{"id":"https://openalex.org/W2059639341","doi":"https://doi.org/10.1021/jm00093a014","title":"Enantiomeric N-substituted N-normetazocines: a comparative study of affinities at .sigma., PCP, and .mu. opioid receptors","display_name":"Enantiomeric N-substituted N-normetazocines: a comparative study of affinities at .sigma., PCP, and .mu. opioid receptors","publication_year":1992,"publication_date":"1992-07-01","ids":{"openalex":"https://openalex.org/W2059639341","doi":"https://doi.org/10.1021/jm00093a014","mag":"2059639341","pmid":"https://pubmed.ncbi.nlm.nih.gov/1322987"},"language":"en","primary_location":{"id":"doi:10.1021/jm00093a014","doi":"https://doi.org/10.1021/jm00093a014","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jm00093a014","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","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/A5112366469","display_name":"F. Ivy Carroll","orcid":"https://orcid.org/0000-0001-9510-765X","observed_orcids":["https://orcid.org/0000-0001-9510-765X"]},"institutions":[{"id":"https://openalex.org/I180297670","display_name":"RTI International","ror":"https://ror.org/052tfza37","country_code":"US","type":"nonprofit","lineage":["https://openalex.org/I137902535","https://openalex.org/I170897317","https://openalex.org/I180297670"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"F. I. Carroll","raw_affiliation_strings":["Chemistry and Life Sciences, Research Triangle Institute, Research Triangle Park, North Carolina 27709"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Chemistry and Life Sciences, Research Triangle Institute, Research Triangle Park, North Carolina 27709","institution_ids":["https://openalex.org/I180297670"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5108393860","display_name":"Philip Abraham","orcid":"https://orcid.org/0009-0009-8711-322X","observed_orcids":["https://orcid.org/0009-0009-8711-322X"]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"P. Abraham","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]},{"author_position":"middle","author":{"id":"https://openalex.org/A5110697839","display_name":"Karol Parham","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"K. Parham","raw_affiliation_strings":["Cntr Drug Discovery"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Cntr Drug Discovery","institution_ids":[]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5103052180","display_name":"Xu Bai","orcid":"https://orcid.org/0000-0003-4877-8383","observed_orcids":["https://orcid.org/0000-0003-4877-8383"]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"X. Bai","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]},{"author_position":"middle","author":{"id":"https://openalex.org/A5080591050","display_name":"X. Zhang","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"X. Zhang","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]},{"author_position":"middle","author":{"id":"https://openalex.org/A5070469235","display_name":"George A. Brine","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"G. A. Brine","raw_affiliation_strings":["Cntr Drug Discovery"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Cntr Drug Discovery","institution_ids":[]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5015241846","display_name":"S. Wayne Mascarella","orcid":"https://orcid.org/0000-0003-0092-8178","observed_orcids":["https://orcid.org/0000-0003-0092-8178"]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"S. W. Mascarella","raw_affiliation_strings":["Cntr Drug Discovery"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Cntr Drug Discovery","institution_ids":[]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5108459067","display_name":"Billy R. Martin","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"B. R. Martin","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]},{"author_position":"middle","author":{"id":"https://openalex.org/A5111838843","display_name":"Everette L. May","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"E. L. May","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]},{"author_position":"middle","author":{"id":"https://openalex.org/A5058146396","display_name":"C Sauss","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"C Sauss","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]},{"author_position":"middle","author":{"id":"https://openalex.org/A5052537774","display_name":"Lisa Di Paolo","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"L Di Paolo","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]},{"author_position":"middle","author":{"id":"https://openalex.org/A5065404552","display_name":"Paul K. Wallace","orcid":"https://orcid.org/0000-0001-7823-9917","observed_orcids":["https://orcid.org/0000-0001-7823-9917"]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"P Wallace","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]},{"author_position":"middle","author":{"id":"https://openalex.org/A5056904475","display_name":"J. M. Walker","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"J. M. Walker","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]},{"author_position":"last","author":{"id":null,"display_name":"W. D. Bowen","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"W. D. Bowen","raw_affiliation_strings":[],"raw_orcid":null,"affiliations":[]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":[],"corresponding_institution_ids":[],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":1.3228,"has_fulltext":false,"cited_by_count":65,"citation_normalized_percentile":{"value":0.80259886,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":89,"max":98},"biblio":{"volume":"35","issue":"15","first_page":"2812","last_page":"2818"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T13047","display_name":"Pharmacological