{"id":"https://openalex.org/W2012730063","doi":"https://doi.org/10.1021/jm00205a011","title":"Synthesis of N-hydroxyacetaminophen, a postulated toxic metabolite of acetaminophen, and its phenolic sulfate conjugate","display_name":"Synthesis of N-hydroxyacetaminophen, a postulated toxic metabolite of acetaminophen, and its phenolic sulfate conjugate","publication_year":1978,"publication_date":"1978-07-01","ids":{"openalex":"https://openalex.org/W2012730063","doi":"https://doi.org/10.1021/jm00205a011","mag":"2012730063","pmid":"https://pubmed.ncbi.nlm.nih.gov/27635"},"language":"en","primary_location":{"id":"doi:10.1021/jm00205a011","doi":"https://doi.org/10.1021/jm00205a011","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jm00205a011","pdf_url":null,"source":{"id":"https://openalex.org/S162030435","display_name":"Journal of Medicinal Chemistry","issn_l":"0022-2623","issn":["0022-2623","1520-4804"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["anvur-scientific","cwts-core","dongbi-a","jufo-3","ki-jl-2","medline","norway-2","poland-200","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of Medicinal Chemistry","raw_type":"journal-article"},"volume":null,"type":"article","is_traditional":true,"indexed_in":["crossref","pubmed"],"open_access":{"is_oa":false,"oa_status":"closed","oa_url":null,"any_repository_has_fulltext":false},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5039536761","display_name":"Mark W. Gemborys","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Mark W. Gemborys","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]},{"author_position":"middle","author":{"id":"https://openalex.org/A5049245360","display_name":"Gordon W. Gribble","orcid":"https://orcid.org/0000-0002-7573-0927","observed_orcids":["https://orcid.org/0000-0002-7573-0927"]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Gordon W. Gribble","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]},{"author_position":"last","author":{"id":"https://openalex.org/A5064553937","display_name":"Gilbert H. Mudge","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Gilbert H. Mudge","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]}],"institutions":[],"countries_distinct_count":0,"institutions_distinct_count":0,"corresponding_author_ids":[],"corresponding_institution_ids":[],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":2.6414,"has_fulltext":false,"cited_by_count":27,"citation_normalized_percentile":{"value":0.88359046,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":88,"max":93},"biblio":{"volume":"21","issue":"7","first_page":"649","last_page":"652"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10375","display_name":"Pharmacogenetics and Drug Metabolism","score":0.30399999022483826,"subfield":{"id":"https://openalex.org/subfields/3004","display_name":"Pharmacology"},"field":{"id":"https://openalex.org/fields/30","display_name":"Pharmacology, Toxicology and Pharmaceutics"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}},"topics":[{"id":"https://openalex.org/T10375","display_name":"Pharmacogenetics and Drug Metabolism","score":0.30399999022483826,"subfield":{"id":"https://openalex.org/subfields/3004","display_name":"Pharmacology"},"field":{"id":"https://openalex.org/fields/30","display_name":"Pharmacology, Toxicology and Pharmaceutics"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}},{"id":"https://openalex.org/T11465","display_name":"Drug-Induced Hepatotoxicity and Protection","score":0.2590000033378601,"subfield":{"id":"https://openalex.org/subfields/3004","display_name":"Pharmacology"},"field":{"id":"https://openalex.org/fields/30","display_name":"Pharmacology, Toxicology and Pharmaceutics"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}},{"id":"https://openalex.org/T12191","display_name":"Physical Organic Chemistry and Reaction Kinetics","score":0.17829999327659607,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}}],"keywords":[{"id":"https://openalex.org/keywords/paracetamol","display_name":"paracetamol","score":0.7990000247955322},{"id":"https://openalex.org/keywords/toxic-metabolites","display_name":"toxic metabolites","score":0.8209999799728394},{"id":"https://openalex.org/keywords/sulfatase","display_name":"sulfatase","score":0.6769999861717224},{"id":"https://openalex.org/keywords/acetylation","display_name":"acetylation","score":0.828000009059906},{"id":"https://openalex.org/keywords/chemical-synthesis","display_name":"chemical synthesis","score":0.746999979019165},{"id":"https://openalex.org/keywords/metabolite-stability","display_name":"metabolite stability","score":0.5809999704360962},{"id":"https://openalex.org/keywords/drug-metabolism","display_name":"drug