{
 "name": "R-(-)-BPAP Evidence Card: census, claims and registry data",
 "version": "1.1",
 "date": "2026-10-26",
 "creator": "Condor Research Editorial",
 "license": "CC BY 4.0",
 "license_url": "https://creativecommons.org/licenses/by/4.0/",
 "url": "https://condorresearch.com/research/r-bpap-evidence-card/",
 "metrics": {
  "records_total": 61,
  "literature_records": 50,
  "patent_families": 11,
  "primary": 31,
  "secondary_lineage": 13,
  "external_mentions": 6,
  "in_pubmed": 47,
  "primary_by_evidence": {
   "ex vivo": 7,
   "in vitro": 6,
   "chemistry": 2,
   "computational": 1,
   "animal": 14,
   "animal PK": 1
  },
  "primary_species_mentions": {
   "rat": 25,
   "mouse": 4,
   "human cells": 3,
   "human cell lines": 1
  },
  "human_studies_registry_only": 1,
  "human_publications": 0,
  "registered_trials": 1,
  "authorship_sensitivity": {
   "A_primary_lineage_author": {
    "n": 29,
    "of": 31,
    "pct": 93.5
   },
   "B_plus_documented_links": {
    "n": 30,
    "of": 31,
    "pct": 96.8
   },
   "C_core_only": {
    "n": 22,
    "of": 31,
    "pct": 71.0
   },
   "D_fujimoto_only": {
    "n": 14,
    "of": 31,
    "pct": 45.2
   },
   "E_pubmed_primary_only": {
    "n": 28,
    "of": 30,
    "pct": 93.3
   },
   "F_biological_primary_only": {
    "n": 26,
    "of": 28,
    "pct": 92.9
   },
   "G_primary_since_2014": {
    "n": 9,
    "of": 9,
    "pct": 100.0
   },
   "H_all_primary_and_secondary": {
    "n": 42,
    "of": 44,
    "pct": 95.5
   },
   "I_all_records_incl_external_mentions": {
    "n": 42,
    "of": 50,
    "pct": 84.0
   }
  },
  "compound_source": {
   "read_open_access_primary_2020_2025": [
    "PMID:30734151",
    "PMID:35955676",
    "PMID:37306892",
    "PMID:39903411"
   ],
   "stating_fujimoto_as_source_or_supporter": 4
  },
  "external_primary": [
   "PMID:16624331"
  ],
  "first_primary": 1999,
  "last_primary": 2025,
  "primary_per_period": {
   "1999-2005": 18,
   "2006-2013": 4,
   "2014-2026": 9
  }
 },
 "doublecode": {
  "n": 47,
  "coder2": "rule-based, blind to coder 1; sees only PubMed metadata",
  "evidence_type": [
   80.9,
   0.75
  ],
  "lineage": [
   100.0,
   1.0
  ],
  "evidence_disagreements": [
   [
    "PMID:10588928",
    "ex vivo",
    "in vitro"
   ],
   [
    "PMID:12147307",
    "in vitro",
    "chemistry"
   ],
   [
    "PMID:12672509",
    "animal",
    "ex vivo"
   ],
   [
    "PMID:12679194",
    "in vitro",
    "chemistry"
   ],
   [
    "PMID:14659999",
    "in vitro",
    "ex vivo"
   ],
   [
    "PMID:15102525",
    "in vitro",
    "chemistry"
   ],
   [
    "PMID:30734151",
    "animal",
    "in vitro"
   ],
   [
    "PMID:18771016",
    "review",
    "animal"
   ],
   [
    "PMID:37686140",
    "review",
    "animal"
   ]
  ],
  "lineage_disagreements": []
 },
 "records": [
  {
   "id": "PMID:10588928",
   "pmid": "10588928",
   "doi": "10.1038/sj.bjp.0702995",
   "year": 1999,
   "kind": "article",
   "evidence": "ex vivo",
   "species": "rat",
   "origin": "core+fujimoto",
   "lineage": true,
   "role": "primary",
   "summary": "First pharmacology of (-)-BPAP; selected from 65 analogues",
   "note": "neuron culture arm used the racemate per a 2011 chapter by the same group",
   "journal": "Br J Pharmacol"
  },
  {
   "id": "PMID:11100977",
   "pmid": "11100977",
   "doi": "10.1023/a:1007050808754",
   "year": 2000,
   "kind": "article",
   "evidence": "in vitro",
   "species": "rat",
   "origin": "fujimoto",
   "lineage": true,
   "role": "primary",
   "summary": "Cortical neuron survival; weak sigma-site displacement",
   "note": "",
   "journal": "Cell Mol Neurobiol"
  },
  {
   "id": "PMID:11377178",
   "pmid": "11377178",
   "doi": "10.1016/s0968-0896(01)00002-5",
   "year": 2001,
   "kind": "article",
   "evidence": "chemistry",
   "species": "rat",
   "origin": "core+fujimoto",
   "lineage": true,
   "role": "primary",
   "summary": "Structure-activity series leading to (-)-BPAP",
   "note": "read in full: 52 racemates itemised in four tables, 4 resolved into enantiomers; screened in a rat shuttle-box test",
   "journal": "Bioorg Med Chem"
  },
  {
   "id": "PMID:11377179",
   "pmid": "11377179",
   "doi": "10.1016/s0968-0896(00)00341-2",
   "year": 2001,
   "kind": "article",
   "evidence": "chemistry",
   "species": "none",
   "origin": "core+fujimoto",
   "lineage": true,
   "role": "primary",
   "summary": "Enantioselective synthesis; (-)-BPAP is R (X-ray)",
   "note": "read in full: specific rotation of both hydrochlorides reported",
   "journal": "Bioorg Med Chem"
  },
  {
   "id": "PMID:11377187",
   "pmid": "11377187",
   "doi": "10.1016/s0968-0896(01)00008-6",
   "year": 2001,
   "kind": "article",
   "evidence": "computational",
   "species": "none",
   "origin": "fujimoto",
   "lineage": true,
   "role": "primary",
   "summary": "Molecular-orbital model of hydroxyl radical trapping",
   "note": "computational only",
   "journal": "Bioorg Med Chem"
  },
  {
   "id": "PMID:11516435",
   "pmid": "11516435",
   "doi": "10.1016/s0014-2999(01)01040-8",
   "year": 2001,
   "kind": "article",
   "evidence": "animal",
   "species": "rat",
   "origin": "core+fujimoto",
   "lineage": true,
   "role": "primary",
   "summary": "Locomotor activity; dopamine-receptor antagonism",
   "note": "",
   "journal": "Eur J Pharmacol"
  },
  {
   "id": "PMID:12147307",
   "pmid": "12147307",
   "doi": "10.1016/s0304-3940(02)00461-5",
   "year": 2002,
   "kind": "article",
   "evidence": "in vitro",
   "species": "mouse",
   "origin": "fujimoto",
   "lineage": true,
   "role": "primary",
   "summary": "Neurotrophin secretion by cultured astrocytes",
   "note": "high-concentration range only",
   "journal": "Neurosci Lett"
  },
  {
   "id": "PMID:12175892",
   "pmid": "12175892",
   "doi": "10.1016/s0024-3205(02)01968-9",
   "year": 2002,
   "kind": "article",
   "evidence": "animal",
   "species": "rat",
   "origin": "core+fujimoto",
   "lineage": true,
   "role": "primary",
   "summary": "3-F-BPAP antagonises the BPAP effect in a learning test",
   "note": "",
   "journal": "Life Sci"
  },
  {
   "id": "PMID:12204771",
   "pmid": "12204771",
   "doi": "10.1016/s0024-3205(02)01969-0",
