generation run 2026-05-10
67 min completedmodel pipeline-v5plan not recordedrun/d9c5559f…Selection
Verification
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- seen / partial
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The model's own caveats
5 further caveats recorded as free text — readable on the working page
Reproduce
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- 28 source keys (listed under Sources)
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17 searches — query, source, results, what was kept and why
| # | source | query | seen | kept | rationale |
|---|---|---|---|---|---|
| 1 | PubMed | DPT dipropyltryptamine pharmacology serotonin receptor | 10 | 4 | DPT is N-propyl analog of EPT; best available pharmacological analog data |
| 2 | WebSearch | EPT N-ethyl-N-propyltryptamine psychedelic drug chemistry | 10 | 3 | Primary sources for history and basic pharmacology information |
| 3 | PMC | EPT crystal structure CaaMTech | 1 | 1 | Primary source for EPT solid-state structure |
| 4 | PubMed | sigma-1 receptor tryptamine DMT hallucinogen endogenous | 10 | 2 | Sigma-1 receptor data relevant to tryptamine class mechanism |
| 5 | PubMed | metabolite markers synthetic tryptamine EPT 5-MeO-EPT drug testing analysis | 1 | 1 | Only published metabolic characterization of EPT specifically |
| 6 | PubMed | substituted tryptamine receptor binding affinity serotonin 5-HT2A | 15 | 2 | Kozell covers structural analog pharmacology; Puigseslloses covers amino-terminal SAR for tryptamines |
| 7 | PubMed · absence | EPT N-ethyl-N-propyltryptamine psychedelic tryptamine | 0 | — | — |
| 8 | OpenAlex | dipropyltryptamine DPT psychotherapy hallucinogen serotonin receptor pharmacology | 10 | 4 | Reviews providing tryptamine class context and DPT human data |
| 9 | WebSearch | DPT dipropyltryptamine Grof psychotherapy clinical human study 1970s | 10 | 2 | Human DPT data for structural analog section |
| 10 | PubChem | EPT tryptamine / N-ethyl-N-propyltryptamine | 1 | 1 | Primary chemical identity verification |
| 11 | WebSearch | EPT ethylpropyltryptamine legal status scheduling Japan novel psychoactive substance | 10 | 3 | Legal status and forensic identification data |
| 12 | WebSearch | EPT ethylpropyltryptamine United States Federal Analog Act Schedule I Australia scheduling | 10 | 2 | Legal status data for jurisdictions |
| 13 | ClinicalTrials.gov · absence | EPT ethylpropyltryptamine tryptamine psychedelic | 0 | — | — |
| 14 | OpenAlex | EPT ethylpropyltryptamine N-ethyl-N-propyltryptamine tryptamine | 1 | 1 | Analytical method development paper covering EPT detection in blood |
| 15 | Crossref | DOI 10.1007/s11419-020-00556-5 | 1 | 1 | Confirms forensic identification paper |
| 16 | PubMed | Chadeayne CaaMTech tryptamine crystal structure hydrofumarate | 3 | 1 | Primary source for EPT structural characterization |
| 17 | PubMed | psychedelic abuse dependence potential tryptamine serotonergic hallucinogen | 5 | 2 | Safety and interaction data for EPT harm reduction section |
58 claims by section — every cited sentence, checked against its source
safety12 · 7 ok
Bergh and colleagues identified unique hydroxy-EPT metabolite markers in postmortem blood, demonstrating the forensic utility of their metabolite identification methodsupported
Metabolite usefulness demonstrated by identification in a human postmortem blood sample with suspected EPT or 4-OH-EPT intoxication. dta.3668
At the class level, classical serotonergic psychedelics (including unsubstituted tryptamines) are generally considered to have low acute physical toxicity relative to their psychoactive dosesupported
Comprehensive review of NPS tryptamines including structure, pharmacology, recreational use, toxicology, analytical methods, and cases of death. 1570159x13666141210222409
Claim in safety — inconclusiveinconclusiveworking →
Claim in safety — inconclusiveinconclusiveworking →
