generation run 2026-05-11
70 min completedmodel pipeline-v5plan not recordedrun/8cbe3e4d…Selection
Verification
- record
- seen / partial
- working
The model's own caveats
1 further caveat recorded as free text — readable on the working page
Reproduce
- inputs
- 21 source keys (listed under Sources)
- plan
- not recorded — template version, prompt hash and git SHA are written from 2026-09 onward
- model
- pipeline-v5
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- none — agent transcripts are persisted from 2026-09 onward
21 searches — query, source, results, what was kept and why
| # | source | query | seen | kept | rationale |
|---|---|---|---|---|---|
| 1 | WebSearch | 3C-P 3,5-dimethoxy-4-propoxyphenylisopropylamine Shulgin PiHKAL history | 10 | 2 | Historical context for discovery timeline |
| 2 | OpenAlex | 3C-P mescaline analog phenethylamine psychedelic amphetamine | 10 | 3 | Selected papers with direct relevance to 3C-P pharmacology and chemical characterization |
| 3 | Erowid | — | — | 1 | Primary historical source for discovery of proscaline; 3C-P mentioned in PiHKAL as related compound |
| 4 | Erowid | — | — | 3 | Community-level harm reduction data for a compound with no published human pharmacology studies |
| 5 | WebSearch | 3C-P phenethylamine legal status scheduling United States United Kingdom | 10 | 1 | Legal status data for major jurisdictions |
| 6 | isomerdesign countyourculture blog | — | — | 1 | Historical context for discovery of proscaline family including 3C-P's phenethylamine progenitor |
| 7 | PubMed | 3C-P 3,5-dimethoxy-4-propoxyphenethylamine psychedelic | 1 | 1 | Only paper directly testing 3C-P in a pharmacological assay |
| 8 | Erowid | — | — | 1 | Primary source for Shulgin's predictions about 3C-P and the related proscaline bioassay |
| 9 | PubChem | 3C-P | 1 | 1 | Primary chemical identity confirmed via PubChem |
| 10 | PubMed Central | — | — | 2 | Only quantitative rodent pharmacology data specifically for 3C-P |
| 11 | PubMed | mescaline analogs phenethylamine serotonin 5-HT2A binding affinity hallucinogen | 3 | 3 | Contextual pharmacology for 5-HT2A agonism in mescaline-class compounds |
| 12 | Erowid | site:erowid.org 3C-P experience report | 10 | 3 | Primary user-report data for 3C-P subjective effects; no controlled human studies exist |
| 13 | PubMed (direct article fetch) | PMID 14761703 | 1 | 1 | Foundational hallucinogens pharmacology review |
| 14 | Multiple sources | 3C-P SMILES molecular formula stereochemistry | — | 1 | Cross-verification of chemical identity data |
| 15 | PubMed | tramadol serotonin syndrome mechanism opioid 5-HT reuptake inhibition | 4 | 1 | Mechanism for dangerous 3C-P + tramadol interaction |
| 16 | WebSearch | 3C-P legal status Australia Canada Germany scheduling | 10 | 1 | Legal status for major jurisdictions required for article |
| 17 | NCATS Inxight Drugs | — | — | 3 | Official chemical identifiers including missing CAS number and SMILES string |
| 18 | PubMed | hallucinogen cross tolerance psychedelic LSD psilocybin mescaline serotonin 5-HT2A receptor | 2 | 2 | Key papers establishing cross-tolerance mechanism relevant to 3C-P tolerance profile |
| 19 | NCATS + PubChem + cross-reference | 3C-P chemical identifiers SMILES CAS stereochemistry | — | 1 | Full chemical identity package for handoff file |
| 20 | WebSearch | Trachsel 2002 phenethylamine synthesis proscaline 3C-P characterization publication | 10 | 1 | Historical synthesis reference for 3C-P |
| 21 | WebSearch | Liechti mescaline clinical study Neuropsychopharmacology 2021 randomized placebo controlled | 10 | 3 | High-quality RCTs on mescaline parent compound; definitive pharmacokinetic and pharmacodynamic data applicable to 3C-P class |
52 claims by section — every cited sentence, checked against its source
safety14 · 7 ok
Claim in safety — inconclusiveinconclusiveworking →
