generation run 2026-05-03
54 min completedmodel pipeline-v5plan not recordedrun/9655b846…Selection
Verification
- record
- seen / partial
- working
The model's own caveats
none raised on this run
Reproduce
- inputs
- 28 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
20 searches — query, source, results, what was kept and why
| # | source | query | seen | kept | rationale |
|---|---|---|---|---|---|
| 1 | Cayman Chemical | — | 1 | 1 | Confirms CAS number not present in seed brief. |
| 2 | PubChem | MiPLA | 1 | 1 | Single unambiguous match for MiPLA. Fills in chemical identity data absent from seed brief. |
| 3 | PubMed | MiPLA lysergamide psychedelic | 5 | 5 | All directly relevant to MiPLA. Huang 1994 is the primary pharmacology paper. Brandt 2022 is the primary forensic/analytical chemistry paper. Tanaka papers document Japanese market appearances. |
| 4 | OpenAlex | MIPLA lysergamide N-methyl-N-isopropyl LSD analog pharmacology | 5 | 1 | Tusiewicz 2024 is directly relevant to forensic analysis of LSD analogs including MIPLA. Ponce 2024 on prodrugs may be relevant for 1cP-MiPLA context. |
| 5 | WebSearch | MiPLA MIPLA lysergamide legal status scheduling UK EU controlled substance | 10 | 2 | Multiple sources confirm legal grey area in EU; controlled in UK, possible analog scheduling in US. |
| 6 | PubMed | N-methyl-N-isopropyl lysergamide hallucinogen | 5 | 0 | Duplicate results. |
| 7 | ClinicalTrials.gov · absence | MiPLA lysergamide psychedelic | 0 | 0 | No trials found. |
| 8 | Bluelight | — | 1 | 3 | Community reports are only available evidence for subjective effects profile; labeled as user-report-only |
| 9 | WebSearch | MiPLA Germany NpSG scheduling 2019 | 10 | 1 | Confirms legal status data for Germany with specific date |
| 10 | PubMed | Brandt Return of the lysergamides LSD analog NPS characterization | 3 | 3 | Establish class pharmacology context for lysergamide NPS characterization |
| 11 | HandWiki | — | 1 | 3 | Verified multiple data points about history and legal status. Hofmann/Sandoz origin is important historical datum not in seed brief. |
| 12 | Google Patents | — | 1 | 1 | Primary source for discovery/synthesis history of MiPLA |
| 13 | PubMed | Psychedelics cardiac 5-HT2B valvulopathy lysergamide LSD | 1 | 1 | Important safety concern for chronic MiPLA use - class-wide cardiac risk |
| 14 | VulcanChem / Web | — | 1 | 2 | SMILES not returned by PubChem API; confirmed from vendor chemical database |
| 15 | Google Patents | — | 1 | 0 | Confirmed MiPLA not in Sandoz/Hofmann patent; HandWiki attribution to Hofmann is likely incorrect - patent is by Pioch/Eli Lilly |
| 16 | PubMed | LSD HPPD hallucinogen persisting perception disorder flashbacks | 8 | 2 | Relevant class safety risk applicable to MiPLA |
| 17 | PubMed | LSD 5-HT2A tolerance receptor downregulation | 1 | 1 | Mechanistic basis for MiPLA tolerance data in seed brief |
| 18 | Multiple | MiPLA potency comparison LSD | 5 | 1 | Multiple convergent sources confirm potency estimate |
| 19 | Research compilation | MiPLA complete data summary | 28 | 1 | Final data compilation for research output |
| 20 | PsychonautWiki | — | 1 | 2 | Dose and duration data confirmed by secondary community harm reduction source |
57 claims by section — every cited sentence, checked against its source
safety10 · 9 ok
Rouaud and colleagues identified structural similarities between psychedelic compounds and known cardiotoxic 5-HT₂B agonists, raising concern for repeated-exposure scenarios such as microdosingsupported
LSD and psilocybin share structural similarities with methysergide, pergolide and fenfluramine... Chronic/microdosing use may raise risk. 02698811231225609
Hallucinogen persisting perception disorder (HPPD): HPPD is documented for LSD-class compounds, with risk present even after a single exposure. No MiPLA-specific HPPD cases have been reported. Flashback phenomena have been documented in controlled LSD studies with healthy participants.supported
HPPD rare but linked to hallucinogen consumption. Can occur after single exposure. LSD most common trigger. brainsci8030047
Hallucinogen persisting perception disorder (HPPD): HPPD is documented for LSD-class compounds, with risk present even after a single exposure. No MiPLA-specific HPPD cases have been reported. Flashback phenomena have been documented in controlled LSD studies with healthy participants.supported
