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psx:substance/2c-b/value/contraindication/fb3d5062-79d6-4e34-8530-2486b26dbf9d@1

valuereferenced by edges — no row of its own

derived from · upstream

feeds · downstream

none recorded

Closure of psx:substance/2c-b/value/contraindication/fb3d5062-79d6-4e34-8530-2486b26dbf9d@1: 1 upstream, 0 downstream.

psx:substance/2c-b/value/contraindication/fb3d5062-79d6-4e34-8530-2486b26dbf9d@1
└─ derived_from  proposal/contraindication/a6e6db6a-d0ed-4170-8355-f5e5608a3595  contraindication · other

indented by distance from this node, not by parentage

1Provenance card

the boundary, as counts

Sources

2920 with DOI

6 strong · 14 moderate · 9 weak

Compilations

12026-04-20T22:24:24.157Z

pipeline-v5 · prompt hash not recorded — run predates 2026-09 · 2 other runs

Decisions

33last ruled 2026-09-29

0 awaiting a ruling

Issued documents

72026-10-19T20:29:15.968Z

notice · info card · emergency

Searches

230 with no results

queries and counts on the build

Claims checked

10155 supported

55 supported · 46 not

Correspondence

0received

consent field ships in Phase 4

Edges

308

derivations recorded for this entity

Complete over 29 sources, 1 compilation, and 33 decisions.Not here: the private journal (never).Working material — drafts, discards, unsupported claims — is listed below and readable on the working page.Cite: psychedex.org/substances/2c-b/archive

2Build

one panel per compilation run

generation run 2026-04-20

68 min completedmodel pipeline-v5plan not recordedrun/2f51e7ee…

Selection

results seen90
selected by the model30
consumed as sources29

Verification

claims checked101
supported52
partially supported3
not supported6
inconclusive40
  • record
  • seen / partial
  • working

The model's own caveats

none raised on this run

Reproduce

inputs
29 source keys (listed under Sources)
plan
not recorded — template version, prompt hash and git SHA are written from 2026-09 onward
model
pipeline-v5
streams
none — agent transcripts are persisted from 2026-09 onward
23 searches — query, source, results, what was kept and why
23 searches for this run
#sourcequeryseenkeptrationale
1OpenAlex2C-B 4-bromo-2,5-dimethoxyphenethylamine psychedelic - citations sorted104Most cited landmark papers on 2C-B pharmacology
2ClinicalTrials.gov2C-B psychedelic11Only registered clinical trial for 2C-B
3WebAlexander Shulgin 2C-B synthesis discovery 1974 PIHKAL history102Historical context and discovery narrative
4PubMedPapaseit Farre 2C-B observational pharmacological effects21First published human observational pharmacology study of 2C-B
5Web/DEA2C-B Schedule I DEA legal status US UK Germany Australia102Legal status across major jurisdictions
6PubChem2C-B compound lookup11Primary chemical identity verification
7ClinicalTrials.govNCT05523401 study details1—Only registered clinical trial for 2C-B
8PubMed4-bromo-2,5-dimethoxyphenethylamine pharmacokinetics metabolism75Primary pharmacokinetic sources
9PubMed2C-B 4-bromo-2,5-dimethoxyphenethylamine pharmacology receptor binding33Key receptor pharmacology papers
10PubMedMallaroni 2C-B psilocybin subjective experience assessment11First controlled clinical study of 2C-B; primary human PK and PD data
11WebNCT05523401 2C-B Basel Holze Liechti published results 2024 2025101First controlled study comparing 2C-B to psilocybin
12DEA/DOJ2C-B Schedule I DEA scheduling history1—Authoritative US/international scheduling history
13PubMed/PMCPapaseit 2018 2C-B observational study pharmacokinetics11Primary human PK data from observational study
14PubMedphenylalkylamine hallucinogen head twitch 2C-B behavioral pharmacology21In vivo 5-HT2A agonism data for 2C-B; hallucinogenic potency benchmark
15ErowidPIHKAL 2C-B entry Shulgin dose duration synthesis11Primary source for Shulgin's characterization and synthesis description
16PubMedNBOMe receptor interaction profiles 2C drugs binding11Contains binding affinity data for 2C-B across multiple receptor types
17PubMed4-bromo-2,5-dimethoxyphenethylamine 5-HT2A antagonist agonist Xenopus oocyte11Key paper on complex 5-HT2A pharmacology of 2C-B
18PubMedGonzalez Torrens Farre 2C-B emotions novel psychoactive drug 201511Characterization of 2C-B as stimulant/hallucinogen/entactogen/empathogen
19PubMed/OpenAlexPapaseit 2018 2C-B referenced works5—Citation graph exploration
20Web/EUDA2C-B EMCDDA European drug report prevalence seizures 2022 2023101Primary EU-level epidemiology and prevalence data
21PubMed2C-B case report poisoning emergency department11Drug testing/detection context for harm reduction
22MultipleSeed data verification against published sources——Quality control and data validation
23Web2C-B Canada legal status controlled substances scheduling101Canadian legal scheduling information
101 claims by section — every cited sentence, checked against its source
safety28 · 15 ok
  • Claim in safety — inconclusiveinconclusiveworking →