Kopra and colleagues characterized psychedelic-related deaths in England, Wales, and Northern Ireland (1997–2022) and found that fatalities, though uncommon, do occur — often in the context of polydrug use or high-risk behavior.supported
Systematic characterization of psychedelic-related deaths 1997-2022. Fatalities associated with psychedelics appear rare. j.pnpbp.2024.111177
Tolerance: Repeated administration of 5-HT₂A agonists produces rapid receptor downregulation in frontal cortexsupported
DOI caused 5-HT2AR downregulation in frontal cortex. acschemneuro.2c00170
Tryptamine-derived hallucinogens (DPT, DiPT) exhibit less tolerance development than phenethylamine hallucinogens (DOI, 2C-T-7) in these assays, suggesting EPT may have a somewhat more favorable tolerance profile than phenethylamine psychedelics.supported
Tolerance developed to HTR elicited by daily DOI but not DPT or DIPT. Phenethylamine-derived hallucinogens may have reduced therapeutic suitability due to rapid tolerance; tryptamine-derived hallucinogens show reduced potential for tolerance development. jpet.114.219337
Claim in safety — inconclusiveinconclusiveworking →
Rached and colleagues document fatalities for MAOIs combined with 5-MeO-DMT, agitation for DMT + MAOI combinations, and rhabdomyolysis for tryptamine-MAOI pairingssupported
Agitation reported for 5-MeO-DMT and DMT with MAOIs. Fatalities reported for MAOIs with 5-MeO-DMT. Rhabdomyolysis reported for 5-MeO-DMT and DMT. s40263-025-01256-7
Claim in safety — inconclusiveinconclusiveworking →
Claim in safety — inconclusiveinconclusiveworking →
CYP2D6 inhibitors: CYP2D6 participates in DMT metabolism via indole hydroxylationsupported
DMT rapidly metabolised by CYP2D6... Formation of mono-, di- and tri-oxygenated metabolites by hydroxylation on the indole core. 00498254.2023.2278488
pharmacology11 · 9 ok
EPT is presumed to act primarily as a partial agonist at 5-HT₂A receptors, the principal target mediating psychedelic effects across the tryptamine classsupported
Affinities, potencies and efficacies of 21 substituted tryptamines at 5-HT1A, 5-HT2A, 5-HT2C receptors and SERT measured using HEK cells. jpet.122.001454
DPT, the closest structural analog, produces full substitution for LSD and psilocybin in drug discrimination assays in rodents and primates, an effect completely antagonized by the selective 5-HT₂A antagonist MDL 100907partially supported
DPT produced partial to full substitution for LSD and psilocybin in drug discrimination assays. 5-HT2A antagonist effects were more profound than 5-HT1A antagonist, suggesting dual receptor mediation. pmid:17905422
DPT, the closest structural analog, produces full substitution for LSD and psilocybin in drug discrimination assays in rodents and primates, an effect completely antagonized by the selective 5-HT₂A antagonist MDL 100907partially supported
DPT produced full substitution for DOM. 5-HT2A antagonists shifted DPT dose-response curves. Schild analysis confirmed 5-HT2A as predominant mediating receptor for DPT hallucinogenic discriminative stimulus effects. jpet.108.145458
DPT also acts as a partial agonist at 5-HT₁A receptors (IC₅₀ ~0.1 µM at human 5-HT₁A), with 5-HT₁A agonism modulating the hallucinogenic effect — DPT's 5-HT₂A-mediated actions mask its 5-HT₁A component in behavioral assayssupported
DPT inhibits [3H]8-OH-DPAT binding with IC50 of 0.1 micromol/l at human 5-HT1a receptor. DPT is a moderate affinity partial agonist at the human 5-HT1a receptor. pmid:15886504
DPT also acts as a partial agonist at 5-HT₁A receptors (IC₅₀ ~0.1 µM at human 5-HT₁A), with 5-HT₁A agonism modulating the hallucinogenic effect — DPT's 5-HT₂A-mediated actions mask its 5-HT₁A component in behavioral assayssupported
DPT showed >95% DOM-lever responding blocked by 5-HT2A antagonist MDL100907. DPT has agonist activity at both 5-HT1A and 5-HT2A receptors. pmid:17551320
