generation run 2026-05-11
79 min completedmodel pipeline-v5plan not recordedrun/32be7481…Selection
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The model's own caveats
2 further caveats recorded as free text — readable on the working page
Reproduce
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16 searches — query, source, results, what was kept and why
| # | source | query | seen | kept | rationale |
|---|---|---|---|---|---|
| 1 | PsychonautWiki | 2C-T comprehensive drug information | 1 | 1 | Community-sourced data corroborating brief seed data |
| 2 | OpenAlex | 2C-T phenethylamine psychedelic Shulgin PiHKAL synthesis | 57 | 3 | Most-cited reviews on 2C drug class pharmacology and toxicology |
| 3 | PubMed | 2C-T 4-methylthio phenethylamine psychedelic serotonin receptor | 1 | 1 | Only published study directly on structure-activity of the 2C-T family including 2C-T-2 and 2C-T-7 |
| 4 | PubMed · absence | 2C-T 4-methylthio-2,5-dimethoxyphenethylamine pharmacology | 0 | — | — |
| 5 | Web/DEA/Federal Register | 2C-T DEA Schedule I controlled substance legal status US UK EU | 10 | 2 | Legal status verification |
| 6 | Erowid/PiHKAL | PiHKAL entry for 2C-T #39 | 1 | 1 | Primary source for 2C-T human psychopharmacology, dosing, and synthesis history |
| 7 | PubMed | Jacob Shulgin sulfur analogues psychotomimetic phenethylamine | 3 | 3 | Complete historical series documenting early thiophenethylamine SAR |
| 8 | PubChem | 2C-T compound lookup by name | 1 | 1 | Verified chemical identity data from PubChem - primary database for chemical metadata |
| 9 | ClinicalTrials.gov · absence | 2C-T phenethylamine psychedelic | 0 | — | — |
| 10 | PubMed | 2C-T-x Shulgin phenethylamine synthesis psychedelic | 10 | 3 | Core historical papers establishing the thiophenethylamine series from which 2C-T derives |
| 11 | WebSearch | 2C-T 2C-T-x MAOI interaction mechanism MAO substrate thiophenethylamine | 10 | 2 | Pharmacological mechanism and MAOI interaction data |
| 12 | PubMed | Luethi 2018 2C-T drugs monoamine receptor profiles | 1 | 1 | Primary receptor binding data for the 2C-T drug class |
| 13 | Multiple sources | Cross-referencing seed data against PiHKAL and PsychonautWiki | 3 | 0 | Cross-reference to identify any seed data discrepancies |
| 14 | PubMed | Wagmann 2019 2C-series MAO human monoamine oxidase interactions | 1 | 1 | Direct evidence for MAO inhibition potential in 2C-series |
| 15 | Erowid | 2C-T Erowid experience report | 1 | 1 | Real-world experience data corroborating PiHKAL descriptions; subjective effects documentation |
| 16 | WebSearch/PsychonautWiki | 2C-T legal status UK Canada Australia Germany | 10 | 2 | International legal status for multiple key jurisdictions |
51 claims by section — every cited sentence, checked against its source
pharmacology11 · 11 ok
The compound binds 5-HT₂A with a Ki of 49 nM, as determined in radioligand displacement assayssupported
2C-T 5-HT2A Ki=49 nM s00213-022-06279-2
In the mouse head-twitch response (HTR) — a validated translational model for 5-HT₂A-mediated hallucinogenic activity in humans (correlation r = 0.9448) — 2C-T shows an ED₅₀ of 13.8 µmol/kg (i.p.).supported
Strong positive correlation (r=0.9448) between HTR potencies in mice and reported hallucinogenic potencies in humans across 36 compounds. j.neuropharm.2019.107933
In the mouse head-twitch response (HTR) — a validated translational model for 5-HT₂A-mediated hallucinogenic activity in humans (correlation r = 0.9448) — 2C-T shows an ED₅₀ of 13.8 µmol/kg (i.p.).supported
2C-T 5-HT2A Ki=49 nM, ED50=13.8 µmol/kg (mouse HTR) s00213-022-06279-2
Across the 2C-T-x class, functional pharmacology reveals partial agonism at both 5-HT₂A and 5-HT₂B receptors, with 5-HT₂B EC₅₀ values of 44–370 nMsupported
5-HT2B EC50 44-370 nM... Partial agonists at 5-HT2A/2B. j.neuropharm.2017.07.012
Monoamine transporter affinity is negligible (NET/DAT/SERT Ki > 4,000 nM), clearly distinguishing 2C-T-class compounds from stimulant phenethylamines.supported
