generation run 2026-05-11
58 min completedmodel pipeline-v5plan not recordedrun/7f8a5582…Selection
Verification
- record
- seen / partial
- working
The model's own caveats
7 further caveats recorded as free text — readable on the working page
Reproduce
- inputs
- 22 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
24 searches — query, source, results, what was kept and why
| # | source | query | seen | kept | rationale |
|---|---|---|---|---|---|
| 1 | PubMed | 2-amino-1-(4-bromo-2,5-dimethoxyphenyl)ethanone | 2 | 2 | Both papers are primary sources directly characterizing bk-2C-B |
| 2 | OpenAlex | bk-2C-B beta-keto 2C-B cathinone phenethylamine | 23 | 0 | Results were not specific enough to bk-2C-B; general NPS reviews not directly relevant |
| 3 | PubMed | Nichols phenethylamine hallucinogen structure activity relationship 5-HT2A | 9 | 2 | Nichols 2018 review is the canonical SAR reference for phenethylamine psychedelics including 2C-B |
| 4 | PubMed | 2C-B pharmacology serotonin receptor binding psychedelic | 6 | 3 | Directly relevant to 2C-B pharmacological class mechanisms |
| 5 | PubChem | bk-2C-B | 1 | 1 | Primary chemical identity data for bk-2C-B confirmed |
| 6 | ClinicalTrials.gov · absence | bk-2C-B beta-keto 2C-B | 0 | 0 | Confirmed no registered clinical trials exist for this substance |
| 7 | PubMed · absence | bk-2C-B beta-keto phenethylamine psychedelic | 0 | 0 | No substance-specific papers found with this query |
| 8 | PubMed | 2C-B human effects subjective psychedelic pharmacokinetics | 3 | 2 | Key human pharmacology studies for the parent compound 2C-B, directly relevant to understanding effects of bk-2C-B as its cathinone analog |
| 9 | PubMed | bk-2C-B new psychoactive substance detection forensic toxicology | 2 | 2 | Documents real-world distribution and forensic identification of bk-2C-B |
| 10 | PubMed | cathinone serotonin 5-HT2A receptor agonist psychedelic hallucinogen | 2 | 1 | Liechti 2015 is canonical reference for cathinone monoamine pharmacology |
| 11 | PubMed | 2C-phenethylamine pharmacokinetics toxicology NPS 2015 | 4 | 1 | Direct pharmacokinetics and toxicology review of 2C-B, highly relevant to bk-2C-B analog |
| 12 | PubMed | get_pubmed_article 29593537, 37253161, 26318099, 32212672, 32249347 | 5 | 3 | Primary human pharmacology data for 2C-B and designer drug mechanisms |
| 13 | WebFetch | PsychonautWiki bk-2C-B page | 1 | 2 | Confirms DB seed data; establishes community-consensus provenance |
| 14 | WebSearch | bk-2C-B history first synthesis 2007 2008 online market | 10 | 1 | Establishes discovery and market history |
| 15 | PubMed | psychedelic tolerance serotonin 5-HT2A receptor downregulation cross-tolerance mechanism | 1 | 1 | Mechanistic basis for tolerance development observed in psychedelics including 2C-B class |
| 16 | Crossref | verify_doi 10.1002/dta.1699 and 10.1002/dta.2200 | 2 | 2 | API verification confirms these are real peer-reviewed publications |
| 17 | PubMed | cathinone beta-keto amphetamine norepinephrine dopamine serotonin transporter reuptake | 3 | 2 | Establish cathinone class mechanism relevant to inferring bk-2C-B pharmacology |
| 18 | WebSearch | bk-2C-B legal status scheduling UK US EU controlled substance | 10 | 2 | Legal status data not available through academic APIs; web search is primary source |
| 19 | Canada Gazette | — | 1 | 1 | Official government source for Canadian scheduling |
| 20 | WebSearch | bk-2C-B SMILES structure CAS number InChI | 10 | 2 | SMILES and CAS number not in PubChem API response; found via web sources |
| 21 | Erowid | — | 25 | 2 | Only community safety data source; cardiac event is safety-critical flag |
| 22 | PubChem | CID 11288812 | 1 | 1 | Verification of chemical identity data |
| 23 | PubMed | systematic analytical characterization new psychoactive substances 2016 | 1 | 0 | Not relevant to bk-2C-B specifically |
| 24 | ClinicalTrials.gov · absence | bk-2C-B | 0 | 0 | Confirms absence of registered clinical studies |