DPT also acts as a substrate (not a blocker) at the serotonin transporter (SERT Ki ~0.594 µM) and vesicular monoamine transporter 2 (VMAT2 Ki ~19 µM), suggesting potential for intraneuronal accumulation via carrier-mediated uptakesupported
DPT inhibits SERT with Ki of 0.594 microM. High binding-to-uptake ratios support tryptamines as transporter substrates at both SERT and VMAT2. s00702-009-0308-8
Claim in pharmacology — inconclusiveinconclusiveworking →
Structure-activity data from 5-MeO-DMT derivatives indicate that the molecular bulk of the N-amino group significantly influences SERT affinity and the selectivity balance between 5-HT₁A and 5-HT₂Asupported
Molecular size of amino group significantly influenced SERT affinity. All examined 5-MeO-tryptamines exhibited selectivity for 5-HT1AR over 5-HT2AR. s41380-024-02506-8
Primary clearance is expected via monoamine oxidase A (MAO-A), by class analogy with DMT, whose rapid inactivation by MAO-A is the dominant metabolic pathway for short-chain dialkyl tryptamines. CYP2D6 participates in DMT metabolism via indole hydroxylation; this enzyme may also contribute to EPT clearancesupported
MAO-A primary clearance; CYP2D6 and CYP2C19 also involved. s13318-023-00822-y
Primary clearance is expected via monoamine oxidase A (MAO-A), by class analogy with DMT, whose rapid inactivation by MAO-A is the dominant metabolic pathway for short-chain dialkyl tryptamines. CYP2D6 participates in DMT metabolism via indole hydroxylation; this enzyme may also contribute to EPT clearancesupported
DMT rapidly metabolised by CYP2D6... Formation of mono-, di- and tri-oxygenated metabolites by hydroxylation on the indole core. 00498254.2023.2278488
Claim in pharmacology — inconclusiveinconclusiveworking →
receptor-pharmacology9 · 8 ok
DPT functions as a 5-HT₂A agonist with hallucinogenic properties confirmed by drug discrimination studies: DPT fully substitutes for LSD and psilocybin in rats, and this discriminative stimulus is abolished by the selective 5-HT₂A antagonist MDL 100907 (M100907)partially supported
DPT produced partial to full substitution for LSD and psilocybin in drug discrimination assays. 5-HT2A antagonist effects were more profound than 5-HT1A antagonist, suggesting dual receptor mediation. pmid:17905422
DPT functions as a 5-HT₂A agonist with hallucinogenic properties confirmed by drug discrimination studies: DPT fully substitutes for LSD and psilocybin in rats, and this discriminative stimulus is abolished by the selective 5-HT₂A antagonist MDL 100907 (M100907)partially supported
DPT produced full substitution for DOM. 5-HT2A antagonists shifted DPT dose-response curves. Schild analysis confirmed 5-HT2A as predominant mediating receptor for DPT hallucinogenic discriminative stimulus effects. jpet.108.145458
Claim in receptor-pharmacology — inconclusiveinconclusiveworking →
DPT acts as a partial agonist at human 5-HT₁A receptors with an IC₅₀ of approximately 0.1 µMsupported
DPT inhibits [3H]8-OH-DPAT binding with IC50 of 0.1 micromol/l at human 5-HT1a receptor. DPT is a moderate affinity partial agonist at the human 5-HT1a receptor. pmid:15886504
Thermodynamic binding analyses have further characterized DPT's interaction at this targetsupported
DPT is a partial agonist at human 5-HT1aR; examined as non-peptide agonist control. Binding is entropy driven. 000312684
In behavioral assays, 5-HT₁A agonism modulates DPT's hallucinogenic effect: the 5-HT₂A-mediated discriminative stimulus masks 5-HT₁A contributions, indicating that the phenomenological output is a composite of activity at both receptorssupported
DPT showed >95% DOM-lever responding blocked by 5-HT2A antagonist MDL100907. DPT has agonist activity at both 5-HT1A and 5-HT2A receptors. pmid:17551320
DPT acts as a substrate at SERT (Ki ~0.594 µM) and VMAT2 (Ki ~19 µM) in a substrate-not-blocker pattern — it is transported into the presynaptic terminal rather than inhibiting reuptake, with subsequent accumulation in synaptic vesiclessupported
