generation run 2026-04-26
54 min completedmodel pipeline-v5plan not recordedrun/5ec763cd…Selection
Verification
- record
- seen / partial
- working
The model's own caveats
none raised on this run
Reproduce
- inputs
- 19 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
18 searches — query, source, results, what was kept and why
| # | source | query | seen | kept | rationale |
|---|---|---|---|---|---|
| 1 | PubChem | DiPT | 1 | 1 | Primary chemical identity verification |
| 2 | Federal Register / WebSearch | DiPT N,N-diisopropyltryptamine legal status scheduling DEA analog act | 10 | 2 | Critical legal status finding - DiPT is currently unscheduled despite DEA attempt |
| 3 | PubMed | DiPT diisopropyltryptamine pharmacology | 15 | 4 | Direct pharmacological relevance to DiPT class or analogues |
| 4 | PubMed | serotonin syndrome MAOI tryptamine interaction serotonin toxicity psychedelic | 1 | 1 | Drug interactions and serotonin toxicity relevant to DiPT safety |
| 5 | PubMed | tryptamine hallucinogen serotonin 5-HT2A receptor binding N-diisopropyl | 1 | 1 | Critical binding affinity data directly relevant to DiPT pharmacology |
| 6 | PubMed | tryptamine serotonin receptor binding affinity substituted Shulgin | 2 | 1 | Comparative tryptamine receptor pharmacology |
| 7 | PubMed | N,N-diisopropyltryptamine auditory psychedelic effects | 3 | 2 | Only two papers directly studying DiPT's pharmacological and neural effects |
| 8 | OpenAlex | DiPT N,N-diisopropyltryptamine psychedelic | 74 | 5 | High-citation landmark papers covering tryptamine receptor pharmacology and toxicology |
| 9 | ClinicalTrials.gov · absence | diisopropyltryptamine DiPT | 0 | 0 | N/A - no results |
| 10 | Erowid / TiHKAL | DiPT TiHKAL entry synthesis dosage effects | 1 | 1 | Primary source for DiPT synthesis history and effects from Shulgin |
| 11 | WebSearch / Purdue Archives | Shulgin 1981 diisopropyltryptamine paper published journal | 10 | 1 | Discovery and publication history of DiPT |
| 12 | WebSearch / UK Isomer Design | UK Misuse of Drugs Act tryptamine generic definition DiPT | 1 | 1 | Legal status confirmation for UK |
| 13 | PMC4194234 | DiPT tryptamine receptor binding transporter data | 1 | 1 | Critical specific pharmacological data for DiPT receptor profile - flags discrepancy with seed data 5-HT1A agonist claim |
| 14 | WebSearch | DiPT Australia schedule 9 Canada controlled substance | 5 | 3 | Legal status across major jurisdictions |
| 15 | Multiple sources cross-reference | Duration discrepancy DiPT: TiHKAL (6-8h) vs seed data (3-6h) vs community sources | 3 | 2 | Duration discrepancy requires editorial review; TiHKAL as primary human source suggests 6-8h may be more accurate |
| 16 | PubMed | serotonin toxicity MAOI tryptamine interaction; psychedelic dependence addiction | 2 | 2 | Drug interactions and tolerance mechanisms applicable to DiPT class |
| 17 | PubMed/OpenAlex | Brogaard synesthesia serotonergic; tryptamine MAO metabolism oral activity; RE104 4-OH-DiPT clinical | 5 | 3 | Synesthesia mechanism relevant to DiPT auditory effects; RE104/4-OH-DiPT data provides closest analogue clinical context |
| 18 | PMC4194234 / Blough 2014 | DiPT tryptamine receptor binding transporter EC50 Ki values | 1 | 3 | Only published paper with quantitative DiPT-specific receptor data |
57 claims by section — every cited sentence, checked against its source
safety14 · 8 ok
Claim in safety — inconclusiveinconclusiveworking →
Claim in safety — inconclusiveinconclusiveworking →
The closest adverse event data within the N,N-diisopropyltryptamine structural class comes from 5-MeO-DiPT, whose 5-methoxy analogue caused rhabdomyolysis and transient acute renal failure in a 23-year-old male following ingestionsupported
5-MeO-DiPT ('Foxy Methoxy') hallucinogenic tryptamine ingestion by a 23-year-old male resulted in rhabdomyolysis and transient acute renal failure. pmid:16610577
Tryptamine class adverse effects include tachycardia, hypertension, hyperthermia, rhabdomyolysis, and serotonin syndrome, with morbidity described as "considerable" in a systematic review of tryptamine toxicologysupported