28-year-old with history of LSD and cannabis use developed HPPD 7 months after stopping LSD. Classic symptoms: persistent visual distortions. cureus.46262
Hallucinogen persisting perception disorder (HPPD): HPPD is documented for LSD-class compounds, with risk present even after a single exposure. No MiPLA-specific HPPD cases have been reported. Flashback phenomena have been documented in controlled LSD studies with healthy participants.supported
Reoccurring drug-like experiences after acute effects have worn off described for both [LSD and psilocybin]... DSM-V distressing manifestation = HPPD. s00213-022-06066-z
De la Fuente Revenga and colleagues demonstrated in mice that tolerance to 5-HT₂A agonist-induced head-twitch responses is observable after a single dose, with progressive receptor density reduction upon repeated administrationsupported
Tolerance observable after single dose. DOI caused 5-HT2AR downregulation in mouse frontal cortex. acschemneuro.2c00170
Gillman documented that phenylpiperidine opioids including tramadol have been involved in fatal serotonin toxicity reactions when combined with agents acting by different serotonergic mechanismssupported
Tramadol and other phenylpiperidine opioids... involved in serotonin toxicity with MAOIs (including fatalities). Only combinations of drugs acting by different serotonergic mechanisms produce life-threatening serotonin toxicity. pmid:16051647
No MiPLA-specific case reports exist, but the mechanistic basis is established for all compounds in this classsupported
Only combinations of drugs acting by different serotonergic mechanisms produce life-threatening serotonin toxicity pmid:16051647
Differentiation requires GC-MS (with attention to the diagnostic iminium ion fragment at m/z 72), GC-FTIR, or LC-MS/MSpartially supported
GC-IR, GC-EI-MS/MS, BSTFA derivatization, LC-Q-MS, LC-MS/MS methods described dta.3103
Claim in safety — inconclusiveinconclusiveworking →
Drug-checking services have misidentified MiPLA as LSD in proficiency testingsupported
MIPLA/LSD confusion identified as a common error in drug checking services due to structural isomerism. ijerph20054628
comparative-pharmacology8 · 5 ok
Claim in comparative-pharmacology — inconclusiveinconclusiveworking →
Claim in comparative-pharmacology — inconclusiveinconclusiveworking →
Claim in comparative-pharmacology — inconclusiveinconclusiveworking →
Drug discrimination ED₅₀ 2–3× higher than LSD in ratssupported
each compound completely substituted with ED50 2-3x larger than LSD pmid:8208787
Forensic blotter dosing of 180–186 µg MiPLA per unit versus typical LSD blotter doses of 75–150 µgsupported
Two blotters found to contain 180 and 186 µg MIPLA per blotter dta.3103
MiPLA occupies a specific position in the lysergamide amide SAR landscape mapped by the Nichols laboratory:supported
Comprehensive SAR review for tryptamines, ergolines, phenethylamines. 5-HT2A as principal target. Key structural features for activity. 7854_2017_475
MiPLA occupies a specific position in the lysergamide amide SAR landscape mapped by the Nichols laboratory:supported
Provides structural insight into optimal amide conformation for 5-HT2A binding. pmid:12213075
The S,S-dimethylazetidine lysergamide, which locks the diethyl groups into a single active conformation, exceeds LSD's potency, confirming that the receptor binding geometry is highly specific.supported
(S,S)-2,4-dimethylazetidine lysergamide most LSD-like... Highest affinity and functional potency at 5-HT2A. pmid:12213075
chemistry7 · 5 ok
On the novel psychoactive substance market, MiPLA has been encountered exclusively on blotter paper at doses of approximately 180–186 µg per unitsupported
Forensic analysis of blotters found to contain MIPLA... Two blotters found to contain 180 and 186 µg MIPLA per blotter dta.3103
Molecular modeling of MiPLA shows low-energy conformations similar to LSD, suggesting conformational flexibility at the receptor is sufficient for activity despite the structural changesupported
Molecular modeling found low-energy conformations similar to LSD. pmid:8208787
Claim in chemistry — inconclusiveinconclusiveworking →
The structural relationship to lsd is that of a positional isomer — the same molecular formula and molecular weight, with carbons redistributed between the two amide nitrogen substituents.supported
MIPLA (N-methyl-N-isopropyl LSD isomer) dta.3103