   "year": 2002,
   "kind": "article",
   "evidence": "ex vivo",
   "species": "rat",
   "origin": "core",
   "lineage": true,
   "role": "primary",
   "summary": "Two bell-shaped concentration-effect curves",
   "note": "read in full: resting release from isolated tissue pieces, 8 rats per point, paired t-tests without multiplicity correction",
   "journal": "Life Sci"
  },
  {
   "id": "PMID:12365195",
   "pmid": "12365195",
   "doi": "10.1007/BF03190451",
   "year": 2002,
   "kind": "article",
   "evidence": "animal PK",
   "species": "rat",
   "origin": "core",
   "lineage": true,
   "role": "primary",
   "summary": "Radiolabel distribution and elimination",
   "note": "read in full: total radioactivity only, 3 rats per time point; one metabolite identified, 7-8 more unidentified",
   "journal": "Eur J Drug Metab Pharmacokinet"
  },
  {
   "id": "PMID:12527038",
   "pmid": "12527038",
   "doi": "10.1016/s0024-3205(02)02411-6",
   "year": 2003,
   "kind": "article",
   "evidence": "animal",
   "species": "rat",
   "origin": "core+fujimoto",
   "lineage": true,
   "role": "primary",
   "summary": "Interaction with L-DOPA in reserpinised rats",
   "note": "",
   "journal": "Life Sci"
  },
  {
   "id": "PMID:12672509",
   "pmid": "12672509",
   "doi": "10.1016/s0024-3205(03)00174-7",
   "year": 2003,
   "kind": "article",
   "evidence": "animal",
   "species": "rat",
   "origin": "core",
   "lineage": true,
   "role": "primary",
   "summary": "Learning-test comparison with alpha-tocopherol and deprenyl",
   "note": "",
   "journal": "Life Sci"
  },
  {
   "id": "PMID:12679194",
   "pmid": "12679194",
   "doi": "10.1016/s0024-3205(03)00191-7",
   "year": 2003,
   "kind": "article",
   "evidence": "in vitro",
   "species": "mouse",
   "origin": "core+fujimoto",
   "lineage": true,
   "role": "primary",
   "summary": "Astrocyte neurotrophins across the full concentration range",
   "note": "",
   "journal": "Life Sci"
  },
  {
   "id": "PMID:12697274",
   "pmid": "12697274",
   "doi": "10.1016/s0024-3205(03)00197-8",
   "year": 2003,
   "kind": "article",
   "evidence": "ex vivo",
   "species": "rat",
   "origin": "core",
   "lineage": true,
   "role": "primary",
   "summary": "Comparison with uptake and MAO inhibitors on evoked release",
   "note": "",
   "journal": "Life Sci"
  },
  {
   "id": "PMID:12697275",
   "pmid": "12697275",
   "doi": "10.1016/s0024-3205(03)00192-9",
   "year": 2003,
   "kind": "article",
   "evidence": "ex vivo",
   "species": "rat",
   "origin": "core",
   "lineage": true,
   "role": "primary",
   "summary": "HPLC of release from discrete brain areas",
   "note": "",
   "journal": "Life Sci"
  },
  {
   "id": "PMID:14659999",
   "pmid": "14659999",
   "doi": "10.1016/j.ejphar.2003.09.044",
   "year": 2003,
   "kind": "article",
   "evidence": "in vitro",
   "species": "human cells, rat",
   "origin": "fujimoto",
   "lineage": true,
   "role": "primary",
   "summary": "Uptake inhibition at human DAT, NET, SERT; no tyramine-like release",
   "note": "read in full; co-author from a US laboratory (Janowsky); cocaine as reference",
   "journal": "Eur J Pharmacol"
  },
  {
   "id": "PMID:15102525",
   "pmid": "15102525",
   "doi": "10.1016/j.lfs.2003.12.001",
   "year": 2004,
   "kind": "article",
   "evidence": "in vitro",
   "species": "human cells",
   "origin": "fujimoto",
   "lineage": true,
   "role": "primary",
   "summary": "Anti-apoptotic effect in SH-SY5Y cells (Bcl-2)",
   "note": "",
   "journal": "Life Sci"
  },
  {
   "id": "PMID:16079507",
   "pmid": "16079507",
   "doi": "10.1248/bpb.28.1524",
   "year": 2005,
   "kind": "article",
   "evidence": "ex vivo",
   "species": "rat",
   "origin": "fujimoto",
   "lineage": true,
   "role": "primary",
   "summary": "BDNF and trkB in mesencephalic slices",
   "note": "",
   "journal": "Biol Pharm Bull"
  },
  {
   "id": "PMID:16624331",
   "pmid": "16624331",
   "doi": "10.1016/j.lfs.2006.03.005",
   "year": 2006,
   "kind": "article",
   "evidence": "in vitro",
   "species": "human cells, rat",
   "origin": "external",
   "lineage": false,
   "role": "primary",
   "summary": "Cytoprotection in PC12 and human brain endothelial cells",
   "note": "no lineage author; same university (neurology)",
   "journal": "Life Sci"
  },
  {
   "id": "DOI:10.1186/1471-2210-7-s2-a32",
   "pmid": null,
   "doi": "10.1186/1471-2210-7-s2-a32",
   "year": 2007,
   "kind": "abstract",
   "evidence": "animal",
   "species": "rat",
   "origin": "core",
   "lineage": true,
   "role": "primary",
   "summary": "Congress abstract: experimental stroke model",
   "note": "Miklya co-author",
   "journal": null
  },
  {
   "id": "PMID:18243357",
   "pmid": "18243357",
   "doi": "10.1016/j.bbr.2007.12.016",
   "year": 2008,
   "kind": "article",
   "evidence": "animal",
   "species": "mouse, rat",
   "origin": "fujimoto",
   "lineage": true,
   "role": "primary",
   "summary": "Forced swim, social interaction and bulbectomy models",
   "note": "read in full: blinded scoring stated; compound synthesised by FP (Fujimoto) Pharmaceutical, first author's affiliation",
   "journal": "Behav Brain Res"
  },
  {
   "id": "PMID:19883738",
   "pmid": "19883738",
   "doi": "10.1016/j.neuroscience.2009.10.055",
   "year": 2010,
   "kind": "article",
   "evidence": "animal",
   "species": "rat",
   "origin": "linked",
   "lineage": false,
   "role": "primary",
   "summary": "Reinstatement of methamphetamine seeking",
   "note": "second author is co-inventor on the Fujimoto substance-dependence patent",
   "journal": "Neuroscience"
  },
  {
   "id": "PMID:24905523",
   "pmid": "24905523",
   "doi": "10.1016/j.pharep.2013.11.003",
   "year": 2014,
   "kind": "article",
   "evidence": "animal",
   "species": "rat",
   "origin": "core",
   "lineage": true,
   "role": "primary",
   "summary": "BPAP as reference compound against rasagiline",
   "note": "read in full: no MAO measurement; MAO-A statement cites the 1999 paper",
   "journal": "Pharmacol Rep"
  },
  {
   "id": "PMID:27777099",
   "pmid": "27777099",
   "doi": "10.1016/j.lfs.2016.10.023",
   "year": 2016,
   "kind": "article",
   "evidence": "animal",
   "species": "rat",
