date = 5 March 2019 | title = 2C-B Is the Drug Taking Over the UK's Clubs | website = VICE | url = https://www.vice.com/en/article/what-is-2cb-and-its-effects/ | access-date = 25 February 2026 | quote = Though research on 2C-B is scant, users also suggest that one’s tolerance to it resets after roughly 48 hours – again different to MDMA, where even taking it once every few months leaves people chasing diminishing highs with increasing amounts. }}</ref>

===Long-term effects=== 2C-B is a potent serotonin 5-HT2B receptor agonist similarly to many other serotonergic psychedelics and hence may pose a risk of cardiac valvulopathy and other complications with frequent long-term use.<ref name="Luethi_2021">{{cite book | vauthors = Luethi D, Liechti ME | date = 2021 | chapter = Drugs of Abuse Affecting 5-HT2B Receptors | title = 5-HT2B Receptors | publisher = Springer International Publishing | volume = 35 | pages = 277–289 | isbn = 978-3-030-55919-9 | doi = 10.1007/978-3-030-55920-5_16 | access-date = 20 November 2025 | series = The Receptors | publication-place = Cham | chapter-url = http://link.springer.com/10.1007/978-3-030-55920-5_16 }}</ref><ref name="McIntyre_2023">{{cite journal | vauthors = McIntyre RS | title = Serotonin 5-HT2B receptor agonism and valvular heart disease: implications for the development of psilocybin and related agents | journal = Expert Opinion on Drug Safety | volume = 22 | issue = 10 | pages = 881–883 | date = 2023 | pmid = 37581427 | doi = 10.1080/14740338.2023.2248883 }}</ref><ref name="Rouaud_2024">{{cite journal | vauthors = Rouaud A, Calder AE, Hasler G | title = Microdosing psychedelics and the risk of cardiac fibrosis and valvulopathy: Comparison to known cardiotoxins | journal = Journal of Psychopharmacology | volume = 38 | issue = 3 | pages = 217–224 | date = March 2024 | pmid = 38214279 | pmc = 10944580 | doi = 10.1177/02698811231225609 }}</ref><ref name="Wso_2023">{{cite journal | vauthors = Wsół A | title = Cardiovascular safety of psychedelic medicine: current status and future directions | journal = Pharmacological Reports | volume = 75 | issue = 6 | pages = 1362–1380 | date = December 2023 | pmid = 37874530 | pmc = 10661823 | doi = 10.1007/s43440-023-00539-4 }}</ref><ref name="Tagen_2023">{{cite journal | vauthors = Tagen M, Mantuani D, van Heerden L, Holstein A, Klumpers LE, Knowles R | title = The risk of chronic psychedelic and MDMA microdosing for valvular heart disease | journal = Journal of Psychopharmacology | volume = 37 | issue = 9 | pages = 876–890 | date = September 2023 | pmid = 37572027 | doi = 10.1177/02698811231190865 }}</ref>

==Overdose== At doses over 20 or 30{{nbsp}}mg orally, frightening hallucinations, as well as tachycardia, hypertension, and hyperthermia, may occur.<ref name="Carmo_2005">{{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 | quote = In humans, it is active at doses between 4 and 30 mg inducing euphoria and increased receptiveness of the visual, auditory, olfactory and tactile sensations (Giroud et al., 1998). Doses between 5 and 10 mg induce amphetamine-like stimulating effects while doses between 10 and 20 mg are required to obtain the hallucinogenic effects of the drug (de Boer et al., 1999a). Higher doses are known to cause frightening hallucinations and sympathomimetic effects such as tachicardia, hypertension and hyperthermia (Velea et al., 1999). | bibcode = 2005Toxgy.206...75C }}</ref><ref name="Nugteren-van_Lonkhuyzen_2015" /><ref name="PiHKAL" /> The fatal dose of 2C-B in humans is unknown but its safety window is thought to be narrower than certain other psychedelics like LSD and psilocybin similarly to the case of mescaline.<ref name="Thomas_2024">{{cite book | vauthors = Thomas K | title = Psychedelic Harm Reduction | date = 2024 | chapter = Toxicology and Pharmacological Interactions of Classic Psychedelics | publisher = Springer Berlin Heidelberg | doi = 10.1007/7854_2024_508 | pmid = 39042251 | series = Current Topics in Behavioral Neurosciences | volume = 77 | pages = 43–62 | publication-place = Berlin, Heidelberg | isbn = 978-3-032-21106-4 }}</ref> It was reported by Alexander Shulgin in his book ''PiHKAL'' (''Phenethylamines I Have Known and Loved'') that a psychologist had accidentally taken a 100{{nbsp}}mg dose orally without apparent harm.<ref name="PiHKAL" /> There are three case reports of 2C-B intoxication in the scientific literature as of 2015 and no deaths have been attributed to 2C-B alone as of 2018.<ref name="Papaseit_2018" /><ref name="Nugteren-van_Lonkhuyzen_2015" />

== Interactions == {{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.<ref name="Dean_2013">{{cite journal | vauthors = Dean BV, Stellpflug SJ, Burnett AM, Engebretsen KM | title = 2C or not 2C: phenethylamine designer drug review | journal = Journal of Medical Toxicology | volume = 9 | issue = 2 | pages = 172–178 | date = June 2013 | pmid = 23494844 | pmc = 3657019 | doi = 10.1007/s13181-013-0295-x | quote = In 1974, 4-bromo-2,5-dimethoxyphenethylamine (2C-B), the first of the 2Cs, was synthesized by Alexander Shulgin as he was exploring homologs from 2,5-dimethoxy-4-bromoamphetamine [3]. 2C-B was manufactured in the 1980s and early 1990s under the names Nexus, Erox, Performax, Toonies, Bromo, Spectrum, and Venus and marketed as MDMA's replacement after MDMA became scheduled in the USA [6, 7]. 2C-B was initially intended for psychotherapy use due to its short 1-h duration of action [3]. Due to 2C-B's significant gastrointestinal effects and lack of empathogenic effects as compared to MDMA, it rapidly fell out of favor for psychotherapy. In 1995, 2C-B was placed on Schedule I of the Controlled Substances Act by the Drug Enforcement Agency (DEA) [6, 7]. However, following the scheduling of 2C-B, other 2C analogues were made available by suppliers as legal alternatives [8]. }}</ref><ref name="Theobald_2007">{{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 = Biochemical Pharmacology | volume = 73 | issue = 2 | pages = 287–297 | date = January 2007 | pmid = 17067556 | doi = 10.1016/j.bcp.2006.09.022 }}</ref> Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C-B.<ref name="Dean_2013" /><ref name="Theobald_2007" /><ref name="Halman_2024">{{cite journal | vauthors = Halman A, Kong G, Sarris J, Perkins D | title = Drug-drug interactions involving classic psychedelics: A systematic review | journal = Journal of Psychopharmacology | volume = 38 | issue = 1 | pages = 3–18 | date = January 2024 | pmid = 37982394 | pmc = 10851641 | doi = 10.1177/02698811231211219 }}</ref><ref name="Rached_2026" /> This may result in overdose and serious toxicity.<ref name="Halman_2024" /><ref name="Dean_2013" /><ref name="Rached_2026" /> There are anecdotal reports of strong potentiation of 2C-B by MAOIs.<ref name="Rached_2026">{{cite journal | vauthors = Rached G, Campana A, Fiani D, Nguyen C, Van den Eynde V, Gillman PK, Barnett BS | title = Safety and Efficacy of Monoamine Oxidase Inhibitors in Patients Who Use Psychoactive Substances: Potential Drug Interactions and Substance Use Disorder Treatment Data | journal = CNS Drugs | date = January 2026 | volume = 40 | issue = 3 | pages = 359–417 | pmid = 41546846 | doi = 10.1007/s40263-025-01256-7 }}</ref> 2C-B may also have interactions with other medications and drugs.<ref name="Inan_2020" />

