{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,30]],"date-time":"2026-07-30T15:03:35Z","timestamp":1785423815355,"version":"3.56.0"},"reference-count":10,"publisher":"International Union of Crystallography (IUCr)","issue":"6","license":[{"start":{"date-parts":[[2026,6,30]],"date-time":"2026-06-30T00:00:00Z","timestamp":1782777600000},"content-version":"vor","delay-in-days":2,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2026,6,30]],"date-time":"2026-06-30T00:00:00Z","timestamp":1782777600000},"content-version":"tdm","delay-in-days":2,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"}],"funder":[{"name":"The Ministry of Health, Labour and Welfare of Japan","award":["JPMH22KC1005"],"award-info":[{"award-number":["JPMH22KC1005"]}]},{"name":"The Ministry of Health, Labour and Welfare of Japan","award":["JPMH25KC1002"],"award-info":[{"award-number":["JPMH25KC1002"]}]}],"content-domain":{"domain":["iucr.org","wiley.com","iucrj.org"],"crossmark-restriction":true},"short-container-title":["IUCrData","IUCr Data","International Union Crystallogr Data","Int Union Cryst Data"],"accepted":{"date-parts":[[2026,6,23]]},"published-print":{"date-parts":[[2026,6,28]]},"abstract":"<jats:p>\n                    The crystal structure of the methanol-solvated hydrochloride salt of the selective \u03ba-opioid receptor agonist (\u00b1)-U50,488, namely, 1-{2-[2-(3,4-dichlorophenyl)-\n                    <jats:italic>N<\/jats:italic>\n                    -methylacetamido]cyclohexyl}pyrrolidin-1-ium chloride methanol monosolvate, C\n                    <jats:sub>19<\/jats:sub>\n                    H\n                    <jats:sub>27<\/jats:sub>\n                    Cl\n                    <jats:sub>2<\/jats:sub>\n                    N\n                    <jats:sub>2<\/jats:sub>\n                    O\n                    <jats:sup>+<\/jats:sup>\n                    \u00b7Cl\n                    <jats:sup>\u2212<\/jats:sup>\n                    \u00b7CH\n                    <jats:sub>3<\/jats:sub>\n                    OH, is reported. The compound crystallized as a racemate of the (\n                    <jats:italic>S<\/jats:italic>\n                    ,\n                    <jats:italic>S<\/jats:italic>\n                    ) and (\n                    <jats:italic>R<\/jats:italic>\n                    ,\n                    <jats:italic>R<\/jats:italic>\n                    ) enantiomers, consistent with the\n                    <jats:italic>anti<\/jats:italic>\n                    -selective nucleophilic substitution used in its synthesis. The cyclohexane ring adopts a chair conformation with an equatorial-equatorial conformation of its 1,2-substituents. Protonation occurs exclusively at the pyrrolidine nitrogen atom, and the pyrrolidine ring displays a half-chair conformation twisted on the bond opposite the nitrogen. In the crystal, the chloride anion forms a hydrogen-bonding network with the protonated pyrrolidine unit, the methanol solvent molecule, and adjacent C\u2014H groups. The crystal packing is further consolidated by C\u2014H...O interactions involving the amide oxygen atom that form centrosymmetric dimers, alongside intermolecular \u03c0-stacking and Cl...O halogen-bonding interactions. This study provides the first structural characterization of the hydrochloride salt form of this widely used pharmacological compound.\n                  <\/jats:p>","DOI":"10.1107\/s2414314626006668","type":"journal-article","created":{"date-parts":[[2026,6,25]],"date-time":"2026-06-25T06:50:06Z","timestamp":1782370206000},"update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":0,"title":["2-(3,4-Dichlorophenyl)-\n                    <i>N<\/i>\n                    -methyl-\n                    <i>N<\/i>\n                    -[2-(pyrrolidin-1-yl)cyclohexyl]acetamide hydrochloride: (\u00b1)-U50,488H"],"prefix":"10.1107","volume":"11","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-1290-0500","authenticated-orcid":true,"given":"Yoshimi","family":"Ichimaru","sequence":"first","affiliation":[{"id":[{"id":"https:\/\/ror.org\/03jqeq923","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Masaaki","family":"Kurihara","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/03jqeq923","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"329","published-online":{"date-parts":[[2026,6,30]]},"reference":[{"key":"zl4100_bb1","doi-asserted-by":"crossref","first-page":"267","DOI":"10.1016\/0883-2889(90)90190-R","volume":"41","author":"Chesis","year":"1990","journal-title":"Int. J. Radiat. Appl. Instrum. Part A. Appl. Radiat. Isot."