metabolism","score":0.35199999809265137}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9258055686950684},{"id":"https://openalex.org/C197336794","wikidata":"https://www.wikidata.org/wiki/Q5161150","display_name":"Conjugate","level":2,"score":0.8175292015075684},{"id":"https://openalex.org/C2777477808","wikidata":"https://www.wikidata.org/wiki/Q407595","display_name":"Metabolite","level":2,"score":0.8117586374282837},{"id":"https://openalex.org/C2778722691","wikidata":"https://www.wikidata.org/wiki/Q57055","display_name":"Acetaminophen","level":2,"score":0.6848233342170715},{"id":"https://openalex.org/C2778343803","wikidata":"https://www.wikidata.org/wiki/Q172290","display_name":"Sulfate","level":2,"score":0.6218492984771729},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.33089759945869446},{"id":"https://openalex.org/C98274493","wikidata":"https://www.wikidata.org/wiki/Q128406","display_name":"Pharmacology","level":1,"score":0.32459700107574463},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.23843449354171753},{"id":"https://openalex.org/C71924100","wikidata":"https://www.wikidata.org/wiki/Q11190","display_name":"Medicine","level":0,"score":0.0},{"id":"https://openalex.org/C134306372","wikidata":"https://www.wikidata.org/wiki/Q7754","display_name":"Mathematical analysis","level":1,"score":0.0},{"id":"https://openalex.org/C33923547","wikidata":"https://www.wikidata.org/wiki/Q395","display_name":"Mathematics","level":0,"score":0.0}],"mesh":[{"descriptor_ui":"D000082","descriptor_name":"Acetaminophen","qualifier_ui":"Q000031","qualifier_name":"analogs & derivatives","is_major_topic":true},{"descriptor_ui":"D000082","descriptor_name":"Acetaminophen","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":false},{"descriptor_ui":"D000082","descriptor_name":"Acetaminophen","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":false},{"descriptor_ui":"D004355","descriptor_name":"Drug Stability","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D006207","descriptor_name":"Half-Life","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D006863","descriptor_name":"Hydrogen-Ion Concentration","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D013431","descriptor_name":"Sulfates","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":false},{"descriptor_ui":"D013696","descriptor_name":"Temperature","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false}],"locations_count":2,"locations":[{"id":"doi:10.1021/jm00205a011","doi":"https://doi.org/10.1021/jm00205a011","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jm00205a011","pdf_url":null,"source":{"id":"https://openalex.org/S162030435","display_name":"Journal of Medicinal Chemistry","issn_l":"0022-2623","issn":["0022-2623","1520-4804"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["anvur-scientific","cwts-core","dongbi-a","jufo-3","ki-jl-2","medline","norway-2","poland-200","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of Medicinal Chemistry","raw_type":"journal-article"},{"id":"pmid:27635","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/27635","pdf_url":null,"source":{"id":"https://openalex.org/S4306525036","display_name":"PubMed","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I1299303238","host_organization_name":"National Institutes of Health","host_organization_lineage":["https://openalex.org/I1299303238"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of medicinal chemistry","raw_type":"Journal Article"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":0,"referenced_works":[],"related_works":["https://openalex.org/W3025984824","https://openalex.org/W2010780015","https://openalex.org/W2059575981","https://openalex.org/W4247406631","https://openalex.org/W2088654713","https://openalex.org/W1503690915","https://openalex.org/W1779657038","https://openalex.org/W2320359099","https://openalex.org/W2063865796","https://openalex.org/W2057206256"],"abstract_inverted_index":{"The":[0,41],"synthesis":[1],"of":[2,10],"N-hydroxyacetaminophen":[3],"(N-acetyl-N-hydroxy-p-aminophenol,":[4],"4),":[5],"a":[6],"postulated":[7],"toxic":[8],"metabolite":[9],"acetaminophen":[11],"(N-acetyl-p-aminophenol,":[12],"3),":[13],"and":[14,34,55,68],"its":[15],"phenolic":[16,72],"sulfate":[17,27,73],"conjugate":[18,74],"(potassium":[19],"N-acetyl-N-hydroxy-p-aminophenyl":[20],"sulfate)":[21],"(13)":[22],"is":[23],"described.":[24],"Potassium":[25],"p-nitrophenyl":[26],"was":[28,59,75],"reduced":[29],"to":[30,38,61],"the":[31,47],"hydroxylamine,":[32],"acetylated,":[33],"treated":[35],"with":[36],"sulfatase":[37],"yield":[39],"N-hydroxyacetaminophen.":[40],"structures":[42],"assigned":[43],"are":[44],"supported":[45],"by":[46],"spectral":[48],"data":[49],"(IR,":[50],"UV,":[51],"MS,":[52],"1H":[53],"NMR,":[54],"13C":[56],"NMR).":[57],"N-Hydroxyacetaminophen":[58],"found":[60],"be":[62],"moderately":[63],"unstable":[64],"at":[65],"physiological":[66],"pH":[67],"temperature,":[69],"whereas":[70],"it":[71],"stable.":[76]},"counts_by_year":[{"year":2022,"cited_by_count":1}],"updated_date":"2026-10-31T12:09:11.096373","created_date":"2016-06-24T00:00:00"}