{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,26]],"date-time":"2026-02-26T15:07:37Z","timestamp":1772118457590,"version":"3.50.1"},"reference-count":53,"publisher":"Wiley","issue":"7","license":[{"start":{"date-parts":[[2019,5,8]],"date-time":"2019-05-08T00:00:00Z","timestamp":1557273600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100000925","name":"National Health and Medical Research Council","doi-asserted-by":"publisher","award":["Project Grant 1107088"],"award-info":[{"award-number":["Project Grant 1107088"]}],"id":[{"id":"10.13039\/501100000925","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100000925","name":"National Health and Medical Research Council","doi-asserted-by":"publisher","award":["Project Grant 1161571"],"award-info":[{"award-number":["Project Grant 1161571"]}],"id":[{"id":"10.13039\/501100000925","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["analyticalsciencejournals.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Drug Testing and Analysis"],"published-print":{"date-parts":[[2019,7]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    5F\u2010PY\u2010PICA and 5F\u2010PY\u2010PINACA are pyrrolidinyl 1\u2010(5\u2010fluoropentyl)ind (az)ole\u20103\u2010carboxamides identified in 2015 as putative synthetic cannabinoid receptor agonist (SCRA) new psychoactive substances (NPS). 5F\u2010PY\u2010PICA, 5F\u2010PY\u2010PINACA, and analogs featuring variation of the 1\u2010alkyl substituent or contraction, expansion, or scission of the pyrrolidine ring were synthesized and characterized by nuclear magnetic resonance (NMR) spectroscopy and liquid chromatography\u2013quadrupole time\u2010of\u2010flight\u2013mass spectrometry (LC\u2013QTOF\u2013MS). In competitive binding experiments against HEK293 cells expressing human cannabinoid receptor type 1 (hCB\n                    <jats:sub>1<\/jats:sub>\n                    ) or type 2 (hCB\n                    <jats:sub>2<\/jats:sub>\n                    ), all analogs showed minimal affinity for CB\n                    <jats:sub>1<\/jats:sub>\n                    (p\n                    <jats:italic>K<\/jats:italic>\n                    <jats:sub>i<\/jats:sub>\n                    \u00a0&lt;\u00a05), although several demonstrated moderate CB\n                    <jats:sub>2<\/jats:sub>\n                    binding (p\n                    <jats:italic>K<\/jats:italic>\n                    <jats:sub>i<\/jats:sub>\n                    5.45\u20136.99). In fluorescence\u2010based membrane potential assays using AtT20\u2010hCB\n                    <jats:sub>1<\/jats:sub>\n                    or \u2010hCB\n                    <jats:sub>2<\/jats:sub>\n                    cells, none of the compounds (at 10\u00a0\u03bcM) produced an effect &gt;50% of the classical cannabinoid agonist CP55,940 (at 1\u00a0\u03bcM) at hCB\n                    <jats:sub>1<\/jats:sub>\n                    , although several showed slightly higher relative efficacy at hCB\n                    <jats:sub>2<\/jats:sub>\n                    . Expansion of the pyrrolidine ring of 5F\u2010PY\u2010PICA to an azepane (\n                    <jats:bold>8<\/jats:bold>\n                    ) conferred the greatest hCB\n                    <jats:sub>2<\/jats:sub>\n                    affinity (p\n                    <jats:italic>K<\/jats:italic>\n                    <jats:sub>i<\/jats:sub>\n                    6.99) and activity (pEC\n                    <jats:sub>50<\/jats:sub>\n                    7.54, E\n                    <jats:sub>max<\/jats:sub>\n                    72%) within the series. Unlike other SCRA NPS evaluated in vivo using radio biotelemetry, 5F\u2010PY\u2010PICA and 5F\u2010PY\u2010PINACA did not produce cannabimimetic effects (hypothermia, bradycardia) in mice at doses up to 10\u00a0mg\/kg.\n                  <\/jats:p>","DOI":"10.1002\/dta.2583","type":"journal-article","created":{"date-parts":[[2019,3,6]],"date-time":"2019-03-06T00:31:57Z","timestamp":1551832317000},"page":"976-989","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":16,"title":["The chemistry and pharmacology of putative synthetic cannabinoid receptor agonist (SCRA) new psychoactive substances (NPS) 5F\u2010PY\u2010PICA, 5F\u2010PY\u2010PINACA, and their analogs"],"prefix":"10.1002","volume":"11","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-4690-4318","authenticated-orcid":false,"given":"Samuel D.","family":"Banister","sequence":"first","affiliation":[{"name":"School of Chemistry The University of Sydney  NSW Australia"},{"name":"Department of Pathology Stanford University  CA USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4912-4499","authenticated-orcid":false,"given":"Richard C.","family":"Kevin","sequence":"additional","affiliation":[{"name":"School of Psychology The University of Sydney  Camperdown NSW Australia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Lewis","family":"Martin","sequence":"additional","affiliation":[{"name":"School of Psychology The University of Sydney  Camperdown NSW Australia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Axel","family":"Adams","sequence":"additional","affiliation":[{"name":"Clinical Toxicology and Environmental Biomonitoring Laboratory University of California  San