  • Claim in safety — inconclusiveinconclusiveworking →

  • Claim in safety — inconclusiveinconclusiveworking →

  • Claim in safety — inconclusiveinconclusiveworking →

  • Claim in safety — inconclusiveinconclusiveworking →

  • Dean et al. reviewed the 2C drug class broadly and identified at least 5 deaths in the published literature attributed to 2C compoundssupported

    At least 5 deaths reported; excited delirium common among fatalities. s13181-013-0295-x

  • Clinical features in severe 2C-class toxicity include sympathomimetic toxidrome, serotonin toxicity syndrome, or excited delirium, with presentations of hallucinations, agitation, aggression, hypertension, tachycardia, seizures, and hyperthermiasupported

    Sympathomimetic and serotonin toxicity presentations. Excited delirium common among fatalities. s13181-013-0295-x

  • Claim in safety — inconclusiveinconclusiveworking →

  • 2C-B is not detected by standard immunoassay drug screenssupported

    These drugs do not reliably trigger a positive result on rapid drug immunoassays. Notes difficulty with laboratory confirmation of 2C drugs. s13181-013-0314-y

  • Specialized analytical methods are required: Kerrigan et al. developed a validated GC-SIM urine method with a limit of detection of 2–10 ng/mL, and Thomann et al. published an LC-MS/MS plasma methodsupported

    GC-MS method for detecting 2C-B and 9 other phenethylamines in urine; LOD 2-10 ng/mL; LOQ 10 ng/mL. pmid:21871155

  • Specialized analytical methods are required: Kerrigan et al. developed a validated GC-SIM urine method with a limit of detection of 2–10 ng/mL, and Thomann et al. published an LC-MS/MS plasma methodsupported

    First human plasma PK study with validated LC-MS/MS method; 30 mg oral dose. j.dmd.2025.100086

  • Mild open-eye hallucinations occurred in 5 of 16 subjects (31%) at doses of 10–20 mg oral in the Papaseit et al. study; these were not characterized as psychotic phenomenasupported

    mild hallucinations (5 subjects) fphar.2018.00206

  • Psilocybin at 15 mg produced greater dysphoria and ego dissolution than 2C-B at 20 mg in the Mallaroni et al. comparison, suggesting a lower acute psychological risk profile at these doses — though the steep dose-response curve documented by Shulgin means small dose increases could substantially alter this profile.supported

    2C-B showed lighter profile; less dysphoria and ego dissolution than psilocybin. cpt.2958

  • Caudevilla-Gálligo et al. reported lower incapacitation with 2C-B compared to ayahuasca or Salvia divinorum in their survey of recreational users.supported

    lower incapacitation than other psychedelics. 0269881111431752

  • Tolerance to 2C-B's psychedelic effects is expected to develop rapidly (within hours to days) through 5-HT₂A receptor downregulation and internalization — a mechanism demonstrated for the class by Wallach et al., who showed that β-arrestin-biased 5-HT₂A agonists induce receptor downregulation and tachyphylaxissupported

    Beta-arrestin-biased ligands block psychedelic effects and induce receptor downregulation and tachyphylaxis. s41467-023-44016-1

  • Claim in safety — inconclusiveinconclusiveworking →

  • Tramadol is a weak serotonin reuptake inhibitor and μ-opioid agonist; combined with 5-HT₂A agonists, the serotonergic burden creates a documented pathway to serotonin toxicitysupported

    Tramadol is a weak serotonin reuptake inhibitor; combinations with serotonergic drugs can precipitate life-threatening serotonin toxicity. pmid:16051647

  • Case reports of tramadol-related serotonin syndrome with serotonergic co-administration support this risksupported

    Case report: lithium addition precipitated serotonin syndrome in patient on tramadol and amitriptyline. bcr-2017-221383

  • Case reports of tramadol-related serotonin syndrome with serotonergic co-administration support this risksupported

    Case report of tramadol-SSRI serotonin syndrome. Tramadol has serotonergic properties that combine with other serotonergic drugs. ajcr.892264

  • Claim in safety — inconclusiveinconclusiveworking →

  • Claim in safety — inconclusiveinconclusiveworking →

  • MAO inhibitors: Since MAO-A and MAO-B are the primary metabolic enzymes for 2C-B, concurrent use of monoamine oxidase inhibitors — including irreversible inhibitors (phenelzine, tranylcypromine), reversible inhibitors (moclobemide), and selective MAO-B inhibitors (selegiline) — would be expected to substantially increase 2C-B plasma exposure, potentially to dangerous levelssupported

