2C-B: Difference between revisions

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| legal = Schedule I (United States)

| mechanism = 5-HT2A partial agonist

| intro = 2C-B, chemically 4-bromo-2,5-dimethoxyphenethylamine, is a synthetic psychedelic phenethylamine first prepared in 1974 by Alexander Shulgin at his home laboratory in Lafayette, California. It is the founding member of the 2C series, a family of 2,5-dimethoxy-4-substituted phenethylamines that Shulgin and his collaborators developed as variations on the mescaline skeleton. 2C-B occupies a distinctive position in the psychedelic medicine landscape: a compound with a mescaline-class structural lineage, a 5-HT2A pharmacology shared with the classical psychedelics, and a subjective character that has been described as bridging the entactogenic register of MDMA and the visionary register of the classical psychedelics. It had a brief legal-sale era in the late 1980s and early 1990s before being placed in Schedule I of the United States Controlled Substances Act in 1995 and Schedule II of the United Nations Convention on Psychotropic Substances in 2001.

| intro = 2C-B, chemically 4-bromo-2,5-dimethoxyphenethylamine, is a synthetic psychedelic phenethylamine first prepared in 1974 by Alexander Shulgin at his home laboratory in Lafayette, California. It is the founding member of the 2C series, a family of 2,5-dimethoxy-4-substituted phenethylamines that Shulgin and his collaborators developed as variations on the mescaline skeleton. 2C-B occupies a distinctive position in the psychedelic medicine landscape: a compound with a mescaline-class structural lineage, a 5-HT2A pharmacology shared with the classical psychedelics, and a subjective character that has been described as bridging the entactogenic register of MDMA and the visionary register of the classical psychedelics. It had a brief legal-sale era in the late 1980s and early 1990s before being placed in Schedule I of the United States Controlled Substances Act, temporarily in 1994 and permanently in 1995, and in Schedule II of the United Nations Convention on Psychotropic Substances in 2001.

| 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.<ref name="shulgin1975">Shulgin AT, Carter MF. Centrally active phenethylamines. Psychopharmacology Communications. 1975;1(1):93-98.</ref>

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.

The compound entered psychotherapeutic underground practice in the late 1970s, where it gained a reputation as a potential adjunct to psychotherapy.<ref name="papaseit2018"/> Interest grew particularly after MDMA was placed in Schedule I, on an emergency basis in 1985 and permanently in 1988,<ref name="blok2020">Blok G. [From Adam to ecstacy; legal use of MDMA in the 1970s and 1980s]. Tijdschrift voor Psychiatrie. 2020;62(8):702-706. PMID 32816299.</ref> 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.<ref name="papaseit2018"/> 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.

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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 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 Drug Enforcement Administration analytical license to possess and study scheduled compounds, and chose to make the chemistry public knowledge in the conviction that the information should not be the property of governments. In 1994 a DEA inspection of his laboratory ended with Shulgin surrendering that license, an episode Ann Shulgin recounts in the opening chapter of the companion volume TiHKAL.<ref name="tihkal-invasion">Shulgin A, Shulgin A. TIHKAL: The Continuation. Berkeley, CA: Transform Press; 1997. Chapter 1, "Invasion".</ref>

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,<ref name="papaseit2018">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.</ref> and groups at Maastricht University and the University of Basel have begun controlled comparisons of 2C-B with psilocybin and MDMA.

The United States Drug Enforcement Administration placed 2C-B in Schedule I on a temporary, emergency basis in January 1994,<ref name="fr1994">Drug Enforcement Administration. Schedules of Controlled Substances: Temporary Placement of 4-Bromo-2,5-dimethoxyphenethylamine Into Schedule I. Final Rule. Federal Register. 1994 Jan 6;59:671.</ref> and made the placement permanent in 1995.<ref name="fr1995">Drug Enforcement Administration. Schedules of Controlled Substances; Placement of 4-Bromo-2,5-Dimethoxyphenethylamine Into Schedule I. Final Rule. Federal Register. 1995 Jun 2;60:28718.</ref> The United Nations Convention on Psychotropic Substances added it to Schedule II in 2001.<ref name="papaseit2018"/> 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,<ref name="papaseit2018">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.</ref> 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.

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