},{"key":"zl4100_bb2","doi-asserted-by":"crossref","first-page":"1354","DOI":"10.1021\/ja00839a011","volume":"97","author":"Cremer","year":"1975","journal-title":"J. Am. Chem. Soc."},{"key":"zl4100_bb3","doi-asserted-by":"crossref","first-page":"676","DOI":"10.1107\/S0108270189009431","volume":"46","author":"Doi","year":"1990","journal-title":"Acta Cryst. C"},{"key":"zl4100_bb4","doi-asserted-by":"crossref","first-page":"339","DOI":"10.1107\/S0021889808042726","volume":"42","author":"Dolomanov","year":"2009","journal-title":"J. Appl. Cryst."},{"key":"zl4100_bb5","doi-asserted-by":"crossref","first-page":"e70075","DOI":"10.1002\/npr2.70075","volume":"45","author":"Kato","year":"2025","journal-title":"Neuropsychopharm Rep."},{"key":"zl4100_bb6","unstructured":"Rigaku OD (2025). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England."},{"key":"zl4100_bb7","doi-asserted-by":"crossref","first-page":"345","DOI":"10.1016\/0014-2999(89)90443-3","volume":"167","author":"Rothman","year":"1989","journal-title":"Eur. J. Pharmacol."},{"key":"zl4100_bb8","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053273314026370","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. A"},{"key":"zl4100_bb9","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053229614024218","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. C"},{"key":"zl4100_bb10","doi-asserted-by":"crossref","first-page":"1125","DOI":"10.1021\/jm00352a005","volume":"25","author":"Szmuszkovicz","year":"1982","journal-title":"J. Med. Chem."}],"container-title":["IUCrData"],"original-title":[],"link":[{"URL":"https:\/\/journals.iucr.org\/x\/issues\/2026\/06\/00\/zl4100\/zl4100.pdf","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/journals.iucr.org\/x\/issues\/2026\/06\/00\/zl4100\/zl4100.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,7,3]],"date-time":"2026-07-03T14:49:08Z","timestamp":1783090148000},"score":1,"resource":{"primary":{"URL":"https:\/\/journals.iucr.org\/paper?S2414314626006668"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,6,28]]},"references-count":10,"journal-issue":{"issue":"6","published-online":{"date-parts":[[2026,6]]}},"alternative-id":["S2414314626006668"],"URL":"https:\/\/doi.org\/10.1107\/s2414314626006668","relation":{"is-supplemented-by":[{"id-type":"doi","id":"10.1107\/S2414314626006668\/zl4100sup1.cif","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2414314626006668\/zl4100Isup2.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2414314626006668\/zl4100Isup3.cml","asserted-by":"subject"}]},"ISSN":["2414-3146"],"issn-type":[{"value":"2414-3146","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,6,28]]},"assertion":[{"value":"IUCrData","order":0,"name":"journal","label":"Publication","explanation":{"URL":"https:\/\/journals.iucr.org\/x"},"group":{"name":"general","label":"General"}},{"value":"data reports","order":1,"name":"content_type","label":"Content type","explanation":{"URL":"https:\/\/journals.iucr.org\/x\/services\/notesforauthors.html"},"group":{"name":"general","label":"General"}},{"value":"Available","URL":"https:\/\/scripts.iucr.org\/cgi-bin\/citedin?zl4100","order":2,"name":"article_metrics","label":"Article metrics","group":{"name":"general","label":"General"}},{"value":"Yes","order":0,"name":"peer_reviewed","label":"Peer reviewed","group":{"name":"peer_review","label":"Peer review"}},{"value":"Single blind","order":1,"name":"review_process","label":"Review process","group":{"name":"peer_review","label":"Peer review"}},{"value":"3 June 2026","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication history"}},{"value":"23 June 2026","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication history"}},{"value":"30 June 2026","order":2,"name":"published_online","label":"Published online","group":{"name":"publication_history","label":"Publication history"}},{"value":"This data article has supporting information","name":"supplementary_materials","label":"Supplementary materials","explanation":{"URL":"https:\/\/scripts.iucr.org\/cgi-bin\/sendsup?zl4100"}},{"value":"\u00a9 2026 Ichimaru and Kurihara","order":0,"name":"copyright","label":"Copyright","explanation":{"URL":"https:\/\/journals.iucr.org\/services\/copyrightpolicy.html"},"group":{"name":"copyright_and_licencing","label":"Copyright and licencing"}},{"value":"Creative Commons Attribution (CC-BY)","order":1,"name":"license","label":"Licence","explanation":{"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},"group":{"name":"copyright_and_licencing","label":"Copyright and licencing"}}],"article-number":"x260666"}}