Morbidity considerable. ijms21239279
Nichols (2016) states that serotonergic psychedelics are "generally considered physiologically safe and do not lead to dependence or addiction" at typical doses, a class-level assessment that applies to DiPT with the caveat that no substance-specific safety data exist.supported
Physiologically safe, not dependence-forming. pr.115.011478
Claim in safety — inconclusiveinconclusiveworking →
Tolerance to DiPT's effects is expected to develop rapidly following the class-level mechanism established for serotonergic psychedelics: repeated administration causes downregulation of 5-HT₂A receptors in the frontal cortexsupported
Daily LSD administration decreases 5-HT2 binding in cortex within 3 days but not after single dose. Psilocybin also reduces 5-HT2 binding. pmid:1969270
Tolerance to DiPT's effects is expected to develop rapidly following the class-level mechanism established for serotonergic psychedelics: repeated administration causes downregulation of 5-HT₂A receptors in the frontal cortexsupported
Repeated DOI induces HTR tolerance and cross-tolerance with LSD via 5-HT2A downregulation in frontal cortex, independent of beta-arrestin-2. acschemneuro.2c00170
Cross-tolerance with other serotonergic psychedelics — including LSD, psilocybin, DMT, and mescaline — is expected through the shared 5-HT₂A downregulation mechanism.supported
Repeated DOI induces HTR tolerance and cross-tolerance with LSD via 5-HT2A downregulation in frontal cortex. acschemneuro.2c00170
Serotonergic psychedelics are classified as non-dependence-formingsupported
Physiologically safe, not dependence-forming. pr.115.011478
Claim in safety — inconclusiveinconclusiveworking →
Claim in safety — inconclusiveinconclusiveworking →
Pharmacokinetic interaction through shared CYP2D6 metabolism is also possible.supported
CYP2D6 plays important polymorphic role in metabolism of IAA drugs of abuse. DDIs can occur at pharmacokinetic and pharmacodynamic levels. s12248-008-9028-5
Claim in safety — inconclusiveinconclusiveworking →
pharmacology10 · 6 ok
Claim in pharmacology — inconclusiveinconclusiveworking →
This 5-HT₂A agonism is the pharmacological basis for hallucinogen-like discriminative stimulus effects confirmed in a DOM drug discrimination model in rats.supported
DOM used as reference hallucinogen training drug. DiPT and other tryptamines evaluated against DOM benchmark. s00213-012-2891-x
Claim in pharmacology — inconclusiveinconclusiveworking →
DiPT is inactive at the 5-HT₁A receptor at concentrations up to 10 µM, distinguishing it from its 5-methoxy analogue 5-meo-dipt, which possesses significant 5-HT₁A activitysupported
5-HT1A inactive at 10 uM. s00213-014-3557-7
Beyond direct receptor agonism, DiPT inhibits the serotonin transporter (SERT) with an IC₅₀ of 288 ± 2.3 nMsupported
SERT 288 nM. s00213-014-3557-7
McKenna and colleagues established that N,N-dialkyl substituent size is a secondary determinant of tryptamine binding affinity at both 5-HT₂A and 5-HT₁A, with groups larger than N,N-diisopropyl producing marked affinity reductionssupported
Size of N,N-dialkyl substituent is secondary determinant; groups larger than N,N-diisopropyl result in marked reduction in affinity at 5-HT2A and 5-HT1A recognition sites. pmid:2139186
This is consistent with behavioral data showing that N,N-diisopropyl compounds are less potent than dimethyl, diethyl, N-methyl-N-ethyl, and N-methyl-N-isopropyl tryptamines in hallucinogen discrimination assays.supported
N,N-diisopropyl compounds less potent than dimethyl, diethyl counterparts. acsptsci.0c00173
Claim in pharmacology — inconclusiveinconclusiveworking →
Claim in pharmacology — inconclusiveinconclusiveworking →
Class-level data for indolealkylamine drugs indicate that CYP2D6 is a primary metabolic enzyme, with CYP2D6 polymorphism representing a risk factor for variable pharmacokinetics and drug-drug interactionssupported
CYP2D6 plays important polymorphic role in metabolism of IAA drugs of abuse. CYP2D6 polymorphism represents additional risk factor. DDIs can occur at pharmacokinetic and pharmacodynamic levels leading to serotonin toxicity. s12248-008-9028-5
