generation run 2026-04-26
65 min completedmodel pipeline-v5plan not recordedrun/9e54c101…Selection
Verification
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- seen / partial
- working
The model's own caveats
none raised on this run
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
12 searches — query, source, results, what was kept and why
| # | source | query | seen | kept | rationale |
|---|---|---|---|---|---|
| 1 | PubMed | 5-MeO-DALT tryptamine pharmacology | 13 | 12 | All directly relevant to 5-MeO-DALT pharmacology, case reports, or tryptamine overview |
| 2 | OpenAlex | 5-MeO-DALT N,N-diallyl-5-methoxytryptamine psychedelic | 10 | 5 | Directly relevant to 5-MeO-DALT pharmacology, case reports, and NPS context |
| 3 | PubChem | 5-MeO-DALT | 1 | 1 | Primary compound identity verification |
| 4 | WHO ECDD Repository | — | 1 | 3 | Official WHO assessment for scheduling decision and physical properties |
| 5 | Web | 5-MeO-DALT legal status scheduling UK US Australia Germany 2024 | 10 | 3 | Comprehensive legal status across jurisdictions |
| 6 | Web | 5-MeO-DALT Shulgin TIHKAL synthesis history | 10 | 2 | Discovery timeline and attribution |
| 7 | Web | WHO ECDD 43rd meeting 5-MeO-DALT critical review recommendation | 10 | 2 | Scheduling recommendation clarity |
| 8 | PubMed | N,N-diallyltryptamine serotonin receptor binding affinity Ki 5-HT2A | 1 | 1 | Critical binding affinity data and discovery confirmation |
| 9 | ClinicalTrials.gov · absence | 5-MeO-DALT diallyltryptamine | 0 | 0 | Confirms absence of registered clinical trials |
| 10 | Web | 5-MeO-DALT Ki nM binding affinity receptor data table | 10 | 1 | Specific Ki and EC50 values for pharmacology section |
| 11 | Web | 5-MeO-DALT melting point hydrochloride freebase physical properties | 10 | 2 | Definitive physical property data |
| 12 | PubMed Central | — | 1 | 1 | Definitive crystallographic/physical property data |
87 claims by section — every cited sentence, checked against its source
safety22 · 20 ok
Acute psychosis, delirium, and severe agitation are documented in case reportssupported
46-year-old man: LOC and visual hallucinations after 3 tablets (32.5 mg/tablet, 11% purity). bkac021
The coroner attributed death to traumatic injuries sustained due to behavioral impairment, not direct pharmacological toxicity.supported
first reported death (mid-2010, trauma under influence). j.pnpbp.2012.05.022
Across four published case reports, the documented acute toxidrome includes:supported
Young healthy male: extreme agitation, tachycardia, diaphoresis, combativeness after standard dose. First published case report. 1556-4029.12367
Across four published case reports, the documented acute toxidrome includes:supported
Case report: acute delirium and rhabdomyolysis associated with 5-MeO-DALT use. aas.12765
Across four published case reports, the documented acute toxidrome includes:supported
29-year-old man with cyclic myoclonus (all extremities, trunk, neck, every ~10 min) after 5-MeO-DALT. wnl.84.14_supplement.p3.013
Across four published case reports, the documented acute toxidrome includes:supported
46-year-old man: LOC and visual hallucinations after 3 tablets (32.5 mg/tablet, 11% purity). bkac021
Musculoskeletal: Rhabdomyolysis (skeletal muscle breakdown) with secondary risk of acute kidney injurysupported
Case report: acute delirium and rhabdomyolysis associated with 5-MeO-DALT use. aas.12765
5-MeO-DALT is not detected by standard immunoassay toxicology screenssupported
not detected by routine screens. bkac021
Claim in safety — not_supportednot supportedworking →
Emergency physicians should consider synthetic tryptamines when patients present with unexplained sympathomimetic or serotonergic toxidrome and negative routine screens.supported
5-MeO-DALT among most prevalent tryptamines; 5-HT2A agonist; 22 new analytical methods 2015-2020. ijms21239279