    MAO-A, MAO-B, cytosolic enzymes, and CYP2D6 identified as key metabolic enzymes. j.dmd.2025.100086

  • Claim in safety — inconclusiveinconclusiveworking →

  • Claim in safety — not_supportednot supportedworking →

  • Cardiovascular disease, uncontrolled hypertension, arrhythmia: Dose-dependent increases in blood pressure and heart rate at recreational doses represent added cardiovascular burden in individuals with compromised cardiac functionsupported

    n=16 recreational users, oral 10-15-20mg. Increased BP/HR. fphar.2018.00206

  • Concurrent MAOI use: MAO-A and MAO-B are the primary metabolic enzymes for 2C-Bsupported

    MAO-A, MAO-B, cytosolic enzymes, and CYP2D6 identified as key metabolic enzymes. j.dmd.2025.100086

  • Claim in safety — inconclusiveinconclusiveworking →

  • Claim in safety — inconclusiveinconclusiveworking →

pharmacology18 · 10 ok
  • Claim in pharmacology — not_supportednot supportedworking →

  • Claim in pharmacology — inconclusiveinconclusiveworking →

  • The psychedelic effects are mediated primarily through 5-HT₂A-Gq signaling rather than β-arrestin2 recruitment, consistent with the signaling pathway model established by Wallach et al. for psychedelic-potential prediction.supported

    5-HT2A-Gq (not beta-arrestin2) efficacy predicts psychedelic potential via head-twitch response magnitude in mice. s41467-023-44016-1

  • In vivo confirmation of 5-HT₂A agonism comes from head-twitch response (HTR) studies in C57BL/6J mice, where 2C-B produced an ED₅₀ of 2.43 μmol/kg — a validated behavioral proxy for hallucinogenic activity in humanssupported

    2C-B ED50=2.43 μmol/kg for head-twitch response in C57BL/6J mice; confirms in vivo 5-HT2A agonism. j.neuropharm.2018.10.037

  • This potency is approximately three-fold lower than DOB (ED₅₀ = 0.75 μmol/kg), consistent with the established potency-reducing effect of removing the alpha-methyl group from phenethylamine psychedelics.supported

    2C-B ED50=2.43 μmol/kg for head-twitch response in C57BL/6J mice. DOB (alpha-methyl analog) ED50=0.75 μmol/kg for comparison. j.neuropharm.2018.10.037

  • Villalobos et al. demonstrated that in Xenopus laevis oocytes expressing rat 5-HT₂A receptors, 2C-B acts as a functional antagonist, blocking 5-HT-induced currents, while maintaining partial agonist activity at 5-HT₂Csupported

    2C-B acts as 5-HT2A antagonist (blocking 5-HT-induced currents) but partial agonist at 5-HT2C in Xenopus oocytes. pmid:15006903

  • This divergence likely reflects differences between heterologous expression systems and intact neural circuits: the robust in vivo HTR data confirm functionally relevant 5-HT₂A agonism in living animals.supported

    2C-B ED50=2.43 μmol/kg for head-twitch response in C57BL/6J mice; confirms in vivo 5-HT2A agonism. j.neuropharm.2018.10.037

  • Claim in pharmacology — inconclusiveinconclusiveworking →

  • Claim in pharmacology — inconclusiveinconclusiveworking →

  • Ray profiled 2C-B alongside 24 other psychedelics at 51 receptor sites in the NIMH Psychoactive Drug Screening Program, demonstrating that phenylalkylamines are "not as selective as generally believed, interacting with 42 of 49 broadly assayed sites"supported

    Receptor affinity pharmacology of 25 psychedelic drugs at 51 receptors, transporters, and ion channels (NIMH-PDSP). Phenylalkylamines interact with 42 of 49 sites tested. journal.pone.0009019

  • Claim in pharmacology — inconclusiveinconclusiveworking →

  • Claim in pharmacology — inconclusiveinconclusiveworking →

  • Metabolism proceeds primarily through MAO-A and MAO-B-mediated oxidative deamination, producing 4-bromo-2,5-dimethoxyphenylacetic acid (BDMPAA) as the major urinary metabolite (73% of human urinary output), with 4-bromo-2-hydroxy-5-methoxyphenylacetic acid (B-2-HMPAA) accounting for 13%supported

    Human urine metabolite profile: 4-bromo-2,5-dimethoxyphenylacetic acid (73%), 4-bromo-2-hydroxy-5-methoxyphenylacetic acid (13%). MAO identified as key metabolic enzyme. j.1556-4029.2012.02289.x

  • Claim in pharmacology — inconclusiveinconclusiveworking →

  • Neither metabolite activates the 5-HT₂A receptor, confirming that the parent compound is solely responsible for psychedelic effectssupported