Claim in safety — inconclusiveinconclusiveworking →
At least five fatalities have been reported for the 2C seriessupported
At least 5 deaths. s13181-013-0295-x
The mescaline systematic review documents hypertension, headache, nausea, and vomiting as the most common adverse effects, with no deaths specifically attributed to pure mescaline.supported
Common AEs: hypertension, headache, nausea, vomiting. Limited quality evidence. ijms27073081
Claim in safety — inconclusiveinconclusiveworking →
Claim in safety — inconclusiveinconclusiveworking →
Cross-tolerance extends to all serotonergic hallucinogens, including lsd, psilocybin, and mescaline, via the shared 5-HT₂A receptor downregulation mechanism.supported
5-HT2A receptor is primary site of hallucinogen action. Cross-tolerance among serotonergic hallucinogens documented. j.bbr.2014.07.016
Cross-tolerance extends to all serotonergic hallucinogens, including lsd, psilocybin, and mescaline, via the shared 5-HT₂A receptor downregulation mechanism.supported
Cross-tolerance between phenylalkylamines and indoleamines. 5-HT2A mediates characteristic effects. j.neuropharm.2011.01.017
Serotonergic hallucinogens as a class are not considered habit-forming and do not produce physical dependencesupported
Hallucinogens physiologically safe, do not produce dependence. pmid:14761703
Tramadol and its active metabolites inhibit the serotonin transporter (SERT) in human cellssupported
Tramadol inhibits human SERT in HEK293 cells. s00204-018-2244-6
Claim in safety — inconclusiveinconclusiveworking →
Severe cases can be fatal.supported
At least 5 deaths. Treatment primarily supportive. s13181-013-0295-x
Claim in safety — inconclusiveinconclusiveworking →
Claim in safety — inconclusiveinconclusiveworking →
pharmacology11 · 8 ok
Both demonstrated approximately 50% greater molar potency than TMA (3,4,5-trimethoxyamphetamine, the α-methyl homolog of mescaline)supported
3C-E and 3C-P were essentially equipotent, both ~50% more potent than TMA. 0269881119826610
Phenylalkylamine hallucinogens are selective 5-HT₂ receptor agonists, in contrast to indoleamine hallucinogens (e.g., LSD, psilocybin) which interact with a broader receptor repertoiresupported
Phenylalkylamine hallucinogens are selective 5-HT2 receptor agonists. j.neuropharm.2011.01.017
Claim in pharmacology — inconclusiveinconclusiveworking →
Direct confirmation that the mescaline-class mechanism is 5-HT₂A-mediated comes from controlled human studies in which co-administration of the selective 5-HT₂A antagonist ketanserin significantly attenuated all subjective effects of mescaline. 3C-P is expected to act via the same receptor mechanism, though no blocking study or receptor binding assay has been performed with this specific compound.supported
Ketanserin attenuated effects, confirming 5-HT2A as primary mechanism. s41398-024-03116-2
The only published quantitative pharmacological study of 3C-P is Halberstadt et al. 2019, which measured the head twitch response (HTR) in C57BL/6J mice — a 5-HT₂A-mediated behavior with established predictive validity for human hallucinogenic potency.supported
HTR experiments conducted with mescaline, escaline, proscaline, TMA, 3C-E, 3C-P, TMA-2, MEM, MPM... Potency relationships in HTR closely parallel human hallucinogenic data. 0269881119826610
The only published quantitative pharmacological study of 3C-P is Halberstadt et al. 2019, which measured the head twitch response (HTR) in C57BL/6J mice — a 5-HT₂A-mediated behavior with established predictive validity for human hallucinogenic potency.supported
Potency relationships in HTR closely parallel human hallucinogenic data. 0269881119826610
Claim in pharmacology — inconclusiveinconclusiveworking →
Claim in pharmacology — inconclusiveinconclusiveworking →
Plasma elimination half-life is approximately 3.5 hours, with Tmax at approximately 2 hours after oral dosingsupported