Online products have documented extreme impurity: one analytically confirmed case found 11% purity in tablets marketed as 5-MeO-DALT, with each tablet containing approximately 3.6 mg of active compound despite a 32.5 mg total tablet weightsupported
3 tablets (32.5 mg/tablet, 11% purity); plasma 7 ng/mL at 8h. LC-MS/MS quantification. bkac021
Acute psychosis, delirium, and severe agitation are documented in case reportssupported
extreme agitation, tachycardia, diaphoresis, combativeness after standard dose. First published case report. 1556-4029.12367
De la Fuente Revenga et al. (2022) demonstrated in mice that DOI-induced HTR tolerance develops within 24 hours of a single dose, involves 5-HT₂A receptor density reduction in frontal cortex, and shows cross-tolerance between psychedelics (DOI↔LSD) but not with non-psychedelic 5-HT₂A agonistspartially supported
Repeated DOI induces HTR tolerance via 5-HT2A downregulation; cross-tolerance between DOI and LSD; nonpsychedelic 5-HT2AR agonists (lisuride) do not induce cross-tolerance. acschemneuro.2c00170
MAO inhibition would reduce 5-MeO-DALT clearance (given O-demethylation and N-dealkylation metabolic pathways potentially involving MAO) while simultaneously increasing synaptic serotonin availability, compounding both pharmacokinetic and pharmacodynamic exposure.supported
Metabolic pathways: aromatic/aliphatic hydroxylation, N-dealkylation, N-oxidation, O-demethylation; phase II glucuronidation/sulfation. s00216-015-8955-0
Tramadol additionally lowers seizure threshold, which may compound risk given the documented myoclonus case.supported
29-year-old man with cyclic myoclonus (all extremities, trunk, neck, every ~10 min) after 5-MeO-DALT. wnl.84.14_supplement.p3.013
Pharmacokinetic interactions: 5-MeO-DALT is metabolized by CYP1A2, CYP2C19, CYP2D6, and CYP3A4supported
CYPs: CYP1A2, CYP2C19, CYP2D6, CYP3A4 for 5-MeO-DALT. s00216-015-8955-0
Drug discrimination data show that 5-MeO-DALT does not substitute for MDMA in trained rats, suggesting different dominant mechanisms and potentially different interaction profiles than entactogens.supported
fully substituted for DOM but not MDMA in drug discrimination. fbp.0000000000000309
Conditions predisposing to rhabdomyolysis: Given the documented case of rhabdomyolysis, individuals with myopathies, metabolic muscle disorders, or conditions increasing rhabdomyolysis susceptibility face elevated risk.supported
Case report: acute delirium and rhabdomyolysis associated with 5-MeO-DALT use. aas.12765
Cardiovascular disease: Tachycardia is documented across case reportssupported
extreme agitation, tachycardia, diaphoresis, combativeness after standard dose. 1556-4029.12367
Claim in safety — not_supportednot supportedworking →
Seizure disorders: Cyclic myoclonus has been documentedsupported
29-year-old man with cyclic myoclonus (all extremities, trunk, neck, every ~10 min) after 5-MeO-DALT. wnl.84.14_supplement.p3.013
Hepatic impairment: 5-MeO-DALT is extensively hepatically metabolized via CYP1A2, CYP2C19, CYP2D6, and CYP3A4supported
CYPs: CYP1A2, CYP2C19, CYP2D6, CYP3A4 for 5-MeO-DALT. s00216-015-8955-0
summary18 · 16 ok
5-MeO-DALT (5-methoxy-N,N-diallyltryptamine) is a synthetic substituted tryptamine psychedelic active orally at 12–20 mg with a total duration of 2–4 hourspartially supported
5-MeO-DALT psychoactive at 12-20 mg self-experiments. j.bmcl.2015.12.053
Among tryptamine psychedelics, it occupies an unusual pharmacological position: high-affinity 5-HT₁A agonism (Ki ≈ 8 nM) coexists with moderate 5-HT₂A agonism, producing a predominantly physical and stimulating experience rather than the deeply visual or introspective states characteristic of classical tryptamines such as DMT or psilocybin.supported
5-HT2A positive and 5-HT1A negative contributions to HTR potency. j.neuropharm.2018.02.028
First synthesized by Alexander Shulgin in May 2004 and distributed to research chemical markets within weeks, 5-MeO-DALT has not entered clinical development — no registered trials existsupported
