2C-B: Difference between revisions

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| bioavailability = Not well characterized

| pregnancy = Not established

| legal = Schedule I (United States)

| legal = [[USLegal:DEA Schedule I|Schedule I]] (United States)

| mechanism = 5-HT2A partial agonist

| intro = 2C-B, chemically 4-bromo-2,5-dimethoxyphenethylamine, is a synthetic psychedelic [[:Category:Phenethylamines|phenethylamine]] first prepared in 1974 by [[Alexander Shulgin]] at his home laboratory in Lafayette, California. It is the founding member of the [[:Category:2C-x series|2C series]], a family of 2,5-dimethoxy-4-substituted phenethylamines that Shulgin and his collaborators developed as variations on the [[Mescaline|mescaline]] skeleton. 2C-B occupies a distinctive position in the psychedelic medicine landscape: a compound with a mescaline-class structural lineage, a [[5-HT2A ~~receptor~~|5-HT2A]] pharmacology shared with the [[:Category:Psychedelics|classical psychedelics]], and a subjective character that has been described as bridging the [[:Category:Empathogens|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 [[Convention on Psychotropic Substances|United Nations Convention on Psychotropic Substances]] in 2001.

| intro = 2C-B, chemically 4-bromo-2,5-dimethoxyphenethylamine, is a synthetic psychedelic [[:Category:Phenethylamines|phenethylamine]] first prepared in 1974 by [[Alexander Shulgin]] at his home laboratory in Lafayette, California. It is the founding member of the [[:Category:2C-x series|2C series]], a family of 2,5-dimethoxy-4-substituted phenethylamines that Shulgin and his collaborators developed as variations on the [[Mescaline|mescaline]] skeleton. 2C-B occupies a distinctive position in the psychedelic medicine landscape: a compound with a mescaline-class structural lineage, a [[Receptor:5-HT2A|5-HT2A]] pharmacology shared with the [[:Category:Psychedelics|classical psychedelics]], and a subjective character that has been described as bridging the [[:Category:Empathogens|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 [[Convention on Psychotropic Substances|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>

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| voice = Commentary

}}

<titration slug="erowid-dose-oral" author="erowid-claude"

title="Oral dose ladder (Erowid)">

Erowid's dosage documentation for oral 2C-B<ref name="erowid-2cb-dose">

Erowid. 2C-B Dosage. Erowid.org.

https://www.erowid.org/chemicals/2cb/2cb_dose.shtml.

Accessed 2026-05-25.</ref> reports the following tiers:

* '''Threshold:''' 2-5 mg

* '''Light:''' 5-15 mg

* '''Common:''' 15-25 mg

* '''Strong:''' 25-50 mg

Timing data are not provided by Erowid for this substance. Nasal

administration has been reported but Erowid does not provide separate

insufflated dose tiers. Note that Erowid's common range (15-25 mg)

approximates but is slightly broader than Shulgin's PiHKAL range

(12-24 mg); both are consistent with the medicine's steep dose-response curve.

</titration>

| effects =

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| pk_metabolism =

| pk_elimination =

| pharmacodynamics = 2C-B is a partial agonist at the serotonin 5-HT2A receptor, with additional activity at [[5-HT2C ~~receptor~~|5-HT2C]] and [[5-HT2B ~~receptor~~|5-HT2B]] and weak inhibition of [[Monoamine transporter|monoamine transporters]].<ref name="nichols2016">Nichols DE. Psychedelics. Pharmacological Reviews. 2016;68(2):264-355. PMID 26841800.</ref> 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 [[:Category:Tryptamines|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.

| pharmacodynamics = 2C-B is a partial agonist at the serotonin 5-HT2A receptor, with additional activity at [[Receptor:5-HT2C|5-HT2C]] and [[Receptor:5-HT2B|5-HT2B]] and weak inhibition of [[Monoamine transporter|monoamine transporters]].<ref name="nichols2016">Nichols DE. Psychedelics. Pharmacological Reviews. 2016;68(2):264-355. PMID 26841800.</ref> 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 [[:Category:Tryptamines|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.

{{ShulginsCorner

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* '''Lithium: seizure and severe-reaction risk.''' Lithium combined with psychedelics including 2C-B is associated with a markedly increased risk of seizures and severe adverse reactions; the mechanism is distinct from serotonin syndrome. Avoid combination.

* '''Psychostimulants: additive cardiovascular load.''' 2C-B itself produces modest sympathomimetic effects (elevated heart rate, mild blood pressure increase); concurrent psychostimulants compound the cardiovascular burden.

* '''CYP interactions: not well characterized.''' Human metabolism of 2C-B has not been comprehensively studied. In vitro work suggests [[~~Pharmacopedia~~:~~Pharmacogenomics sandbox/Enzyme~~ CYP2D6|CYP2D6]] and [[~~Pharmacopedia~~:~~Pharmacogenomics sandbox/Enzyme~~ CYP3A4|CYP3A4]] involvement; strong inhibitors of these enzymes may increase 2C-B exposure.

* '''CYP interactions: not well characterized.''' Human metabolism of 2C-B has not been comprehensively studied. In vitro work suggests [[Enzyme:CYP2D6|CYP2D6]] and [[Enzyme:CYP3A4|CYP3A4]] involvement; strong inhibitors of these enzymes may increase 2C-B exposure.

| pregnancy_details = Not characterized. 2C-B has not been studied in human pregnancy; no preclinical reproductive toxicology data are available in the public literature. The compound's Schedule I status precludes systematic study under conventional regulatory frameworks. Avoid in pregnancy on first-principles grounds.

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