Monte and colleagues confirmed that (R)-configured lysergamides are consistently more potent at both 5-HT₂A and 5-HT₁A receptor sites; the (S)-epimers show dramatically reduced or absent psychedelic activitysupported
(R)-lysergamides consistently more potent than (S)-amides at 5-HT2A and 5-HT1A sites. (R)-pentyllysergamide ~20x more active than (S). pmid:7699712
Claim in chemistry — inconclusiveinconclusiveworking →
The most potent known configuration is the conformationally constrained S,S-dimethylazetidine lysergamide, which maps the precise binding pose of the diethylamide moiety within the 5-HT₂A receptor.supported
(S,S)-2,4-dimethylazetidine lysergamide most LSD-like. Provides structural insight into optimal amide conformation for 5-HT2A binding. Highest affinity and functional potency at 5-HT2A. pmid:12213075
pharmacology7 · 6 ok
The only substance-specific pharmacological characterization derives from Huang and colleagues, who demonstrated that MiPLA fully substitutes for lsd in rats trained to discriminate LSD (0.08 mg/kg) from saline, with an ED₅₀ approximately 2–3× higher than LSDsupported
each compound completely substituted with ED50 2-3x larger than LSD pmid:8208787
DOI preferentially labels 5-HT₂A sites, while ketanserin also labels 5-HT₂C; the divergence may reflect differential affinity across receptor subtypes or distinct binding modes at the two radioligand sites.supported
KI similar to LSD, but had 4-5x lower affinities than LSD at [3H]ketanserin 5-HT2 binding sites pmid:8208787
By class inference from LSD pharmacology, MiPLA is expected to interact with dopamine D₁ and D₂ receptors and trace amine-associated receptor 1 (TAAR₁)supported
LSD and lysergamide analogs tested at D1 and D2 dopamine receptors. All bind with agonist profiles to both subtypes. pmid:7568626
By class inference from LSD pharmacology, MiPLA is expected to interact with dopamine D₁ and D₂ receptors and trace amine-associated receptor 1 (TAAR₁)supported
Two temporal phases of LSD action: early 5-HT2A-mediated (LSD30) and later D2-mediated (LSD90) j.neuropharm.2011.02.006
By class inference from LSD pharmacology, MiPLA is expected to interact with dopamine D₁ and D₂ receptors and trace amine-associated receptor 1 (TAAR₁)supported
Also modulates dopamine D2, TAAR1 at higher doses ijms17111834
For context, lsd administered orally achieves Tmax of approximately 1.1 hours with an elimination half-life of approximately 2.7 hours at microdoses (5–20 µg), exhibiting dose-proportional plasma levelspartially supported
LSD 5/10/20 µg in 23 healthy subjects. Tmax 1.1 h, half-life 2.7 h. cpt.2057
Claim in pharmacology — inconclusiveinconclusiveworking →
summary7 · 6 ok
N-Methyl-N-isopropyllysergamide (MiPLA) is a semisynthetic ergoline psychedelic and structural isomer of lsd sharing the identical molecular weight (323.4 g/mol) but exhibiting approximately 33–50% of LSD's potency by weightpartially supported
each compound completely substituted with ED50 2-3x larger than LSD pmid:8208787
N-Methyl-N-isopropyllysergamide (MiPLA) is a semisynthetic ergoline psychedelic and structural isomer of lsd sharing the identical molecular weight (323.4 g/mol) but exhibiting approximately 33–50% of LSD's potency by weightpartially supported
MIPLA (N-methyl-N-isopropyl LSD isomer) dta.3103
Claim in summary — inconclusiveinconclusiveworking →
It received its only published pharmacological characterization in 1994 through the Nichols laboratory at Purdue University, then remained obscure until appearing on novel psychoactive substance markets around 2019supported
Three LSD derivatives identified from paper sheet products in Japan (Sept 2019 – Mar 2020): 1cP-LSD, MIPLA, and 1B-LSD yakushi.20-00124
MiPLA acts as an agonist at 5-HT₂A receptors — fully substituting for LSD in drug discrimination assays with an ED₅₀ 2–3× higher than LSD — and binds 5-HT₁A sites with affinity comparable to LSDsupported
each compound completely substituted with ED50 2-3x larger than LSD... displaced [3H]8-OH-DPAT from hippocampal homogenates with KI similar to LSD pmid:8208787
Tolerance develops rapidly via 5-HT₂A receptor downregulation in frontal cortex, with cross-tolerance to other serotonergic psychedelics and a reported 14-day full resetpartially supported
Tolerance observable after single dose. Cross-tolerance between psychedelic DOI and LSD. DOI caused 5-HT2AR downregulation in mouse frontal cortex. acschemneuro.2c00170