==Pharmacology== ===Pharmacodynamics=== {| class="wikitable floatright" style="font-size:small;" |+ {{Nowrap|2C-B activities}} |- ! Target !! Affinity (Ki, nM) |- | 5-HT1A || 130–311 |- | 5-HT1B || 104 |- | 5-HT1D || 26 |- | 5-HT1E || 120 |- | 5-HT1F || {{Abbr|ND|No data}} |- | 5-HT2A || 0.66–32 (Ki) 1.20–689 ({{Abbrlink|EC50|half-maximal effective concentration}}) 4–101% ({{Abbrlink|Emax|maximal efficacy}}) |- | 5-HT2B || 13.5–97 (Ki) 12.6–130 ({{Abbr|EC50|half-maximal effective concentration}}) 52–97% ({{Abbr|Emax|maximal efficacy}}) |- | 5-HT2C || 32–90 (Ki) 0.03–493 ({{Abbr|EC50|half-maximal effective concentration}}) 50–116% ({{Abbr|Emax|maximal efficacy}}) |- | 5-HT3 || >10,000 |- | 5-HT4 || {{Abbr|ND|No data}} |- | 5-HT5A || >10,000 |- | 5-HT6 || 320 |- | 5-HT7 || 210 |- | α1A || >10,000 |- | α1B || >10,000 |- | α1D || {{Abbr|ND|No data}} |- | α2A || 309–320 |- | α2B || >10,000 |- | α2C || 103 |- | β1 || >10,000 |- | β2 || >10,000 |- | β3 || {{Abbr|ND|No data}} |- | D1 || 12,000 |- | D2 || 2,200–25,200 |- | D3 || 7,116–10,000 |- | D4 || >10,000 |- | D5 || >10,000 |- | H1–H4 || >10,000 |- | M1–M2 || >10,000 |- | M3 || 822 |- | M4–M5 || >10,000 |- | I1 || 2,155 |- | σ1 || >10,000 |- | σ2 || >10,000 |- | {{Abbrlink|TAAR1|Trace amine-associated receptor 1}} || 90–3,000 (Ki) (rodent) 3,300–7,190 ({{Abbr|EC50|half-maximal effective concentration}}) (human) |- | {{Abbrlink|SERT|Serotonin transporter}} || 9,700–13,300 (Ki) 18,000–312,900 ({{Abbrlink|IC50|half-maximal inhibitory concentration}}) |- | {{Abbrlink|NET|Norepinephrine transporter}} || 27,400–31,000 (Ki) 44,000–122,000 ({{Abbr|IC50|half-maximal inhibitory concentration}}) |- | {{Abbrlink|DAT|Dopamine transporter}} || 6,500–>30,000 (Ki) 132,000–231,000 ({{Abbr|IC50|half-maximal inhibitory concentration}}) |- | {{Abbrlink|MAO-A|Monoamine oxidase A}} || 125,000 ({{Abbr|IC50|half-maximal inhibitory concentration}}) |- | {{Abbrlink|MAO-B|Monoamine oxidase B}} || 58,000 ({{Abbr|IC50|half-maximal inhibitory concentration}}) |- class="sortbottom" | colspan="2" style="width: 1px; background-color:var(--background-color-notice-subtle,#eaecf0); color:inherit; 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 | vauthors = Liu T | 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="Ray_2010">{{cite journal | vauthors = Ray TS | title = Psychedelics and the human receptorome | journal = PLOS ONE | volume = 5 | issue = 2 | date = February 2010 | pmid = 20126400 | pmc = 2814854 | doi = 10.1371/journal.pone.0009019 | bibcode = 2010PLoSO...5.9019R | doi-access = free | article-number = e9019 }}</ref><ref name="Rickli_2015">{{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 | pages = 546–553 | date = December 2015 | pmid = 26318099 | doi = 10.1016/j.neuropharm.2015.08.034 }}</ref><ref name="Nugteren-van_Lonkhuyzen_2015" /><ref name="Wallach_2023">{{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 | date = December 2023 | title = Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential | journal = Nature Communications | volume = 14 | issue = 1 | article-number = 8221 | doi = 10.1038/s41467-023-44016-1 | pmc = 10724237 | pmid = 38102107 | bibcode = 2023NatCo..14.8221W }}</ref> <ref name="Marcher-Rrsted_2020">{{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 Chemical Neuroscience | volume = 11 | issue = 9 | pages = 1238–1244 | date = May 2020 | pmid = 32212672 | doi = 10.1021/acschemneuro.0c00129 }}</ref><ref name="Luethi_2018a">{{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 }}</ref><ref name="Rudin_2022">{{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 | doi = 10.1096/fasebj.2022.36.S1.R2121 | article-number = fasebj.2022.36.S1.R2121 | issn = 0892-6638 | doi-access = free | url = https://www.researchgate.net/publication/360423277 }}</ref><ref name="Pottie_2020" /><ref name="Acuna-Castillo_2002">{{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 = British Journal of Pharmacology | volume = 136 | issue = 4 | pages = 510–519 | date = June 2002 | pmid = 12055129 | pmc = 1573376 | doi = 10.1038/sj.bjp.0704747 }}</ref><ref name="McCorvy_2013">{{cite thesis | vauthors = McCorvy JD | title = Mapping the binding site of the 5-HT2A receptor using mutagenesis and ligand libraries: Insights into the molecular actions of psychedelics | date = 16 January 2013 | degree = Ph.D. | publisher = Purdue University | via = Purdue e-Pubs | url = https://docs.lib.purdue.edu/dissertations/AAI3545320/ | archive-url = https://web.archive.org/web/20250515110801/https://docs.lib.purdue.edu/dissertations/AAI3545320/ | archive-date = 15 May 2025 | access-date = 27 May 2025 | url-status =live}}</ref><ref name="Flanagan_2021">{{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 Pharmacology & Translational Science | volume = 4 | issue = 2 | pages = 488–502 | date = April 2021 | pmid = 33860179 | pmc = 8033619 | doi = 10.1021/acsptsci.0c00063 }}</ref><ref name="Wagmann_2019">{{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 Testing and Analysis | volume = 11 | issue = 2 | pages = 318–324 | date = February 2019 | pmid = 30188017 | doi = 10.1002/dta.2494 | url = https://researchonline.ljmu.ac.uk/id/eprint/9155/1/DTA-18-0224.R1.pdf }}</ref><ref name="Zwartsen_2017">{{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 = Toxicology in Vitro | volume = 45 | issue = Pt 1 | pages = 60–71 | date = December 2017 | pmid = 28506818 | doi = 10.1016/j.tiv.2017.05.010 | bibcode = 2017ToxVi..45...60Z }}</ref><ref name="Simmler_2016">{{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 = The Journal of Pharmacology and Experimental Therapeutics | volume = 357 | issue = 1 | pages = 134–144 | date = April 2016 | pmid = 26791601 | doi = 10.1124/jpet.115.229765 | url = 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 | access-date = 2025-05-10 | url-status = bot: unknown | archive-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 | archive-date = 2025-05-09 }}</ref> |}

2C-B acts as a potent partial agonist of the serotonin 5-HT2 receptors, including of the serotonin 5-HT2A and 5-HT2C receptors and to a lesser extent of the serotonin 5-HT2B receptor.<ref name="Wallach_2023" /><ref name="Rickli_2015" /><ref name="Ray_2010" /> In one study, it had {{Abbrlink|EC50|half-maximal effective concentration}} ({{Abbrlink|Emax|maximal efficacy}}) values of 1.2{{nbsp}}nM (101%) at the serotonin 5-HT2A receptor, 13{{nbsp}}nM (97%) at the serotonin 5-HT2B receptor, and 0.63{{nbsp}}nM (98%) at the serotonin 5-HT2C receptor.<ref name="Wallach_2023" /> In earlier studies, 2C-B was found to be a low-efficacy serotonin 5-HT2A and 5-HT2C receptor partial agonist or even antagonist.<ref name="Moya_2007">{{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 = 1054–1061 | date = June 2007 | pmid = 17337633 | doi = 10.1124/jpet.106.117507 | s2cid = 11651502 | citeseerx = 10.1.1.690.3752 }}</ref><ref name="Villalobos_2004">{{cite journal | vauthors = Villalobos CA, Bull P, Sáez P, Cassels BK, Huidobro-Toro JP | title = 4-Bromo-2,5-dimethoxyphenethylamine (2C-B) and structurally related phenylethylamines are potent 5-HT2A receptor antagonists in Xenopus laevis oocytes | journal = British Journal of Pharmacology | volume = 141 | issue = 7 | pages = 1167–1174 | date = April 2004 | pmid = 15006903 | pmc = 1574890 | doi = 10.1038/sj.bjp.0705722 }}</ref><ref name="Nugteren-van_Lonkhuyzen_2015" /> However, subsequent studies have consistently found higher efficacy of 2C-B at these receptors.<ref name="Wallach_2023" /><ref name="Rickli_2015" /><ref name="Ray_2010" /> In addition to the serotonin 5-HT2 receptors, 2C-B also shows lower affinity for other serotonin receptors, such as the serotonin 5-HT1A and 5-HT1B receptors among others.<ref name="Ray_2010" /><ref name="Rickli_2015" /><ref name="Nugteren-van_Lonkhuyzen_2015" /> However, while 2C-B itself was not assessed, other 2C derivatives showed little activity as serotonin 5-HT1A receptor agonists ({{Abbr|EC50|half-maximal effective concentration}} = >3,000{{nbsp}}nM).<ref name="Eshleman_2014" />

