generation run 2026-05-03
50 min completedmodel pipeline-v5plan not recordedrun/a1bf87a7…Selection
Verification
- record
- seen / partial
- working
The model's own caveats
none raised on this run
Reproduce
- inputs
- 25 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
17 searches — query, source, results, what was kept and why
| # | source | query | seen | kept | rationale |
|---|---|---|---|---|---|
| 1 | PubChem | 2C-C | 1 | 1 | Primary chemical identity verification |
| 2 | PubMed | 25C-NBOMe detection forensic blood urine | 3 | 1 | Directly documents 2C-C in human biological samples |
| 3 | ClinicalTrials.gov · absence | 2C-C phenethylamine psychedelic | 0 | — | Confirmed no trials exist |
| 4 | PubMed | hallucinogen tolerance cross-tolerance tryptamine phenethylamine serotonin | 6 | 3 | Document cross-tolerance mechanisms relevant to 2C-class drugs |
| 5 | PubMed | 2C-C 5-HT2A receptor binding affinity phenethylamine hallucinogen | 3 | 2 | Eshleman 2014 directly measures 2C-C receptor binding and function |
| 6 | PubMed | designer phenethylamine 2C drugs novel psychoactive substance prevalence | 4 | 2 | Gil-Martins 2025 is most comprehensive review of 2C/NBOMe drugs |
| 7 | OpenAlex | 2C-C phenethylamine psychedelic serotonin receptor | 424 | 1 | Most cited paper with direct 2C drug receptor profile data |
| 8 | PubMed | 2C-C 4-chloro-2,5-dimethoxyphenethylamine pharmacology | 2 | 2 | Both papers directly study 2C-C pharmacology |
| 9 | Web search + Wikipedia | 2C-C legal status DEA scheduling UK EU controlled substance | 5 | 4 | Key jurisdictions for legal status section |
| 10 | Erowid | PiHKAL entry #22 2C-C | 1 | 1 | Primary historical source - Shulgin's own characterization of 2C-C |
| 11 | PsychonautWiki | 2C-C dose duration pharmacology | 1 | 1 | Confirms seed data in brief is community-consistent |
| 12 | PubChem (direct) | CID 29979100 | 1 | 1 | Chemical verification |
| 13 | OpenAlex | 2C-B 2C-I phenethylamine receptor binding | 10 | 3 | Class-level pharmacology papers relevant to 2C-C mechanism |
| 14 | Web search | Australia 2C-C Schedule 9 Poisons Standard | 3 | — | Legal status research - unconfirmed for Australia specifically |
| 15 | PubMed | hallucinogen tolerance cross-tolerance 5-HT2A receptor | 6 | 2 | Tolerance mechanism directly applicable to 2C-class |
| 16 | Canada Controlled Drugs and Substances Act | 2C-phenethylamine Schedule III Canada | 1 | 1 | Canada legal status confirmed |
| 17 | Web search | 2C-C CAS number SMILES structure | 5 | 2 | CAS number and SMILES not returned by PubChem API |
57 claims by section — every cited sentence, checked against its source
safety15 · 14 ok
Kim et al. (2021) documented neurotoxicity in rodents following high-dose 2C-C administration:supported
High doses induced microglial activation (neuroinflammation) in striatum. s00204-021-02980-x
The only identified case documenting 2C-C in a human fatality involved 25C-NBOMe poisoning, in which 2C-C was detected at low concentrations (0.12 ng/mL blood, 0.38 ng/mL urine) as a metabolite of the primary toxic agent rather than as the cause of death.supported
Accidental death associated with 25C-NBOMe. 2C-C detected in blood (0.12 ng/mL) and urine (0.38 ng/mL) alongside 25C-NBOMe, likely as metabolite. bkw035
Class-level acute toxicity for 2C compounds includes presentations consistent with sympathomimetic toxidrome or serotonin toxicity: agitation, hallucinations, aggression, hypertension, tachycardia, seizures, and hyperthermiasupported
Sympathomimetic and serotonin toxicity presentations. s13181-013-0295-x
At least five deaths have been reported in the broader 2C drug class literature, with excited delirium as a consistent finding among fatalitiessupported
At least 5 deaths reported; excited delirium common among fatalities. s13181-013-0295-x
Published human data for 2C-B (10–20 mg oral) confirmed increased systolic and diastolic blood pressure and heart rate. 2C-C is expected to produce similar cardiovascular effects, though potentially at higher absolute doses given its lower potencysupported