Synthesis details available from 2004; limited pharmacological literature; controlled in few countries. j.pnpbp.2012.05.022
The published evidence base comprises receptor binding and behavioral pharmacology studies in rodents, metabolic characterization in rat and human liver microsomes, and four clinical case reports of adverse presentationssupported
DALT and 5-MeO-DALT binding at 45 receptor and transporter sites; HTR assay in mice. j.neuropharm.2018.02.028
The published evidence base comprises receptor binding and behavioral pharmacology studies in rodents, metabolic characterization in rat and human liver microsomes, and four clinical case reports of adverse presentationssupported
Binding at 45 receptors: 5-HT1A and 5-HT2B ~10-80 nM; 5-HT2A 250-730 nM. j.bmcl.2015.12.053
The published evidence base comprises receptor binding and behavioral pharmacology studies in rodents, metabolic characterization in rat and human liver microsomes, and four clinical case reports of adverse presentationssupported
Metabolic pathways: aromatic/aliphatic hydroxylation, N-dealkylation, N-oxidation, O-demethylation; phase II glucuronidation/sulfation. CYPs: CYP1A2, CYP2C19, CYP2D6, CYP3A4 for 5-MeO-DALT. s00216-015-8955-0
The published evidence base comprises receptor binding and behavioral pharmacology studies in rodents, metabolic characterization in rat and human liver microsomes, and four clinical case reports of adverse presentationssupported
Young healthy male: extreme agitation, tachycardia, diaphoresis, combativeness after standard dose. First published case report. 1556-4029.12367
The published evidence base comprises receptor binding and behavioral pharmacology studies in rodents, metabolic characterization in rat and human liver microsomes, and four clinical case reports of adverse presentationssupported
46-year-old man: LOC and visual hallucinations after 3 tablets (32.5 mg/tablet, 11% purity); plasma 7 ng/mL at 8h. bkac021
Claim in summary — inconclusiveinconclusiveworking →
Claim in summary — not_supportednot supportedworking →
Multiple regression analysis of head twitch response potency across the DALT series (R² = 0.87) shows 5-HT₂A binding positively predicts hallucinogenic activity while 5-HT₁A binding negatively modulates it — a buffering effect likely underlying the compound's muted visual profile.supported
5-HT2A positive and 5-HT1A negative contributions to HTR potency. j.neuropharm.2018.02.028
Case reports document delirium, rhabdomyolysis, and cyclic myoclonus as serious adverse events; one indirect fatality occurred when an intoxicated individual was struck by a vehiclesupported
Young healthy male: extreme agitation, tachycardia, diaphoresis, combativeness after standard dose; physical restraint and IV sedation required. First published case report. 1556-4029.12367
Case reports document delirium, rhabdomyolysis, and cyclic myoclonus as serious adverse events; one indirect fatality occurred when an intoxicated individual was struck by a vehiclesupported
Case report: acute delirium and rhabdomyolysis associated with 5-MeO-DALT use. aas.12765
Case reports document delirium, rhabdomyolysis, and cyclic myoclonus as serious adverse events; one indirect fatality occurred when an intoxicated individual was struck by a vehiclesupported
29-year-old man with cyclic myoclonus (all extremities, trunk, neck, every ~10 min) after 5-MeO-DALT. wnl.84.14_supplement.p3.013
Case reports document delirium, rhabdomyolysis, and cyclic myoclonus as serious adverse events; one indirect fatality occurred when an intoxicated individual was struck by a vehiclesupported
first reported death (mid-2010, trauma under influence). j.pnpbp.2012.05.022
The compound is not detected by standard immunoassay toxicology screens, creating a significant clinical diagnostic gapsupported
not detected by routine screens. bkac021
Tolerance is expected to develop rapidly via 5-HT₂A receptor downregulation but has not been confirmed substance-specificallysupported