67 claims by section — every cited sentence, checked against its source
safety19 · 10 ok
Substituted cathinones as a class produce tachycardia, hypertension, and, in severe toxicity, hyperthermia, metabolic acidosis, and rhabdomyolysispartially supported
Adverse effects include tachycardia, hypertension, agitation, seizures, paranoia, hyperthermia. sar.s37257
The parent compound 2C-B increases blood pressure and heart rate at therapeutic doses in humanssupported
Increased BP/HR. fphar.2018.00206
The parent compound 2C-B increases blood pressure and heart rate at therapeutic doses in humanssupported
Transient pressor effects. cpt.2958
Heating βk-2C-B produces at least 12 pyrolysis products, none of which have been toxicologically characterizedsupported
12 pyrolysis products detected and verified by synthesis. Unknown pyrolysis product toxicity adds safety concern for inhalation route. dta.2200
Claim in safety — inconclusiveinconclusiveworking →
Claim in safety — inconclusiveinconclusiveworking →
Claim in safety — inconclusiveinconclusiveworking →
Claim in safety — inconclusiveinconclusiveworking →
Paranoia and agitation: The cathinone component may contribute additional risk of paranoia, agitation, and anxiety beyond what is typical for serotonergic psychedelics alone.supported
Adverse effects include tachycardia, hypertension, agitation, seizures, paranoia, hyperthermia. sar.s37257
Tolerance. Serotonergic psychedelic 5-HT₂A agonists produce rapid, near-complete tachyphylaxis mediated by 5-HT₂A receptor downregulation in the frontal cortex, a process independent of β-arrestin-2 and occurring after even single-dose administrationpartially supported
Repeated DOI induces progressive HTR decrease. 5-HT2AR downregulation in frontal cortex. Tolerance mechanism independent of beta-arrestin-2. acschemneuro.2c00170
Cross-tolerance exists within the psychedelic class (demonstrated between LSD and DOI in animal models)supported
Cross-tolerance between DOI and LSD. acschemneuro.2c00170
Cathinones as a class possess reinforcing properties in animal models of self-administration, but psychedelic phenethylamines are generally considered to have low dependence potential because rapid tolerance development prevents the sustained, escalating use patterns that drive dependence formationsupported
High abuse potential. No specific antidote. sar.s37257
Claim in safety — inconclusiveinconclusiveworking →
Claim in safety — inconclusiveinconclusiveworking →
Claim in safety — inconclusiveinconclusiveworking →
Claim in safety — inconclusiveinconclusiveworking →
Seizure disorders: Both cathinone-class stimulants and serotonergic psychedelics have been associated with seizure threshold reduction.supported
Adverse effects include tachycardia, hypertension, agitation, seizures, paranoia, hyperthermia. sar.s37257
Hepatic impairment: If CYP2D6 is involved in metabolism (by analogy to 2C-B-FLY), altered hepatic function could affect clearance. This is speculative.supported
2C-B-fly metabolized by CYP2D6 in HLM and by MAO-A. j.toxlet.2018.07.018
Claim in safety — inconclusiveinconclusiveworking →
pharmacology12 · 10 ok
Cathinone-type novel psychoactive substances function primarily as monoamine uptake inhibitors at the norepinephrine transporter (NET), dopamine transporter (DAT), and serotonin transporter (SERT), with cathinones generally demonstrating greater dopaminergic versus serotonergic selectivity compared to their non-beta-keto amphetamine analogssupported
Cathinones classified by transporter inhibition vs monoamine efflux. Cathinones have more dopaminergic vs serotonergic properties than non-beta-keto amphetamine analogs. 7854_2016_20
Cathinone-type novel psychoactive substances function primarily as monoamine uptake inhibitors at the norepinephrine transporter (NET), dopamine transporter (DAT), and serotonin transporter (SERT), with cathinones generally demonstrating greater dopaminergic versus serotonergic selectivity compared to their non-beta-keto amphetamine analogssupported