Dose-proportional PK, Tmax ~2h, t½ ~3.5h s41398-024-03116-2
Mean subjective effect duration at pharmacologically active doses (500 mg mescaline sulfate equivalent) is 11.1 hours, with a range of 6.4–14 hours across doses.supported
Mescaline effect duration mean 11.1h s41386-023-01607-2
Mean subjective effect duration at pharmacologically active doses (500 mg mescaline sulfate equivalent) is 11.1 hours, with a range of 6.4–14 hours across doses.supported
effect duration 6.4-14h s41398-024-03116-2
receptor-pharmacology7 · 7 ok
The compound's classification as a 5-HT₂A/5-HT₂C agonist rests on structural class membership — it is a 3,5-dimethoxy-4-alkoxy-substituted amphetamine, a pharmacological class defined by selective 5-HT₂ receptor agonism — and on its activity in the murine head twitch response, a behavior mediated exclusively by 5-HT₂A receptors.supported
Phenylalkylamine hallucinogens are selective 5-HT2 receptor agonists... 5-HT2A mediates characteristic effects. j.neuropharm.2011.01.017
The compound's classification as a 5-HT₂A/5-HT₂C agonist rests on structural class membership — it is a 3,5-dimethoxy-4-alkoxy-substituted amphetamine, a pharmacological class defined by selective 5-HT₂ receptor agonism — and on its activity in the murine head twitch response, a behavior mediated exclusively by 5-HT₂A receptors.supported
HTR experiments conducted with... 3C-P... Potency relationships in HTR closely parallel human hallucinogenic data. 0269881119826610
While no direct binding data exist for 3C-P, extensive receptor interaction profiling has been performed on structurally related compounds in the 2,5-dimethoxy-4-substituted phenethylamine and amphetamine seriessupported
Receptor binding affinities of 2C-O and DO-alkoxy derivatives at 5-HT1A, 5-HT2A, 5-HT2C, TAAR1, alpha-adrenergic, D2 and monoamine transporters. fphar.2019.01423
While no direct binding data exist for 3C-P, extensive receptor interaction profiling has been performed on structurally related compounds in the 2,5-dimethoxy-4-substituted phenethylamine and amphetamine seriessupported
Characterized receptor binding profiles of NBOMe drugs vs 2C drugs and LSD. Provides 5-HT2A binding data for phenethylamine psychedelics. j.neuropharm.2015.08.034
The divergent structure-activity relationships between these two substitution patterns — documented in the HTR assay — suggest that receptor selectivity and binding kinetics may also differsupported
HTR experiments conducted with mescaline, escaline, proscaline, TMA, 3C-E, 3C-P, TMA-2, MEM, MPM. 0269881119826610
Homology modeling of the 5-HT₂A receptor with mescaline-class ligands indicates that the 3,4,5-substitution pattern requires conformational freedom for efficacious binding, a constraint not present in the 2,4,5 series.supported
3 and 5 methoxy groups must remain conformationally mobile to enable receptor activation. pmid:9301661
The prolonged subjective duration (10–16 hours) relative to the expected plasma half-life (estimated at 3–5 hours based on mescaline analog data) could reflect extended receptor occupancy, slow tissue redistribution, the contribution of active metabolites, or some combination thereofsupported
Mescaline effect duration mean 11.1h; plasma t½ ~3.5h s41386-023-01607-2
comparative-pharmacology6 · 5 ok
Mescaline at pharmacologically active doses (300–500 mg sulfate salt, oral) produces altered states of consciousness comparable in intensity to LSD 100 μg and psilocybin 20 mgsupported
Mescaline 300/500mg vs LSD 100μg vs psilocybin 20mg. Subjective effects comparable at equivalent doses. s41386-023-01607-2
Mescaline's adverse effect profile includes nausea, headache, hypertension, and tachycardia as the most common events. 3C-P's more stimulant-dominant phenomenology, operating at dramatically lower absolute doses (20–40 mg vs 300–500 mg), suggests partial pharmacological differentiation despite structural similaritypartially supported