    Metabolites BDMPAA and B-2-HMPAA do not activate serotonin 2A receptor. j.dmd.2025.100086

  • CYP2D6 contributes a minor metabolic pathway.partially supported

    MAO-A, MAO-B, cytosolic enzymes, and CYP2D6 identified as key metabolic enzymes. j.dmd.2025.100086

  • Claim in pharmacology — inconclusiveinconclusiveworking →

  • A significant species difference exists in metabolic routing: O-demethylation followed by N-acetylation is the major pathway in rats but only a minor fraction in human urinesupported

    Human urine metabolite profile: 4-bromo-2,5-dimethoxyphenylacetic acid (73%)... MAO identified as key metabolic enzyme. Species differences from rat. j.1556-4029.2012.02289.x

summary12 · 6 ok
  • Claim in summary — inconclusiveinconclusiveworking →

  • Claim in summary — inconclusiveinconclusiveworking →

  • Claim in summary — inconclusiveinconclusiveworking →

  • Claim in summary — not_supportednot supportedworking →

  • 2C-B acts as a partial agonist at serotonin 5-HT₂A, 5-HT₂B, and 5-HT₂C receptors, with in vivo 5-HT₂A agonism confirmed by a head-twitch response ED₅₀ of 2.43 μmol/kg in mice — approximately three-fold less potent than its alpha-methylated analog DOBsupported

    2C-B ED50=2.43 μmol/kg for head-twitch response in C57BL/6J mice; confirms in vivo 5-HT2A agonism. DOB (alpha-methyl analog) ED50=0.75 μmol/kg for comparison. j.neuropharm.2018.10.037

  • Metabolism proceeds primarily through MAO-A/MAO-B-mediated oxidative deamination to inactive metabolites, with CYP2D6 as a minor pathway; plasma half-life is 1.43 hours at 20 mg oral.partially supported

    2C-B: Tmax 2.43h, t1/2 1.43h. cpt.2958

  • Metabolism proceeds primarily through MAO-A/MAO-B-mediated oxidative deamination to inactive metabolites, with CYP2D6 as a minor pathway; plasma half-life is 1.43 hours at 20 mg oral.partially supported

    MAO-A, MAO-B, cytosolic enzymes, and CYP2D6 identified as key metabolic enzymes. Metabolites BDMPAA and B-2-HMPAA do not activate serotonin 2A receptor. First human plasma PK study with validated LC-MS/MS method; 30 mg oral dose. j.dmd.2025.100086

  • The subjective experience spans visual intensification, color enhancement, and sensory amplification alongside entactogenic qualities — pleasure and sociability comparable to mdma — that scale steeply with dose into full psychedelic territorysupported

    psychedelic + entactogen profile; lower incapacitation than other psychedelics. 0269881111431752

  • The subjective experience spans visual intensification, color enhancement, and sensory amplification alongside entactogenic qualities — pleasure and sociability comparable to mdma — that scale steeply with dose into full psychedelic territorysupported

    2C-B classified as stimulant, hallucinogen, entactogen and/or empathogen. 643878

  • Claim in summary — inconclusiveinconclusiveworking →

  • Claim in summary — inconclusiveinconclusiveworking →

  • Tolerance develops rapidly through 5-HT₂A receptor downregulation, consistent with the serotonergic psychedelic class, though no substance-specific study confirms thissupported

    Beta-arrestin-biased ligands block psychedelic effects and induce receptor downregulation and tachyphylaxis. s41467-023-44016-1

pharmacokinetic-detail10 · 10 ok
  • Mallaroni et al. measured plasma concentrations in 22 healthy subjects following 20 mg oral administration in a double-blind, placebo-controlled design:supported

    First double-blind placebo-controlled comparison of 2C-B (20mg) vs psilocybin (15mg) in 22 healthy subjects. cpt.2958

  • Papaseit et al. measured oral fluid concentrations in 16 subjects at doses of 10–20 mg (mean 15.94 mg):supported

    n=16 recreational users, oral 10-15-20mg. fphar.2018.00206

  • Thomann et al. conducted the first validated LC-MS/MS pharmacokinetic and metabolite analysis using plasma from subjects who received 30 mg oral 2C-B, identifying BDMPAA and B-2-HMPAA as the primary plasma metabolitessupported

    Metabolites BDMPAA and B-2-HMPAA do not activate serotonin 2A receptor. First human plasma PK study with validated LC-MS/MS method; 30 mg oral dose. j.dmd.2025.100086

  • This study confirmed MAO-A, MAO-B, and cytosolic enzymes as the primary BDMPAA-forming pathway, with CYP2D6 identified as a minor metabolic contributor.supported

    MAO-A, MAO-B, cytosolic enzymes, and CYP2D6 identified as key metabolic enzymes. j.dmd.2025.100086