   "origin": "core",
   "lineage": true,
   "role": "primary",
   "summary": "Lifespan cohort of 200 rats; reported longer lifespan",
   "note": "read in full: does not mention tumours; same cohort as the 2017 paper",
   "journal": "Life Sci"
  },
  {
   "id": "PMID:28623006",
   "pmid": "28623006",
   "doi": "10.1016/j.lfs.2017.06.010",
   "year": 2017,
   "kind": "article",
   "evidence": "animal",
   "species": "rat, human cell lines",
   "origin": "core",
   "lineage": true,
   "role": "primary",
   "summary": "Tumour manifestation in a longevity study; medulloblastoma lines",
   "note": "read in full: same 200-rat cohort as the 2016 paper (second endpoint)",
   "journal": "Life Sci"
  },
  {
   "id": "PMID:30734151",
   "pmid": "30734151",
   "doi": "10.1007/s12253-019-00603-6",
   "year": 2020,
   "kind": "article",
   "evidence": "animal",
   "species": "mouse",
   "origin": "core",
   "lineage": true,
   "role": "primary",
   "summary": "Lung adenocarcinoma xenograft",
   "note": "compound supplied by Fujimoto",
   "journal": "Pathol Oncol Res"
  },
  {
   "id": "PMID:31610214",
   "pmid": "31610214",
   "doi": "10.1016/j.bbr.2019.112290",
   "year": 2020,
   "kind": "article",
   "evidence": "animal",
   "species": "rat",
   "origin": "core",
   "lineage": true,
   "role": "primary",
   "summary": "Anxiety-like behaviour, glutamate receptor phosphorylation",
   "note": "",
   "journal": "Behav Brain Res"
  },
  {
   "id": "PMID:35853552",
   "pmid": "35853552",
   "doi": "10.1016/j.neuint.2022.105404",
   "year": 2022,
   "kind": "article",
   "evidence": "animal",
   "species": "rat",
   "origin": "core",
   "lineage": true,
   "role": "primary",
   "summary": "Chronic mild stress; gene expression",
   "note": "",
   "journal": "Neurochem Int"
  },
  {
   "id": "PMID:35955676",
   "pmid": "35955676",
   "doi": "10.3390/ijms23158543",
   "year": 2022,
   "kind": "article",
   "evidence": "ex vivo",
   "species": "rat",
   "origin": "core",
   "lineage": true,
   "role": "primary",
   "summary": "TAAR1 link via EPPTB in striatal slices",
   "note": "work partly supported by Fujimoto (acknowledgement)",
   "journal": "Int J Mol Sci"
  },
  {
   "id": "PMID:37306892",
   "pmid": "37306892",
   "doi": "10.1007/s11357-023-00821-6",
   "year": 2024,
   "kind": "article",
   "evidence": "animal",
   "species": "rat",
   "origin": "core",
   "lineage": true,
   "role": "primary",
   "summary": "Aged experienced rats: no effect on cognition or lifespan",
   "note": "compound a gift from Fujimoto",
   "journal": "Geroscience"
  },
  {
   "id": "PMID:39903411",
   "pmid": "39903411",
   "doi": "10.1007/s11064-025-04337-7",
   "year": 2025,
   "kind": "article",
   "evidence": "ex vivo",
   "species": "rat",
   "origin": "core",
   "lineage": true,
   "role": "primary",
   "summary": "TAAR1 and dopamine-GABA interaction in striatum",
   "note": "compound received from Fujimoto",
   "journal": "Neurochem Res"
  },
  {
   "id": "PMID:11607046",
   "pmid": "11607046",
   "doi": "10.1111/j.1527-3458.2001.tb00202.x",
   "year": 2001,
   "kind": "review",
   "evidence": "review",
   "species": "",
   "origin": "core",
   "lineage": true,
   "role": "secondary",
   "summary": "Antiaging compounds: deprenyl and BPAP",
   "note": "",
   "journal": "CNS Drug Rev"
  },
  {
   "id": "PMID:12834268",
   "pmid": "12834268",
   "doi": "10.1023/a:1024224311289",
   "year": 2003,
   "kind": "review",
   "evidence": "review",
   "species": "",
   "origin": "core",
   "lineage": true,
   "role": "secondary",
   "summary": "Enhancer regulation: the neurochemical concept",
   "note": "",
   "journal": "Neurochem Res"
  },
  {
   "id": "PMID:15093948",
   "pmid": "15093948",
   "doi": "10.1016/j.pnpbp.2003.11.016",
   "year": 2004,
   "kind": "review",
   "evidence": "review",
   "species": "",
   "origin": "core+fujimoto",
   "lineage": true,
   "role": "secondary",
   "summary": "Endogenous enhancer substances and synthetic derivatives",
   "note": "",
   "journal": "Prog Neuropsychopharmacol Biol Psychiatry"
  },
  {
   "id": "PMID:15825676",
   "pmid": "15825676",
   "doi": null,
   "year": 2004,
   "kind": "review",
   "evidence": "review",
   "species": "",
   "origin": "core",
   "lineage": true,
   "role": "secondary",
   "summary": "Alzheimer's prevention: a proposed three-arm trial",
   "note": "proposal; no registration located",
   "journal": "Neuropsychopharmacol Hung"
  },
  {
   "id": "PMID:15825677",
   "pmid": "15825677",
   "doi": null,
   "year": 2004,
   "kind": "review",
   "evidence": "review",
   "species": "",
   "origin": "core",
   "lineage": true,
   "role": "secondary",
   "summary": "Enhancer substances in major depression (proposal)",
   "note": "",
   "journal": "Neuropsychopharmacol Hung"
  },
  {
   "id": "PMID:16023777",
   "pmid": "16023777",
   "doi": "10.1016/j.pnpbp.2005.06.004",
   "year": 2006,
   "kind": "review",
   "evidence": "review",
   "species": "",
   "origin": "core",
   "lineage": true,
   "role": "secondary",
   "summary": "Major depression and enhancer substances",
   "note": "",
   "journal": "Prog Neuropsychopharmacol Biol Psychiatry"
  },
  {
   "id": "PMID:18771016",
   "pmid": "18771016",
   "doi": null,
   "year": 2008,
   "kind": "article",
   "evidence": "review",
   "species": "",
   "origin": "core",
   "lineage": true,
   "role": "secondary",
   "summary": "Deprenyl vs J-508 and rasagiline (Hungarian)",
   "note": "BPAP as background",
   "journal": "Neuropsychopharmacol Hung"
  },
  {
   "id": "PMID:20962359",
   "pmid": "20962359",
   "doi": null,
   "year": 2010,
   "kind": "review",
   "evidence": "review",
   "species": "",
   "origin": "core",
   "lineage": true,
   "role": "secondary",
   "summary": "Enhancer substances and liposomal delivery (Hungarian)",
   "note": "",
   "journal": "Neuropsychopharmacol Hung"
  },
  {
   "id": "DOI:10.5772/18654",
   "pmid": null,
   "doi": "10.5772/18654",
   "year": 2011,
   "kind": "chapter",
   "evidence": "review",
   "species": "",
   "origin": "core",
   "lineage": true,
   "role": "secondary",
   "summary": "The Knoll concept (InTech chapter)",