2C-B has been reported to be an allosteric or non-competitive serotonin transporter (SERT) inhibitor or serotonin reuptake inhibitor, albeit of very low potency.<ref name="Saez-Briones_2019">{{cite journal | vauthors = Sáez-Briones P, Castro-Castillo V, Díaz-Véliz G, Valladares L, Barra R, Hernández A, Cassels BK | date = 2019 | title = Aromatic Bromination Abolishes the Psychomotor Features and Pro-social Responses of MDMA ("Ecstasy") in Rats and Preserves Affinity for the Serotonin Transporter (SERT) | journal = Frontiers in Pharmacology | volume = 10 | article-number = 157 | doi = 10.3389/fphar.2019.00157 | doi-access = free | pmc = 6403168 | pmid = 30873030 | quote = Interestingly, 2C-B (4-bromo-2,5-dimethoxyphenylethylamine), an entactogenic psychedelic (González et al., 2015) that does not enhance the head-shake response in rats and possesses low affinity for the 5-HT2A receptor (Nelson et al., 1999) has been shown to be a low-affinity, non-competitive selective SERT blocker (Montgomery et al., 2007). The binding and functional data reported in the present work support this notion. }}</ref><ref name="Montgomery_2007">{{cite journal | vauthors = Montgomery T, Buon C, Eibauer S, Guiry PJ, Keenan AK, McBean GJ | title = Comparative potencies of 3,4-methylenedioxymethamphetamine (MDMA) analogues as inhibitors of [3H]noradrenaline and [3H]5-HT transport in mammalian cell lines | journal = British Journal of Pharmacology | volume = 152 | issue = 7 | pages = 1121–1130 | date = December 2007 | pmid = 17891159 | pmc = 2095113 | doi = 10.1038/sj.bjp.0707473 | quote = 2CB was the only analogue analysed that did not demonstrate competitive binding at SERT. This suggests that 2CB binds to the transporter independently of the substrate site. }}</ref><ref name="Potts_2022">{{cite book | vauthors = Potts AJ, Thomas SH, Hill SL | date = 2022 | chapter = Pharmacology and toxicology of N-Benzyl-phenylethylamines (25X-NBOMe) hallucinogens | title = Novel Psychoactive Substances | publisher = Elsevier | pages = 279–300 | isbn = 978-0-12-818788-3 | doi = 10.1016/b978-0-12-818788-3.00008-5 | quote = 2C-B, the 2C analogue of 25B-NBOMe, also had a preferential inhibitory effect on hSERT, but with an IC50 ten-times greater (EC50 54 micromolar) than 25B-NBOMe or 25INBOMe. A similar pattern of comparatively weaker interactions with hNET and hDAT (IC50 166 micromolar and 240 micromolar, respectively) was also observed. [42] The IC50 values for 2C-B and 25X-NBOMes were significantly greater than the drug-concentrations identified in human plasma and predicted in human cerebrospinal fluid [42] and therefore the significance of interactions with monoamine transporters in human toxicity is not clear. }}</ref><ref name="Canal_2018">{{cite book | vauthors = Canal CE | title = New Psychoactive Substances | chapter = Serotonergic Psychedelics: Experimental Approaches for Assessing Mechanisms of Action | volume = 252 | pages = 227–260 | date = 2018 | pmid = 29532180 | doi = 10.1007/164_2018_107 | pmc = 6136989 | isbn = 978-3-030-10560-0 | series = Handbook of Experimental Pharmacology | quote = Intriguingly, 2C-B, traditionally viewed as a selective 5-HT 2 agonist, has an inhibitory potency at SERT similar to MDMA (Montgomery et al. 2007); similar effects were observed with DIPT (Rickli et al. 2016). Moreover, DMT causes serotonin efflux from SERT with efficacies similar to MDMA (Rickli et al. 2016). }}</ref><ref name="Nugteren-van_Lonkhuyzen_2015" /><ref name="Caudevilla-Galligo_2012">{{cite journal | vauthors = Caudevilla-Gálligo F, Riba J, Ventura M, González D, Farré M, Barbanoj MJ, Bouso JC | 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 | date = July 2012 | pmid = 22234927 | doi = 10.1177/0269881111431752 | quote = 4-Bromo-2,5-dimethoxyphenethylamine (2C-B, Nexus, Afro) is one of these synthetic drugs. At the chemical level, 2C-B is structurally related to mescaline and was first synthesized in the mid-1970s (Shulgin and Carter, 1975). It gained certain popularity as a legal substitute for MDMA after its prohibition in 1985 (Bouso et al., 2008). In some European countries 2C-B was legally sold as an aphrodisiac under the brand names Nexus, Erox and Performax in stores specialized in psychoactive products, the so-called smart shops (US Department of Justice, 2001). [...] To date, very little scientific research has been conducted on 2C-B. The drug is known to be orally active and its effects are mediated by its action as a partial 5-HT2A and 5-HT2C receptor agonist. In addition, 2C-B is a substrate and an inhibitor of the serotonin transporter (SERT) (McLean et al., 2006; Montgomery et al., 2007). Regarding its psychotropic properties, 2C-B has been reported to induce 'perceptual enhancement' and euphoria at doses of 8–10mg but to lack hallucinogenic or psychotomimetic effects (Shulgin and Carter, 1975). These authors also stated that the effects last 6–8h and that they are milder than those of classical psychedelics such as lysergic acid diethylamide (LSD). | s2cid = 35535891 }}</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 agents of serotonin, norepinephrine, or dopamine ({{Abbr|EC50|half-maximal effective concentration}} = >100,000{{nbsp}}nM or "inactive").<ref name="Nagai_2007">{{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 = European Journal of Pharmacology | volume = 559 | issue = 2–3 | pages = 132–137 | date = March 2007 | pmid = 17223101 | doi = 10.1016/j.ejphar.2006.11.075 }}</ref><ref name="Eshleman_2014">{{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 | volume = 231 | issue = 5 | pages = 875–888 | date = March 2014 | pmid = 24142203 | pmc = 3945162 | doi = 10.1007/s00213-013-3303-6 }}</ref>

2C-B produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.<ref name="Wallach_2023" /> It also shows potent and efficacious anti-inflammatory effects in preclinical research.<ref name="Flanagan_2021a">{{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 Pharmacology & Translational Science | volume = 4 | issue = 2 | pages = 488–502 | date = April 2021 | pmid = 33860179 | pmc = 8033619 | doi = 10.1021/acsptsci.0c00063 }}</ref>

===Pharmacokinetics=== ====Absorption==== 2C-B appears to have relatively low oral bioavailability.<ref name="Mallaroni_2023" /> The time to peak levels is 2.0 to 2.4{{nbsp}}hours.<ref name="HolzeArikciThomann2025" /><ref name="Mallaroni_2023" /> Peak levels of 2C-B have been reported to be 2.5{{nbsp}}ng/mL with 10{{nbsp}}mg orally, 3.3 to 4.6{{nbsp}}ng/mL with 20{{nbsp}}mg orally, and 5.4 to 6.4{{nbsp}}ng/mL with 30{{nbsp}}mg orally.<ref name="HolzeArikciThomann2025" /><ref name="Thomann_2025" /><ref name="Mallaroni_2023" /> The peak levels of 2C-B metabolites have also been described.<ref name="HolzeArikciThomann2025">{{cite journal | title = ACNP 64th Annual Meeting: Poster Abstracts P584-P872 | journal = Neuropsychopharmacology | volume = 51 | issue = Suppl 1 | pages = 410–571 | date = January 2026 | pmid = 41507446 | doi = 10.1038/s41386-025-02281-2 | pmc = 12783840 | publisher = Nature Publishing Group | pmc-embargo-date = January 1, 2027 }}</ref>

====Distribution==== The volume of distribution and plasma protein binding of 2C-B are unknown.<ref name="DrugBank" />

====Metabolism==== 2C-B appears to undergo substantial first-pass metabolism.<ref name="Mallaroni_2023" /> It 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.<ref name="Carmo_2005" /> Deamination of 2C-B is mediated by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B.<ref name="Dean_2013" /><ref name="Theobald_2007" /><ref name="Thomann_2025" />

