generation run 2026-04-24
57 min completedmodel pipeline-v5plan not recordedrun/349bc17e…Selection
Verification
- record
- seen / partial
- working
The model's own caveats
none raised on this run
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
- streams
- none — agent transcripts are persisted from 2026-09 onward
13 searches — query, source, results, what was kept and why
| # | source | query | seen | kept | rationale |
|---|---|---|---|---|---|
| 1 | OpenAlex | 5-MeO-MiPT tryptamine psychedelic | 10 | 5 | High-citation papers providing pharmacology context and reviews relevant to 5-MeO-MiPT |
| 2 | PubMed | 5-MeO-MiPT tryptamine pharmacology | 10 | 10 | All directly relevant to 5-MeO-MiPT pharmacology, toxicology, and clinical reports |
| 3 | PubChem | 5-MeO-MiPT | 1 | 1 | Primary chemical identity verification |
| 4 | PubMed | 5-methoxytryptamine serotonin 5-HT1A 5-HT2A binding hallucinogen | 1 | 1 | Provides comparative receptor binding context for 5-methoxy substituted tryptamines |
| 5 | ClinicalTrials.gov · absence | 5-MeO-MiPT | 0 | — | No trials to select |
| 6 | PubMed Central | 5-MeO-MiPT binding affinity Ki receptor | 1 | 1 | Critical binding affinity data for 5-MeO-MiPT receptor pharmacology |
| 7 | Federal Register / Erowid | 5-MeO-MiPT DEA scheduling US legal status | 2 | 2 | Key legal status information for primary article |
| 8 | PubMed | Repke Shulgin tryptamine N-methyl N-isopropyl 1985 psychotomimetic | 1 | 1 | Foundational discovery paper for 5-MeO-MiPT |
| 9 | Web Search | 5-MeO-MiPT UK Germany Canada Australia legal status | 5 | — | International legal status data for multiple jurisdictions |
| 10 | Erowid TiHKAL | 5-MeO-MIPT TiHKAL entry | 1 | 1 | Primary source for Shulgin's human self-experiment data and synthesis description |
| 11 | Web Search | 5-MeO-MiPT physical properties melting point solubility | 5 | 1 | Physical property data not available through structured APIs |
| 12 | PMC Web | Bassi 2024 5-MeO-MiPT cardiorespiratory poisoning | 1 | 1 | Key human poisoning case details and preclinical pharmacological data |
| 13 | PubChem | CID 2763156 | 1 | 1 | Verification of chemical identity data |
70 claims by section — every cited sentence, checked against its source
safety18 · 11 ok
Claim in safety — inconclusiveinconclusiveworking →
Altunci et al. (2021) conducted the first published in vivo acute toxicity and histotoxicological study of 5-MeO-MiPTsupported
In vivo acute toxicity and histotoxicological study of 5-MeO-MiPT. balkanmedj.galenos.2020.2019.11.68
Claim in safety — inconclusiveinconclusiveworking →
Zhao et al. (2024a) demonstrated that chronic 5-MeO-MiPT injection over 30 days in zebrafish produces behavioral inhibition, anxiety-like behavior, and disruption of the liver-brain pathway via the Gαq/11-PLCβ signaling cascadepartially supported
30-day zebrafish injection study. 5-MeO-MiPT acts via Galphaq/11-PLCbeta signaling. Behavioral inhibition. j.ecoenv.2024.116969
Claim in safety — inconclusiveinconclusiveworking →
Claim in safety — inconclusiveinconclusiveworking →
Case reports describe agitated, disinhibited behavior: the Grafinger (2018) forensic case involved a male found naked and aggressive, and the Shimizu (2007) case documented a substance-related mental disorder presentation, though polydrug context complicates attribution.supported
Substance-related mental disorder complicated by polydrug use. pmid:16876302
Claim in safety — inconclusiveinconclusiveworking →