Repeated DOI induces HTR tolerance via 5-HT2A downregulation; cross-tolerance between DOI and LSD. acschemneuro.2c00170
Human pharmacokinetic parameters remain uncharacterized beyond a single plasma concentration datapoint.supported
plasma 7 ng/mL at 8h. LC-MS/MS quantification. bkac021
pharmacology15 · 14 ok
Psychedelic-type effects are mediated principally through 5-HT₂A receptor agonism, while concurrent high-affinity 5-HT₁A agonism (Ki = 7.95 ± 0.52 nM) negatively modulates the behavioral expression of 5-HT₂A-mediated activity.supported
5-HT2A positive and 5-HT1A negative contributions to HTR potency. j.neuropharm.2018.02.028
Klein et al. (2018) quantified this relationship using multiple regression analysis of head twitch response (HTR) potency across the DALT series. 5-HT₂A binding affinity made a significant positive contribution to HTR potency (R² = 0.87 for the full model), while 5-HT₁A affinity contributed negatively — consistent with 5-HT₁A agonism buffering the hallucinogenic responsesupported
rank order of potency for HTR; 5-HT2A positive and 5-HT1A negative contributions to HTR potency. j.neuropharm.2018.02.028
Two comprehensive receptor screening studies have characterized 5-MeO-DALT at 45 receptor and transporter sites each, with additional functional data from Kozell et al. (2023) and Pottie et al. (2019).supported
Binding at 45 receptors: 5-HT1A and 5-HT2B ~10-80 nM; 5-HT2A 250-730 nM. Also binds alpha2 adrenergic, sigma, H1, SERT, NET. j.bmcl.2015.12.053
Two comprehensive receptor screening studies have characterized 5-MeO-DALT at 45 receptor and transporter sites each, with additional functional data from Kozell et al. (2023) and Pottie et al. (2019).supported
DALT and 5-MeO-DALT binding at 45 receptor and transporter sites. j.neuropharm.2018.02.028
Two comprehensive receptor screening studies have characterized 5-MeO-DALT at 45 receptor and transporter sites each, with additional functional data from Kozell et al. (2023) and Pottie et al. (2019).supported
21 substituted tryptamines at 5-HT1A, 5-HT2A, 5-HT2C, SERT. jpet.122.001454
Two comprehensive receptor screening studies have characterized 5-MeO-DALT at 45 receptor and transporter sites each, with additional functional data from Kozell et al. (2023) and Pottie et al. (2019).supported
beta-arrestin2 recruitment bioassay; 5-MeO-DALT used as test compound alongside LSD and mescaline; EC50 values reported. acs.analchem.9b03104
The sole human plasma datapoint derives from a clinical case report: 7 ng/mL at 8 hours post-ingestion of approximately 10.7 mg oralsupported
46-year-old man: LOC and visual hallucinations after 3 tablets (32.5 mg/tablet, 11% purity); plasma 7 ng/mL at 8h. bkac021
Metabolic fate has been characterized in rat urine with confirmation in pooled human liver microsomes (pHLM)supported
Metabolic pathways: aromatic/aliphatic hydroxylation, N-dealkylation, N-oxidation, O-demethylation; phase II glucuronidation/sulfation. s00216-015-8955-0
The principal cytochrome P450 enzymes involved are CYP1A2, CYP2C19, CYP2D6, and CYP3A4, consistent with metabolism data for related DALT derivatives.supported
CYPs: CYP1A2, CYP2C19, CYP2D6, CYP3A4 for 5-MeO-DALT. s00216-015-8955-0
The principal cytochrome P450 enzymes involved are CYP1A2, CYP2C19, CYP2D6, and CYP3A4, consistent with metabolism data for related DALT derivatives.supported
O-demethylation, hydroxylation, N-dealkylation for DALT derivatives; CYP1A2, CYP2C19, CYP2D6, CYP3A4 involvement. dta.2197
The recommended urinary detection targets are the N,O-bis-dealkyl metabolite (loss of both allyl groups and the methoxy group) and its glucuronide conjugate. 5-MeO-DALT is not detected by standard immunoassay toxicology screens; confirmed identification requires LC-MS/MSsupported
Target urine markers: N,O-bis-dealkyl metabolite and glucuronide. s00216-015-8955-0
The recommended urinary detection targets are the N,O-bis-dealkyl metabolite (loss of both allyl groups and the methoxy group) and its glucuronide conjugate. 5-MeO-DALT is not detected by standard immunoassay toxicology screens; confirmed identification requires LC-MS/MSsupported