Cardiac 5-HT₂B activation under chronic exposure is a theoretical concernsupported
Chronic/microdosing use may raise risk 02698811231225609
pharmacokinetic-detail6 · 4 ok
For comparison, LSD oral pharmacokinetics in healthy volunteers show Tmax of approximately 1.1 hours and elimination half-life of approximately 2.7 hours at microdoses (5–20 µg), with dose-proportional increases in Cmax and AUCpartially supported
LSD 5/10/20 µg in 23 healthy subjects (double-blind RCT). Tmax 1.1 h, half-life 2.7 h. cpt.2057
Claim in pharmacokinetic-detail — inconclusiveinconclusiveworking →
Claim in pharmacokinetic-detail — inconclusiveinconclusiveworking →
1cP-MiPLA (4-(cyclopropanecarbonyl)-N-methyl-N-isopropyl-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide) has appeared on illicit marketssupported
1cP-AL-LAD, 1cP-MIPLA, 1V-LSD and LSZ identified in sheet products in Japan s11419-023-00661-1
By analogy with 1cP-LSD — which is a confirmed esterase-hydrolyzable prodrug of LSD — and 1P-ETH-LAD, 1cP-MiPLA is expected to undergo hydrolytic cleavage of the N1-cyclopropanoyl group to release MiPLA as the active metabolitesupported
1CP-LSD prodrug confirmed: hydrolysis to LSD in human serum. dta.2789
By analogy with 1cP-LSD — which is a confirmed esterase-hydrolyzable prodrug of LSD — and 1P-ETH-LAD, 1cP-MiPLA is expected to undergo hydrolytic cleavage of the N1-cyclopropanoyl group to release MiPLA as the active metabolitesupported
1P-ETH-LAD hydrolyzed to ETH-LAD in human serum, suggesting prodrug status. dta.2196
history5 · 4 ok
Brandt and colleagues subsequently reported forensic analysis of blotters containing MiPLA at doses of approximately 180–186 µg per unit and developed analytical methods to differentiate it from lsd and LAMPA (N-methyl-N-propyl lysergamide).supported
Two blotters found to contain 180 and 186 µg MIPLA per blotter... Techniques to differentiate from LSD and LAMPA dta.3103
Claim in history — inconclusiveinconclusiveworking →
Tanaka and colleagues documented MiPLA in paper sheet products seized in Japan between September 2019 and March 2020, representing the first published forensic identificationsupported
Three LSD derivatives identified from paper sheet products in Japan (Sept 2019 – Mar 2020): 1cP-LSD, MIPLA, and 1B-LSD yakushi.20-00124
By 2023, a prodrug variant — 1cP-MiPLA (N1-cyclopropanoyl-MiPLA) — had appeared on Japanese marketssupported
1cP-AL-LAD, 1cP-MIPLA, 1V-LSD and LSZ identified in sheet products in Japan s11419-023-00661-1
A European drug-checking proficiency test in 2023 identified MiPLA/LSD confusion as among the most common analytical errors, arising from identical molecular weight and similar UV spectrasupported
MIPLA/LSD confusion identified as a common error in drug checking services due to structural isomerism. ijerph20054628
receptor-pharmacology4 · 3 ok
Claim in receptor-pharmacology — inconclusiveinconclusiveworking →
LSD and close structural analogs interact with dopamine D₁ receptors (Ki in the low-nanomolar range for LSD) and exhibit a biphasic pharmacological profile involving early 5-HT₂A-mediated effects followed by later dopaminergic contributionspartially supported
LSD and lysergamide analogs tested at D1 and D2 dopamine receptors. All bind with agonist profiles to both subtypes. pmid:7568626
LSD and close structural analogs interact with dopamine D₁ receptors (Ki in the low-nanomolar range for LSD) and exhibit a biphasic pharmacological profile involving early 5-HT₂A-mediated effects followed by later dopaminergic contributionssupported
Two temporal phases of LSD action: early 5-HT2A-mediated (LSD30) and later D2-mediated (LSD90). j.neuropharm.2011.02.006
TAAR₁ activation has also been documented for LSDsupported
Also modulates dopamine D2, TAAR1 at higher doses. ijms17111834
clinical-evidence1 · 0 ok
Claim in clinical-evidence — inconclusiveinconclusiveworking →
legal-status1 · 1 ok
MiPLA satisfies both criteria: it is a structural isomer of LSD with demonstrated LSD-like pharmacological activitysupported
each compound completely substituted with ED50 2-3x larger than LSD pmid:8208787
neuroscience1 · 1 ok
As a 5-HT₂A receptor agonist that fully substitutes for LSD in drug discrimination, MiPLA is expected to engage the same neural systems documented for classical serotonergic psychedelics:supported
each compound completely substituted... displaced [125I]DOI from rat cortical homogenates... KI similar to LSD pmid:8208787