  • MAO-mediated oxidative deamination produces an aldehyde intermediate, which is subsequently oxidized by aldehyde dehydrogenase to BDMPAA (4-bromo-2,5-dimethoxyphenylacetic acid), accounting for 73% of human urinary metabolitessupported

    Human urine metabolite profile: 4-bromo-2,5-dimethoxyphenylacetic acid (73%)... MAO identified as key metabolic enzyme. j.1556-4029.2012.02289.x

  • BDMPAA is pharmacologically inactive at 5-HT₂Asupported

    Metabolites BDMPAA and B-2-HMPAA do not activate serotonin 2A receptor. j.dmd.2025.100086

  • The secondary metabolite B-2-HMPAA (4-bromo-2-hydroxy-5-methoxyphenylacetic acid) accounts for 13% of urinary output, with a minor alcohol metabolite (4-bromo-2,5-dimethoxyphenylethyl alcohol) contributing approximately 4.5%.supported

    4-bromo-2-hydroxy-5-methoxyphenylacetic acid (13%), alcohol metabolite (4.5%). j.1556-4029.2012.02289.x

  • These acetamide metabolites are only minor fractions in human urinesupported

    Human urine metabolite profile: 4-bromo-2,5-dimethoxyphenylacetic acid (73%), 4-bromo-2-hydroxy-5-methoxyphenylacetic acid (13%), alcohol metabolite (4.5%). Species differences from rat. j.1556-4029.2012.02289.x

  • Rohanova et al. characterized 2C-B pharmacokinetics in rats following subcutaneous administration:supported

    Rat SC disposition; half-life ~1.1 h; volume of distribution 16 L/kg; high brain:serum ratio (max 13.9); rapid BBB penetration; lung retention. j.toxlet.2008.01.017

  • Since MAO-A and MAO-B are the primary metabolic enzymes, concurrent administration of monoamine oxidase inhibitors would be expected to substantially increase 2C-B systemic exposuresupported

    MAO-A, MAO-B, cytosolic enzymes, and CYP2D6 identified as key metabolic enzymes. j.dmd.2025.100086

receptor-pharmacology9 · 5 ok
  • Claim in receptor-pharmacology — not_supportednot supportedworking →

  • Hansen et al. used 2C-B as the reference compound for a 48-member N-benzyl phenethylamine series, establishing its binding at 5-HT₂A and 5-HT₂C as the pharmacological foundation for the entire NBOMe drug classsupported

    48-compound SAR study using 2C-B as template; 5-HT2A affinity from subnanomolar to micromolar across series. cn400216u

  • Claim in receptor-pharmacology — inconclusiveinconclusiveworking →

  • Claim in receptor-pharmacology — inconclusiveinconclusiveworking →

  • In intact animals, 2C-B produces robust 5-HT₂A-mediated behavioral responses (HTR ED₅₀ = 2.43 μmol/kg)supported

    2C-B ED50=2.43 μmol/kg for head-twitch response in C57BL/6J mice; confirms in vivo 5-HT2A agonism. j.neuropharm.2018.10.037

  • In Xenopus laevis oocytes expressing rat 5-HT₂A receptors, however, Villalobos et al. found 2C-B to act as a functional antagonist, blocking serotonin-induced ion currents, while retaining partial agonist activity at 5-HT₂Csupported

    2C-B acts as 5-HT2A antagonist (blocking 5-HT-induced currents) but partial agonist at 5-HT2C in Xenopus oocytes. pmid:15006903

  • The 5-HT₂A-Gq signaling pathway, rather than β-arrestin2 recruitment, appears to mediate the psychedelic effects, and the oocyte current assay may preferentially detect different downstream signaling events than those responsible for hallucinogenic activity.supported

    5-HT2A-Gq (not beta-arrestin2) efficacy predicts psychedelic potential via head-twitch response magnitude in mice. s41467-023-44016-1

  • Ray's NIMH-PDSP screen demonstrated that 2C-B interacts with 42 of 49 assayed receptor sites, including serotonin, dopamine, adrenergic, and histamine targetssupported

    Phenylalkylamines interact with 42 of 49 sites tested. Diversity of receptor interaction underlies qualitative diversity of drug effects. journal.pone.0009019

  • Claim in receptor-pharmacology — inconclusiveinconclusiveworking →

comparative-pharmacology6 · 2 ok
  • The only published direct head-to-head comparison comes from Mallaroni et al., using 2C-B 20 mg vs. psilocybin 15 mg oral in 22 subjects.supported

    First double-blind placebo-controlled comparison of 2C-B (20mg) vs psilocybin (15mg) in 22 healthy subjects. cpt.2958

  • Claim in comparative-pharmacology — inconclusiveinconclusiveworking →

  • Claim in comparative-pharmacology — inconclusiveinconclusiveworking →

  • Claim in comparative-pharmacology — inconclusiveinconclusiveworking →

  • Claim in comparative-pharmacology — inconclusiveinconclusiveworking →

  • Rickli et al. profiled 2C-B alongside 2c-c, 2C-D, 2c-e, 2c-i, and mescaline in a comprehensive multi-receptor panel with comparison to lsdsupported