LC-MS/MS quantification; not detected by routine screens. bkac021
Claim in pharmacology — not_supportednot supportedworking →
Validated LC-MS/MS methods for detection in blood, urine, and oral fluid have been published.supported
HPLC-MS-MS validated for 77 NPS including 5-MeO-DALT in blood, urine, oral fluid. bkaa103
Validated LC-MS/MS methods for detection in blood, urine, and oral fluid have been published.supported
LC-MS/MS method for 182 NPS in whole blood; fast, cost-effective, applicable to clinical and postmortem toxicology. dta.3170
pharmacokinetic-detail8 · 7 ok
The recommended urinary detection targets are the N,O-bis-dealkyl metabolite (loss of both allyl groups and the methoxy group) and its glucuronide conjugate.supported
Target urine markers: N,O-bis-dealkyl metabolite and glucuronide. s00216-015-8955-0
The only published human plasma measurement is a single datapoint: 7 ng/mL at 8 hours after oral ingestion of approximately 10.7 mgsupported
46-year-old man: LOC and visual hallucinations after 3 tablets (32.5 mg/tablet, 11% purity); plasma 7 ng/mL at 8h. bkac021
Michely et al. (2015) characterized the metabolic fate of 5-MeO-DALT using rat urine analysis with confirmatory incubation in pooled human liver microsomes (pHLM).supported
Metabolic pathways: aromatic/aliphatic hydroxylation, N-dealkylation, N-oxidation, O-demethylation; phase II glucuronidation/sulfation. CYPs: CYP1A2, CYP2C19, CYP2D6, CYP3A4 for 5-MeO-DALT. s00216-015-8955-0
The principal CYP enzymes mediating Phase I metabolism are CYP1A2, CYP2C19, CYP2D6, and CYP3A4supported
CYPs: CYP1A2, CYP2C19, CYP2D6, CYP3A4 for 5-MeO-DALT. s00216-015-8955-0
This CYP profile is consistent with data from structurally related DALT derivatives including 5-MeO-2-Me-DALT, 5-MeO-2-Me-ALCHT, and 5-MeO-2-Me-DIPT.supported
O-demethylation, hydroxylation, N-dealkylation for DALT derivatives; CYP1A2, CYP2C19, CYP2D6, CYP3A4 involvement. dta.2197
5-MeO-DALT is not detected by standard immunoassay toxicology screens — a significant clinical limitation documented across multiple case reportssupported
not detected by routine screens. bkac021
Claim in pharmacokinetic-detail — not_supportednot supportedworking →
Confirmed detection requires LC-MS/MS methodology, which has been validated for blood, urine, and oral fluid matrices.supported
HPLC-MS-MS validated for 77 NPS including 5-MeO-DALT in blood, urine, oral fluid. bkaa103
receptor-pharmacology6 · 5 ok
Binding affinity data for 5-MeO-DALT derive from two comprehensive screening studies — Cozzi and Daley (2016) and Klein et al. (2018) — with receptor-specific values from Kozell et al. (2023).supported
Binding at 45 receptors: 5-HT1A and 5-HT2B ~10-80 nM; 5-HT2A 250-730 nM. j.bmcl.2015.12.053
Binding affinity data for 5-MeO-DALT derive from two comprehensive screening studies — Cozzi and Daley (2016) and Klein et al. (2018) — with receptor-specific values from Kozell et al. (2023).supported
DALT and 5-MeO-DALT binding at 45 receptor and transporter sites. j.neuropharm.2018.02.028
Binding affinity data for 5-MeO-DALT derive from two comprehensive screening studies — Cozzi and Daley (2016) and Klein et al. (2018) — with receptor-specific values from Kozell et al. (2023).supported
21 substituted tryptamines at 5-HT1A, 5-HT2A, 5-HT2C, SERT. jpet.122.001454
Claim in receptor-pharmacology — inconclusiveinconclusiveworking →
Additional binding has been reported at α₂A, α₂B, and α₂C adrenergic receptors (nanomolar-to-low-micromolar range), σ₁ and σ₂ receptors (micromolar affinity), H₁ histamine receptors (nanomolar affinity for some DALT analogs), DAT (micromolar range), and κ opioid receptorssupported
Also binds alpha2 adrenergic, sigma, H1, SERT, NET. j.bmcl.2015.12.053
In a β-arrestin2 recruitment assay at the 5-HT₂A receptor, Pottie et al. (2019) confirmed 5-MeO-DALT activation with an EC₅₀ in the low-micromolar to submicromolar range, comparable to mescaline in the same assay system.supported