Receptor Mechanisms and Effects","score":0.9984999895095825,"subfield":{"id":"https://openalex.org/subfields/1312","display_name":"Molecular Biology"},"field":{"id":"https://openalex.org/fields/13","display_name":"Biochemistry, Genetics and Molecular Biology"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}},"topics":[{"id":"https://openalex.org/T13047","display_name":"Pharmacological Receptor Mechanisms and Effects","score":0.9984999895095825,"subfield":{"id":"https://openalex.org/subfields/1312","display_name":"Molecular Biology"},"field":{"id":"https://openalex.org/fields/13","display_name":"Biochemistry, Genetics and Molecular Biology"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}},{"id":"https://openalex.org/T11178","display_name":"Receptor Mechanisms and Signaling","score":0.00039999998989515007,"subfield":{"id":"https://openalex.org/subfields/1312","display_name":"Molecular Biology"},"field":{"id":"https://openalex.org/fields/13","display_name":"Biochemistry, Genetics and Molecular Biology"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}},{"id":"https://openalex.org/T10814","display_name":"Neuropeptides and Animal Physiology","score":0.0003000000142492354,"subfield":{"id":"https://openalex.org/subfields/2804","display_name":"Cellular and Molecular Neuroscience"},"field":{"id":"https://openalex.org/fields/28","display_name":"Neuroscience"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}}],"keywords":[{"id":"https://openalex.org/keywords/sigma-1-receptor","display_name":"sigma-1 receptor","score":0.8050000071525574},{"id":"https://openalex.org/keywords/pcp-receptor","display_name":"PCP receptor","score":0.8169999718666077},{"id":"https://openalex.org/keywords/mu-opioid-receptor","display_name":"mu-opioid receptor","score":0.9290000200271606},{"id":"https://openalex.org/keywords/enantioselectivity","display_name":"enantioselectivity","score":0.8009999990463257},{"id":"https://openalex.org/keywords/receptor-binding-affinity","display_name":"receptor binding affinity","score":0.7649999856948853},{"id":"https://openalex.org/keywords/structure-activity-relationship","display_name":"structure-activity relationship","score":0.8730000257492065},{"id":"https://openalex.org/keywords/pentazocine","display_name":"pentazocine","score":0.7630000114440918},{"id":"https://openalex.org/keywords/receptor-selectivity","display_name":"receptor selectivity","score":0.5870000123977661}],"concepts":[{"id":"https://openalex.org/C2778805511","wikidata":"https://www.wikidata.org/wiki/Q1713","display_name":"Citation","level":2,"score":0.6330500841140747},{"id":"https://openalex.org/C518677369","wikidata":"https://www.wikidata.org/wiki/Q202833","display_name":"Social media","level":2,"score":0.46492838859558105},{"id":"https://openalex.org/C2780283098","wikidata":"https://www.wikidata.org/wiki/Q4688960","display_name":"Affinities","level":2,"score":0.44505465030670166},{"id":"https://openalex.org/C23123220","wikidata":"https://www.wikidata.org/wiki/Q816826","display_name":"Information retrieval","level":1,"score":0.42934104800224304},{"id":"https://openalex.org/C41008148","wikidata":"https://www.wikidata.org/wiki/Q21198","display_name":"Computer science","level":0,"score":0.3534628748893738},{"id":"https://openalex.org/C15744967","wikidata":"https://www.wikidata.org/wiki/Q9418","display_name":"Psychology","level":0,"score":0.33255213499069214},{"id":"https://openalex.org/C161191863","wikidata":"https://www.wikidata.org/wiki/Q199655","display_name":"Library science","level":1,"score":0.31168708205223083},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.2754114866256714},{"id":"https://openalex.org/C136764020","wikidata":"https://www.wikidata.org/wiki/Q466","display_name":"World Wide Web","level":1,"score":0.26913201808929443},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.22482618689537048}],"mesh":[{"descriptor_ui":"D000818","descriptor_name":"Animals","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D001921","descriptor_name":"Brain","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":false},{"descriptor_ui":"D006168","descriptor_name":"Guinea Pigs","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D008297","descriptor_name":"Male","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D009294","descriptor_name":"Narcotics","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":false},{"descriptor_ui":"D010620","descriptor_name":"Phenazocine","qualifier_ui":"Q000031","qualifier_name":"analogs & derivatives","is_major_topic":true},{"descriptor_ui":"D010620","descriptor_name":"Phenazocine","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":false},{"descriptor_ui":"D010622","descriptor_name":"Phencyclidine","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":false},{"descriptor_ui":"D011919","descriptor_name":"Rats, Inbred Strains","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D011957","descriptor_name":"Receptors, Opioid","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":true},{"descriptor_ui":"D013237","descriptor_name":"Stereoisomerism","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D013379","descriptor_name":"Substrate