   "note": "cited in 2023 for 'early clinical findings'; no human BPAP data in our reading",
   "journal": null
  },
  {
   "id": "DOI:10.2174/978160805470111201010006",
   "pmid": null,
   "doi": "10.2174/978160805470111201010006",
   "year": 2012,
   "kind": "chapter",
   "evidence": "review",
   "species": "",
   "origin": "core",
   "lineage": true,
   "role": "secondary",
   "summary": "Bentham e-book chapter on the CAE effect",
   "note": "read in full (purchased); no human BPAP data; confirms racemate in the 1999 culture experiment",
   "journal": null
  },
  {
   "id": "PMID:27480491",
   "pmid": "27480491",
   "doi": "10.1038/mp.2016.127",
   "year": 2016,
   "kind": "review",
   "evidence": "review",
   "species": "",
   "origin": "core",
   "lineage": true,
   "role": "secondary",
   "summary": "Selegiline after 50 years",
   "note": "",
   "journal": "Mol Psychiatry"
  },
  {
   "id": "PMID:31743738",
   "pmid": "31743738",
   "doi": "10.1016/j.ejphar.2019.172793",
   "year": 2020,
   "kind": "article",
   "evidence": "review",
   "species": "",
   "origin": "core+fujimoto",
   "lineage": true,
   "role": "secondary",
   "summary": "In memoriam of Joseph Knoll",
   "note": "",
   "journal": "Eur J Pharmacol"
  },
  {
   "id": "PMID:37686140",
   "pmid": "37686140",
   "doi": "10.3390/ijms241713334",
   "year": 2023,
   "kind": "article",
   "evidence": "mention",
   "species": "",
   "origin": "core",
   "lineage": true,
   "role": "secondary",
   "summary": "Selegiline vs rasagiline; discusses BPAP",
   "note": "declares partial support by Fujimoto",
   "journal": "Int J Mol Sci"
  },
  {
   "id": "PMID:26300737",
   "pmid": "26300737",
   "doi": null,
   "year": 2015,
   "kind": "review",
   "evidence": "mention",
   "species": "",
   "origin": "external",
   "lineage": false,
   "role": "mention",
   "summary": "Sympathoadrenergic modulation of haematopoiesis (table entry)",
   "note": "",
   "journal": "Front Cell Neurosci"
  },
  {
   "id": "PMID:25995827",
   "pmid": "25995827",
   "doi": null,
   "year": 2015,
   "kind": "article",
   "evidence": "mention",
   "species": "",
   "origin": "external",
   "lineage": false,
   "role": "mention",
   "summary": "Benzofuran carboxamides; BPAP cited as precedent",
   "note": "",
   "journal": "Biomol Ther (Seoul)"
  },
  {
   "id": "PMID:32429435",
   "pmid": "32429435",
   "doi": null,
   "year": 2020,
   "kind": "review",
   "evidence": "mention",
   "species": "",
   "origin": "external",
   "lineage": false,
   "role": "mention",
   "summary": "Benzofuran synthesis review",
   "note": "calls (-)-BPAP a 'prescribed' antidepressant",
   "journal": "Molecules"
  },
  {
   "id": "PMID:36840015",
   "pmid": "36840015",
   "doi": null,
   "year": 2023,
   "kind": "review",
   "evidence": "mention",
   "species": "",
   "origin": "external",
   "lineage": false,
   "role": "mention",
   "summary": "Dopamine-related drugs as anti-inflammatories",
   "note": "",
   "journal": "Pharmaceutics"
  },
  {
   "id": "PMID:40816452",
   "pmid": "40816452",
   "doi": null,
   "year": 2025,
   "kind": "review",
   "evidence": "mention",
   "species": "",
   "origin": "external",
   "lineage": false,
   "role": "mention",
   "summary": "Meta-analysis of deprenyl longevity experiments",
   "note": "reports the 2016 BPAP result; omits the 2024 null study",
   "journal": "Ageing Res Rev"
  },
  {
   "id": "PMID:41284116",
   "pmid": "41284116",
   "doi": null,
   "year": 2025,
   "kind": "article",
   "evidence": "mention",
   "species": "",
   "origin": "external",
   "lineage": false,
   "role": "mention",
   "summary": "Lung adenocarcinoma risk model; cites BPAP xenograft",
   "note": "",
   "journal": "Discov Oncol"
  }
 ],
 "patent_families": [
  {
   "priority": "1997-08-07",
   "assignee": "Fujimoto Brothers",
   "inventors": "Yoneda F; Knoll J",
   "subject": "Ethylamine derivatives with bicyclic rings (benzofuran class)",
   "members": "WO1999007667A1; HU228759B1; IL129322A; SI9820009A"
  },
  {
   "priority": "1998-10-29",
   "assignee": "Fujimoto Brothers",
   "inventors": "Yoneda F; Knoll J",
   "subject": "Optically active (-)-BPAP, substantially free of the (+)-isomer",
   "members": "WO2000026204A1; US6391914B1; EP1052259; CA2317036C; JP2000136187A"
  },
  {
   "priority": "2000-04-11",
   "assignee": "Fujimoto",
   "inventors": "Yoneda F; Oka T; Watanabe M; Yasusa T",
   "subject": "Process for optically active aminopentane derivatives",
   "members": "WO2001077074; JP2001294583A; AU4474201A"
  },
  {
   "priority": "2001-09-14",
   "assignee": "Fujimoto",
   "inventors": "Yoneda F; Knoll J",
   "subject": "Trifluoropropylaminopentane derivative (3-F-BPAP)",
   "members": "JP2003081960A"
  },
  {
   "priority": "2001-09-19",
   "assignee": "Fujimoto",
   "inventors": "Yoneda F; Knoll J",
   "subject": "Apoptosis inhibitor",
   "members": "JP2003089695A; JP2003089643A"
  },
  {
   "priority": "2004-11-25",
   "assignee": "Fujimoto",
   "inventors": "Yamamoto T; Yoneda F",
   "subject": "Use against substance dependence (relapse)",
   "members": "US8318799B2; EP1815853; CA2589289C; IL183028; KR20070091610"
  },
  {
   "priority": "2005-06-28",
   "assignee": "Fujimoto",
   "inventors": "Yoneda F; Watanabe M",
   "subject": "Process and intermediates for the optically active compound",
   "members": "US7807840B2; US8178686B2; EP1905760B1; CA2612290C; AU2006263167"
  },
  {
   "priority": "2007-06-21",
   "assignee": "Fujimoto",
   "inventors": "Yoneda F; Ohde H; Hoshino N",
   "subject": "Formulation",
   "members": "WO2008156160A1; EP2158908B1; US20100137429A1; CA2690945C; CN101677988A; JP5754885B2"
  },
  {
   "priority": "2013-12-25",
   "assignee": "Fujimoto",
   "inventors": "Togashi H; Hiraide S",
   "subject": "Attention-deficit/hyperactivity disorder use",
   "members": "WO2015098591A1; AU2014371437B2; CN106163514A"
  },
  {
   "priority": "2014-12-05",
   "assignee": "Fujimoto; Semmelweis University",
   "inventors": "Knoll J; Miklya I",
   "subject": "Tumour-manifestation suppression (family 1)",
   "members": "WO2016088111A1; US10258598B2; EP3226851B1; CN107205966A"
  },
  {
   "priority": "2014-12-05",
   "assignee": "Fujimoto; Semmelweis University",