    In vitro receptor interaction profiles of NBOMe drugs vs 2C drugs (including 2C-B) and LSD. j.neuropharm.2015.08.034

clinical-evidence5 · 2 ok
  • Claim in clinical-evidence — inconclusiveinconclusiveworking →

  • The first published human pharmacological study of 2C-B used an observational design with 16 experienced recreational users at doses of 10–20 mg oral.supported

    n=16 recreational users, oral 10-15-20mg. fphar.2018.00206

  • Pharmacokinetic data from the 30 mg arm have been published by Thomann et al., but the primary comparative outcome results — the trial's core objective of head-to-head comparison across three doses of 2C-B against active comparators — have not appeared in peer-reviewed publication as of April 2026supported

    First human plasma PK study with validated LC-MS/MS method; 30 mg oral dose. j.dmd.2025.100086

  • Claim in clinical-evidence — inconclusiveinconclusiveworking →

  • Claim in clinical-evidence — inconclusiveinconclusiveworking →

neuroscience4 · 2 ok
  • Claim in neuroscience — inconclusiveinconclusiveworking →

  • Claim in neuroscience — inconclusiveinconclusiveworking →

  • The entactogenic component — pleasure and sociability without significant monoamine release — may reflect a distinct balance of 5-HT₂A versus 5-HT₂C activation, or contributions from the broad receptorome interactions documented by Ray.supported

    Diversity of receptor interaction underlies qualitative diversity of drug effects. Phenylalkylamines interact with 42 of 49 sites tested. journal.pone.0009019

  • How does 2C-B's functional antagonism at 5-HT₂A in heterologous expression systems reconcile with its clear 5-HT₂A-mediated behavioral effects in vivo? This preparation-dependent pharmacology remains mechanistically unexplained.supported

    2C-B acts as 5-HT2A antagonist (blocking 5-HT-induced currents) but partial agonist at 5-HT2C in Xenopus oocytes. pmid:15006903

chemistry3 · 2 ok
  • Claim in chemistry — not_supportednot supportedworking →

  • The absence of an alpha-methyl group on the ethylamine chain differentiates 2C-B from the corresponding amphetamine analog DOB (2,5-dimethoxy-4-bromoamphetamine), which is approximately three-fold more potent and substantially longer-acting.supported

    DOB (alpha-methyl analog) ED50=0.75 μmol/kg for comparison. j.neuropharm.2018.10.037

  • 2C-B also serves as the parent compound for the NBOMe series: N-benzylation at the amine produces 25B-NBOMe, a full 5-HT₂A agonist with dramatically increased potency and a substantially different safety profilesupported

    Reviews NBOMe structure-activity relationships, behavioral pharmacology, metabolism, and toxicity. 2C-B identified as reference compound for the 2C-X class. 7854_2016_64

effects-overview3 · 1 ok
  • Claim in effects-overview — inconclusiveinconclusiveworking →

  • Claim in effects-overview — inconclusiveinconclusiveworking →

  • Relative to psilocybin, 2C-B produces less dysphoria, less ego dissolution, and shorter duration at comparable recreational doses, while retaining equivalent psychomotor and spatial memory impairmentsupported

    2C-B showed lighter profile; less dysphoria and ego dissolution than psilocybin. Similar cognitive impairment. Effects resolved within 6h in 86.3% vs 63.6% for psilocybin. cpt.2958

history3 · 0 ok
  • Claim in history — inconclusiveinconclusiveworking →

  • Claim in history — not_supportednot supportedworking →

  • Claim in history — inconclusiveinconclusiveworking →

Other runs

  1. brief run2026-09-27completed2 minrun/bbeaebff…
  2. brief run2026-09-29completed3 minrun/f7a99940…