n=16 recreational users, oral 10-15-20mg 2C-B. Increased BP/HR. fphar.2018.00206
Gil-Martins et al. (2025) reviewed cardiovascular complications of the 2C/NBOMe class, including hypertension and arrhythmia.supported
Comprehensive review of psychedelic pathways of 2C and NBOMe designer drugs; serotonergic interactions, cardiovascular complications, neurotoxicity, abuse potential. j.toxrep.2025.101890
Claim in safety — inconclusiveinconclusiveworking →
Targeted LC-MS/MS methods are required for confirmation.supported
LC-MS/MS method for 15 designer psychostimulants in urine including 2C-C. LOD 0.5 ng/mL. 1556-4029.12306
Acute psychological distress ("bad trips"): anxiety, panic, paranoia, dysphoria, confusion. Risk correlates with dose, set, and setting. The 2C class review by Dean et al. (2013) documents agitation, aggression, and dysphoria among intoxication presentations.supported
Excited delirium common among fatalities. Sympathomimetic and serotonin toxicity presentations. s13181-013-0295-x
This mechanism is blocked by 5-HT₂A antagonist pretreatment and is independent of β-arrestin2 signaling.supported
Tolerance involves 5-HT2A receptor downregulation; independent of beta-arrestin-2. acschemneuro.2c00170
Smith et al. (2014) demonstrated that phenethylamine hallucinogens (DOI, 2C-T-7) develop insurmountable cross-tolerance, and that phenethylamine-class compounds develop tolerance more rapidly than tryptaminessupported
Tolerance developed to HTR elicited by DOI and 2C-T-7 but not tryptamines DPT/DIPT. Cross-tolerance between phenethylamine hallucinogens. Suggests phenethylamines may have greater tolerance liability than tryptamines. jpet.114.219337
However, Kim et al. (2021) demonstrated dose-dependent conditioned place preference in mice and increased self-administration in rats — preclinical indicators of abuse potential that challenge the conventional "non-addictive" characterization of serotonergic psychedelicssupported
2C-C and 2C-P produced conditioned place preference in mice and increased self-administration in rats, suggesting abuse potential. s00204-021-02980-x
Gil-Martins et al. (2025) further examined abuse potential across the 2C and NBOMe classessupported
Comprehensive review of psychedelic pathways of 2C and NBOMe designer drugs; serotonergic interactions, cardiovascular complications, neurotoxicity, abuse potential. j.toxrep.2025.101890
Coadministration with a 5-HT₂A agonist creates a dual serotonergic burden with substantially elevated serotonin syndrome risksupported
Case report of possible serotonin syndrome with tramadol and SSRI combination. Documents serotonergic mechanism of tramadol. pmid:9034418
The dopaminergic involvement demonstrated for 2C-C at high doses may compound with dopaminergic stimulants.supported
Affected D1/D2 dopamine receptor expression, DAT phosphorylation in nucleus accumbens and medial prefrontal cortex. s00204-021-02980-x
comparative-pharmacology8 · 4 ok
Papaseit et al. (2018) provided the only published controlled human pharmacology data for a halogenated 2C compound, studying 2C-B at 10–20 mg oral in recreational userssupported
n=16 recreational users, oral 10-15-20mg 2C-B. Increased BP/HR. Euphoria, perceptual changes, mild hallucinations (5 subjects). fphar.2018.00206
Claim in comparative-pharmacology — inconclusiveinconclusiveworking →
Claim in comparative-pharmacology — inconclusiveinconclusiveworking →
Claim in comparative-pharmacology — inconclusiveinconclusiveworking →
The N-benzyl moiety dramatically increases 5-HT₂A binding affinity, resulting in a potency increase of approximately 10–20x in vivopartially supported
NBOMes displayed higher affinity for 5-HT2A than 2C counterparts but weaker in functional assays. j.neuropharm.2018.02.033
Claim in comparative-pharmacology — inconclusiveinconclusiveworking →
2C-C appears as a metabolite of 25C-NBOMe in vivo, formed via hepatic N-debenzylation.supported
NBOMe metabolism includes N-dealkylation back to 2C-C analog. fnins.2020.00078