   "inventors": "Knoll J; Miklya I",
   "subject": "Tumour-manifestation suppression (family 2)",
   "members": "WO2016088112A1; US10258599B2; EP3226852B1; RU2714893C2; JP6875278B2"
  }
 ],
 "human_studies": [
  {
   "register": "EudraCT",
   "id": "2006-000361-11",
   "sponsor": "Fujimoto Pharmaceutical Corporation",
   "country": "United Kingdom",
   "design": "open-label, single site, no placebo, no randomisation, sequential levels",
   "participants": 10,
   "recruitment": "2006-09 to 2007-02",
   "global_end": "2007-03-30 (results record) / 2007-04-02 (protocol record)",
   "results_posted": "2022-07-21",
   "statistics": "descriptive only",
   "serious_adverse_events": 0,
   "peer_reviewed_publication": null
  }
 ],
 "claims": [
  {
   "claim": "BPAP is a TAAR1 agonist",
   "where": "vendor pages; forum guides",
   "evidence": "The TAAR1 link rests on one group's experiments in rat striatal slices, where the TAAR1 antagonist EPPTB reversed the BPAP effect. No binding, cAMP or knockout experiment on TAAR1 itself was located.",
   "verdict": "Not established",
   "sources": [
    "PMID:35955676",
    "PMID:39903411"
   ]
  },
  {
   "claim": "BPAP is about 100 to 130 times more potent than selegiline",
   "where": "Wikipedia; vendor pages",
   "evidence": "The figure comes from a rat learning test (tetrabenazine shuttle box), the screen used to rank the analogues: about 130 times selegiline and about 100 times PPAP. It is a ratio in one assay, not a general potency measure, and has not been measured in people.",
   "verdict": "Narrower than claimed",
   "sources": [
    "PMID:10588928",
    "PMID:11377178"
   ]
  },
  {
   "claim": "BPAP extends lifespan",
   "where": "longevity forums; one 2025 meta-analysis",
   "evidence": "One cohort of 200 rats (40 per group), reported by the developers in 2016, showed longer mean lifespan in both BPAP groups by pairwise t-tests, which survive a Bonferroni correction in our recalculation (p = 0.03 and 0.04). The printed five-group F statistic corresponds to p = 0.09, while the paper's own table of means gives p = 0.035, so the omnibus test is at best modest. The same cohort's 2017 report shows that tumour manifestation also differed between groups, which the 2016 paper does not mention. A 2024 study in aged rats found no effect on lifespan or cognition.",
   "verdict": "Conflicting rodent data",
   "sources": [
    "PMID:27777099",
    "PMID:28623006",
    "PMID:37306892"
   ]
  },
  {
   "claim": "BPAP has never been tested in humans",
   "where": "forums; review pages",
   "evidence": "One human study exists, registered only in the EU Clinical Trials Register (EudraCT 2006-000361-11): an open-label, single-site UK study in 10 adults with Parkinson's disease, sponsored by Fujimoto, completed in 2007, with summary results posted in July 2022 and no peer-reviewed publication located. It is absent from ClinicalTrials.gov and ISRCTN.",
   "verdict": "Incorrect: one small registry-only study",
   "sources": [
    "eudract",
    "eudract_res"
   ]
  },
  {
   "claim": "Clinical data show BPAP works in Parkinson's disease",
   "where": "a 2023 paper ('early clinical findings'); forums",
   "evidence": "The only human data are the EudraCT summary results: no placebo, no randomisation, no statistical analysis, 10 participants. The 2023 statement cites a 2011 chapter that, in our reading, reports no human BPAP data.",
   "verdict": "Not supported",
   "sources": [
    "eudract_res",
    "PMID:37686140",
    "DOI:10.5772/18654"
   ]
  },
  {
   "claim": "BPAP is an approved or prescribed antidepressant",
   "where": "a 2020 synthesis review",
   "evidence": "No approval was located in the EMA medicines dataset or Drugs@FDA. The review lists (-)-BPAP among 'prescribed agents'.",
   "verdict": "Incorrect",
   "sources": [
    "PMID:32429435"
   ]
  },
  {
   "claim": "BPAP is a pure 'enhancer' and not a reuptake inhibitor",
   "where": "forum guides",
   "evidence": "Uptake inhibition at human dopamine and noradrenaline transporters was measured in 2003 at nanomolar concentrations. Whether the 'enhancer' effect is separate from uptake inhibition depends on the model and has been tested mainly by the originating group.",
   "verdict": "Contradicted in part",
   "sources": [
    "PMID:14659999",
    "PMID:12697274"
   ]
  },
  {
   "claim": "BPAP does not inhibit MAO",
   "where": "vendor pages",
   "evidence": "Reported as leaving MAO practically unchanged in the low range. MAO-A inhibition at high concentrations is stated in 2014 with a citation to the 1999 paper and is invoked in 2022 for the second peak; the 2014 study did not measure MAO activity itself.",
   "verdict": "Partly supported",
   "sources": [
    "PMID:24905523",
    "PMID:35955676"
   ]
  },
  {
   "claim": "More is not better: the effect follows a bell-shaped curve",
   "where": "forum guides; vendor pages",
   "evidence": "Two bell-shaped concentration-effect ranges are reported ex vivo by the developers, and a similar pattern in cultured cells by one group without a developer author. The mechanism is unexplained and the pattern has not been studied in people.",
   "verdict": "Reported preclinically",
   "sources": [
    "PMID:12204771",
    "PMID:16624331"
   ]
  },
  {
   "claim": "BPAP suppresses tumours",
   "where": "patent summaries; forum guides",
   "evidence": "Fewer tumours were observed in the BPAP groups of one rat cohort; that cohort (the 2016-2017 longevity study) reported fewer spontaneous fibromyxosarcomas in BPAP groups (8 and 7 of 40, against 20 of 40 with saline), and one mouse xenograft study reported slower tumour growth; both come from the developers' network. No independent replication was located.",
   "verdict": "Reported preclinically",
   "sources": [
    "PMID:28623006",
    "PMID:30734151"
   ]
  },
  {
   "claim": "BPAP is neuroprotective or raises BDNF",
   "where": "vendor pages; forums",
   "evidence": "Neurotrophin and anti-apoptotic effects were measured in astrocyte cultures, brain slices and a neuroblastoma line, mostly in the high concentration range; no in vivo human measurement exists.",
   "verdict": "Preclinical only",