3Sources

29 consumed · sorted by year · feeds = sections resting on it

Sources
yearsourcetierstatusfeeds
2025Liquid chromatography-tandam mass spectrometry-based pharmacokinetic and metabolic analysis of 4-bromo-2,5-dimethoxyphenethylamine and its metabolites in human plasmaThomann J, Rudin D, Kraus S, Arikci D, Holze F, Liechti ME, Luethi D · Drug Metabolism and Dispositiondoi:10.1016/j.dmd.2025.100086strongconsumed6 sections
2024EUDA European Drug Report 2024/2023: New Psychoactive SubstancesEuropean Union Drugs Agency (EUDA)url:ebab85faaf312ad8weakconsumedcited only
2023Assessment of the Acute Effects of 2C-B vs. Psilocybin on Subjective Experience, Mood, and CognitionMallaroni P, Mason NL, Reckweg JT, Paci R, Ritscher S, Toennes SW, Theunissen EL, Kuypers KPC, Ramaekers JG · Clinical Pharmacology and Therapeuticsdoi:10.1002/cpt.2958strongconsumed8 sections
2023Identification of 5-HT2A receptor signaling pathways associated with psychedelic potentialWallach J, Cao AB, Calkins MM, Heim AJ, Lanham JK, et al. · Nature Communicationsdoi:10.1038/s41467-023-44016-1moderateconsumed4 sections
2020Novel Phenethylamines and Their Potential Interactions With Prescription Drugs: A Systematic Critical ReviewInan F, Brunt TM, Contrucci RR, Hondebrink L, Franssen EJF · Therapeutic Drug Monitoringdoi:10.1097/ftd.0000000000000725strongconsumedcited only
2019Comparison of the behavioral responses induced by phenylalkylamine hallucinogens and their tetrahydrobenzodifuran ("FLY") and benzodifuran ("DragonFLY") analogsHalberstadt AL, Chatha M, Stratford A, Grill M, Brandt SD · Neuropharmacologydoi:10.1016/j.neuropharm.2018.10.037moderateconsumed4 sections
2018Acute Pharmacological Effects of 2C-B in Humans: An Observational StudyPapaseit E, Farre M, Perez-Mana C, Torrens M, Ventura M, Pujadas M, de la Torre R, Gonzalez D · Frontiers in Pharmacologydoi:10.3389/fphar.2018.00206moderateconsumed8 sections
2017Pharmacology and Toxicology of N-Benzylphenethylamine (NBOMe) HallucinogensHalberstadt AL · Current Topics in Behavioral Neurosciencesdoi:10.1007/7854_2016_64strongconsumed2 sections
2017Serotonin syndrome in patients with headache disordersPrakash S, Adroja B, Parekh H · BMJ Case Reportsdoi:10.1136/bcr-2017-221383weakconsumed1 section
2016Canada Gazette: Regulations Amending Food and Drug Regulations (Part J — 2C-phenethylamines)Health Canadaurl:c1bfc79f6343981bweakconsumedcited only
2015Acute Effects of the Novel Psychoactive Drug 2C-B on EmotionsGonzalez D, Torrens M, Farre M · BioMed Research Internationaldoi:10.1155/2015/643878moderateconsumed2 sections
2015Pharmacokinetics, pharmacodynamics and toxicology of new psychoactive substances (NPS): 2C-B, 4-fluoroamphetamine and benzofuransNugteren-van Lonkhuyzen JJ, van Riel AJ, Brunt TM, Hondebrink L · Drug and Alcohol Dependencedoi:10.1016/j.drugalcdep.2015.10.011moderateconsumed1 section
2015Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs)Rickli A, Luethi D, Reinisch J, Buchy D, Hoener MC, Liechti ME · Neuropharmacologydoi:10.1016/j.neuropharm.2015.08.034moderateconsumed1 section
2015Synthesis and pharmacological evaluation of N-benzyl substituted 4-bromo-2,5-dimethoxyphenethylamines as 5-HT2A/2C partial agonistsHansen M, Jacobsen SE, Plunkett S, Liebscher GE, McCorvy JD, Brauner-Osborne H, Kristensen JL · Bioorganic & Medicinal Chemistrydoi:10.1016/j.bmc.2014.12.011moderateconsumed1 section
201425I-NBOMe: clinical case with unique confirmatory testingStellpflug SJ, Kealey SE, Hegarty CB, Janis GC · Journal of Medical Toxicologydoi:10.1007/s13181-013-0314-yweakconsumed1 section
2014Synthesis and Structure-Activity Relationships of N-Benzyl Phenethylamines as 5-HT2A/2C AgonistsHansen M, Phonekeo K, Paine JS, Leth-Petersen S, Begtrup M, Brauner-Osborne H, Kristensen JL · ACS Chemical Neurosciencedoi:10.1021/cn400216umoderateconsumed1 section
2014Transient serotonin syndrome caused by concurrent use of tramadol and selective serotonin reuptake inhibitorShakoor M, Ayub S, Ahad A, Ayub Z · American Journal of Case Reportsdoi:10.12659/ajcr.892264weakconsumedcited only
20132C or Not 2C: Phenethylamine Designer Drug ReviewDean BV, Stellpflug SJ, Burnett A, Engebretsen KM · Journal of Medical Toxicologydoi:10.1007/s13181-013-0295-xstrongconsumed2 sections
2013Analysis of 4-bromo-2,5-dimethoxyphenethylamine abuser's urine: identification and quantitation of urinary metabolitesKanamori T, Nagasawa K, Kuwayama K, Tsujikawa K, Iwata YT, Inoue H · Journal of Forensic Sciencesdoi:10.1111/j.1556-4029.2012.02289.xweakconsumed2 sections
20124-Bromo-2,5-dimethoxyphenethylamine (2C-B): presence in the recreational drug market in Spain, pattern of use and subjective effectsCaudevilla-Galligo F, Riba J, Ventura M, Gonzalez D, Farre M, Barbanoj MJ, Bouso JC · Journal of Psychopharmacologydoi:10.1177/0269881111431752moderateconsumed3 sections
2011Simultaneous detection of ten psychedelic phenethylamines in urine by gas chromatography-mass spectrometryKerrigan S, Banuelos S, Perrella L, Hardy B · Journal of Analytical Toxicologypmid:21871155moderateconsumed1 section
2010Psychedelics and the human receptoromeRay TS · PLoS ONEdoi:10.1371/journal.pone.0009019moderateconsumed3 sections
2008Disposition of 4-bromo-2,5-dimethoxyphenethylamine (2C-B) and its metabolite in rats after subcutaneous administrationRohanova M, Palenicek T, Balikova M · Toxicology Lettersdoi:10.1016/j.toxlet.2008.01.017moderateconsumed1 section
2005Monoamine oxidase inhibitors, opioid analgesics and serotonin toxicity.Gillman PK · British Journal of Anaesthesiapmid:16051647strongconsumed1 section
20044-Bromo-2,5-dimethoxyphenethylamine (2C-B) and structurally related phenylethylamines are potent 5-HT2A receptor antagonists in Xenopus laevis oocytesVillalobos CA, Bull P, Saez P, Cassels BK, Huidobro-Toro JP · British Journal of Pharmacologypmid:15006903moderateconsumed3 sections
20034-Bromo-2,5-Dimethoxyphenethylamine (2C-B): DEA Drug Information BulletinUS Drug Enforcement Administrationurl:1cba1ab68b495e4aweakconsumedcited only
2002In vivo metabolism of 4-bromo-2,5-dimethoxyphenethylamine (2C-B) in the rat: identification of urinary metabolitesKanamori T, Inoue H, Iwata Y, Ohmae Y, Kishi T · Journal of Analytical Toxicologypmid:11916016moderateconsumed1 section
20012C-B (Nexus) Reappears on the Club Drug Scene — NDIC Information BulletinNational Drug Intelligence Centerurl:e001befec07dc1efweakconsumedcited only
1991PiHKAL: A Chemical Love Story — Entry #20: 2C-BShulgin A, Shulgin Aurl:1b18c0f13f256828weakconsumedcited only