Cross-tolerance between classical psychedelics (DOI and LSD) was confirmed, mediated through 5-HT₂A receptor activation.supported
Cross-tolerance observed between DOI and LSD but not with nonpsychedelic 5-HT2A agonists. acschemneuro.2c00170
The Zhao et al. (2024a) zebrafish study noted its findings offer "novel insights into the toxicological effects and addiction mechanisms" but did not characterize dependence or withdrawal directly.supported
Insights into toxicological effects and addiction mechanisms. j.ecoenv.2024.116969
As a 5-HT₂A agonist, 5-MeO-MiPT carries a class-level serotonin syndrome risk when combined with monoamine oxidase inhibitors (MAOIs), selective serotonin reuptake inhibitors (SSRIs), serotonin-norepinephrine reuptake inhibitors (SNRIs), and other serotonergic compoundssupported
Serotonergic drugs associated with acute serotonin syndrome, hyperthermia, seizures, hyponatremia. Tryptamines and hallucinogenic phenethylamines are 5-HT2A direct agonists. fpsyt.2017.00152
Although 5-MeO-MiPT itself does not significantly inhibit SERT, its direct receptor agonism at 5-HT₂A provides sufficient serotonergic activity to contribute to serotonin syndrome in combination.supported
5-MeO-MiPT shows EC50 at 5-HT2A of ~7.82 nM; inactive as SERT inhibitor above 10,000 nM. s00213-014-3557-7
The dual serotonergic mechanism (tramadol's SERT inhibition plus 5-MeO-MiPT's 5-HT₂A agonism) elevates serotonin syndrome risksupported
Serotonergic drugs associated with acute serotonin syndrome. Tryptamines and hallucinogenic phenethylamines are 5-HT2A direct agonists. fpsyt.2017.00152
The Grafinger (2018) forensic case documents concurrent cocaine and 5-MeO-MiPT use with severe agitation, and the Shimizu (2007) case involved co-ingestion with methylonesupported
Case report of 27-year-old male intoxicated with methylone (120 mg) + 5-MeO-MIPT (76 mg). pmid:16876302
Claim in safety — inconclusiveinconclusiveworking →
Concomitant use of MAOIs, SSRIs, SNRIs, tramadol, or lithium is contraindicated due to serotonin syndrome risk.supported
Serotonergic drugs associated with acute serotonin syndrome, hyperthermia, seizures, hyponatremia. Tryptamines and hallucinogenic phenethylamines are 5-HT2A direct agonists. fpsyt.2017.00152
Given the compound's hepatic metabolism via phase I oxidative pathways and the zebrafish evidence for liver-brain pathway disruption, hepatic impairment may alter metabolism and increase exposuresupported
Primary metabolites via demethylation and hydroxylation. dta.2245
Claim in safety — inconclusiveinconclusiveworking →
pharmacology12 · 9 ok
Blough et al. (2014) measured a functional EC₅₀ of 7.82 ± 1.5 nM with an Emax of 101 ± 3%, confirming full agonist efficacypartially supported
5-MeO-MiPT shows EC50 at 5-HT2A of ~7.82 nM s00213-014-3557-7
Arrestin recruitment at 5-HT₂A was negligible (EC₅₀ >10,000 nM), indicating strongly G-protein-biased signalingpartially supported
inactive as SERT inhibitor above 10,000 nM. s00213-014-3557-7
At the G-protein level, Nonaka et al. (2007) demonstrated that 5-MeO-MiPT stimulates [³⁵S]GTPγS binding in rat brain membranes, with a potency rank among 5-methoxytryptamines of: 5-MeO-DMT > 5-MeO-DALT > 5-MeO-AMT ≥ 5-MeO-MiPT > 5-MeO-DiPT > DPT ≥ AMT.partially supported
Rank order potency among 5-methoxy tryptamines: 5-MeO-DMT > 5-MeO-DALT > 5-MeO-AMT >= 5-MeO-MIPT > 5-MeO-DIPT. pmid:18057721
The compound is essentially inactive at the serotonin transporter (SERT IC₅₀ >10,000 nM)supported
inactive as SERT inhibitor above 10,000 nM. s00213-014-3557-7
