2C-B
History
The compound that became 2C-B emerged from Shulgin's systematic exploration of the structure-activity relationships of mescaline analogs, a program he had begun in the mid-1960s. Shulgin's hypothesis was that modifications to the trimethoxyphenethylamine skeleton might yield compounds active at lower doses than mescaline's, with subjective profiles that varied in characteristic ways with the substituent at the 4-position of the phenyl ring. 2C-B, with bromine at the 4-position, was one of the most striking results. The first published description appeared in 1975 in Psychopharmacology Communications, the short-lived journal that was one of the few outlets willing to publish Shulgin's work in that era.[1]
The compound entered psychotherapeutic underground practice in the late 1970s, particularly after MDMA was placed in Schedule I, on an emergency basis in 1985 and permanently in 1988, removing that medicine from the limited circle of therapists who had been using it adjunctively. 2C-B was, for a window of years, legal in the United States and in much of Europe, and was used by some therapists as an MDMA-adjacent option for couples and individual work. Commercial sale began in the late 1980s under the brand names Eroxan and Nexus, marketed initially in pharmacies and smartshops as an aphrodisiac. The Nexus product became particularly identified with South Africa, where it had a brief and conspicuous run as a legal sex-positive medicine in the early 1990s before the Medicines Control Council scheduled it.
Commentary
The full account of the synthesis, qualitative effects, and dose range was published in 1991 in Shulgin and Shulgin's PiHKAL: A Chemical Love Story, the first half of which is autobiographical and the second half of which is a methodical catalog of 179 phenethylamines that Shulgin and his collaborators synthesized and self-tested. The book included full experimental procedures and was published as a deliberate political act: Shulgin held a Schedule I research license from the United States Drug Enforcement Administration and chose to make the chemistry public knowledge in the conviction that the information should not be the property of governments. The DEA revoked his license in 1994, two years after a raid on his Lafayette laboratory.
The United States placed 2C-B in Schedule I of the Controlled Substances Act in 1995. The United Nations Convention on Psychotropic Substances added it to Schedule II in 2001. Most other jurisdictions scheduled the compound on similar timelines. For roughly a decade after the US scheduling, 2C-B circulated as a clandestine product in European and South American party scenes, often sold as MDMA or under one of the brand names that survived the legal sale era. In the 2010s and 2020s a small body of formal clinical research has emerged: an observational study at the Universitat Autònoma de Barcelona reported the acute pharmacology of oral 2C-B in experienced users,[2] and groups at Maastricht University and the University of Basel have begun controlled comparisons of 2C-B with psilocybin and MDMA.
2C-B is not licensed as a medicine in any major jurisdiction. Formal clinical investigation is in early stages. Underground therapeutic use continues in the lineage that began with the late-1970s Shulgin circle. The compound's role in the modern psychedelic-medicine landscape is uncertain: its shorter duration and lower dose-response slope make it logistically tractable, but the limited modern clinical data and the absence of major-trial sponsorship have kept it on the margins of the renaissance that has gathered around psilocybin and MDMA.Experience
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Narrative
Commentary
Effects
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Pharmacodynamics
2C-B is a partial agonist at the serotonin 5-HT2A receptor, with additional activity at 5-HT2C and 5-HT2B and weak inhibition of monoamine transporters.[3] The pharmacological profile is intermediate between the classical 5-HT2A psychedelics such as LSD and psilocybin and the entactogens such as MDMA. The 5-HT2A action is the principal driver of the psychedelic component; the transporter activity may contribute to the entactogenic character at lower doses. Oral 2C-B has an onset of roughly 45 to 75 minutes and a duration of approximately four to eight hours, which is shorter than psilocybin and considerably shorter than LSD. The compound is structurally a phenethylamine in the mescaline lineage rather than a tryptamine; the 4-bromo substituent on the 2,5-dimethoxyphenethylamine scaffold confers substantially higher 5-HT2A affinity than mescaline's 3,4,5-trimethoxy parent compound, accounting for the dose-potency difference.
Narrative
Narrative
Interactions
Key interaction concerns for 2C-B specifically:
- Serotonergic medicines: serotonin syndrome risk. Concurrent use of SSRIs, SNRIs, MAOIs, tramadol, lithium, dextromethorphan, or other strongly serotonergic agents carries serotonin syndrome risk and should be avoided. MAOI co-administration is particularly dangerous.
- Stimulants: additive cardiovascular load. 2C-B itself produces modest sympathomimetic effects (elevated heart rate, mild blood pressure increase); concurrent stimulants compound the cardiovascular burden.
- CYP interactions: not well characterized. Human metabolism of 2C-B has not been comprehensively studied. In vitro work suggests CYP2D6 and CYP3A4 involvement; strong inhibitors of these enzymes may increase 2C-B exposure.
Pregnancy and lactation
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See also
References
- ↑ Shulgin AT, Carter MF. Centrally active phenethylamines. Psychopharmacology Communications. 1975;1(1):93-98.
- ↑ Papaseit E, Farré M, Pérez-Mañá C, Torrens M, et al. Acute Pharmacological Effects of 2C-B in Humans: An Observational Study. Frontiers in Pharmacology. 2018;9:206. PMID 29593537.
- ↑ Nichols DE. Psychedelics. Pharmacological Reviews. 2016;68(2):264-355. PMID 26841800.