All potent NE uptake inhibitors. Cathinones differ in DA vs 5-HT inhibition profiles. None exhibit binding to monoamine receptors at relevant concentrations. j.neuropharm.2013.11.008
Substituted cathinones act as central nervous system stimulants primarily through catecholamine release and/or reuptake blockade at NET and DAT.supported
They act via catecholamine release and reuptake blockade. sar.s37257
The 2,5-dimethoxy motif contributes to in vivo potency at 5-HT₂A beyond what receptor affinity alone predictssupported
The motif appears important for in vivo potency beyond what receptor affinity alone predicts. acschemneuro.0c00129
However, phenethylamine analogs (2C-x class) exhibit lower intrinsic activity at 5-HT₂A than their phenylisopropylamine counterparts (DOx class), and the additional beta-keto modification may further reduce 5-HT₂A intrinsic activity or potency relative to 2C-Bsupported
Phenylisopropylamine analogs have significantly higher intrinsic activities at 5-HT2A than phenethylamine analogs. Beta-keto modification would further modify intrinsic activity. pmid:16277614
Claim in pharmacology — inconclusiveinconclusiveworking →
Parent compound 2C-B reference data. In the only published human pharmacokinetic assessment, oral 2C-B reached peak salivary concentrations (Tmax) approximately 1 hour after administrationsupported
Salivary Tmax 1h. fphar.2018.00206
Subjective effects of 2C-B (20 mg oral) largely resolved within 6 hours in a controlled within-subjects studysupported
2C-B 20mg vs psilocybin 15mg. Duration resolved within 6 hours. cpt.2958
Both studies documented increases in blood pressure and heart rate.supported
Increased BP/HR. fphar.2018.00206
Both studies documented increases in blood pressure and heart rate.supported
Transient pressor effects. cpt.2958
Claim in pharmacology — inconclusiveinconclusiveworking →
The structurally related compound 2C-B-FLY is metabolized by CYP2D6 in human liver microsomes and by MAO-A, suggesting CYP2D6 involvement is plausible for βk-2C-B, though undemonstrated.supported
2C-B-fly metabolized by CYP2D6 in HLM and by MAO-A. j.toxlet.2018.07.018
chemistry8 · 5 ok
This single structural modification places βk-2C-B at the intersection of two pharmacological traditions: the 4-bromo-2,5-dimethoxyphenyl aromatic scaffold that defines the 2C-x psychedelic series, and the alpha-aminoketone backbone that defines the cathinone stimulant class.supported
First reported test purchase and characterization of bk-2C-B. Identity confirmed by NMR, GC-MS, LC-MS. dta.1699
This single structural modification places βk-2C-B at the intersection of two pharmacological traditions: the 4-bromo-2,5-dimethoxyphenyl aromatic scaffold that defines the 2C-x psychedelic series, and the alpha-aminoketone backbone that defines the cathinone stimulant class.supported
Cathinones classified by transporter inhibition vs monoamine efflux. Cathinones have more dopaminergic vs serotonergic properties than non-beta-keto amphetamine analogs. 7854_2016_20
Claim in chemistry — inconclusiveinconclusiveworking →
Power et al. characterized both the commercially purchased material and the independently synthesized reference standardsupported
First reported test purchase and characterization of bk-2C-B... Synthesis via Delépine reaction. HCl/HBr salt mixture in purchased sample. dta.1699
The synthesized HCl salt and the purchased mixed salt exhibit distinct polymorphic crystal forms, confirmed by single-crystal X-ray diffraction.supported
X-ray crystallography confirmed polymorph structure. HCl/HBr salt mixture in purchased sample. dta.1699
The synthesis route employed by Power et al. proceeded through alpha-bromination of 1-(4-bromo-2,5-dimethoxyphenyl)ethanone (the corresponding acetophenone), followed by hexamethylenetetramine quaternization and acid hydrolysis to yield the free amine, which was converted to the hydrochloride salt.supported