no monoamine transporter activity (Ki >4000 nM) j.neuropharm.2017.07.012
Jacob and Shulgin demonstrated in 1981 that 4-thiomescaline and related thiophenethylamines serve as substrates for MAO in vitro, but found no correlation between MAO substrate activity and psychotomimetic potencysupported
All five compounds serve as MAO substrates in vitro; no correlation between MAO degradation and psychotomimetic potency. pmid:7310812
Wagmann et al. subsequently showed that 2C-series compounds exhibit weak-to-moderate MAO-A inhibition in vitro (IC₅₀ = 10–125 µM across 17 tested compounds), though 2C-T was not individually reportedsupported
17 phenethylamine drugs (2C-series) tested for MAO-A and MAO-B inhibition in vitro. 13 showed MAO-A inhibition, 11 showed MAO-B inhibition. IC50 values ranged 10-125 microM for MAO-A. dta.2494
The practical significance is metabolic: MAO enzymes represent the primary degradative pathway for 2C-T, and co-administration with MAOIs can potentiate effects by slowing oxidative deamination.supported
MAOI + phenethylamines may cause serotonin toxicity and hypertensive emergency. s40263-025-01256-7
The 2C-T-x class also displays high affinity for rat trace amine-associated receptor 1 (TAAR1; Ki = 5–68 nM) but does not interact with human TAAR1partially supported
rat TAAR1 5-68 nM j.neuropharm.2017.07.012
The following parameters are inferred from structural analogy to 2c-b, which has been characterized in a human observational study:supported
Observational study: 16 healthy experienced drug users took oral 2C-B. fphar.2018.00206
Tmax: Estimated 1–2 hours (2C-B Tmax ≈ 1 hour)supported
Max plasma concentrations at 1h (2C-B) fphar.2018.00206
receptor-pharmacology9 · 9 ok
2C-T binds to the 5-HT₂A receptor with a Ki of 49 nM, placing it at the upper (least potent) end of the 2C-T-x series range (1–54 nM)supported
2C-T 5-HT2A Ki=49 nM; 2C-T-2 Ki=9 nM; 2C-T-7 Ki=5.3 nM. s00213-022-06279-2
2C-T binds to the 5-HT₂A receptor with a Ki of 49 nM, placing it at the upper (least potent) end of the 2C-T-x series range (1–54 nM)supported
5-HT2A Ki 1-54 nM j.neuropharm.2017.07.012
In the mouse head-twitch response assay, 2C-T produces an ED₅₀ of 13.8 µmol/kg (i.p.), confirming hallucinogenic-range activity at this receptor.supported
2C-T ED50=13.8 µmol/kg (mouse HTR) s00213-022-06279-2
Extension from methylthio to ethylthio produces the most dramatic potency increase (approximately 5-fold in Ki, approximately 10-fold in HTR ED₅₀), with further chain elongation yielding diminishing returns.supported
2C-T Ki=49 nM, ED50=13.8 µmol/kg; 2C-T-2 Ki=9 nM, ED50=1.44; 2C-T-7 Ki=5.3 nM, ED50=2.12. s00213-022-06279-2
Across the 2C-T-x class, Luethi et al. characterized the following binding and activity ranges:supported
Characterized monoamine receptor and transporter interaction profiles of 2C-T drugs. j.neuropharm.2017.07.012
The negligible monoamine transporter affinity (Ki > 4,000 nM) across all 2C-T-x compounds cleanly separates their pharmacology from stimulant phenethylamines, which achieve their effects through transporter-mediated monoamine release or reuptake inhibition.supported
no monoamine transporter activity (Ki >4000 nM) j.neuropharm.2017.07.012
The 2C series displays weak-to-moderate MAO inhibition in vitro: among 17 tested 2C compounds, 13 inhibited MAO-A and 11 inhibited MAO-B, with MAO-A IC₅₀ values of 10–125 µM. 2C-T was not individually reported in this assay, but the class-level data indicate inhibitory potency three to four orders of magnitude weaker than clinical MAOIssupported
17 phenethylamine drugs (2C-series) tested for MAO-A and MAO-B inhibition in vitro. 13 showed MAO-A inhibition, 11 showed MAO-B inhibition. IC50 values ranged 10-125 microM for MAO-A. dta.2494
The primary relevance of MAO to 2C-T pharmacology is metabolic: as an MAO substrate, 2C-T is degraded by oxidative deamination, and exogenous MAO inhibition slows this clearance pathway.supported
All five compounds serve as MAO substrates in vitro. pmid:7310812