Phenethylamine hallucinogens develop tolerance more rapidly than tryptamines — an experimentally demonstrated difference with clinical relevance for dosing intervals.supported
Tolerance developed to HTR elicited by DOI and 2C-T-7 but not tryptamines DPT/DIPT. Suggests phenethylamines may have greater tolerance liability than tryptamines. jpet.114.219337
pharmacology8 · 3 ok
Claim in pharmacology — inconclusiveinconclusiveworking →
Claim in pharmacology — inconclusiveinconclusiveworking →
The psychedelic potential of 5-HT₂A agonists correlates specifically with Gq-coupled phospholipase C/IP₃ signaling rather than β-arrestin2 recruitment, as demonstrated by head-twitch response studies in micesupported
5-HT2A-Gq (not beta-arrestin2) efficacy predicts psychedelic potential via head-twitch response. Beta-arrestin-biased ligands block psychedelic effects. s41467-023-44016-1
Elmore et al. (2018) confirmed that 2C-C at 0.1–3.0 mg/kg (subcutaneous, rats) induced characteristic 5-HT₂A-mediated behaviors — wet dog shakes and back muscle contractions — fully abolished by the selective 5-HT₂A antagonist M100907supported
2C-C tested at 0.1-3.0 mg/kg sc. M100907 pretreatment reversed all behaviors. j.neuropharm.2018.02.033
Claim in pharmacology — inconclusiveinconclusiveworking →
Claim in pharmacology — inconclusiveinconclusiveworking →
Claim in pharmacology — inconclusiveinconclusiveworking →
In a fatality attributed to 25C-NBOMe, 2C-C was detected at 0.12 ng/mL in blood and 0.38 ng/mL in urine.supported
2C-C detected in blood (0.12 ng/mL) and urine (0.38 ng/mL) alongside 25C-NBOMe, likely as metabolite. bkw035
pharmacokinetic-detail6 · 4 ok
Elimination: 2C-C was detected in urine at 0.38 ng/mL in a 25C-NBOMe fatality case, confirming renal excretion of at least the intact parent compound or minimally modified metabolites.supported
2C-C detected in blood (0.12 ng/mL) and urine (0.38 ng/mL) alongside 25C-NBOMe, likely as metabolite. bkw035
The following estimates are drawn from structural analogy with 2C-B, for which limited human data exist:supported
n=16 recreational users, oral 10-15-20mg 2C-B. fphar.2018.00206
Claim in pharmacokinetic-detail — inconclusiveinconclusiveworking →
Kerrigan et al. (2014) validated a forensic LC-MS/MS method for 2C-C detection in urine with a limit of detection (LOD) of 0.5 ng/mL and a linear range of 0.5–100 ng/mLsupported
LC-MS/MS method for 15 designer psychostimulants in urine including 2C-C. LOD 0.5 ng/mL. Linear 0.5-100 ng/mL. 1556-4029.12306
GC-EI-MS and HPLC-electrospray-MS screening methods have also been published for the broader phenethylamine classsupported
GC-EI-MS screening method for designer tryptamines and phenethylamines in blood and urine. pmid:15516287
Claim in pharmacokinetic-detail — inconclusiveinconclusiveworking →
summary6 · 6 ok
The compound's primary research significance lies in comparative pharmacology — it serves as the chloro reference point in structure-activity relationship studies of halogenated phenethylamines — and in preclinical abuse liability modeling.supported
Reviews SAR for classic serotonergic hallucinogens (tryptamines, ergolines, phenethylamines). 5-HT2A as principal target. Key structural features for activity in phenethylamine class discussed. 7854_2017_475
The compound's primary research significance lies in comparative pharmacology — it serves as the chloro reference point in structure-activity relationship studies of halogenated phenethylamines — and in preclinical abuse liability modeling.supported
2C-C and 2C-P produced conditioned place preference in mice and increased self-administration in rats, suggesting abuse potential. s00204-021-02980-x
In vitro binding data exist but numerical Ki values remain inaccessible outside the full text of a single comparative studysupported
In vitro receptor binding and function data for 2C-C, 2C-D, 2C-E, 2C-I, 2C-T-2, and DOC. s00213-013-3303-6
Behaviorally, 2C-C induces 5-HT₂A-mediated responses in rats (wet dog shakes, back muscle contractions) fully blocked by the selective antagonist M100907supported