Synthesis via Delépine reaction. dta.1699
Claim in chemistry — inconclusiveinconclusiveworking →
Claim in chemistry — inconclusiveinconclusiveworking →
pharmacokinetic-detail6 · 4 ok
Mallaroni et al. (2023), in a double-blind, placebo-controlled, within-subjects study (n=22), found that subjective effects of oral 2C-B (20 mg) largely resolved within 6 hourssupported
Double-blind placebo-controlled within-subjects study, n=22. 2C-B 20mg vs psilocybin 15mg. Duration resolved within 6 hours. cpt.2958
The study documented dose-dependent increases in systolic and diastolic blood pressure and heart rate.supported
Observational study, n=16, oral 2C-B 10-20mg. Increased BP/HR. fphar.2018.00206
Nugteren-van Lonkhuyzen et al. (2015) reviewed the pharmacokinetics, pharmacodynamics, and toxicology of 2C-B and related NPS compounds, providing additional context for the 2C-x class.supported
Reviews PK, PD and toxicology of 2C-B as a frequently detected NPS in Europe. j.drugalcdep.2015.10.011
Claim in pharmacokinetic-detail — inconclusiveinconclusiveworking →
Onset. Community consensus places oral onset at 20–70 minutes, somewhat slower and more variable than the approximately 1-hour Tmax reported for 2C-B.supported
Salivary Tmax 1h. fphar.2018.00206
Claim in pharmacokinetic-detail — inconclusiveinconclusiveworking →
receptor-pharmacology6 · 6 ok
Nichols (2018) confirms 5-HT₂A as the primary pharmacological target for the psychedelic effects of 2C-B and related phenethylaminessupported
5-HT2A receptor is principal target. Reviews 2C-B and related compounds. 7854_2017_475
Ray (2010) reported multi-receptor affinity data for 2C-B from the NIMH Psychoactive Drug Screening Program (PDSP), confirming activity at 5-HT₂A, 5-HT₂C, and additional serotonergic and adrenergic sitessupported
Receptor affinity pharmacology of 25 psychedelic drugs at 51 receptors/transporters/ion channels (NIMH-PDSP). Includes 2C-B receptor binding data. journal.pone.0009019
Rickli et al. (2015) characterized the receptor interaction profiles of 2C-x compounds including 2C-B in transfected cell systems, providing Ki values at monoamine transporters and serotonin receptors.supported
In vitro characterization of 2C drugs including 2C-B at monoamine transporters and receptors. Provides binding affinity data for 2C-B class. j.neuropharm.2015.08.034
Kolaczynska et al. (2019) profiled related 4-alkoxy-substituted 2,5-dimethoxyphenethylamines, reporting 5-HT₂A Ki values ranging from 61 to 4400 nM across this chemical class.supported
In vitro receptor binding of alkoxy-substituted 2,5-dimethoxyphenethylamines. 5-HT2A Ki values 61-4400 nM. fphar.2019.01423
Reduced 5-HT₂A intrinsic activity. Parrish and Nichols (2005) demonstrated that phenylisopropylamine analogs (DOx class) exhibit significantly higher intrinsic activities at 5-HT₂A than phenethylamine analogs (2C-x class) in phospholipase C activation assayssupported
Phenylisopropylamine analogs have significantly higher intrinsic activities at 5-HT2A than phenethylamine analogs. pmid:16277614
Shift toward dopaminergic selectivity. Cathinones as a class demonstrate greater dopaminergic versus serotonergic transporter selectivity compared to their non-beta-keto amphetamine analogssupported
Cathinones have more dopaminergic vs serotonergic properties than non-beta-keto amphetamine analogs. 7854_2016_20
comparative-pharmacology5 · 4 ok
The more pronounced stimulant character reported by users aligns with the cathinone scaffold's predicted shift toward dopaminergic/noradrenergic transporter activity.supported
Cathinones have more dopaminergic vs serotonergic properties than non-beta-keto amphetamine analogs. 7854_2016_20
The more pronounced stimulant character reported by users aligns with the cathinone scaffold's predicted shift toward dopaminergic/noradrenergic transporter activity.supported