DPT inhibits SERT with Ki of 0.594 microM. High binding-to-uptake ratios support tryptamines as transporter substrates at both SERT and VMAT2. s00702-009-0308-8
Whether EPT behaves as a SERT substrate has not been tested, but non-ring-substituted tryptamines consistently exhibit SERT interaction in class surveys.supported
Affinities, potencies and efficacies of 21 substituted tryptamines at 5-HT1A, 5-HT2A, 5-HT2C receptors and SERT measured using HEK cells. jpet.122.001454
Structure-activity analysis of 5-MeO-DMT derivatives demonstrates that increasing N-alkyl bulk modulates the SERT-to-5-HT₁A/5-HT₂A selectivity ratiosupported
Molecular size of amino group significantly influenced SERT affinity. All examined 5-MeO-tryptamines exhibited selectivity for 5-HT1AR over 5-HT2AR. s41380-024-02506-8
history6 · 2 ok
Claim in history — inconclusiveinconclusiveworking →
Claim in history — inconclusiveinconclusiveworking →
Claim in history — inconclusiveinconclusiveworking →
Schuller and colleagues subsequently included EPT in a validated 96-well electromembrane extraction method for tryptamine analogs in whole blood, confirming its status as a tracked forensic analyte.supported
Simultaneous extraction of 20 tryptamines from whole blood including EPT using 96-well EME. Method validated for 16 tryptamines, LOD 0.15-0.75 nM. EPT is among the 20 analytes covered. j.talo.2022.100171
Richards and colleagues used intramuscular DPT as a short-acting psychedelic adjunct in brief psychotherapy with cancer patients experiencing existential distresssupported
30 cancer patients with psychological distress received ~12h conventional psychotherapy and a single DPT-assisted session. DPT used as a short-acting psychedelic adjunct to therapy. ngub-v4rm-t7dc-xth3
Claim in history — inconclusiveinconclusiveworking →
summary6 · 5 ok
The published literature consists of a single crystal structure of its hydrofumarate salt and an in vitro metabolite characterization using human liver microsomessupported
The solid-state structures of the hydrofumarate salts of EPT and MALT are reported. s2056989020008683
The published literature consists of a single crystal structure of its hydrofumarate salt and an in vitro metabolite characterization using human liver microsomessupported
Major in vitro EPT metabolites: hydroxylation, N-dealkylation, and carbonylation. dta.3668
As a non-ring-substituted dialkyl tryptamine, EPT is presumed to act primarily as a partial agonist at 5-HT₂A and 5-HT₁A receptors, by structural analogy with DPTsupported
5-HT2A antagonist effects were more profound than 5-HT1A antagonist, suggesting dual receptor mediation. pmid:17905422
One human postmortem case involving suspected EPT or 4-hydroxy-EPT has been documented, though full clinical details remain unpublishedsupported
Metabolite usefulness demonstrated by identification in a human postmortem blood sample with suspected EPT or 4-OH-EPT intoxication. dta.3668
Claim in summary — inconclusiveinconclusiveworking →
Tolerance develops through 5-HT₂A receptor downregulation, with cross-tolerance to other serotonergic psychedelicssupported
DOI caused 5-HT2AR downregulation in frontal cortex. Cross-tolerance between DOI and LSD. acschemneuro.2c00170
comparative-pharmacology5 · 5 ok
DPT's pharmacodynamic profile — full 5-HT₂A agonism confirmed by drug discrimination and selective antagonism, partial 5-HT₁A agonism, and SERT substrate behavior — provides the strongest available predictor of EPT's receptor activitysupported
DPT produced partial to full substitution for LSD and psilocybin in drug discrimination assays. 5-HT2A antagonist effects were more profound than 5-HT1A antagonist, suggesting dual receptor mediation. pmid:17905422
DPT's pharmacodynamic profile — full 5-HT₂A agonism confirmed by drug discrimination and selective antagonism, partial 5-HT₁A agonism, and SERT substrate behavior — provides the strongest available predictor of EPT's receptor activitysupported