There is species differentiation in the metabolism of 2C-B.<ref name="Carmo_2005" /> Mice hepatocytes produce 4-bromo-2,5-dimethoxyphenol (BDMP), a previously unknown metabolite.<ref name="Carmo_2005" /> 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="Carmo_2005" />

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="Thomann_2025" />

Another known metabolite of 2C-B is 2-OH-2C-B (2-DM-2C-B; B-2-HMPEA).<ref name="Kanamori_2003">{{cite journal | vauthors = Kanamori T, Tsujikawa K, Ohmae Y, Iwata Y, Inoue H, Inouye Y, Kishi T | title = Excretory Profile of 4-Bromo-2,5-dimethoxyphenethylamine (2C-B) in Rat. | journal = Journal of Health Science | volume = 49 | issue = 2 | pages = 166–169 | date = 2003 | doi = 10.1248/jhs.49.166 | issn = 1344-9702 | url = http://www.jstage.jst.go.jp/article/jhs/49/2/49_2_166/_article | access-date = 2 February 2026 }}</ref><ref name="Carmo_2004">{{cite journal | vauthors = Carmo H, de Boer D, Remião F, Carvalho F, dos Reys LA, de Lourdes Bastos M | title = Metabolism of the designer drug 4-bromo-2,5-dimethoxyphenethylamine (2C-B) in mice, after acute administration | journal = Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences | volume = 811 | issue = 2 | pages = 143–152 | date = November 2004 | pmid = 15522713 | doi = 10.1016/j.jchromb.2004.08.026 }}</ref><ref name="Kanamori_2005">{{cite journal | vauthors = Kanamori T, Tsujikawa K, Ohmae Y, Iwata YT, Inoue H, Kishi T, Nakahama T, Inouye Y | title = A study of the metabolism of methamphetamine and 4-bromo-2,5-dimethoxyphenethylamine (2C-B) in isolated rat hepatocytes | journal = Forensic Science International | volume = 148 | issue = 2–3 | pages = 131–137 | date = March 2005 | pmid = 15639607 | doi = 10.1016/j.forsciint.2004.04.084 }}</ref><ref name="Carmo_2005a">{{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 }}</ref><ref name="Kanamori_2011">{{cite journal | vauthors = Kanamori T, Kuwayama K, Tsujikawa K, Miyaguchi H, Togawa-Iwata Y, Inoue H | title = A model system for prediction of the in vivo metabolism of designer drugs using three-dimensional culture of rat and human hepatocytes | journal = Forensic Toxicology | volume = 29 | issue = 2 | pages = 142–151 | date = 2011 | doi = 10.1007/s11419-011-0116-3 | issn = 1860-8965 | url = http://link.springer.com/10.1007/s11419-011-0116-3 | access-date = 2 February 2026 }}</ref><ref name="Kanamori_2013">{{cite journal | vauthors = Kanamori T, Nagasawa K, Kuwayama K, Tsujikawa K, Iwata YT, Inoue H | title = Analysis of 4-bromo-2,5-dimethoxyphenethylamine abuser's urine: identification and quantitation of urinary metabolites | journal = Journal of Forensic Sciences | volume = 58 | issue = 1 | pages = 279–287 | date = January 2013 | pmid = 23066942 | doi = 10.1111/j.1556-4029.2012.02289.x }}</ref><ref name="Thomann_2025a">{{cite journal | vauthors = Thomann J, Rudin D, Kraus S, Arikci D, Holze F, Liechti ME, Luethi D | title = Liquid chromatography-tandem mass spectrometry-based pharmacokinetic and metabolic analysis of 4-bromo-2,5-dimethoxyphenethylamine and its metabolites in human plasma | journal = Drug Metabolism and Disposition | volume = 53 | issue = 6 | date = June 2025 | pmid = 40408905 | doi = 10.1016/j.dmd.2025.100086 | quote = In addition to the primary metabolic pathway involving MAO and aldehyde-oxidizing enzymes, CYP2D6 rapidly degraded 2C-B, suggesting its role in this metabolic pathway. However, neither BDMPAA nor B-2-HMPAA was detected, and the identities of the resulting metabolites remain unknown. In rats, cytochrome P450 enzymes have been implicated in a major demethylation pathway that converts 2C-B into 4-bromo-2-hydroxy-5-methoxyphenethylamine or 4-bromo-5-hydroxy-2-methoxyphenethylamine, a process that may also occur to a lesser extent in humans (Carmo et al, 2005; Kanamori et al, 2013) | article-number = 100086 }}</ref><ref name="Meyer_2010">{{cite journal | vauthors = Meyer MR, Maurer HH | title = Metabolism of designer drugs of abuse: an updated review | journal = Current Drug Metabolism | volume = 11 | issue = 5 | pages = 468–482 | date = June 2010 | pmid = 20540700 | doi = 10.2174/138920010791526042 }}</ref><ref name="Meyer_2012">{{cite book | vauthors = Meyer MR, Maurer HH | date = 18 April 2012 | chapter = Drugs of Abuse (Including Designer Drugs) | title = Metabolism of Drugs and Other Xenobiotics | publisher = Wiley | pages = 429–463 | isbn = 978-3-527-32903-8 | doi = 10.1002/9783527630905.ch16 }}</ref><ref name="Papaseit_2018a">{{cite book | vauthors = Papaseit E, Pérez-Mañá C, González D, Fonseca F, Torrens M, Farré M | date = 10 October 2018 | chapter = Clinical Effects of 2C-B Abuse | title = Handbook of Novel Psychoactive Substances | publisher = Routledge | pages = 291–303 | isbn = 978-1-315-15808-2 | doi = 10.4324/9781315158082-16 | publication-place = New York, NY }}</ref> This compound is active and has similarly potency as a serotonin 5-HT2A receptor agonist as 2C-B itself ''in vitro''.<ref name="McCorvy_2013" />

====Elimination==== The elimination half-life of 2C-B in humans is 1.2 to 2.5{{nbsp}}hours.<ref name="HolzeArikciThomann2025" /><ref name="Papaseit_2018" /><ref name="Mallaroni_2023" /><ref name="Thomann_2025" />

==Chemistry== 2C-B, also known as 4-bromo-2,5-dimethoxyphenethylamine, is a substituted phenethylamine of the 2C family, also known as the 4-substituted 2,5-dimethoxyphenethylamines.<ref name="PiHKAL" /><ref name="Shulgin_2011" /><ref name="Trachsel_2013" /> It is a synthetic analogue of the naturally occurring phenethylamine psychedelic mescaline found in peyote and certain other cacti.<ref name="Anilanmert_2018" /><ref name="Vari_2019">{{cite journal | vauthors = Varì MR, Pichini S, Giorgetti R, Busardò FP | title = New psychoactive substances—Synthetic stimulants | journal = WIREs Forensic Science | volume = 1 | issue = 2 | date = 2019 | doi = 10.1002/wfs2.1197 | article-number = e1197 | issn = 2573-9468 | doi-access = free | quote = In addition, simple variations of mescaline (a natural phenylethylamine occurring in the peyote cactus (Lophophora williamsii (Lem.) J.M. Coult.)) led to the synthesis of powerful hallucinogenic substances, e.g., 4-bromo-2,5-dimethoxyphenethylamine (2C-B), synthesized by Shulgin in 1974. }}</ref><ref name="PiHKAL" />

===Synthesis=== The chemical synthesis of 2C-B has been described.<ref name="PiHKAL" /><ref name="Shulgin_2011">{{cite book | vauthors = Shulgin A, Manning T, Daley P | year = 2011 | title = The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds | publisher = Transform Press | volume = 1 | isbn = 978-0-9630096-3-0 | location = Berkeley }}</ref><ref name="Shulgin_1975" />

===Identification=== Exposing compounds to the reagents gives a colour change which is indicative of the compound under test.{{Citation needed|date=November 2025}}

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

===Analogues and derivatives=== Analogues of 2C-B include 2C-I, 2C-C, DOB, 4C-B, 2C-B-FLY, and 25B-NBOMe, among others.<ref name="PiHKAL" /><ref name="Shulgin_2011" /><ref name="Trachsel_2013">{{cite book | vauthors = Trachsel D, Lehmann D, Enzensperger C | year = 2013 | title = Phenethylamine: von der Struktur zur Funktion | language = de | publisher = Nachtschatten-Verlag | edition = 1 | isbn = 978-3-03788-700-4 | url = https://books.google.com/books?id=-Us1kgEACAAJ | location = Solothurn | trans-title = Phenethylamines: From Structure to Function | series = Nachtschatten-Science | oclc = 858805226 }}</ref><ref name="Duan_2024" />