All potent NE uptake inhibitors. Cathinones differ in DA vs 5-HT inhibition profiles. j.neuropharm.2013.11.008
Claim in comparative-pharmacology — inconclusiveinconclusiveworking →
Unlike βk-2C-B, 2C-B-FLY has published metabolic data showing CYP2D6-mediated metabolism and potent MAO-A inhibitionsupported
2C-B-fly metabolized by CYP2D6 in HLM and by MAO-A. MAO-A inhibition Ki 0.352 µM. j.toxlet.2018.07.018
Kolaczynska et al. (2019) profiled 4-alkoxy-substituted 2,5-dimethoxyphenethylamines, finding 5-HT₂A Ki values spanning 61–4400 nM across the class. βk-2C-B cannot be placed in this affinity landscape without direct binding data, but the beta-keto modification is expected to shift its position toward lower potency at 5-HT₂A based on the intrinsic activity reduction demonstrated for side-chain-modified phenethylamines.supported
In vitro receptor binding of alkoxy-substituted 2,5-dimethoxyphenethylamines. 5-HT2A Ki values 61-4400 nM. fphar.2019.01423
summary5 · 5 ok
The first peer-reviewed characterization — analytical identification by NMR, GC-MS, LC-HRMS, and X-ray crystallography of a test-purchased sample — was published by Power et al. in 2015partially supported
Identity confirmed by NMR, GC-MS, LC-MS. X-ray crystallography confirmed polymorph structure. dta.1699
Its dual classification as a norepinephrine–dopamine reuptake inhibitor and serotonin 5-HT₂A/₂C receptor agonist is inferred entirely from its hybrid structure: the 4-bromo-2,5-dimethoxyphenyl ring shared with 2c-b predicts serotonergic psychedelic activity, while the beta-keto carbonyl defines the cathinone scaffold associated with monoamine transporter inhibitionsupported
The 2,5-dimethoxyphenethylamine scaffold confers potent 5-HT2AR agonist activity. acschemneuro.0c00129
Its dual classification as a norepinephrine–dopamine reuptake inhibitor and serotonin 5-HT₂A/₂C receptor agonist is inferred entirely from its hybrid structure: the 4-bromo-2,5-dimethoxyphenyl ring shared with 2c-b predicts serotonergic psychedelic activity, while the beta-keto carbonyl defines the cathinone scaffold associated with monoamine transporter inhibitionsupported
Cathinones classified by transporter inhibition vs monoamine efflux. Cathinones have more dopaminergic vs serotonergic properties than non-beta-keto amphetamine analogs. 7854_2016_20
Heating the compound produces at least 12 pyrolysis products of uncharacterized toxicity, making inhalation routes particularly hazardoussupported
12 pyrolysis products detected and verified by synthesis. Unknown pyrolysis product toxicity adds safety concern for inhalation route. dta.2200
Tolerance develops rapidly via presumed 5-HT₂A receptor downregulation, consistent with the serotonergic psychedelic class, and the compound is not considered habit-formingsupported
5-HT2AR downregulation in frontal cortex. Tolerance mechanism independent of beta-arrestin-2. acschemneuro.2c00170
history4 · 4 ok
The first formal analytical characterization was published by Power et al. in 2015supported
First reported test purchase and characterization of bk-2C-B. dta.1699
Power et al. also completed an independent synthesis for reference standard comparison.supported
Synthesis via Delépine reaction. dta.1699
Odoardi et al. documented its presence among novel psychoactive substances seized in Italian forensic laboratories over that periodsupported
Italian NPS seizure analysis 2013-2015, 162 samples. bk-2C-B detected among seized materials. j.forsciint.2016.01.037
Consortium in Italy subsequently confirmed the compound's identity in seized materials using LC-MS/MS and NMR spectroscopy.supported
Multidisciplinary NPS identification using LC-MS/MS, GC-MS, and NMR; identified bk-2C-B in seized materials. 14756366.2017.1333987
clinical-evidence2 · 2 ok
The study was observational, unblinded, and lacked a placebo control.supported
Observational study, n=16, oral 2C-B 10-20mg. fphar.2018.00206
Effects largely resolved within 6 hours.supported
Duration resolved within 6 hours. cpt.2958