The primary relevance of MAO to 2C-T pharmacology is metabolic: as an MAO substrate, 2C-T is degraded by oxidative deamination, and exogenous MAO inhibition slows this clearance pathway.supported
MAOI + phenethylamines may cause serotonin toxicity and hypertensive emergency. s40263-025-01256-7
summary8 · 7 ok
With a 5-HT₂A binding affinity of Ki = 49 nM — approximately ten-fold weaker than its ethylthio and propylthio congeners — 2C-T is the least potent member of the series, active at oral doses of 60–100 mg with a total duration of 3–6 hours.partially supported
2C-T 5-HT2A Ki=49 nM; 2C-T-2 Ki=9 nM; 2C-T-7 Ki=5.3 nM. Increasing alkylthio chain length markedly increases potency. s00213-022-06279-2
Claim in summary — inconclusiveinconclusiveworking →
2C-T acts as a partial agonist at 5-HT₂A receptors (Ki = 49 nM; mouse head-twitch response ED₅₀ = 13.8 µmol/kg), with negligible monoamine transporter affinity (Ki > 4,000 nM) distinguishing it from stimulant phenethylaminespartially supported
2C-T 5-HT2A Ki=49 nM, ED50=13.8 µmol/kg (mouse HTR) s00213-022-06279-2
2C-T acts as a partial agonist at 5-HT₂A receptors (Ki = 49 nM; mouse head-twitch response ED₅₀ = 13.8 µmol/kg), with negligible monoamine transporter affinity (Ki > 4,000 nM) distinguishing it from stimulant phenethylaminessupported
Partial agonists at 5-HT2A/2B. no monoamine transporter activity (Ki >4000 nM). j.neuropharm.2017.07.012
The class exhibits weak in vitro MAO inhibitory activity, though 2C-T is more accurately characterized as an MAO substrate than a clinically meaningful inhibitor.partially supported
All five compounds serve as MAO substrates in vitro; no correlation between MAO degradation and psychotomimetic potency. pmid:7310812
The class exhibits weak in vitro MAO inhibitory activity, though 2C-T is more accurately characterized as an MAO substrate than a clinically meaningful inhibitor.partially supported
IC50 values ranged 10-125 microM for MAO-A. MAO inhibition cannot be excluded as pharmacological contributor for 2C-series compounds. dta.2494
The broader 2C class has been associated with sympathomimetic toxicity and at least five deaths involving higher-potency congeners in polydrug contextssupported
At least 5 deaths reported; excited delirium common among fatalities. Sympathomimetic and serotonin toxicity presentations. s13181-013-0295-x
The principal pharmacological risk is potentiation by MAO inhibitors, which slow oxidative deaminationsupported
MAOI + phenethylamines may cause serotonin toxicity and hypertensive emergency. s40263-025-01256-7
safety7 · 4 ok
The 2C drug class has been associated with a recognizable toxidrome at supratherapeutic doses:supported
Sympathomimetic and serotonin toxicity presentations. Hallucinations, agitation, hypertension, tachycardia, seizures, hyperthermia. s13181-013-0295-x
Claim in safety — inconclusiveinconclusiveworking →
Partial agonism at 5-HT₂B receptors is documented for the 2C-T-x class (EC₅₀ 44–370 nM)supported
5-HT2B EC50 44-370 nM... Partial agonists at 5-HT2A/2B. j.neuropharm.2017.07.012
Serotonin toxicity — characterized by hyperthermia, neuromuscular excitability, and altered mental status — is the principal danger.{{/Warning}}supported
MAOI + phenethylamines may cause serotonin toxicity and hypertensive emergency. s40263-025-01256-7
Claim in safety — inconclusiveinconclusiveworking →
Claim in safety — inconclusiveinconclusiveworking →
Concurrent MAO inhibitor use: prescription MAOIs, reversible MAOIs, and MAO-inhibiting plant preparations (ayahuasca, Syrian rue) — risk of serotonin syndrome and uncontrolled sympathomimetic crisissupported
MAOI + phenethylamines may cause serotonin toxicity and hypertensive emergency. Fatalities reported for MAOI + 5-MeO-DMT, amphetamines, MDMA, meperidine. s40263-025-01256-7
history6 · 1 ok
Claim in history — inconclusiveinconclusiveworking →
Claim in history — inconclusiveinconclusiveworking →
Claim in history — inconclusiveinconclusiveworking →
