{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,2]],"date-time":"2026-09-02T07:15:46Z","timestamp":1788333346834,"version":"build-2803163510"},"reference-count":31,"publisher":"American Chemical Society (ACS)","issue":"3","license":[{"start":{"date-parts":[[2015,2,4]],"date-time":"2015-02-04T00:00:00Z","timestamp":1423008000000},"content-version":"vor","delay-in-days":365,"URL":"https:\/\/pubs.acs.org\/page\/policy\/authorchoice_termsofuse.html"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2014,2,13]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>2-[(Diphenylmethyl)sulfinyl]acetamide (modafinil, (\u00b1)-1) is a unique dopamine uptake inhibitor that binds the dopamine transporter (DAT) differently than cocaine and may have potential for the treatment of psychostimulant abuse. To further investigate structural requirements for this divergent binding mode, novel thio- and sulfinylacetamide and ethanamine analogues of (\u00b1)-1 were synthesized wherein (1) the diphenyl rings were substituted with methyl, trifluoromethyl, and halogen substituents and (2) substituents were added to the terminal amide\/amine nitrogen. Halogen substitution of the diphenyl rings of (\u00b1)-1 gave several amide analogues with improved binding affinity for DAT and robust selectivity over the serotonin transporter (SERT), whereas affinity improved at SERT over DAT for the p-halo-substituted amine analogues. Molecular docking studies, using a subset of analogues with DAT and SERT homology models, and functional data obtained with DAT (A480T) and SERT (T497A) mutants defined a role for TM10 in the substrate\/inhibitor S1 binding sites of DAT and SERT.<\/jats:p>","DOI":"10.1021\/jm401754x","type":"journal-article","created":{"date-parts":[[2014,2,4]],"date-time":"2014-02-04T13:57:51Z","timestamp":1391522271000},"page":"1000-1013","source":"Crossref","is-referenced-by-count":53,"title":["Elucidation of Structural\nElements for Selectivity\nacross Monoamine Transporters: Novel 2-[(Diphenylmethyl)sulfinyl]acetamide\n(Modafinil) Analogues"],"prefix":"10.1021","volume":"57","author":[{"given":"Oluyomi M.","family":"Okunola-Bakare","sequence":"first","affiliation":[{"name":"National Institute on Drug Abuse\u2500Intramural Research Program, National Institutes of Health , , , ,","place":["Baltimore, Maryland, United States, 21224"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jianjing","family":"Cao","sequence":"additional","affiliation":[{"name":"National Institute on Drug Abuse\u2500Intramural Research Program, National Institutes of Health , , , ,","place":["Baltimore, Maryland, United States, 21224"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Theresa","family":"Kopajtic","sequence":"additional","affiliation":[{"name":"National Institute on Drug Abuse\u2500Intramural Research Program, National Institutes of Health , , , ,","place":["Baltimore, Maryland, United States, 21224"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jonathan L.","family":"Katz","sequence":"additional","affiliation":[{"name":"National Institute on Drug Abuse\u2500Intramural Research Program, National Institutes of Health , , , ,","place":["Baltimore, Maryland, United States, 21224"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Claus J.","family":"Loland","sequence":"additional","affiliation":[{"name":"Copenhagen University , , ,","place":["Copenhagen, Denmark, DK-1165"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lei","family":"Shi","sequence":"additional","affiliation":[{"name":"Weill Medical College of Cornell University , , , ,","place":["New York, New York, United States, 10065"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Amy Hauck","family":"Newman","sequence":"additional","affiliation":[{"name":"National Institute on Drug Abuse\u2500Intramural Research Program, National Institutes of Health , , , ,","place":["Baltimore, Maryland, United States, 21224"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2014,2,4]]},"reference":[{"key":"2026090202481706000_cit1","doi-asserted-by":"crossref","first-page":"405","DOI":"10.1016\/j.biopsych.2012.03.022","article-title":"R-Modafinil (Armodafinil):\nA Unique\nDopamine Uptake Inhibitor and Potential Medication for Psychostimulant\nAbuse","volume":"72","author":"Loland","year":"2012","journal-title":"Biol. Psychiatry"},{"key":"2026090202481706000_cit2","doi-asserted-by":"crossref","first-page":"415","DOI":"10.1007\/s00213-013-3232-4","article-title":"The Neurobiology\nof\nModafinil as an Enhancer of Cognitive Performance and a Potential\nTreatment for Substance Use Disorders","volume":"229","author":"Mereu","year":"2013","journal-title":"Psychopharmacology"},{"key":"2026090202481706000_cit3","doi-asserted-by":"crossref","first-page":"e25790","DOI":"10.1371\/journal.pone.0025790","article-title":"The Atypical Stimulant\nand Nootropic Modafinil Interacts\nwith the Dopamine Transporter in a Different Manner Than Classical\nCocaine-like Inhibitors","volume":"6","author":"Schmitt","year":"2011","journal-title":"PLoS One"},{"key":"2026090202481706000_cit4","doi-asserted-by":"crossref","first-page":"49","DOI":"10.1111\/j.1369-1600.2012.00506.x","article-title":"Modafinil\nAttenuates Reinstatement of Cocaine Seeking: Role for Cystine-Glutamate\nExchange and Metabotropic Glutamate Receptors","volume":"19","author":"Mahler","year":"2014","journal-title":"Addict. Biol."},{"key":"2026090202481706000_cit5","doi-asserted-by":"crossref","first-page":"1477","DOI":"10.1038\/sj.npp.1301534","article-title":"Modafinil: A Review of Neurochemical Actions and Effects\non Cognition","volume":"33","author":"Minzenberg","year":"2008","journal-title":"Neuropsychopharmacology"},{"key":"2026090202481706000_cit6","doi-asserted-by":"crossref","first-page":"337","DOI":"10.1007\/s00213-010-1828-5","article-title":"Modafinil Effects\non Reinstatement of Methamphetamine\nSeeking in a Rat Model of Relapse","volume":"210","author":"Reichel","year":"2010","journal-title":"Psychopharmacology"},{"key":"2026090202481706000_cit7","doi-asserted-by":"crossref","first-page":"919","DOI":"10.1017\/S1461145711000988","article-title":"Chronic Modafinil\nEffects on Drug-Seeking Following\nMethamphetamine Self-Administration in Rats","volume":"15","author":"Reichel","year":"2012","journal-title":"Int. J. 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