Specificity","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D017450","descriptor_name":"Receptors, Opioid, mu","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D017478","descriptor_name":"Receptors, Phencyclidine","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D017480","descriptor_name":"Receptors, sigma","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D017981","descriptor_name":"Receptors, Neurotransmitter","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":true},{"descriptor_ui":"D051381","descriptor_name":"Rats","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false}],"locations_count":2,"locations":[{"id":"doi:10.1021/jm00093a014","doi":"https://doi.org/10.1021/jm00093a014","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jm00093a014","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:1322987","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/1322987","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":"Comparative Study"}],"best_oa_location":null,"sustainable_development_goals":[{"display_name":"Good health and well-being","id":"https://metadata.un.org/sdg/3","score":0.46810001134872437}],"study_designs":[],"awards":[{"id":"https://openalex.org/G3458438798","display_name":null,"funder_award_id":"DA05721","funder_id":"https://openalex.org/F4320337347","funder_display_name":"National Institute on Drug Abuse"},{"id":"https://openalex.org/G3600523153","display_name":null,"funder_award_id":"DA02396","funder_id":"https://openalex.org/F4320337347","funder_display_name":"National Institute on Drug Abuse"},{"id":"https://openalex.org/G6357648671","display_name":"Inhalation of Drugs of Abuse","funder_award_id":"R01DA002396","funder_id":"https://openalex.org/F4320337347","funder_display_name":"National Institute on Drug Abuse"},{"id":"https://openalex.org/G728949196","display_name":null,"funder_award_id":"DA00490","funder_id":"https://openalex.org/F4320337347","funder_display_name":"National Institute on Drug Abuse"}],"funders":[{"id":"https://openalex.org/F4320337347","display_name":"National Institute on Drug Abuse","ror":"https://ror.org/00fq5cm18"}],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":0,"referenced_works":[],"related_works":["https://openalex.org/W2950869122","https://openalex.org/W2078712122","https://openalex.org/W2013207405","https://openalex.org/W2071657064","https://openalex.org/W2082152906","https://openalex.org/W2950128627","https://openalex.org/W6987488887","https://openalex.org/W1973750932","https://openalex.org/W2525804344","https://openalex.org/W4291778529"],"abstract_inverted_index":{"The":[0,94,117,126],"optical":[1],"antipodes":[2],"of":[3,17,138],"N-allyl-N-normetazocine":[4],"(2;":[5],"SKF":[6],"10047,":[7],"NANM)":[8],"were":[9,63,120],"the":[10,15,18,28,48,88,106,111,123,139,151,155,166,171,176],"original":[11],"compounds":[12],"used":[13],"for":[14,47,67,87,105,122,154,170],"classification":[16],"sigma":[19,49,89,107,124,177],"receptor":[20,79,108,173],"as":[21,27],"distinct":[22],"from":[23],"other":[24],"receptors":[25],"such":[26],"PCP":[29,73,112,156,172],"(NMDA),":[30],"opioid,":[31],"and":[32,45,65,75,101,113,179],"dopamine":[33],"receptors.":[34,116],"Later":[35],"studies":[36],"showed":[37,97,130],"that":[38,143],"(+)-N-(dimethylallyl)-N-normetazocine":[39],"[(+)-4,":[40],"(+)-pentazocine]":[41],"was":[42,165],"more":[43],"potent":[44],"selective":[46,168],"receptor.":[50,157],"In":[51],"order":[52],"to":[53,110,135,175],"gain":[54],"additional":[55],"structure-activity":[56],"relationship":[57],"information,":[58],"several":[59],"N-substituted":[60,118],"N-normetazocine":[61],"analogs":[62],"prepared":[64],"evaluated":[66],"their":[68],"sigma-1":[69],"([3H]-(+)-3-PPP":[70],"or":[71],"[3H]-(+)-pentazocine),":[72],"([3H]TCP),":[74],"mu":[76,114,180],"opioid":[77,115,181],"([3H]DAMGO)":[78],"binding":[80],"affinities.":[81],"(+)-N-Benzyl-N-normetazocine":[82],"[(+)-10)]":[83],"possessed":[84,150],"subnanomolar":[85],"affinities":[86],"site,":[90],"Ki":[91],"=":[92,147,162],"0.67.":[93],"analog":[95],"(+)-10":[96],"greater":[98],"than":[99,183],"14,000-":[100],"2400-fold":[102],"selectivity,":[103],"respectively,":[104],"relative":[109,134,174],"N-normetazocines":[119],"enantioselective":[121],"site.":[125],"(+)-N-benzyl":[127],"analog,":[128],"(+)-10,":[129],"a":[131],"55-fold":[132],"selectivity":[133],"(-)-10.":[136],"Analysis":[137],"data":[140],"also":[141],"revealed":[142],"(+)-normetazocine":[144],"[(+)-1]":[145],"[Ki":[146],"30":[148],"nM]":[149],"highest":[152],"affinity":[153],"However,":[158],"(+)-metazocine":[159],"[(+)-5]":[160],"(Ki":[161],"41":[163],"nM)":[164],"most":[167],"compound":[169],"(51-fold)":[178],"(greater":[182],"200-fold)":[184],"sites.":[185]},"counts_by_year":[{"year":2026,"cited_by_count":3},{"year":2025,"cited_by_count":1},{"year":2024,"cited_by_count":2},{"year":2023,"cited_by_count":1},{"year":2022,"cited_by_count":1},{"year":2021,"cited_by_count":3},{"year":2020,"cited_by_count":2},{"year":2019,"cited_by_count":1},{"year":2018,"cited_by_count":1},{"year":2017,"cited_by_count":4},{"year":2016,"cited_by_count":3},{"year":2015,"cited_by_count":2},{"year":2014,"cited_by_count":4},{"year":2013,"cited_by_count":2},{"year":2012,"cited_by_count":4}],"updated_date":"2026-10-31T12:09:11.096373","created_date":"2016-06-24T00:00:00"}