   "sources": [
    "PMID:12679194",
    "PMID:16079507",
    "PMID:15102525"
   ]
  },
  {
   "claim": "BPAP is safe or free of side effects",
   "where": "forums",
   "evidence": "The EudraCT summary lists no serious adverse events or deaths in 10 participants in a short exploratory protocol, with non-serious events in some. Ten people in an uncontrolled study cannot establish safety, and no full repeat-dose toxicology report was located; the only published pharmacokinetic study is in rats and measured total radioactivity rather than the parent compound.",
   "verdict": "Not established",
   "sources": [
    "eudract_res",
    "PMID:12365195"
   ]
  },
  {
   "claim": "BPAP is a peptide",
   "where": "vendor and affiliate pages titled 'BPAP peptide'",
   "evidence": "BPAP is a small benzofuran amine (C16H23NO), not a peptide.",
   "verdict": "Incorrect",
   "sources": []
  },
  {
   "claim": "BPAP is not prohibited in sport",
   "where": "forums",
   "evidence": "BPAP is not named on the WADA 2026 List. Section S0 prohibits pharmacological substances with no current governmental approval for human therapeutic use that are not addressed elsewhere; no approval of BPAP was located. No WADA statement on BPAP was located.",
   "verdict": "Not named; S0 wording applies",
   "sources": [
    "wada"
   ]
  }
 ],
 "mechanisms": [
  {
   "statement": "Enhances electrically evoked release of noradrenaline, dopamine and serotonin",
   "year": "1999",
   "status": "measured",
   "source": "PMID:10588928",
   "who": "lineage, ex vivo rat"
  },
  {
   "statement": "Two separate bell-shaped concentration ranges of effect",
   "year": "2002",
   "status": "measured",
   "source": "PMID:12204771",
   "who": "lineage; resting release from isolated rat brain pieces, 8 rats per point; not seen in every region"
  },
  {
   "statement": "Higher range attributed to sigma-receptor binding",
   "year": "2002",
   "status": "proposed",
   "source": "PMID:12204771",
   "who": "lineage, discussion; later replaced by MAO-A (below)"
  },
  {
   "statement": "'Enhancer receptors' may be trace amine receptors",
   "year": "2002",
   "status": "proposed",
   "source": "PMID:12204771",
   "who": "lineage, hypothesis in the discussion"
  },
  {
   "statement": "Weak displacement at sigma sites; survival effect blocked by a sigma antagonist",
   "year": "2000",
   "status": "measured",
   "source": "PMID:11100977",
   "who": "lineage co-authors, rat neurons"
  },
  {
   "statement": "Hydroxyl radical scavenging",
   "year": "2001",
   "status": "computational",
   "source": "PMID:11377187",
   "who": "lineage, molecular-orbital model only"
  },
  {
   "statement": "Inhibits dopamine and noradrenaline uptake, and serotonin uptake at about 12-15 times higher concentration",
   "year": "2003",
   "status": "measured",
   "source": "PMID:14659999",
   "who": "lineage with a US co-author, human transporters in HEK293 cells; at least 3 independent experiments; cocaine as reference"
  },
  {
   "statement": "No tyramine-like (releaser) action on catecholamines",
   "year": "2003",
   "status": "measured",
   "source": "PMID:14659999",
   "who": "rat synaptosomes"
  },
  {
   "statement": "Raises neurotrophin (NGF, BDNF, GDNF) output",
   "year": "2002",
   "status": "measured",
   "source": "PMID:12147307",
   "who": "mouse astrocytes, high range only"
  },
  {
   "statement": "Anti-apoptotic, Bcl-2 induction",
   "year": "2004",
   "status": "measured",
   "source": "PMID:15102525",
   "who": "human neuroblastoma cells"
  },
  {
   "statement": "MAO-A inhibition at high (micromolar) concentrations",
   "year": "2014",
   "status": "cited",
   "source": "PMID:24905523",
   "who": "lineage; the 2022 paper cites 2014, which cites 1999; the 2014 paper did not measure MAO"
  },
  {
   "statement": "Distinct sites on VMAT2 as the main mechanism",
   "year": "2017",
   "status": "proposed",
   "source": "PMID:28623006",
   "who": "lineage, stated in an abstract"
  },
  {
   "statement": "TAAR1 mediates the effect (reversed by EPPTB)",
   "year": "2022",
   "status": "indirect",
   "source": "PMID:35955676",
   "who": "lineage, rat striatal slices; no receptor assay"
  },
  {
   "statement": "TAAR1-D2 heterodimerisation explains the falling limb",
   "year": "2025",
   "status": "proposed",
   "source": "PMID:39903411",
   "who": "lineage, stated as speculation"
  }
 ],
 "reanalysis": {
  "date": "2026-10-26",
  "assumptions": "grupos independientes de n = 40 (como declaran los autores); SD = SEM x sqrt(40); t de Student de dos colas con\ndf = 78; Bonferroni para 4 comparaciones con el control; Fisher exacto bilateral para las tablas 2x2; potencia por\naproximación normal (alfa bilateral 0,05; potencia 80 %).",
  "longevity_2016": {
   "n_per_group": 40,
   "control_mean_weeks": 94.23,
   "control_sem": 3.48,
   "pairwise": [
    {
     "group": "BPAP group 1 (authors' 'specific' range)",
     "mean_weeks": 107.0,
     "sem": 3.14,
     "diff_weeks": 12.77,
     "t": 2.72,
     "p_two_sided": 0.0079,
     "p_bonferroni_4": 0.032,
     "cohens_d": 0.61
    },
    {
     "group": "BPAP group 2 (authors' 'non-specific' range)",
     "mean_weeks": 107.0,
     "sem": 3.45,
     "diff_weeks": 12.77,
     "t": 2.61,
     "p_two_sided": 0.011,
     "p_bonferroni_4": 0.044,
     "cohens_d": 0.58
    },
    {
     "group": "selegiline group 1",
     "mean_weeks": 101.6,
     "sem": 3.38,
     "diff_weeks": 7.37,
     "t": 1.52,
     "p_two_sided": 0.1328,
     "p_bonferroni_4": 0.531,
     "cohens_d": 0.34
    },
    {
     "group": "selegiline group 2",
     "mean_weeks": 105.2,
     "sem": 3.07,
     "diff_weeks": 10.97,
     "t": 2.36,
     "p_two_sided": 0.0206,
     "p_bonferroni_4": 0.082,
     "cohens_d": 0.53
    }
   ],
   "anova": {
    "reported": "F(4,195) = 2.0356, reported as P < 0.05 (Fig. 3)",
    "p_of_printed_F": 0.091,
    "F_recomputed_from_table_2_means_and_sems": 2.64,
    "p_recomputed_from_table_2": 0.035,
    "note": "Table 2 prints F = 2.632, p = 0.0356, consistent with the recomputation; the F printed in Figure 3 (2.0356) is inconsistent with it and is most likely a typographical error."