comparative-pharmacology5 · 4 ok
This potency reduction tracks with McKenna and colleagues' binding data showing that substituent size beyond N,N-diisopropyl produces marked affinity loss at both 5-HT₂A and 5-HT₁A.supported
groups larger than N,N-diisopropyl result in marked reduction in affinity at 5-HT2A and 5-HT1A recognition sites. pmid:2139186
Gatch and colleagues (2021) demonstrated that N,N-diisopropyl compounds are consistently less potent hallucinogens than dimethyl, diethyl, N-methyl-N-ethyl, and N-methyl-N-isopropyl tryptamines in DOM discrimination assayssupported
N,N-diisopropyl compounds less potent than dimethyl, diethyl counterparts. acsptsci.0c00173
Carbonaro and colleagues (2013) explicitly note that DiPT "is known for its production of auditory distortions," a characteristic not shared by other tryptamines tested in the same discrimination paradigmsupported
the synthetic hallucinogen N,N-diisopropyltryptamine (DiPT) is known for its production of auditory distortions. s00213-012-2891-x
Claim in comparative-pharmacology — inconclusiveinconclusiveworking →
Critically, 5-MeO-DiPT has a documented adverse event profile — including a published case of rhabdomyolysis and acute renal failure in a 23-year-old male — that DiPT lacks, though this absence likely reflects lower prevalence rather than lower intrinsic risk.supported
5-MeO-DiPT ('Foxy Methoxy') hallucinogenic tryptamine ingestion by a 23-year-old male resulted in rhabdomyolysis and transient acute renal failure. pmid:16610577
pharmacokinetic-detail5 · 2 ok
Claim in pharmacokinetic-detail — inconclusiveinconclusiveworking →
Claim in pharmacokinetic-detail — inconclusiveinconclusiveworking →
For comparative context, the closely related 4-hydroxy analogue (4-OH-DiPT, studied as prodrug RE104) shows a plasma half-life of approximately 40 minutes following subcutaneous administration in ratssupported
RE104 prodrug of 4-OH-DiPT. Half-life 40 min after s.c. in rats. acschemneuro.4c00058
Claim in pharmacokinetic-detail — inconclusiveinconclusiveworking →
Class-level data indicate that indolealkylamine drugs are substrates for CYP2D6, with CYP2D6 genetic polymorphism identified as a risk factor for pharmacokinetic variability and drug-drug interactionssupported
CYP2D6 plays important polymorphic role in metabolism of IAA drugs of abuse. CYP2D6 polymorphism represents additional risk factor. DDIs can occur at pharmacokinetic and pharmacodynamic levels. s12248-008-9028-5
receptor-pharmacology5 · 4 ok
The most comprehensive receptor and transporter binding data for DiPT derive from Blough and colleagues (2014), who evaluated the compound (designated compound 22) across serotonin receptor subtypes and monoamine transporters.supported
DiPT (compound 22): 5-HT2A EC50 33.5 nM 110% efficacy (full agonist); 5-HT1A inactive at 10 uM; SERT 288 nM; DAT 4788 nM; NET >10,000 nM; no beta-arrestin at 5-HT2A. s00213-014-3557-7
This dual mechanism — 5-HT₂A agonism combined with moderate SERT inhibition — is shared by several tryptamine psychedelics and may contribute to serotonergic effects beyond those mediated by direct receptor activation.supported
DiPT (compound 22): 5-HT2A EC50 33.5 nM 110% efficacy (full agonist); SERT 288 nM. s00213-014-3557-7
McKenna and colleagues (1990) systematically evaluated the influence of N,N-dialkyl substituent size on tryptamine binding affinities across 21 indolealkylamine derivativessupported
Affinities of 21 indolealkylamine derivatives at 5-HT1A, 5-HT2A, 5-HT2B. pmid:2139186
Behavioral pharmacology confirms this pattern — N,N-diisopropyl tryptamines are less potent hallucinogens than their dimethyl, diethyl, and mixed N-alkyl counterparts in DOM discrimination assays.supported
N,N-diisopropyl compounds less potent than dimethyl, diethyl counterparts. acsptsci.0c00173
Claim in receptor-pharmacology — inconclusiveinconclusiveworking →
summary5 · 3 ok
Serotonergic psychedelics as a class are considered physiologically safe at typical doses and do not produce dependencesupported
Physiologically safe, not dependence-forming. pr.115.011478