This finding is corroborated by Nagai et al. (2007), who demonstrated only weak monoamine reuptake inhibition and minimal monoamine release in rat synaptosomes, and by Rickli et al. (2016), who found no significant interaction with SERT or the norepinephrine transporter (NET)supported
5-MeO-MiPT inhibits monoamine reuptake but has minimal effects on monoamine release in rat brain synaptosomes. pmid:17223101
Claim in pharmacology — inconclusiveinconclusiveworking →
Claim in pharmacology — inconclusiveinconclusiveworking →
However, Warren et al. (2024) demonstrated via cryo-EM structural studies that 5-methoxytryptamines as a class engage 5-HT₁A, with the 5-methoxy substitution promoting receptor engagement — though their primary ligand was 5-MeO-DMT, not 5-MeO-MiPTsupported
Cryo-EM structures of 5-HT1A with 5-MeO-DMT and analogues. SAR of 5-methoxytryptamines at 5-HT1A and 5-HT2A. s41586-024-07403-2
Ray (2010) profiled 25 psychedelics across 51 receptor targets using NIMH-PDSP data, demonstrating that psychedelic tryptamines interact with a broader array of monoamine receptors than 5-HT₂A alone — including 5-HT₂B, 5-HT₁A, 5-HT₆, 5-HT₇, and in some cases sigma receptors.supported
Receptor affinity pharmacology of 25 psychedelic drugs at 51 receptors, transporters, and ion channels (NIMH-PDSP). Psychedelic drugs interact with 42 of 49 sites tested. journal.pone.0009019
Grafinger et al. (2018) characterized 5-MeO-MiPT metabolism using pooled human liver microsomes (pHLM) and forensic biological samplessupported
Seven phase I metabolites identified in vitro; 4 in blood, 7 in urine in vivo. Primary metabolites via demethylation and hydroxylation. dta.2245
Claim in pharmacology — inconclusiveinconclusiveworking →
In the Grafinger (2018) forensic case, blood concentration was 160 ng/mL and urine concentration was 3,380 ng/mLsupported
Blood concentration 160 ng/mL, urine 3380 ng/mL. dta.2245
receptor-pharmacology10 · 7 ok
Claim in receptor-pharmacology — inconclusiveinconclusiveworking →
The most comprehensive functional characterization of 5-MeO-MiPT at serotonin targets comes from Blough et al. (2014):supported
5-MeO-MiPT shows EC50 at 5-HT2A of ~7.82 nM; inactive as SERT inhibitor above 10,000 nM. s00213-014-3557-7
The SERT inactivity is independently confirmed by Nagai et al. (2007), who found weak reuptake inhibition and minimal monoamine release in rat synaptosomes, and by Rickli et al. (2016), who demonstrated no significant SERT or NET interaction for 5-MeO-MiPT — contrasting with 5-MeO-AMT and certain other tryptamines that do engage monoamine transporters.supported
5-MeO-MiPT inhibits monoamine reuptake but has minimal effects on monoamine release in rat brain synaptosomes. pmid:17223101
Claim in receptor-pharmacology — inconclusiveinconclusiveworking →
Nonaka et al. (2007) demonstrated [³⁵S]GTPγS binding stimulation by 5-MeO-MiPT in rat brain membranessupported
5-MeO-MiPT stimulates G protein binding in rat brain membranes. pmid:18057721
Among 5-methoxytryptamines tested, 5-MeO-MiPT ranked below 5-MeO-DMT, 5-MeO-DALT, and was approximately equipotent with 5-MeO-AMT, but more potent than 5-MeO-DiPT.supported
Rank order potency among 5-methoxy tryptamines: 5-MeO-DMT > 5-MeO-DALT > 5-MeO-AMT >= 5-MeO-MIPT > 5-MeO-DIPT. pmid:18057721
Claim in receptor-pharmacology — inconclusiveinconclusiveworking →