DOB and 4C-B are α-alkyl derivatives of 2C-B, specifically the amphetamine (α-methyl) and phenylisobutylamine (α-ethyl) derivatives, respectively.<ref name="PiHKAL" /><ref name="Shulgin_2011" /><ref name="Trachsel_2013" /> β-Substituted derivatives of 2C-B such as BOB (β-methoxy-2C-B), BOH-2C-B (β-hydroxy-2C-B), βk-2C-B (β-keto-2C-B), and β-methyl-2C-B (BMB) have been described.<ref name="PiHKAL" /><ref name="Shulgin_2011" /><ref name="Trachsel_2013" /> βk-2C-B shows dramatically reduced potency and efficacy as a serotonin 5-HT2A receptor agonist compared to 2C-B.<ref name="Pottie_2020">{{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 = Archives of Toxicology | volume = 94 | issue = 10 | pages = 3449–3460 | date = October 2020 | pmid = 32627074 | doi = 10.1007/s00204-020-02836-w | hdl-access = free | bibcode = 2020ArTox..94.3449P | hdl = 1854/LU-8687071 }}</ref>

A variety of ''N''-substituted derivatives of 2C-B have been tested, including ''N''-methyl-2C-B, ''N'',''N''-dimethyl-2C-B, ''N''-ethyl-2C-B and ''N''-benzyl-2C-B.<ref name="Glennon_1994" /> Most simple alkyl derivatives were considerably less potent than 2C-B, with ''N''-ethyl-2C-B for instance having a 40{{nbsp}}times lower affinity for the serotonin 5-HT2A receptor.<ref name="Glennon_1994" /> The ''N''-benzyl derivative however was found to have higher affinity than 2C-B itself, with ''N''-(4-bromobenzyl)-2C-B binding even more tightly.<ref name="Glennon_1994">{{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 = 1929–1935 | 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 | vauthors = Heim R | title = Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur: Entwicklung eines neuen Struktur-Wirkungskonzepts | date = March 19, 2004 | url = http://www.diss.fu-berlin.de/diss/receive/FUDISS_thesis_000000001221 | trans-title = Synthesis and pharmacology of potent 5-HT2A receptor agonists which have a partial N-2-methoxybenzyl structure: Development of a new structure-activity concept | language = de | publisher = Free University of Berlin | access-date = August 1, 2014 }}</ref> and 25B-NBOH. Another ''N''-substituted derivative, 2C-B-AN, is an ''N''-benzylphenethylamine-like prodrug of 2C-B.<ref name="Trachsel_2013" /><ref name="Elliott_2020">{{cite journal | vauthors = Elliott SP, Holdbrook T, Brandt SD | title = Prodrugs of New Psychoactive Substances (NPS): A New Challenge | journal = Journal of Forensic Sciences | volume = 65 | issue = 3 | pages = 913–920 | date = May 2020 | pmid = 31943218 | doi = 10.1111/1556-4029.14268 }}</ref><ref name="Ponce_2024">{{cite journal | vauthors = Ponce JD | title = The use of prodrugs as drugs of abuse | journal = WIREs Forensic Science | volume = 6 | issue = 3 | date = 2024 | doi = 10.1002/wfs2.1514 | article-number = e1514 | issn = 2573-9468 | doi-access = free }}</ref>

2C-DB (6-bromo-2C-B) is a ring-substituted derivative of 2C-B.<ref name="Trachsel_2013" /> TWEETIO derivatives of 2C-B, in which one or both of the methoxy groups of 2C-B are extended to ethoxy groups, exist as well, such as 2CB-2-EtO.<ref name="PiHKAL" /><ref name="Shulgin_2003a">{{cite book | vauthors = Shulgin AT | year = 2003 | veditors = Laing RR | chapter = Basic Pharmacology and Effects | title = Hallucinogens: A Forensic Drug Handbook | publisher = Elsevier Science | pages = 67–137 | isbn = 978-0-12-433951-4 | url = https://books.google.com/books?id=l1DrqgobbcwC | access-date = 1 February 2025 | series = Forensic Drug Handbook Series | chapter-url = https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=6bb3a7499da8e9852b39cd4db16891147c83f5c6 }}</ref><ref name="Jacob_1994a">{{cite journal | vauthors = Jacob P, Shulgin AT | title = Structure-activity relationships of the classic hallucinogens and their analogs | journal = NIDA Research Monograph | volume = 146 | pages = 74–91 | date = 1994 | pmid = 8742795 | url = https://archives.nida.nih.gov/sites/default/files/monograph146.pdf#page=79 | archive-url = https://web.archive.org/web/20230805004551/https://archives.nida.nih.gov/sites/default/files/monograph146.pdf#page=79 | archive-date = August 5, 2023 }}</ref><ref name="Trachsel_2013" /> ASR-2001 (2CB-5PrO) is a propoxy TWEETIO and another notable analogue of 2C-B which is under development for treatment of psychiatric disorders.<ref name="Busby_2023">{{cite web | vauthors = Busby M | title = The Heirs to a Vault of Novel Psychedelics Take a Trip Into the Unknown | date = 2 November 2023 | website = DoubleBlind Mag | url = https://doubleblindmag.com/sasha-shulgin-legacy/ | access-date = 19 April 2025 }}</ref><ref name="Busby_2025">{{cite web | vauthors = Busby M | title = What Happens When You Inherit 500 Psychedelic Compounds? | date = 30 March 2025 | website = DoubleBlind Mag | url = https://doubleblindmag.com/what-happens-when-you-inherit-500-psychedelic-compounds/ | access-date = 19 April 2025 }}</ref><ref name="Kargbo_2025">{{cite journal | vauthors = Kargbo RB | title = Innovative Approaches in Psychedelics, AI, and Communication: A Multi-Domain Perspective | journal = ACS Medicinal Chemistry Letters | volume = 16 | issue = 4 | pages = 514–516 | date = April 2025 | pmid = 40236531 | pmc = 11995231 | doi = 10.1021/acsmedchemlett.5c00114 }}</ref>

FLY derivatives of 2C-B like 2C-B-FLY, 2C-B-DRAGONFLY, and 2C-B-BUTTERFLY are analogues in which the methoxy groups of 2C-B on the phenyl ring have been cyclized into furan or other rings to form benzodifuran and other tricyclic compounds.<ref name="Shulgin_2011" /><ref name="Trachsel_2013" />

2-OH-2C-B is the 2-''O''-desmethylated analogue of 2C-B and shows similar potency as a serotonin 5-HT2A receptor agonist ''in vitro''.<ref name="McCorvy_2013" />

Cyclized phenethylamine derivatives of 2C-B in which the side chain has been cyclized in some way include DOB-CR (2C-B-CR), 2CB-Ind, 2C-B-5-hemiFLY-α6 (BNAP), 2CB7 (2C-B-5-hemiFLY-β7), TCB-2 (2CBCB), 2C-B-PYR, 2C-B-3PIP, 2C-B-3PIP-NBOMe, 2C-B-3PIP-POMe, 2CBecca, 2CJP, 2CLisaB, ZC-B, 2C-B-aminorex (2C-B-AR), and 2C-B-morpholine (2C-B-MOR), among others.<ref name="Trachsel_2013" /><ref name="Duan_2024">{{cite journal | vauthors = Duan W, Cao D, Wang S, Cheng J | title = Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants | journal = Chemical Reviews | volume = 124 | issue = 1 | pages = 124–163 | date = January 2024 | pmid = 38033123 | doi = 10.1021/acs.chemrev.3c00375 }}</ref><ref name="Nichols_2018">{{cite book | vauthors = Nichols DE | date = 2018 | title = Chemistry and Structure-Activity Relationships of Psychedelics | volume = 36 | pages = 1–43 | isbn = 978-3-662-55878-2 | doi = 10.1007/7854_2017_475 | pmid = 28401524 | series = Current Topics in Behavioral Neurosciences }}</ref> Other related cyclized compounds, while not technically phenethylamines or 2C-B derivatives, include 2C-B-BZP and 2C-B-PP.<ref name="Trachsel_2013" /><ref name="Shulgin_2011" />

A notable positional isomer of 2C-B is the scaline and mescaline analogue 4-bromomescaline (4-Br-3,5-DMPEA).<ref name="PiHKAL" /><ref name="Trachsel_2013" /><ref name="McCorvy_2013" />