2C-C tested at 0.1-3.0 mg/kg sc. M100907 pretreatment reversed all behaviors. j.neuropharm.2018.02.033
Rodent studies demonstrate neurotoxicity (microglial activation, memory impairment) and abuse potential (conditioned place preference, self-administration) at high doses, a finding that contrasts with the conventional low-abuse-liability framing of serotonergic psychedelicssupported
2C-C and 2C-P produced conditioned place preference in mice and increased self-administration in rats, suggesting abuse potential. High doses decreased locomotor activity, motor performance, and memory test scores. High doses induced microglial activation (neuroinflammation) in striatum. s00204-021-02980-x
Tolerance develops rapidly via 5-HT₂A receptor downregulation, with cross-tolerance to other phenethylamine and tryptamine hallucinogenspartially supported
Tolerance developed to HTR elicited by DOI and 2C-T-7 but not tryptamines DPT/DIPT. Cross-tolerance between phenethylamine hallucinogens. jpet.114.219337
neuroscience5 · 1 ok
Claim in neuroscience — inconclusiveinconclusiveworking →
Claim in neuroscience — inconclusiveinconclusiveworking →
Claim in neuroscience — inconclusiveinconclusiveworking →
The Gq signaling pathway — rather than β-arrestin2 recruitment — is the specific transduction arm associated with psychedelic behavioral markers (head-twitch response)supported
5-HT2A-Gq (not beta-arrestin2) efficacy predicts psychedelic potential via head-twitch response. s41467-023-44016-1
Claim in neuroscience — inconclusiveinconclusiveworking →
receptor-pharmacology5 · 4 ok
Eshleman et al. (2014) is the only published study reporting in vitro receptor binding and transporter interaction data for 2C-C specifically, in a comparative panel including 2C-D, 2C-E, 2C-I, 2C-T-2, and DOCsupported
In vitro receptor binding and function data for 2C-C, 2C-D, 2C-E, 2C-I, 2C-T-2, and DOC. Includes transporter binding. s00213-013-3303-6
Claim in receptor-pharmacology — inconclusiveinconclusiveworking →
Elmore et al. (2018) demonstrated that 25C-NBOMe (the N-2-methoxybenzyl derivative of 2C-C) was substantially more potent than 2C-C in vivo, consistent with the higher 5-HT₂A binding affinity conferred by the N-benzyl moiety.partially supported
NBOMes displayed higher affinity for 5-HT2A than 2C counterparts but weaker in functional assays. j.neuropharm.2018.02.033
Ray (2010) profiled 25 psychedelics across 51 receptors using the NIMH Psychoactive Drug Screening Program (PDSP); 2C-C was not among the compounds studiedsupported
Receptor affinity pharmacology of 25 psychedelic drugs at 51 receptors, transporters, and ion channels (NIMH-PDSP). Note: 2C-C was not among the 25 drugs assayed. journal.pone.0009019
Eshleman et al. (2014) characterized 2C-C's interactions with monoamine transporters (DAT, NET, SERT)supported
Includes transporter binding, mouse locomotion, and rat drug discrimination data. s00213-013-3303-6
clinical-evidence3 · 3 ok
Kim et al. (2021) conducted the most comprehensive preclinical characterization, examining locomotor activity, motor coordination (rota-rod), memory (Y-maze, novel object recognition, passive avoidance), conditioned place preference, self-administration, and neurochemistry in rodentssupported
High doses decreased locomotor activity, motor performance, and memory test scores. Conditioned place preference in mice and increased self-administration in rats. Affected D1/D2 dopamine receptor expression, DAT phosphorylation. s00204-021-02980-x
Eshleman et al. (2014) combined in vitro receptor/transporter binding with mouse locomotion and rat drug discriminationsupported
In vitro receptor binding and function data for 2C-C... Includes transporter binding, mouse locomotion, and rat drug discrimination data. s00213-013-3303-6
Elmore et al. (2018) characterized in vivo behavioral pharmacology including 5-HT₂A-mediated responses.supported
Investigated in vitro and in vivo pharmacology... 2C-C tested at 0.1-3.0 mg/kg sc. M100907 pretreatment reversed all behaviors. j.neuropharm.2018.02.033
chemistry1 · 0 ok
Claim in chemistry — inconclusiveinconclusiveworking →