Warren et al. (2024) characterized 5-methoxytryptamine engagement at 5-HT₁A using cryo-EM structural pharmacology, demonstrating that the 5-methoxy substitution promotes 5-HT₁A receptor binding as a class effect — but the primary ligand studied was 5-MeO-DMTsupported
Cryo-EM structures of 5-HT1A with 5-MeO-DMT and analogues. SAR of 5-methoxytryptamines at 5-HT1A and 5-HT2A. s41586-024-07403-2
Gatch et al. (2021) trained rats to discriminate DOM (2,5-dimethoxy-4-methylamphetamine) from saline and found that 5-MeO-MiPT fully substituted for DOM, with potency at or below that of DOM itselfsupported
5-MeO-MiPT fully substituted for DOM discriminative stimulus in rats. acsptsci.0c00173
This confirms classical hallucinogen-like discriminative stimulus properties, consistent with 5-HT₂A-mediated pharmacology, and implies an abuse liability profile comparable to that of other classical psychedelics.supported
Results suggest hallucinogen-like abuse liability similar to DOM. acsptsci.0c00173
summary7 · 6 ok
5-MeO-MiPT was first synthesized by Repke, Grotjahn, and Shulgin in 1985, with expanded qualitative reporting in Shulgin's 1997 TiHKAL monographsupported
Eight N-methyl-N-isopropyltryptamines with various aromatic oxygen substituents evaluated for hallucinogenic activity in man. 5-MeO-MiPT (compound 4, Ar 5-OCH3) showed substantial increase in potency and oral activity compared to symmetrical dimethyl homologue. pmid:4009612
5-MeO-MiPT is a full agonist at the serotonin 5-HT₂A receptor (EC₅₀ ≈ 7.82 nM, Emax 101%) with markedly G-protein-biased signaling — arrestin recruitment is negligible (EC₅₀ >10,000 nM)partially supported
5-MeO-MiPT shows EC50 at 5-HT2A of ~7.82 nM; inactive as SERT inhibitor above 10,000 nM. s00213-014-3557-7
5-MeO-MiPT is a full agonist at the serotonin 5-HT₂A receptor (EC₅₀ ≈ 7.82 nM, Emax 101%) with markedly G-protein-biased signaling — arrestin recruitment is negligible (EC₅₀ >10,000 nM)partially supported
5-MeO-MiPT shows EC50 at 5-HT2A of ~7.82 nM; inactive as SERT inhibitor above 10,000 nM. s00213-014-3557-7
The compound is essentially inactive at the serotonin transporter (SERT IC₅₀ >10,000 nM), distinguishing it from entactogenic tryptaminessupported
inactive as SERT inhibitor above 10,000 nM. s00213-014-3557-7
Claim in summary — inconclusiveinconclusiveworking →
Chronic zebrafish exposure studies demonstrate liver-brain pathway disruption and histopathological tissue damagepartially supported
Seven pathways significantly affected including liver-brain pathway. j.ecoenv.2024.116044
Tolerance follows the standard 5-HT₂A agonist pattern — rapid receptor downregulation with near-complete reset within approximately 7 days, conferring an inherent brake on compulsive redosingpartially supported
Repeated DOI administration causes progressive HTR tolerance and 5-HT2A receptor downregulation in frontal cortex. acschemneuro.2c00170
neuroscience6 · 0 ok
Claim in neuroscience — inconclusiveinconclusiveworking →
Claim in neuroscience — inconclusiveinconclusiveworking →
Claim in neuroscience — inconclusiveinconclusiveworking →
Claim in neuroscience — inconclusiveinconclusiveworking →
Claim in neuroscience — inconclusiveinconclusiveworking →
Claim in neuroscience — inconclusiveinconclusiveworking →
comparative-pharmacology5 · 3 ok
Nonaka et al. (2007) established a G-protein activation potency rank via [³⁵S]GTPγS binding: 5-MeO-DMT > 5-MeO-DALT > 5-MeO-AMT ≥ 5-MeO-MiPT > 5-MeO-DiPT > DPT ≥ AMT. 5-MeO-MiPT thus falls in the mid-range of the series for G-protein coupling potency.partially supported
