{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,4]],"date-time":"2026-09-04T22:22:01Z","timestamp":1788560521472,"version":"build-2803163510"},"reference-count":60,"publisher":"International Union of Crystallography (IUCr)","issue":"1","license":[{"start":{"date-parts":[[2022,1,1]],"date-time":"2022-01-01T00:00:00Z","timestamp":1640995200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2022,1,1]],"date-time":"2022-01-01T00:00:00Z","timestamp":1640995200000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"}],"funder":[{"DOI":"10.13039\/100000015","name":"U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences","doi-asserted-by":"publisher","award":["DE-AC02-06CH11357"],"award-info":[{"award-number":["DE-AC02-06CH11357"]}],"id":[{"id":"10.13039\/100000015","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["iucr.org","wiley.com","iucrj.org"],"crossmark-restriction":true},"short-container-title":["Acta Crystallogr C Struct Chem","Acta Crystallogr C","Acta Crystallogr C Cryst Struct Commun","Acta Cryst C","Acta Cryst C Struct Chem","Acta Cryst Sect C","Acta Cryst Sect C Struct Chem","Acta Crystallogr Sect C","Acta Crystallogr Sect C Struct Chem","Acta Crystallogr Sect C Cryst Struct Commun"],"accepted":{"date-parts":[[2021,12,10]]},"published-print":{"date-parts":[[2022,1,1]]},"abstract":"<jats:p>\n                    Psilocybin {systematic name: 3-[2-(dimethylamino)ethyl]-1\n                    <jats:italic>H<\/jats:italic>\n                    -indol-4-yl dihydrogen phosphate} is a zwitterionic tryptamine natural product found in numerous species of fungi known for their psychoactive properties. Following its structural elucidation and chemical synthesis in 1959, purified synthetic psilocybin has been evaluated in clinical trials and has shown promise in the treatment of various mental health disorders. In a recent process-scale crystallization investigation, three crystalline forms of psilocybin were repeatedly observed: Hydrate A, Polymorph A, and Polymorph B. The crystal structure for Hydrate A was solved previously by single-crystal X-ray diffraction. This article presents new crystal structure solutions for the two anhydrates, Polymorphs A and B, based on Rietveld refinement using laboratory and synchrotron X-ray diffraction data, and density functional theory (DFT) calculations. Utilizing the three solved structures, an investigation was conducted\n                    <jats:italic>via<\/jats:italic>\n                    Rietveld method (RM) based quantitative phase analysis (QPA) to estimate the contribution of the three different forms in powder X-ray diffraction (PXRD) patterns provided by different sources of bulk psilocybin produced between 1963 and 2021. Over the last 57 years, each of these samples quantitatively reflect one or more of the hydrate and anhydrate polymorphs. In addition to quantitatively evaluating the composition of each sample, this article evaluates correlations between the crystal forms present, corresponding process methods, sample age, and storage conditions. Furthermore, revision is recommended on characterizations in recently granted patents that include descriptions of crystalline psilocybin inappropriately reported as a single-phase `isostructural variant.' Rietveld refinement demonstrated that the claimed material was composed of approximately 81% Polymorph A and 19% Polymorph B, both of which have been identified in historical samples. In this article, we show conclusively that all published data can be explained in terms of three well-defined forms of psilocybin and that no additional forms are needed to explain the diffraction patterns.\n                  <\/jats:p>","DOI":"10.1107\/s2053229621013164","type":"journal-article","created":{"date-parts":[[2021,12,20]],"date-time":"2021-12-20T07:54:04Z","timestamp":1639986844000},"page":"36-55","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":10,"title":["Psilocybin: crystal structure solutions enable phase analysis of prior art and recently patented examples"],"prefix":"10.1107","volume":"78","author":[{"given":"Alexander M.","family":"Sherwood","sequence":"first","affiliation":[{"id":[{"id":"https:\/\/ror.org\/02ebkdp37","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Robert B.","family":"Kargbo","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/02ebkdp37","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kristi W.","family":"Kaylo","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/02ebkdp37","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7593-6063","authenticated-orcid":true,"given":"Nicholas V.","family":"Cozzi","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Poncho","family":"Meisenheimer","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/02ebkdp37","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6610-541X","authenticated-orcid":true,"given":"James A.","family":"Kaduk","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/02ehan050","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"329","published-online":{"date-parts":[[2022,1,1]]},"reference":[{"key":"wp3022_bb1","doi-asserted-by":"crossref","first-page":"129","DOI":"10.1016\/j.ijpharm.2004.02.017","volume":"276","author":"Airaksinen","year":"2004","journal-title":"Int. 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