   },
   "survivors_over_2_years": {
    "saline": {
     "n_over_2y": 14,
     "of": 40,
     "fisher_p_vs_saline": null
    },
    "selegiline group 1": {
     "n_over_2y": 19,
     "of": 40,
     "fisher_p_vs_saline": 0.364
    },
    "selegiline group 2": {
     "n_over_2y": 22,
     "of": 40,
     "fisher_p_vs_saline": 0.115
    },
    "BPAP group 1": {
     "n_over_2y": 23,
     "of": 40,
     "fisher_p_vs_saline": 0.072
    },
    "BPAP group 2": {
     "n_over_2y": 22,
     "of": 40,
     "fisher_p_vs_saline": 0.115
    }
   },
   "power_at_n40_for_observed_difference": 0.74,
   "n_per_group_for_80pct_power": 47,
   "n_per_group_for_80pct_power_bonferroni4": 67,
   "tumours_mentioned_in_2016_paper": false
  },
  "tumour_2017_same_cohort": {
   "saline": {
    "with_tumour": 20,
    "of": 40,
    "risk_difference_vs_saline": null,
    "fisher_p_vs_saline": null
   },
   "selegiline group 1": {
    "with_tumour": 15,
    "of": 40,
    "risk_difference_vs_saline": 0.125,
    "fisher_p_vs_saline": 0.3675
   },
   "selegiline group 2": {
    "with_tumour": 11,
    "of": 40,
    "risk_difference_vs_saline": 0.225,
    "fisher_p_vs_saline": 0.0656
   },
   "BPAP group 1": {
    "with_tumour": 8,
    "of": 40,
    "risk_difference_vs_saline": 0.3,
    "fisher_p_vs_saline": 0.0093
   },
   "BPAP group 2": {
    "with_tumour": 7,
    "of": 40,
    "risk_difference_vs_saline": 0.325,
    "fisher_p_vs_saline": 0.0041
   }
  },
  "optical_rotation_HCl": {
   "R_HCl": [
    {
     "value": -4.08,
     "c_g_per_100ml": 4.0,
     "solvent": "MeOH",
     "source": "PMID 11377178"
    },
    {
     "value": -4.23,
     "c_g_per_100ml": 4.4,
     "solvent": "MeOH",
     "source": "PMID 11377179"
    }
   ],
   "S_HCl": [
    {
     "value": 4.01,
     "c_g_per_100ml": 4.0,
     "solvent": "MeOH",
     "source": "PMID 11377178"
    },
    {
     "value": 5.11,
     "c_g_per_100ml": 0.44,
     "solvent": "MeOH",
     "source": "PMID 11377179"
    }
   ]
  },
  "rotation_if_contaminated_with_S": {
   "0% S": -4.08,
   "5% S": -3.67,
   "10% S": -3.26,
   "25% S": -2.04,
   "50% S": -0.0
  },
  "transporters_2003": {
   "uptake_IC50_nM": {
    "DAT": 42.3,
    "NET": 52,
    "SERT": 640
   },
   "binding_Ki_nM": {
    "DAT": 16.3,
    "NET": 211,
    "SERT": 638
   },
   "cocaine_uptake_IC50_nM": {
    "DAT": 524,
    "NET": 370,
    "SERT": 419
   }
  },
  "transporter_ratios": {
   "SERT_over_DAT_uptake": 15.1,
   "SERT_over_NET_uptake": 12.3,
   "cocaine_over_BPAP_DAT_uptake": 12.4,
   "cocaine_over_BPAP_NET_uptake": 7.1,
   "cocaine_over_BPAP_SERT_uptake": 0.65
  },
  "sar_2001": {
   "racemates_itemised_in_tables_1_to_4": 52,
   "per_table": {
    "phenyl/furyl/thienyl (4a-4q)": 17,
    "methylenedioxy (5a-5k)": 11,
    "naphthyl (6a-6n)": 14,
    "indolyl/benzothienyl/benzofuryl (7a-7j)": 10
   },
   "racemates_resolved": 4,
   "enantiomers_reported": 8,
   "note": "The 1999 paper speaks of 65 newly synthesised compounds; the 2001 paper itemises 52 racemates plus 8 enantiomers (60 substances). Compound 4p carries a citation to earlier work."
  }
 },
 "identity": {
  "tool": "RDKit 2026.09.1",
  "date": "2026-10-26",
  "proton_mass": 1.007276467,
  "molecules": [
   {
    "key": "R",
    "name": "(R)-(-)-BPAP free base",
    "pubchem_cid": 9816303,
    "smiles": "CCCN[C@H](CCC)Cc1cc2ccccc2o1",
    "formula": "C16H23NO",
    "inchikey": "LJHIBIVAYHQPBT-CQSZACIVSA-N",
    "mw_average": 245.37,
    "monoisotopic_parent": 245.178,
    "ion_[M+H]+": 246.1852,
    "stereocentres": [
     [
      3,
      "R"
     ]
    ],
    "clogp_crippen_parent": 4.14,
    "tpsa_parent": 25.2,
    "hbd": 1,
    "hba": 2,
    "rotatable_bonds": 7
   },
   {
    "key": "S",
    "name": "(S)-(+)-BPAP free base",
    "pubchem_cid": 67426312,
    "smiles": "CCCN[C@@H](CCC)Cc1cc2ccccc2o1",
    "formula": "C16H23NO",
    "inchikey": "LJHIBIVAYHQPBT-AWEZNQCLSA-N",
    "mw_average": 245.37,
    "monoisotopic_parent": 245.178,
    "ion_[M+H]+": 246.1852,
    "stereocentres": [
     [
      3,
      "S"
     ]
    ],
    "clogp_crippen_parent": 4.14,
    "tpsa_parent": 25.2,
    "hbd": 1,
    "hba": 2,
    "rotatable_bonds": 7
   },
   {
    "key": "rac",
    "name": "BPAP, stereochemistry undefined (racemate)",
    "pubchem_cid": 9859674,
    "smiles": "CCCNC(CCC)Cc1cc2ccccc2o1",
    "formula": "C16H23NO",
    "inchikey": "LJHIBIVAYHQPBT-UHFFFAOYSA-N",
    "mw_average": 245.37,
    "monoisotopic_parent": 245.178,
    "ion_[M+H]+": 246.1852,
    "stereocentres": [
     [
      3,
      "?"