4Docket

one filing per activity — decisions, correspondence, reports

  1. 0012026-04-20revisionRevision 1

    Initial LLM generation (v5 pipeline, wiki)

    psx:substance/2c-b/version/1
  2. 0022026-06-04proposal29 value proposals approved together

    one review action inferred from a shared reviewer and instant — the graph records one activity per proposal

    29 items in this filing

    • dose_tier · light
    • dose_tier · common
    • dose_tier · strong
    • dose_tier · heavy
    • timeline · oral · onset
    • timeline · oral · come_up
    • timeline · oral · peak
    • timeline · oral · plateau
    • timeline · oral · resolution
    • timeline · oral · afterglow
    • toxicity
    • dependence · full
    • withdrawal
    • tolerance
    • dosage · oral
    • duration · oral · onset
    • duration · oral · come_up
    • duration · oral · peak
    • duration · oral · offset
    • duration · oral · total
    • duration · oral · aftereffects
    • contraindication · cardiovascular
    • contraindication · psychiatric
    • contraindication · psychiatric
    • contraindication · neurological
    • contraindication · other
    • contraindication · other
    • contraindication · pregnancy_breastfeeding
    psx:substance/2c-b/proposal/dose_tier/14f39341-c95e-42bf-89a3-2b2a17ab896d
  3. 0032026-06-04publicationPublication — backfill
  4. 0042026-09-27revisionr1.a1

    no edit summary recorded

    psx:substance/2c-b/version/2
  5. 0052026-09-29publicationPublication — publishagent-psx (local dev)

5Issued documents

what the notice, info card and emergency page said, by hash

Issued documents
documentcontent hashissuedfrom versionsuperseded
emergencyc15c760aabf6f0fcf5b6fc6b…2026-10-19 20:29Revision 2current
info_card44403e053a9d45e0e736d31f…2026-10-19 20:29Revision 2current
info_card8238ed62360c039a78460b91…2026-09-29 10:22Revision 2superseded2026-10-19
notice53ffc98bc5c175e403d133df…2026-09-29 10:22Revision 2current
emergency3f0909c25c714d225b4bb3e3…2026-09-04 04:27Revision 1superseded2026-10-19
info_cardb6ebfbbaeeef5d78cdb42d97…2026-09-04 04:27Revision 1superseded2026-09-29
notice64878b43a1d2932a5305f55b…2026-09-04 04:27Revision 1superseded2026-09-29