{{Hidden | header = Chemical structures of 2C-B analogues and derivatives | content = {{Gallery | height = 120 | width = 180 | File:2C-B.svg | class1=skin-invert-image | 2C-B (4-bromo-2,5-DMPEA) | File:2C-I2DACS.svg | class2=skin-invert-image | 2C-I (4-iodo-2,5-DMPEA) | File:2C-C.svg | class3=skin-invert-image | 2C-C (4-chloro-2,5-DMPEA) | File:2C-D 2DACS.svg | class4=skin-invert-image | 2C-D (4-methyl-2,5-DMPEA) | File:2C-E.svg | class5=skin-invert-image | 2C-E (4-ethyl-2,5-DMPEA) | File:DOB-racemic-skeletal.svg | class6=skin-invert-image | DOB (α-methyl-2C-B) | File:2,5-dimethoxy-4-methylamphetamine.svg | class7=skin-invert-image | DOM (α-methyl-2C-D) | File:4C-B Structure.svg | class8=skin-invert-image | 4C-B (α-ethyl-2C-B) | File:Β-Methyl-2C-B.svg | class9=skin-invert-image | β-Methyl-2C-B (BMB) | File:ΒOH-2C-B.svg | class10=skin-invert-image | BOH-2C-B (BOHB; β-hydroxy-2C-B) | File:4-bromo-2,5,beta-trimethoxy-phenethylamine.svg | class11=skin-invert-image | BOB (β-methoxy-2C-B) | File:Βk-2C-B-skeletal.svg | class12=skin-invert-image | βk-2C-B (β-keto-2C-B) | File:2C-DB.svg | class13=skin-invert-image | 2C-DB (6-bromo-2C-B) | File:2CB-2-EtO.svg | class14=skin-invert-image | 2CB-2-EtO | File:ASR-2001.svg | class15=skin-invert-image | ASR-2001 (2CB-5PrO) | File:N-Methyl-2C-B.svg | class16=skin-invert-image | ''N''-Methyl-2C-B (2C-B-M) | File:N-Ethyl-2C-B.svg | class17=skin-invert-image | ''N''-Ethyl-2C-B | File:25B-NB.svg | class18=skin-invert-image | 25B-NB (''N''-benzyl-2C-B) | File:2C-B-NBOMe-skeletal.svg | class19=skin-invert-image | 25B-NBOMe | File:25B-NBOH.svg | class20=skin-invert-image | 25B-NBOH | File:2C-B-AN.svg | class21=skin-invert-image | 2C-B-AN | File:DOB-NDEPA.svg | class22=skin-invert-image | DOB-NDEPA | File:2C-B-FLY chemical structure.svg | class23=skin-invert-image | 2C-B-FLY | File:2C-B-DRAGONFLY.svg | class24=skin-invert-image | 2C-B-DRAGONFLY | File:2C-B-BUTTERFLY Structure.svg | class25=skin-invert-image | 2C-B-BUTTERFLY | File:DOB-CR.svg | class26=skin-invert-image | DOB-CR (2C-B-CR; DOB-THIQ) | File:TCB-2.svg | class27=skin-invert-image | TCB-2 (2CBCB) | File:2CB-Ind chemical structure.svg | class28=skin-invert-image | 2CB-Ind | File:2C-B-5-hemiFLY-α6.svg | class29=skin-invert-image | 2C-B-5-hemiFLY-α6 (BNAP) | File:2CB7 structure.svg | class30=skin-invert-image | 2CB7 (2C-B-5-hemiFLY-β7) | File:ZC-B structure.svg | class31=skin-invert-image | ZC-B (2C-B-AZET) | File:2C-B-PYR.svg | class32=skin-invert-image | 2C-B-PYR | File:2C-B-3PIP.svg | class33=skin-invert-image | 2C-B-3PIP | File:2C-B-3PIP-NBOMe.svg | class34=skin-invert-image | 2C-B-3PIP-NBOMe | File:2C-B-3PIP-POMe.svg | class35=skin-invert-image | 2C-B-3PIP-POMe | File:2CBecca.svg | class36=skin-invert-image | 2CBecca | File:2CJP structure.svg | class37=skin-invert-image | 2CJP | File:2CLisaB.svg | class38=skin-invert-image | 2CLisaB | File:DMBMPP.svg | class39=skin-invert-image | DMBMPP (juncosamine) | File:2C-B-aminorex.svg | class40=skin-invert-image | 2C-B-aminorex (2C-B-AR) | File:2C-B-morpholine.svg | class41=skin-invert-image | 2C-B-morpholine (2C-B-MOR) | File:2C-B-BZP.svg | class42=skin-invert-image | 2C-B-BZP | File:2C-B-PP Structure.svg | class43=skin-invert-image | 2C-B-PP | File:2-OH-2C-B.svg | class44=skin-invert-image | 2-OH-2C-B (2-DM-2C-B) | File:Desoxybromoscaline.svg | class45=skin-invert-image | 4-Bromomescaline (4-Br-3,5-DMPEA) | File:Mescaline Structural Formulae bondline.svg | class46=skin-invert-image | mescaline (3,4,5-TMPEA) }} }}

==History== 2C-B was first synthesized and evaluated by American chemist Alexander Shulgin in 1974.<ref name="Poulie_2020" /><ref name="Dean_2013" /><ref name="Wills_2012" /> He described the properties and effects of 2C-B in humans, along with those of 2C-D, in the scientific literature in 1975.<ref name="Passie_2018" /><ref name="Wills_2012" /><ref name="PiHKAL" /><ref name="Shulgin_1975">{{cite journal | vauthors = Shulgin AT, Carter MF | title = Centrally active phenethylamines | journal = Psychopharmacology Communications | volume = 1 | issue = 1 | pages = 93–98 | date = 1975 | pmid = 1223994 | url = https://isomerdesign.com/bitnest/external/Psychopharmacol.Commun/1.1.93 }}</ref> Shulgin proposed 2C-B and 2C-D for use in psychedelic-assisted psychotherapy.<ref name="Shulgin_1975" /><ref name="Dean_2013" /> However, it was reportedly abandoned for such purposes due to gastrointestinal side effects and lack of entactogenic effects.<ref name="Nugteren-van_Lonkhuyzen_2015" /><ref name="Dean_2013" /> 2C-B was Shulgin's favorite psychedelic of his own creations, though he only tried it a few times.<ref name="Morris2010">{{cite web | author = Hamilton Morris | date = 2 May 2010 | title = The Last Interview With Alexander Shulgin: Which, Technically, Was Not an Interview at All | website = vice.com | publisher = Vice Media | url = https://web.archive.org/web/20201018023408/http://www.vice.com/en/article/avjewz/the-last-interview-with-alexander-shulgin-423-v17n5 | archive-date = 27 March 2025 | archive-url = https://isomerdesign.com/bitnest/external/Vice/v17n5_us17 | quote = Ask Shulgin what his favorite psychedelic is and he will say “2CB”5 without hesitation. Ask him how many times he has taken it and he’ll say “a few.” This is a guy who has had approximately 10,000 psychedelic experiences. No drug, not even his cherished 2C-B, tastes better than the untasted. }}</ref><ref name="Biello2008">{{cite web | vauthors = Biello D | date = 20 March 2008 | title = Self-Experimenters: Psychedelic Chemist Explores the Surreality of Inner Space, One Drug at a Time | website = Scientific American | url = https://www.scientificamerican.com/article/self-experimenter-chemist-explores-new-psychedelics/ | access-date = 11 February 2026 | quote = His personal favorite, which he describes as "extraordinarily comfortable and quite erotic," is known simply as 2C-B for its chemical makeup. }}</ref><ref name="Kent2014">{{cite web | vauthors = Kent JL | date = September 10, 2014 | title = Godfather of Ecstasy: Alexander Shulgin's Last Trip | language = en-US | website = High Times | url = https://hightimes.com/culture/godfather-of-ecstasy-alexander-shulgins-last-trip/ | access-date = April 15, 2023 | archive-date = 2020-03-11 | archive-url = https://web.archive.org/web/20200311075358/https://hightimes.com/culture/godfather-of-ecstasy-alexander-shulgins-last-trip/ | url-status = dead | quote = When I ask Ann about his favorite among all the chemical compounds he’d created, she answers immediately: “It would have to be 2C-B. He was always very proud of that one. He called it the ‘Great Teacher’ … although I preferred 2C-B-FLY a bit more.” [...] Although Shulgin worked with many types of drugs, his favorites were the phenethylamines, psychedelics that are more thoughtful than overpowering. }}</ref><ref name="Kent2022">{{cite web | vauthors = Kent J | date = 17 June 2022 | title = Remembering Psychedelic Chemist Alexander Shulgin | website = Psychedelic Spotlight | url = https://psychedelicspotlight.com/remembering-psychedelic-chemist-alexander-shulgin/ | access-date = 11 February 2026 | quote = Shulgin’s favorite drug was LSD, [...] When I ask Ann what Sasha’s favorite of his own chemicals is she knows immediately. “It would have to be 2C-B. He was always very proud of that one. He called it the Great Teacher. Although I preferred 2C-B-Fly a bit more.” }}</ref>

