2C-B: Difference between revisions
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MDElliottMD (talk | contribs) Build out 2C-B from stub: history, pharmacodynamics, dosing + harm-reduction titration, 5 ShulginsCorner quotes (PiHKAL #20), interactions, Pharmaceutical origin tag |
MDElliottMD (talk | contribs) Citation pass on 2C-B history: add DEA Federal Register rules (59 FR 671, 60 FR 28718), Papaseit 2018 and Blok 2020 cites; correct the DEA-license account (TiHKAL Invasion), give both 2C-B scheduling dates |
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| legal = Schedule I (United States) | | legal = Schedule I (United States) | ||
| mechanism = 5-HT2A partial agonist | | 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> | | 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. | ||
{{ShulginsCorner | {{ShulginsCorner | ||
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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 | 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 | 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. | 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. | ||
Revision as of 21:11, 21 May 2026
Psychedelic, Phenethylamine, 2C-x series
2C-B
Nexus, Eroxan (historical, late-1980s through mid-1990s)
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.
Mescaline, MDMA, Psilocybin, LSD
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, where it gained a reputation as a potential adjunct to psychotherapy.[2] Interest grew particularly after MDMA was placed in Schedule I, on an emergency basis in 1985 and permanently in 1988,[3] 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.[2] 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.
Shulgin's Corner
If there is anything ever found to be an effective aphrodisiac, it will probably be patterned after 2C-B in structure.
Alexander Shulgin, PiHKAL, Recipe #20, pp. 503-506
Commentary
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 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.[4]
The United States Drug Enforcement Administration placed 2C-B in Schedule I on a temporary, emergency basis in January 1994,[5] and made the placement permanent in 1995.[6] The United Nations Convention on Psychotropic Substances added it to Schedule II in 2001.[2] 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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Problems
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+ Add a problemTitration strategies
Reported oral dose magnitudes0
PiHKAL #20 reports an oral dosage range of 12-24 mg with a duration of 4-8 hours. The dose-response curve is steep across this range; Shulgin's commentary observes that every 2 mg can make a profound change in response, and the practical implication is that 2C-B does not tolerate the kind of dose imprecision that is forgiving with longer-duration psychedelics such as psilocybin or LSD. Doses below 12 mg are described as threshold or "museum level" in the Shulgin literature, producing perceptual shifts subtle enough to allow ordinary public activity. The Papaseit 2018 observational study at the Universitat Autònoma de Barcelona characterized acute pharmacology in experienced users at doses comparable to the PiHKAL range and is the closest the modern clinical literature comes to a controlled human pharmacokinetic study; doses substantially above 24 mg are not characterized in the formal literature and the few case reports available describe adverse psychological events.
Shulgin's Corner
A day at the Stanford museum. Things were visually rich, yet I felt that I was reasonably inconspicuous. The Rodin sculptures were very personal and not terribly subtle. I saw Escher things in the ceiling design, when I decided to sit in a foyer somewhere and simply pretend to rest.
Anonymous (quoted in PiHKAL), Recipe #20, pp. 503-506
Narrative
Narrative
Harm reduction considerations0
2C-B is a Schedule I controlled substance in the United States with no approved medical use and no legal supply chain that guarantees product identity or purity; in modern markets it is frequently misrepresented as MDMA or substituted with other compounds, including the structurally similar but pharmacologically distinct DOB. Onset after oral administration is typically 45-75 minutes; the long onset combined with the steep dose-response curve drives a common harm pattern in which inexperienced users redose during the onset window and overshoot the intended dose. Combinations with serotonergic medicines (SSRIs, SNRIs, MAOIs, tramadol, lithium, dextromethorphan) carry serotonin syndrome risk and should be avoided; combinations with stimulants increase cardiovascular load. The general harm-reduction principles for psychedelic experiences (set, setting, sober companion, advance arrangement of supportive contacts) apply to 2C-B as they do to other 5-HT2A agonists.
Shulgin's Corner
The 2C-B experience is one of the shortest of any major psychedelic drug. Wherever you might be, hang on. In an hour or so you will be approaching familiar territory again.
Alexander Shulgin, PiHKAL, Recipe #20, pp. 503-506
Commentary
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.[7] 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.
Shulgin's Corner
The drug effect first became known to me as a shift of colors toward golden and rose tones. Pigments in the room became intensified. Shapes became rounder, more organic. A sensation of lightness and rivulets of warmth began seeping through my body.
Anonymous (quoted in PiHKAL), Recipe #20, pp. 503-506
Narrative
Narrative
Shulgin's Corner
I am totally into my body. I am aware of every muscle and nerve in my body. The night is extraordinary — moon full. Unbelievably erotic, quiet and exquisite, almost unbearable.
Anonymous (quoted in PiHKAL), Recipe #20, pp. 503-506
Narrative
Narrative
Interactions
MDMA exp 5.0/5 outcome n/a (n=1) no reports yet
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How did it go? (-100 worst, +100 best)
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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Relevant Literature
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See also
References
- ↑ Shulgin AT, Carter MF. Centrally active phenethylamines. Psychopharmacology Communications. 1975;1(1):93-98.
- ↑ 2.0 2.1 2.2 2.3 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.
- ↑ 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.
- ↑ Shulgin A, Shulgin A. TIHKAL: The Continuation. Berkeley, CA: Transform Press; 1997. Chapter 1, "Invasion".
- ↑ 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.
- ↑ 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.
- ↑ Nichols DE. Psychedelics. Pharmacological Reviews. 2016;68(2):264-355. PMID 26841800.
Summary
Classes
Psychedelic, Phenethylamine, 2C-x series
Common uses
Pharmacy
Pharmacology
Routes
Oral, insufflated
Onset
45-75 min (oral)
Duration
4-8 h
Half-life
Not well characterized
Bioavailability
Not well characterized
Pregnancy
Not established
Legal status
Schedule I (United States)
Purported mechanism
5-HT2A partial agonist