Rank order potency among 5-methoxy tryptamines: 5-MeO-DMT > 5-MeO-DALT > 5-MeO-AMT >= 5-MeO-MIPT > 5-MeO-DIPT. pmid:18057721
Claim in comparative-pharmacology — inconclusiveinconclusiveworking →
Gatch et al. (2021) showed 5-MeO-MiPT fully substitutes for DOM in drug discrimination assays, with potency at or below DOM itselfsupported
5-MeO-MiPT fully substituted for DOM discriminative stimulus in rats. acsptsci.0c00173
Claim in comparative-pharmacology — inconclusiveinconclusiveworking →
Repke et al. (1985) established that 5-MeO-MiPT shows "a substantial increase in potency as well as oral activity when compared to the symmetrical dimethyl homologues"supported
5-MeO-MiPT (compound 4, Ar 5-OCH3) showed substantial increase in potency and oral activity compared to symmetrical dimethyl homologue. pmid:4009612
history5 · 3 ok
The earliest published human toxicity case involved a 27-year-old Japanese male in 2007 who ingested a mixture containing approximately 76 mg of 5-MeO-MiPT alongside 120 mg of methylone, resulting in a substance-related mental disorder presentationsupported
Case report of 27-year-old male intoxicated with methylone (120 mg) + 5-MeO-MIPT (76 mg). Substance-related mental disorder complicated by polydrug use. pmid:16876302
Claim in history — inconclusiveinconclusiveworking →
The paper examined eight N-methyl-N-isopropyltryptamines bearing different aromatic oxygen substituents for hallucinogenic activity. 5-MeO-MiPT — designated compound 4, the 5-methoxy derivative — demonstrated "a substantial increase in potency as well as oral activity when compared to the symmetrical dimethyl homologues"supported
Eight N-methyl-N-isopropyltryptamines with various aromatic oxygen substituents evaluated for hallucinogenic activity in man. 5-MeO-MiPT (compound 4, Ar 5-OCH3) showed substantial increase in potency and oral activity compared to symmetrical dimethyl homologue. pmid:4009612
It was first identified in forensic and law-enforcement contexts in Italy in 2014 and was subsequently seized in Germany and Switzerland by at least 2016partially supported
5-MeO-MiPT first identified on Italian national territory in 2014. s00213-024-06526-8
Claim in history — inconclusiveinconclusiveworking →
clinical-evidence4 · 2 ok
Analysis revealed approximately 60% methylone (120 mg) and 38% 5-MeO-MiPT (76 mg)supported
Case report of 27-year-old male intoxicated with methylone (120 mg) + 5-MeO-MIPT (76 mg). pmid:16876302
Claim in clinical-evidence — inconclusiveinconclusiveworking →
Claim in clinical-evidence — inconclusiveinconclusiveworking →
Bassi et al. (2024) derived their mouse pharmacotoxicology study directly from the Italian human poisoning case, testing 5-MeO-MiPT at pharmacologically relevant doses in micesupported
Preclinical mouse study on pharmaco-toxicological effects; derived from a human poisoning case. s00213-024-06526-8
pharmacokinetic-detail3 · 3 ok
Grafinger et al. (2018) provide the only published metabolic characterization, using pooled human liver microsomes (pHLM) and biological samples from a forensic case.supported
Seven phase I metabolites identified in vitro; 4 in blood, 7 in urine in vivo. dta.2245
These metabolites are recommended as urinary biomarkers for forensic and clinical detection.supported
4 in blood, 7 in urine in vivo. Primary metabolites via demethylation and hydroxylation. dta.2245
In the forensic case reported by Grafinger et al. (2018), four metabolites were detected in blood and seven in urinesupported
4 in blood, 7 in urine in vivo. dta.2245