2C-B was legitimately marketed and sold as an over-the-counter sexual enhancer under brand names like Erox in several European countries such as Germany in the 1980s and early 1990s.<ref name="Poulie_2020" /><ref name="DOJ2006">{{cite web | title = Information Bulletin 2C-B (Nexus) Reappears on the Club Drug Scene | date = 1 January 2006 | website = Department of Justice | url = https://www.justice.gov/archive/ndic/pubs0/665/index.htm | access-date = 14 November 2025 }}</ref><ref name="Anilanmert_2018" /><ref name="Caudevilla-Galligo_2012" /><ref name="Johnson_2018">{{cite book | vauthors = Johnson C | date = 5 June 2018 | title = Magic Medicine: A Trip Through the Intoxicating History and Modern-Day Use of Psychedelic Plants and Substances | publisher = Fair Winds Press | isbn = 978-1-63159-428-1 | url = https://books.google.com/books?id=N-NfDwAAQBAJ&pg=PA25 | quote = During its legal heyday, a German company even marketed it as an aphrodisiac called Erox. Dutch "smart shops" also sold 2C-B as an Ecstasy-like legal high under the name "Nexus." }}</ref> It was manufactured by the German pharmaceutical company Drittewelle and was sold in adult stores, smart shops, and some nightclubs.<ref name="Poulie_2020">{{cite journal | vauthors = Poulie CB, Jensen AA, Halberstadt AL, Kristensen JL | title = DARK Classics in Chemical Neuroscience: NBOMes | journal = ACS Chemical Neuroscience | volume = 11 | issue = 23 | pages = 3860–3869 | date = December 2020 | pmid = 31657895 | pmc = 9191638 | doi = 10.1021/acschemneuro.9b00528 | quote = However, 2C-B was emergency scheduled by the Drug Enforcement Administration (DEA) in 1994, due to its appearance on the recreational drug market as a replacement for 3,4-methylenedioxy methamphetamine (MDMA) (which had been scheduled in 1985). At that time, 2C-B was still being legally manufactured by the German company Drittewelle under the trade name of Erox and sold in Dutch "head-shops" under the name Nexus. In March 2001, the UN Commission on Narcotic Drugs added 2C-B to Schedule II of the Convention on Psychotropic Substances. }}</ref><ref name="DOJ2006" /><ref name="Caudevilla-Galligo_2012" /><ref name="Erowid2002">{{cite web | title = Drittewelle 2C-B Packaging | year = 2002 | url = https://www.erowid.org/chemicals/show_image.php?i=2cb/2cb_pack2.jpg | publisher = Erowid.org | access-date = 25 September 2013 }}</ref> In addition, 2C-B was sold in Dutch smart shops as an ecstasy-like legal high under names like Nexus.<ref name="Poulie_2020" /><ref name="Johnson_2018" /> 2C-B was first encountered as a novel recreational designer drug in the United States in 1985.<ref name="Wills_2012" /> It was advertised and used as an MDMA substitute after MDMA was made illegal around this time.<ref name="Dean_2013" /><ref name="Wills_2012">{{cite book | vauthors = Wills B, Erickson T | date = 9 March 2012 | veditors = Barceloux DG | chapter = Psychoactive Phenethylamine, Piperazine, and Pyrrolidinophenone Derivatives | title = Medical Toxicology of Drug Abuse: Synthesized Chemicals and Psychoactive Plants | publisher = Wiley | pages = 156–192 | isbn = 978-0-471-72760-6 | doi = 10.1002/9781118105955.ch10 | quote = DOSE EFFECT: Anecdotal data suggests that recreational doses of 2C-B range from 4—30 mg with lower doses (4—10 mg) producing entactogenic effects, whereas high doses (10— 20 mg) cause psychedelic and sympathomimetic effects. }}</ref><ref name="Anilanmert_2018" />

2C-B has been said to have been legally sold in Southern Africa from 1993 to 1996 and used as an 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''".<ref>{{cite web | title = 2CB chosen over traditional entheogen's by South African healers. | date = 2008-03-27 | 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>

The drug became a controlled substance in the United States in 1994.<ref name="Poulie_2020" /><ref name="Dean_2013" /><ref name="Wills_2012" /><ref name="Anilanmert_2018" /> It also became a controlled substance in most other countries in the mid-1990s.<ref name="Caudevilla-Galligo_2012" /> In addition, 2C-B was placed in Schedule II of the United Nations Convention on Psychotropic Substances and hence became an internationally controlled substance in 2001.<ref name="Nugteren-van_Lonkhuyzen_2015" /><ref name="Papaseit_2018" /> Following 2C-B's restriction, many other 2C psychedelics, such as 2C-E and 2C-I, emerged as designer drugs.<ref name="Dean_2013" /> Nonetheless, 2C-B is the most popular of the 2C psychedelics.<ref name="Wills_2012" /><ref name="Anilanmert_2018" /><ref name="Palamar_2020" /><ref name="Mallaroni_2022" /> Subsequent to their emergence, numerous other 2C drugs besides 2C-B have also been made controlled substances throughout the world.<ref name="Anilanmert_2018" /> In addition to other 2Cs, derivatives of 2C-B such as 2C-B-FLY and 25B-NBOMe have been developed and emerged as well-known novel designer drugs.<ref name="PiHKAL" /><ref name="Shulgin_2011" /><ref name="Trachsel_2013" /> 2C-B-FLY was Ann Shulgin's favorite psychedelic, which she especially enjoyed in terms of enhanced eroticism, and preferred "a bit more" than 2C-B.<ref name="HighTimes2014">{{cite web | title=Godfather of Ecstasy: Alexander Shulgin's Last Trip | website=High Times | date=10 September 2014 | url=https://hightimes.com/culture/godfather-of-ecstasy-alexander-shulgins-last-trip/ | access-date=15 November 2025}}</ref><ref name="Kent2014" /><ref name="Kent2022" /><ref name="Cooke2021">{{cite web | vauthors = Cooke J | date = 1 July 2021 | title = 2C-B-FLY: Is It The Best Psychedelic For Arousal & Sexual Intimacy? | website = Tripsitter | url = https://tripsitter.com/2cb-fly/ | access-date = 26 March 2025 | quote = The overall sentiment for [2C-B-FLY] is that it’s one of the most enjoyable of the research psychedelics. Ann Shulgin — wife of Alexander Shulgin and co-author of the books TiHKAL and PiHKAL — once stated that 2C-B-FLY was one of her favorite psychedelics. }}</ref><ref name="Hufford2007">{{cite journal | vauthors = Hufford S | title = An Interview with Ann Shulgin on Psychedelics and Self-Discovery | journal = MAPS Newsletter | volume = 17 | issue = 2 | pages = 23–24 | date = 2007 | publisher = Multidisciplinary Association for Psychedelic Studies | url = https://maps.org/news-letters/v17n2/v17n2_annshulgin-23.pdf | quote = In one recent case, I said often, too often, that something called 2CB Fly was absolutely great for me. To me, it’s the loveliest thing, especially for eroticism. But I found out that it’s not interesting to anybody else. I realized that having said that, I was putting things in motion. The Internet was full of 2CB Fly, and people were asking about it and I thought “uh-oh.” It turned out that it’s a disappointment to most other people. So if I say what my favorite psychedelics are, it’s almost meaningless for other people, because they have to find their allies very carefully. }}</ref><ref name="BLTC2021">{{cite AV media | people=Connie Littlefield (director, writer), Siobhan Flanagan, Alexander Shulgin (subject), Ann Shulgin (subject), Paul F. Daley (subject), Myron Stolaroff (subject), Jean Stolaroff (subject), Wendy Perry Tucker (subject), Tania Manning (subject), Greg Manning (subject), Keeper Trout (subject), Earth and Fire Erowid, others | date=2021 | title=Better Living Through Chemistry | url=https://betterlivingthroughchemistry.org/ | archive-url=https://tubitv.com/movies/100015889/better-living-through-chemistry | archive-date=21 September 2021 | type=Motion picture | language=English | location= | publisher=Better Living Through Film, Incorporated | time=~49:50}}</ref>