Common AEs: hypertension, headache, nausea, vomiting. ijms27073081
This establishes that extending the 4-position alkoxy chain from methyl (TMA) to ethyl (3C-E) increases potency, but further extension to propyl (3C-P) does not yield additional gains — suggesting a potency plateau at the ethoxy chain length in this regiochemistry.supported
3C-E and 3C-P were essentially equipotent, both ~50% more potent than TMA. 0269881119826610
The only head-to-head pharmacological comparison involving 3C-P is the Halberstadt et al. 2019 HTR study, which tested multiple mescaline-class compounds under identical conditions:supported
HTR experiments conducted with mescaline, escaline, proscaline, TMA, 3C-E, 3C-P, TMA-2, MEM, MPM. 0269881119826610
Claim in comparative-pharmacology — inconclusiveinconclusiveworking →
This divergence indicates that the two regiochemistries engage the 5-HT₂A receptor through different binding geometries, consistent with earlier homology modeling work showing that the 3,4,5 pattern requires conformational flexibility for efficacious receptor engagement.supported
3 and 5 methoxy groups must remain conformationally mobile to enable receptor activation. pmid:9301661
chemistry3 · 1 ok
This regiochemical difference confers fundamentally distinct structure-activity relationships: in the 3,4,5-substitution pattern, extending the 4-position alkoxy chain from methyl to ethyl to propyl progressively increases hallucinogenic potency, whereas in the 2,4,5-series such homologation does not alter potency.partially supported
3C-E and 3C-P were essentially equipotent, both ~50% more potent than TMA. 0269881119826610
Claim in chemistry — inconclusiveinconclusiveworking →
Claim in chemistry — inconclusiveinconclusiveworking →
clinical-evidence3 · 3 ok
One murine head twitch response studysupported
HTR experiments conducted with mescaline, escaline, proscaline, TMA, 3C-E, 3C-P, TMA-2, MEM, MPM. 0269881119826610
Structural analog inference from mescaline clinical datasupported
Randomized double-blind placebo-controlled crossover in 32 healthy participants. Mescaline 300/500mg... s41386-023-01607-2
Structural analog inference from mescaline clinical datasupported
Randomized double-blind crossover in 16 healthy subjects: mescaline 100-800mg... s41398-024-03116-2
neuroscience3 · 1 ok
Claim in neuroscience — inconclusiveinconclusiveworking →
For mescaline specifically, controlled studies confirm that its subjective effects are entirely attributable to 5-HT₂A agonism, as demonstrated by complete attenuation with the selective antagonist ketanserin.partially supported
Ketanserin attenuated effects, confirming 5-HT2A as primary mechanism. s41398-024-03116-2
Claim in neuroscience — inconclusiveinconclusiveworking →
summary3 · 2 ok
No clinical pharmacological characterization has been published; the sole quantitative study is a murine head twitch response assay establishing an ED₅₀ of 2.45 mg/kg.supported
3C-P ED50=2.45 mg/kg (molar 8.47 μmol/kg) 0269881119826610
3C-P is presumed to act as a 5-HT₂A/5-HT₂C receptor agonist based on structural class membership and its capacity to elicit the head twitch response in mice — a behavior selectively mediated by 5-HT₂A activationsupported
Potency relationships in HTR closely parallel human hallucinogenic data. 0269881119826610
Claim in summary — inconclusiveinconclusiveworking →
history1 · 1 ok
The sole published pharmacological study was conducted by Halberstadt and colleagues in 2019, establishing 3C-P's potency in the murine head twitch response assaysupported
HTR experiments conducted with mescaline, escaline, proscaline, TMA, 3C-E, 3C-P, TMA-2, MEM, MPM. 3C-P ED50=2.45 mg/kg 0269881119826610
pharmacokinetic-detail1 · 0 ok
Claim in pharmacokinetic-detail — inconclusiveinconclusiveworking →