     ]
    ],
    "clogp_crippen_parent": 4.14,
    "tpsa_parent": 25.2,
    "hbd": 1,
    "hba": 2,
    "rotatable_bonds": 7
   },
   {
    "key": "R_HCl",
    "name": "(R)-(-)-BPAP hydrochloride (FPFS-1169)",
    "pubchem_cid": 11984587,
    "smiles": "CCCN[C@H](CCC)Cc1cc2ccccc2o1.Cl",
    "formula": "C16H24ClNO",
    "inchikey": "GKKNDWKXWAVGOK-PFEQFJNWSA-N",
    "mw_average": 281.83,
    "monoisotopic_parent": 245.178,
    "ion_[M+H]+": 246.1852,
    "stereocentres": [
     [
      3,
      "R"
     ]
    ],
    "clogp_crippen_parent": 4.14,
    "tpsa_parent": 25.2,
    "hbd": 1,
    "hba": 2,
    "rotatable_bonds": 7
   },
   {
    "key": "3FBPAP",
    "name": "3-F-BPAP (antagonist analogue)",
    "pubchem_cid": 10125543,
    "smiles": "CCCC(Cc1cc2ccccc2o1)NCCC(F)(F)F",
    "formula": "C16H20F3NO",
    "inchikey": "JCZRCOLYSDAPPW-UHFFFAOYSA-N",
    "mw_average": 299.34,
    "monoisotopic_parent": 299.1497,
    "ion_[M+H]+": 300.157,
    "stereocentres": [
     [
      3,
      "?"
     ]
    ],
    "clogp_crippen_parent": 4.69,
    "tpsa_parent": 25.2,
    "hbd": 1,
    "hba": 2,
    "rotatable_bonds": 7
   },
   {
    "key": "PPAP",
    "name": "1-phenyl-2-propylaminopentane (PPAP), stereo undefined",
    "pubchem_cid": 10262369,
    "smiles": "CCCNC(CCC)Cc1ccccc1",
    "formula": "C14H23N",
    "inchikey": "PBENSVGEGPJNFJ-UHFFFAOYSA-N",
    "mw_average": 205.34,
    "monoisotopic_parent": 205.183,
    "ion_[M+H]+": 206.1903,
    "stereocentres": [
     [
      3,
      "?"
     ]
    ],
    "clogp_crippen_parent": 3.4,
    "tpsa_parent": 12.0,
    "hbd": 1,
    "hba": 1,
    "rotatable_bonds": 7
   },
   {
    "key": "sigmaPPAP",
    "name": "N-(3-phenylpropyl)-1-phenyl-2-aminopropane, the unrelated sigma ligand also called (-)PPAP",
    "pubchem_cid": null,
    "smiles": "CC(Cc1ccccc1)NCCCc1ccccc1",
    "formula": "C18H23N",
    "inchikey": "CYWPIEBWQAZHQX-UHFFFAOYSA-N",
    "mw_average": 253.39,
    "monoisotopic_parent": 253.183,
    "ion_[M+H]+": 254.1903,
    "stereocentres": [
     [
      1,
      "?"
     ]
    ],
    "clogp_crippen_parent": 3.84,
    "tpsa_parent": 12.0,
    "hbd": 1,
    "hba": 1,
    "rotatable_bonds": 7
   }
  ],
  "derived": {
   "R_S_racemate_same_exact_mass_and_ion": true,
   "free_base_fraction_of_HCl_salt_mass": 0.8706,
   "salt_mass_excess_vs_free_base_pct": 14.9
  },
  "note": "Enantiomers have identical mass, ions and 2D descriptors: an achiral LC-MS or HPLC-UV result cannot distinguish R from S or from the racemate. Crippen cLogP is an atom-additive estimate, not a measurement."
 },
 "homonyms": {
  "date": "2026-10-26",
  "query": "BPAP[tiab]",
  "n": 399,
  "counts": {
   "bicyclic polyprenylated acylphloroglucinols (plant chemistry)": 8,
   "bilevel positive airway pressure": 156,
   "bisphenol AP (environmental chemistry and toxicology)": 125,
   "other meaning": 26,
   "the compound R-(-)-BPAP": 40,
   "back-propagating action potentials (neurophysiology)": 5,
   "benzoyl-Phe-Ala-Pro (ACE enzyme substrate)": 39
  }
 },
 "authorship_benchmark": [
  {
   "key": "bpap",
   "compound": "R-(-)-BPAP (curated census)",
   "query": "raw/census_pmids.txt",
   "records": 47,
   "with_affiliation": 47,
   "origin_with_affiliation": 31,
   "pct_origin": 66.0,
   "pct_origin_narrow": 57.4,
   "pct_origin_nonreview": 69.4,
   "n_nonreview": 36,
   "pct_origin_since_2014": 66.7,
   "n_since_2014": 18
  },
  {
   "key": "ppap",
   "compound": "(-)-PPAP",
   "query": "(PPAP[tiab] OR \"1-phenyl-2-propylaminopentane\"[tiab] OR \"phenylpropylaminopentane\"[tiab]) AND (deprenyl[tiab] OR selegiline[tiab] OR enhancer[tiab] OR catecholamin*[tiab] OR dopamin*[tiab] OR noradrenal*[tiab])",
   "records": 19,
   "with_affiliation": 19,
   "origin_with_affiliation": 10,
   "pct_origin": 52.6,
   "pct_origin_narrow": 47.4,
   "pct_origin_nonreview": 50.0,
   "n_nonreview": 18,
   "pct_origin_since_2014": 100.0,
   "n_since_2014": 1
  },
  {
   "key": "selegiline",
   "compound": "Selegiline / (-)-deprenyl",
   "query": "selegiline[tiab] OR deprenyl[tiab]",
   "records": 3231,
   "with_affiliation": 2734,
   "origin_with_affiliation": 151,
   "pct_origin": 5.5,
   "pct_origin_narrow": 3.1,
   "pct_origin_nonreview": 5.0,
   "n_nonreview": 2226,
   "pct_origin_since_2014": 4.7,
   "n_since_2014": 601
  }
 ],
 "reddit": {
  "source": "Condor passes of 25-26 Oct 2026 (Apify search, PullPush archive); not re-queried",
  "apify_unique_posts_matching_BPAP": 124,
  "homonym_airway_pressure": 115,
  "profile_pages": 1,
  "about_compound": 8,
  "about_compound_6m_to_2026-10-25": 7,
  "about_compound_previous_6m": 1,
  "pullpush_regex_matches_recent_5.5m": {
   "posts": 64,
   "comments": 229
  },
  "pullpush_regex_matches_previous_5.5m": {
   "posts": 86,
   "comments": 282
  },
  "pullpush_note": "PullPush counts are regex matches on 'bpap'; the top subreddits include sleep-apnoea forums, so they mix the homonym with the compound."
 }
}