DPT inhibits [3H]8-OH-DPAT binding with IC50 of 0.1 micromol/l at human 5-HT1a receptor. DPT is a moderate affinity partial agonist at the human 5-HT1a receptor. pmid:15886504
DPT's pharmacodynamic profile — full 5-HT₂A agonism confirmed by drug discrimination and selective antagonism, partial 5-HT₁A agonism, and SERT substrate behavior — provides the strongest available predictor of EPT's receptor activitysupported
DPT inhibits SERT with Ki of 0.594 microM. High binding-to-uptake ratios support tryptamines as transporter substrates at both SERT and VMAT2. s00702-009-0308-8
Structure-activity data from 5-MeO-DMT derivatives confirm that N-alkyl size modulates the SERT-to-5-HT₁A/5-HT₂A selectivity ratio, predicting that EPT falls between DET and DPT in binding profile — though no direct measurement confirms this.supported
Molecular size of amino group significantly influenced SERT affinity. All examined 5-MeO-tryptamines exhibited selectivity for 5-HT1AR over 5-HT2AR. s41380-024-02506-8
Tryptamine-derived hallucinogens (DPT, DiPT) exhibit less tolerance development than phenethylamine-derived hallucinogens (DOI, 2C-T-7) in mouse head-twitch response assayssupported
Tolerance developed to HTR elicited by daily DOI but not DPT or DIPT. Phenethylamine-derived hallucinogens may have reduced therapeutic suitability due to rapid tolerance; tryptamine-derived hallucinogens show reduced potential for tolerance development. jpet.114.219337
pharmacokinetic-detail5 · 3 ok
Claim in pharmacokinetic-detail — inconclusiveinconclusiveworking →
Claim in pharmacokinetic-detail — inconclusiveinconclusiveworking →
The study further demonstrated the forensic utility of these metabolite markers by identifying unique hydroxy-EPT species in a human postmortem blood sample.supported
Metabolite usefulness demonstrated by identification in a human postmortem blood sample with suspected EPT or 4-OH-EPT intoxication. EPT known to form metabolites by indole ring hydroxylation among others. dta.3668
MAO-A is the expected primary clearance enzyme for EPT, by direct analogy with DMT's well-characterized MAO-A-dependent metabolism. CYP2D6 contributes to DMT metabolism via indole hydroxylation; the predominance of hydroxylated metabolites in EPT's in vitro profile is consistent with CYP2D6 involvement, though the specific CYP isoforms responsible have not been identified for EPT.supported
MAO-A primary clearance; CYP2D6 and CYP2C19 also involved. s13318-023-00822-y
MAO-A is the expected primary clearance enzyme for EPT, by direct analogy with DMT's well-characterized MAO-A-dependent metabolism. CYP2D6 contributes to DMT metabolism via indole hydroxylation; the predominance of hydroxylated metabolites in EPT's in vitro profile is consistent with CYP2D6 involvement, though the specific CYP isoforms responsible have not been identified for EPT.supported
DMT rapidly metabolised by CYP2D6... Formation of mono-, di- and tri-oxygenated metabolites by hydroxylation on the indole core. 00498254.2023.2278488
chemistry2 · 1 ok
Claim in chemistry — inconclusiveinconclusiveworking →
Crystal structure data confirm conformational flexibility of the N-ethyl chain, which exhibits a two-component positional disorder with 50% occupancy for each orientation in the solid state.supported
The ethyl group of the EPT cation is modeled as a two-component disorder with 50% occupancy. s2056989020008683
clinical-evidence2 · 1 ok
Richards and colleagues administered intramuscular DPT to cancer patients in brief psychotherapy sessions addressing existential distress, and separate investigations explored DPT-assisted psychotherapy for alcohol use disordersupported
30 cancer patients with psychological distress received ~12h conventional psychotherapy and a single DPT-assisted session. DPT used as a short-acting psychedelic adjunct to therapy. ngub-v4rm-t7dc-xth3
Claim in clinical-evidence — inconclusiveinconclusiveworking →