Claim in summary — inconclusiveinconclusiveworking →
The compound's unique auditory selectivity attracted renewed mechanistic interest when Hurst and Bajo proposed the first neural model for DiPT's frequency-selective pitch distortion in 2026.supported
Hurst and Bajo propose the neural mechanisms for this effect and its use as potential therapeutic for tinnitus. fcag093
DiPT acts as a full agonist at the serotonin 5-HT₂A receptor (EC₅₀ = 33.5 ± 1.5 nM, 110% intrinsic efficacy relative to serotonin) with a G-protein-biased signaling profile — no β-arrestin₂ recruitment is detectable at concentrations up to 10 µMsupported
DiPT (compound 22): 5-HT2A EC50 33.5 nM 110% efficacy (full agonist); no beta-arrestin at 5-HT2A. s00213-014-3557-7
Claim in summary — inconclusiveinconclusiveworking →
history4 · 3 ok
Claim in history — inconclusiveinconclusiveworking →
The first peer-reviewed animal pharmacology study directly evaluating DiPT was published by Carbonaro and colleagues in 2013, confirming hallucinogen-like discriminative stimulus effects in a DOM drug discrimination model in ratssupported
DOM used as reference hallucinogen training drug. DiPT and other tryptamines evaluated against DOM benchmark. s00213-012-2891-x
Blough and colleagues (2014) provided the first quantitative receptor pharmacology data, establishing DiPT's EC₅₀ at 5-HT₂A and its transporter binding profile.supported
DiPT (compound 22): 5-HT2A EC50 33.5 nM 110% efficacy (full agonist); SERT 288 nM; DAT 4788 nM; NET >10,000 nM. s00213-014-3557-7
In 2026, Hurst and Bajo published the first mechanistic hypothesis for DiPT's frequency-selective auditory distortion — termed "diptogenia" — proposing neural mechanisms by which 5-HT₂A receptor agonism in auditory cortical circuits preferentially disrupts tonotopic processingsupported
Hurst and Bajo propose the neural mechanisms for this effect and its use as potential therapeutic for tinnitus. fcag093
neuroscience4 · 2 ok
Hurst and Bajo (2026) proposed the first mechanistic framework, termed "diptogenia," in which DiPT's particular binding profile at 5-HT₂A receptors preferentially disrupts tonotopic processing in auditory cortexsupported
Hurst and Bajo propose the neural mechanisms for this effect and its use as potential therapeutic for tinnitus. fcag093
Claim in neuroscience — inconclusiveinconclusiveworking →
Brogaard (2013) reviewed evidence that serotonin system perturbation — particularly 5-HT₂A agonism — can induce cross-modal binding and synesthetic experiences through disinhibition of normally segregated sensory processing streams.supported
Excessive serotonin increases excitability and connectedness of sensory brain regions via direct projection and disinhibited feedback mechanisms. fnhum.2013.00657
Claim in neuroscience — inconclusiveinconclusiveworking →
clinical-evidence3 · 2 ok
Claim in clinical-evidence — inconclusiveinconclusiveworking →
Bryson and colleagues (2024) published preclinical characterization demonstrating serotonergic psychedelic activity and antidepressant-like effects in rodent behavioral models.supported
Short-duration (2-3h) psychedelic effects. Significant antidepressant effect in forced swim test. acschemneuro.4c00058
Ludbrook and colleagues (2025) reported a Phase 1 single-ascending-dose, randomized, double-blind, placebo-controlled study of subcutaneous RE104 in healthy volunteerssupported
First formal human evaluation of RE104, a prodrug of 4-OH-DiPT (4-hydroxy-N,N-diisopropyltryptamine). Safety, PK, PD characterized. jcp.0000000000002047
chemistry1 · 0 ok
Claim in chemistry — inconclusiveinconclusiveworking →
effects-overview1 · 1 ok
Where psilocybin and LSD reshape the visual field and emotional landscape, DiPT leaves vision largely untouched and instead restructures auditory reality — a dissociation between sensory modalities that is pharmacologically unique within the 5-HT₂A agonist class.supported
Serotonergic hallucinogens such as LSD and DMT produce distinctive visual effects, whereas the synthetic hallucinogen N,N-diisopropyltryptamine (DiPT) is known for its production of auditory distortions. s00213-012-2891-x