==Society and culture== ===Names=== Brand names and street names of 2C-B include Nexus, Venus, Bromo, Erox, Perfomax, Bees, Toonies, Spectrum, XTC, and Synergy, among others.<ref name="Dean_2013" /><ref name="Wills_2012" /><ref name="Cole_2002" /><ref name="DEA - Evaluation Section">{{cite web | title = 2C-B Street Names | date = February 1, 2011 | url = https://www.deadiversion.usdoj.gov/drug_chem_info/bromo_dmp.pdf | 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>

Street purity of 2C-B, when tested, has been found to be relatively high.<ref name="Cole_2002" /> 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="Caudevilla-Galligo_2012" /> 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="de_Boer_1999" />

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 | date = May 2001 | 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 }}</ref>

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

2C-B is a scheduled drug in most jurisdictions.<ref>{{cite web | title = Erowid 2C-B page | url = http://www.erowid.org/chemicals/2cb/2cb_law.shtml }}</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 | title = Last Argentina Controlled Drugs List | url = http://www.cicad.oas.org/fortalecimiento_institucional/legislations/PDF/AR/decreto_299.pdf | 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 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 | title = CDSA Schedule II | url = http://isomerdesign.com/Cdsa/schedule.php?schedule=3&section=ALL&structure=C | 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 }}</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 | title = Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines) | date = 2016-05-04 | url = http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php | work = Canada Gazette | publisher = Government of Canada, Public Works and Government Services Canada, Public Services and Procurement Canada, Integrated Services Branch, Canada }}</ref>

====Chile==== In August 2007, 2C-B, along with many other psychologically active substances,<ref>{{Cite web | 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. | trans-title = Approves Regulations of Law No. 20,000 That Sanctions the Illicit Trafficking of Narcotics and Psychotropic Substances and Replaces Law No. 19,366. | url = http://www.ispch.cl/sites/default/files/5_agencia_reguladora/decreto_867_07.pdf }}</ref> was added to Ley 20.000, known as the Ley de drogas.

====Czech Republic==== Possession of more than 200{{nbsp}}mg of 2C-B is punishable with a two years jail sentence.<ref>{{cite web | title = Erowid Psychoactive Vaults : Drug Laws: Czech Republic | url = https://www.erowid.org/psychoactives//law/countries/law_czech.shtml | 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 | title = Bekendtgørelse om euforiserende stoffer | date = 2008-07-01 | url = https://www.retsinformation.dk/Forms/R0710.aspx?id=137169 | access-date = 2013-10-01 | language = da }}</ref>

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

====Finland==== Scheduled in the "government decree on substances, preparations and plants considered to be narcotic drugs".<ref>{{Cite web | title = Valtioneuvoston asetus huumausaineina pidettävistä aineista, valmisteista ja kasveista | 543/2008 | Lainsäädäntö | Finlex | url = https://finlex.fi/fi/lainsaadanto/2008/543 | website = finlex.fi }}</ref>

====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 | title = Italy Drug Schedule (Tabella I) | url = http://www.salute.gov.it/medicinaliSostanze/paginaInternaMedicinaliSostanze.jsp?id=7&menu=strumenti | 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 | title = Norway Drug Schedule | url = http://www.lovdata.no/for/sf/ho/xo-19780630-0008.html }}</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 | 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) | url = http://base.garant.ru/70237124/ | 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 {{Lang|swe|Lagen om förbud mot vissa hälsofarliga varor|italic=no}} (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 | title = Förordning (1999:58) om förbud mot vissa hälsofarliga varo | date = 1999-02-25 | url = http://www.notisum.se/rnp/sls/fakta/a9990058.HTM | access-date = 2013-10-01 | language = sv | archive-date = 2013-10-04 | archive-url = https://web.archive.org/web/20131004215233/http://www.notisum.se/rnp/sls/fakta/a9990058.HTM }}</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 | title = Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 1997:12) om förteckningar över narkotika: LVFS 2002:4 | url = http://www.lakemedelsverket.se/upload/lvfs/LVFS_2002-4.pdf | 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 }}</ref> but mislabeled "2-CB" in the document. However, this was corrected in a new document, LVFS 2009:22<ref>{{cite web | title = Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 1997:12) om förteckningar över narkotika: LVFS 2009:22 | url = http://www.lakemedelsverket.se/upload/lvfs/LVFS_2009-22.pdf | 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 }}</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 | date = 2011-08-18 | title = Verzeichnis aller betäubungsmittelhaltigen Stoffe | language = de | website = Swissmedic | publisher = Swiss Agency for Therapeutic Products | page = 2 | url = http://www.swissmedic.ch/produktbereiche/00447/00536/index.html?lang=en&download=NHzLpZeg7t,lnp6I0NTU042l2Z6ln1ad1IZn4Z2qZpnO2Yuq2Z6gpJCDdn12hGym162epYbg2c_JjKbNoKSn6A--&.pdf | access-date = 2013-11-30 | archive-date = 2012-03-15 | archive-url = https://web.archive.org/web/20120315071907/http://www.swissmedic.ch/produktbereiche/00447/00536/index.html?lang=en | trans-title = Directory of all narcotics-containing substances }}</ref>

====United Kingdom==== 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.<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 Schedule I controlled substance. This became permanent law on June 2, 1995,<ref name="fed_reg_1995">{{Cite web | title = Federal Register, Volume 60 Issue 106 (Friday, June 2, 1995) | date = 1994-06-02 | 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 | title = Federal Register, Volume 59 Issue 243 (Tuesday, December 20, 1994) | date = 1994-12-20 | 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>

==Research== 2C-B has been studied and suggested for more widespread use in psychedelic-assisted psychotherapy.<ref name="Sessa_2016" /><ref name="Mallaroni_2023" /><ref name="Shulgin_1975" /><ref name="Dean_2013" />

== References == {{Reflist}}

== External links == {{Div col|colwidth=30em}} * [https://isomerdesign.com/pihkal/explore/20 2C-B - Isomer Design] * [https://psychonautwiki.org/wiki/2C-B 2C-B - PsychonautWiki] * [https://www.erowid.org/chemicals/2cb/2cb.shtml 2C-B - Erowid] * [https://www.erowid.org/library/books_online/pihkal/pihkal020.shtml 2C-B - PiHKAL - Erowid] * [https://isomerdesign.com/pihkal/read/pk/20 2C-B - PiHKAL - Isomer Design] * [https://archive.org/details/shulgin-index-vol-1/page/20/mode/1up?view=theater 2C-B - The Shulgin Index] * [https://www.bluelight.org/xf/threads/125910 The Big & Dandy 2C-B Thread - Bluelight] * [https://shulginfoundation.org/molecular-memoirs-2c-b-the-warm-hug/ Molecular Memoirs: 2C-B, The “Warm Hug” - The Shulgin Foundation] * [https://www.psychedelics.com/articles/2c-b-alexander-shulgin/ 2C-B, the Forgotten Psychedelic: Understanding the “Love Child” of Alexander and Ann Shulgin - Psychedelics.com] * [https://psychedelicspotlight.com/forgotten-psychedelics-what-is-2c-b/ Forgotten Psychedelics: What Is 2C-B? - Psychedelic Spotlight] * [https://psychedelicreview.com/is-2c-b-a-psychedelic-drug/ Is 2C-B a Psychedelic Drug? - Psychedelic Science Review (PSR)] * [https://tripsitter.com/2cb/ 2C-B: Effects, Dosage, & Safety - Tripsitter] * [https://tripsit.me/factsheets/2c-b 2C-B - TripSit] * [https://healingmaps.com/2c-b-effects-dosage/ 2C-B – Graceful, Erotic, and Sensual? - HealingMaps] * [https://psychedelichealth.co.uk/2023/06/23/2c-b-lsd-mdma-baby/ 2C-B: If LSD and MDMA had a baby - PsychedelicHealth] * [https://www.vice.com/en/article/what-is-2cb-and-its-effects/ 2C-B Is the Drug Taking Over the UK's Clubs - Vice] {{Div col end}}

Category:5-HT2A agonists Category:5-HT2B agonists Category:5-HT2C agonists Category:2C (psychedelics) Category:Alexander Shulgin Category:Anti-inflammatory agents Category:Aphrodisiacs Category:Bromobenzene derivatives Category:Designer drugs Category:Entactogens Category:Entheogens Category:O-methylated phenols Category:PiHKAL Category:Psychedelic-assisted therapy Category:Psychedelic phenethylamines Category:Stimulants Category:Substances discovered in the 1970s

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