beta-arrestin2 recruitment bioassay; 5-MeO-DALT used as test compound alongside LSD and mescaline; EC50 values reported. acs.analchem.9b03104
comparative-pharmacology5 · 2 ok
5-MeO-DALT dose-dependently increased locomotor activity in mice, with peak stimulation at 10 mg/kg and suppression at 25 mg/kg — a biphasic pattern distinct from the dose-dependent locomotor depression characteristically observed with NBOMe-class compounds.partially supported
5-MeO-DALT: dose-dependent locomotor increase (peak 10 mg/kg). fbp.0000000000000309
Claim in comparative-pharmacology — inconclusiveinconclusiveworking →
In the [³⁵S]GTPγS binding assay, 5-MeO-DMT ranked as the most potent tryptamine tested, with 5-MeO-DALT secondsupported
G protein activation: 5-MeO-DALT second most potent tryptamine (behind 5-MeO-DMT). Rank: 5-MeO-DMT > 5-MeO-DALT > 5-MeO-AMT > 5-MeO-MIPT > 5-MeO-DIPT > DPT > AMT. pmid:18057721
Claim in comparative-pharmacology — inconclusiveinconclusiveworking →
Claim in comparative-pharmacology — inconclusiveinconclusiveworking →
history4 · 1 ok
Claim in history — inconclusiveinconclusiveworking →
The first reported death involving 5-MeO-DALT occurred in mid-2010 in the United Kingdom, when a man in his mid-20s was struck by a lorry while intoxicated — an indirect fatality attributed to behavioral impairment rather than direct pharmacological toxicity.supported
first reported death (mid-2010, trauma under influence). j.pnpbp.2012.05.022
Claim in history — inconclusiveinconclusiveworking →
Claim in history — inconclusiveinconclusiveworking →
clinical-evidence3 · 1 ok
Claim in clinical-evidence — inconclusiveinconclusiveworking →
Claim in clinical-evidence — inconclusiveinconclusiveworking →
This case — presented as a conference abstract rather than a full peer-reviewed publication — represents the first documented neurological presentation of 5-MeO-DALT-induced myoclonus.supported
First report of myoclonus as neurological presentation of 5-MeO-DALT. wnl.84.14_supplement.p3.013
chemistry2 · 1 ok
Claim in chemistry — inconclusiveinconclusiveworking →
Molecules form zigzag chains along the b-axis via N–H⋯N hydrogen bonds (N⋯N distance = 2.988 Å), adopting a colorless plate morphology.supported
N-H...N hydrogen bonds form zigzag chains. Colorless plate crystals. s2414314620004988
effects-overview2 · 1 ok
The 5-MeO-DALT experience is shaped by its unusual dual-receptor pharmacology: high 5-HT₁A affinity appears to buffer the 5-HT₂A-mediated visual and perceptual intensity typical of classical tryptamines, producing a state that is fundamentally more somatic and stimulating than introspective or visionarysupported
5-HT2A positive and 5-HT1A negative contributions to HTR potency. j.neuropharm.2018.02.028
Claim in effects-overview — inconclusiveinconclusiveworking →
neuroscience2 · 2 ok
As a 5-HT₂A receptor agonist confirmed by head twitch response activity and DOM drug discrimination substitution, 5-MeO-DALT is expected to engage the neural circuits established for serotonergic psychedelics: activation of 5-HT₂A receptors on layer V pyramidal neurons in the prefrontal cortex, disruption of thalamocortical gating, dissolution of default mode network (DMN) integrity, and increased global functional connectivity and neural entropysupported
HTR assay in mice; 5-HT2A positive and 5-HT1A negative contributions to HTR potency. j.neuropharm.2018.02.028
As a 5-HT₂A receptor agonist confirmed by head twitch response activity and DOM drug discrimination substitution, 5-MeO-DALT is expected to engage the neural circuits established for serotonergic psychedelics: activation of 5-HT₂A receptors on layer V pyramidal neurons in the prefrontal cortex, disruption of thalamocortical gating, dissolution of default mode network (DMN) integrity, and increased global functional connectivity and neural entropysupported
fully substituted for DOM but not MDMA in drug discrimination. fbp.0000000000000309