Francisco CA USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Christa","family":"Macdonald","sequence":"additional","affiliation":[{"name":"School of Medical Sciences The University of Auckland  Auckland New Zealand"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6945-2254","authenticated-orcid":false,"given":"Jamie J.","family":"Manning","sequence":"additional","affiliation":[{"name":"School of Medical Sciences The University of Auckland  Auckland New Zealand"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Rochelle","family":"Boyd","sequence":"additional","affiliation":[{"name":"Faculty of Medicine and Health Sciences Macquarie University  NSW Australia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Michael","family":"Cunningham","sequence":"additional","affiliation":[{"name":"Division of Medicinal Chemistry, Department of Biomolecular Sciences, School of Pharmacy The University of Mississippi  MS USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Marc Y.","family":"Stevens","sequence":"additional","affiliation":[{"name":"Department of Radiology Stanford University  CA USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Iain S.","family":"McGregor","sequence":"additional","affiliation":[{"name":"School of Psychology The University of Sydney  Camperdown NSW Australia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5997-6898","authenticated-orcid":false,"given":"Michelle","family":"Glass","sequence":"additional","affiliation":[{"name":"School of Medical Sciences The University of Auckland  Auckland New Zealand"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2538-2001","authenticated-orcid":false,"given":"Mark","family":"Connor","sequence":"additional","affiliation":[{"name":"Faculty of Medicine and Health Sciences Macquarie University  NSW Australia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Roy R.","family":"Gerona","sequence":"additional","affiliation":[{"name":"Clinical Toxicology and Environmental Biomonitoring Laboratory University of California  San Francisco CA USA"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2019,5,8]]},"reference":[{"key":"e_1_2_6_2_1","unstructured":"United Nations Office on Drugs and Crime.World Drug Report 2018. 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National Forensic Laboratory Ljubljana Slovenia.2015. Available athttps:\/\/www.policija.si\/apps\/nfl_response_web\/seznam.php. Accessed 29 September 2018."},{"key":"e_1_2_6_43_1","unstructured":"European Project RESPONSE.Analytical Report 5F\u2010PY\u2010PINACA (C17H22FN3O) [1\u2010(5\u2010fluoropentyl)indazol\u20103\u2010yl]\u2010pyrrolidin\u20101\u2010yl\u2010methanone. National Forensic Laboratory Ljubljana Slovenia.2015. Available athttps:\/\/www.policija.si\/apps\/nfl_response_web\/seznam.php. Accessed 29 September 2018."},{"key":"e_1_2_6_44_1","doi-asserted-by":"publisher","DOI":"10.1021\/acschemneuro.7b00267"},{"key":"e_1_2_6_45_1","doi-asserted-by":"publisher","DOI":"10.1002\/dta.2362"},{"key":"e_1_2_6_46_1","doi-asserted-by":"publisher","DOI":"10.1021\/acschemneuro.5b00107"},{"key":"e_1_2_6_47_1","doi-asserted-by":"publisher","DOI":"10.1021\/acschemneuro.6b00137"},{"key":"e_1_2_6_48_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bbamcr.2011.05.010"},{"key":"e_1_2_6_49_1","doi-asserted-by":"publisher","DOI":"10.1111\/bph.13866"},{"key":"e_1_2_6_50_1","doi-asserted-by":"publisher","DOI":"10.1177\/1087057112461376"},{"key":"e_1_2_6_51_1","doi-asserted-by":"publisher","DOI":"10.1002\/hup.2601"},{"key":"e_1_2_6_52_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.drugalcdep.2017.07.029"},{"key":"e_1_2_6_53_1","article-title":"Functional effects of synthetic cannabinoids versus Delta(9) \u2010THC in mice on body temperature, nociceptive threshold, anxiety, cognition, locomotor\/exploratory parameters and depression","author":"Schreiber S","year":"2018","journal-title":"Addict Biol"},{"key":"e_1_2_6_54_1","doi-asserted-by":"publisher","DOI":"10.1021\/acschemneuro.5b00112"}],"container-title":["Drug Testing and Analysis"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fdta.2583","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/dta.2583","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/dta.2583","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/dta.2583","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,13]],"date-time":"2025-10-13T20:18:48Z","timestamp":1760386728000},"score":1,"resource":{"primary":{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/10.1002\/dta.2583"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,5,8]]},"references-count":53,"journal-issue":{"issue":"7","published-print":{"date-parts":[[2019,7]]}},"alternative-id":["10.1002\/dta.2583"],"URL":"https:\/\/doi.org\/10.1002\/dta.2583","archive":["Portico"],"relation":{"has-preprint":[{"id-type":"doi","id":"10.1101\/430959","asserted-by":"object"}]},"ISSN":["1942-7603","1942-7611"],"issn-type":[{"value":"1942-7603","type":"print"},{"value":"1942-7611","type":"electronic"}],"subject":[],"published":{"date-parts":[[2019,5,8]]},"assertion":[{"value":"2018-09-29","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2019-02-28","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2019-05-08","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}