These papers established the structure-activity relationships for 4-alkylthio-substituted phenethylamines and amphetamines, demonstrating that sulfur substitution at the 4-position of the 2,5-dimethoxyphenethylamine scaffold produced compounds with psychotomimetic activity while also serving as substrates for monoamine oxidase.partially supported
3- and 4-thiomescaline found to be psychotomimetics in man. All five compounds serve as MAO substrates in vitro. pmid:7310812
Claim in history — inconclusiveinconclusiveworking →
Claim in history — inconclusiveinconclusiveworking →
comparative-pharmacology3 · 3 ok
The progression from methylthio (2C-T) to ethylthio (2C-T-2) to n-propylthio (2C-T-7) reflects a consistent increase in 5-HT₂A affinity and in vivo potency, with the methylthio-to-ethylthio step producing the most dramatic gain:partially supported
2C-T Ki=49 nM, ED50=13.8 µmol/kg; 2C-T-2 Ki=9 nM, ED50=1.44; 2C-T-7 Ki=5.3 nM, ED50=2.12. s00213-022-06279-2
2c-b (4-bromo-2,5-dimethoxyphenethylamine) is the most pharmacologically characterized member of the 2C family. 2C-B has been studied in controlled human settings, with published pharmacokinetic data (Tmax ≈ 1 h, duration 4–6 h) and a randomized comparison with psilocybin. 2C-T shares the 2,5-dimethoxyphenethylamine scaffold with 2C-B but substitutes a methylthio group for the bromine at position 4supported
Observational study: 16 healthy experienced drug users took oral 2C-B. Max plasma concentrations at 1h (2C-B). fphar.2018.00206
2c-b (4-bromo-2,5-dimethoxyphenethylamine) is the most pharmacologically characterized member of the 2C family. 2C-B has been studied in controlled human settings, with published pharmacokinetic data (Tmax ≈ 1 h, duration 4–6 h) and a randomized comparison with psilocybin. 2C-T shares the 2,5-dimethoxyphenethylamine scaffold with 2C-B but substitutes a methylthio group for the bromine at position 4supported
Double-blind, placebo-controlled study. 2C-B (20 mg) vs psilocybin (15 mg). 2C-B produced psychedelic alterations of consciousness with shorter duration than psilocybin (~6 hours). cpt.2958
clinical-evidence2 · 2 ok
The closest controlled human data within the 2C drug class come from studies of 2c-b, including an observational pharmacology study and a randomized crossover trial comparing 2C-B to psilocybinsupported
Observational study: 16 healthy experienced drug users took oral 2C-B. fphar.2018.00206
The closest controlled human data within the 2C drug class come from studies of 2c-b, including an observational pharmacology study and a randomized crossover trial comparing 2C-B to psilocybinsupported
Double-blind, placebo-controlled study. 2C-B (20 mg) vs psilocybin (15 mg) in 22 psychedelic-experienced participants. cpt.2958
pharmacokinetic-detail2 · 2 ok
This mechanism underlies the documented risk of serotonin toxicity when phenethylamine psychedelics are combined with MAOIssupported
MAOI + phenethylamines may cause serotonin toxicity and hypertensive emergency. s40263-025-01256-7
The following parameter estimates are extrapolated from the structural analog 2c-b, for which limited human data exist, and from community-reported duration data.supported
Observational study: 16 healthy experienced drug users took oral 2C-B. Max plasma concentrations at 1h (2C-B). fphar.2018.00206
chemistry1 · 1 ok
Chain extension of the thioether to ethylthio yields 2c-t-2, to n-propylthio yields 2c-t-7, and to butylthio yields 2C-T-19 — each step increasing 5-HT₂A affinity and in vivo potency.supported
2C-T Ki=49 nM; 2C-T-2 Ki=9 nM; 2C-T-7 Ki=5.3 nM. Increasing alkylthio chain length markedly increases potency. s00213-022-06279-2
legal-status1 · 0 ok
Claim in legal-status — inconclusiveinconclusiveworking →
neuroscience1 · 1 ok
As a 5-HT₂A partial agonist, the compound is expected to engage the same neural circuitry as other serotonergic psychedelics, including:supported
Receptor affinity pharmacology of 25 psychedelic drugs at 51 receptors. Phenylalkylamines interact with 42 of 49 sites. Diversity of receptor interaction underlies qualitative diversity of drug effects. journal.pone.0009019