{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,3]],"date-time":"2026-03-03T21:40:20Z","timestamp":1772574020991,"version":"3.50.1"},"reference-count":29,"publisher":"Wiley","issue":"9-10","license":[{"start":{"date-parts":[[2025,7,31]],"date-time":"2025-07-31T00:00:00Z","timestamp":1753920000000},"content-version":"vor","delay-in-days":30,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["analyticalsciencejournals.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Labelled Comp Radiopharmac"],"published-print":{"date-parts":[[2025,7]]},"abstract":"<jats:title>ABSTRACT<\/jats:title><jats:p>Three novel <jats:sup>14<\/jats:sup>C\u2010labelled isotopologues of the psychoactive agents psilocin, psilocybin and 5\u2010methoxy\u2010<jats:italic>N<\/jats:italic>,<jats:italic>N<\/jats:italic>\u2010dimethyltryptamine (5\u2010MeO\u2010DMT) were synthesised, all labelled at the 2\u2010position of the indole. The syntheses involved incorporating the 3\u2010dimethylaminoethyl substituent common to all three substances onto a 4\u2010 or 5\u2010substituted indole intermediate via successive treatments with oxalyl chloride, dimethylamine and reduction with lithium aluminium hydride.<\/jats:p><jats:p>Psilocybin\u2010<jats:italic>2<\/jats:italic>\u2010<jats:sup>14<\/jats:sup><jats:italic>C<\/jats:italic> with a specific activity of 234\u2009\u03bcCi\/mg exhibited limited stability, but a 5.5\u2010fold radio dilution with unlabelled psilocybin afforded material that maintained a radiochemical purity exceeding 97.5% after 1\u2010month storage at \u2264\u2009\u221270\u00b0C. The stability of 5\u2010MeO\u2010DMT\u2010<jats:italic>2<\/jats:italic>\u2010<jats:sup>14<\/jats:sup><jats:italic>C<\/jats:italic> succinate salt with a specific activity of 173\u2009\u03bcCi\/mg was assessed over a more extended storage period, and after 6\u2009months at \u2264\u2009\u221270\u00b0C the radiochemical purity was 98.0%, supporting its use in long\u2010term studies.<\/jats:p><jats:p>The radiolabelled psilocybin\u2010<jats:italic>2<\/jats:italic>\u2010<jats:sup>14<\/jats:sup><jats:italic>C<\/jats:italic> and 5\u2010MeO\u2010DMT\u2010<jats:italic>2<\/jats:italic>\u2010<jats:sup>14<\/jats:sup><jats:italic>C<\/jats:italic> succinate represent new tools for in\u00a0vivo pharmacokinetic and metabolic studies with psychedelic tryptamines. These novel derivatives may offer enhanced metabolic stability and facilitate more precise ADME and mass balance studies. Future research will explore their behaviour in biological systems to support necessary studies toward regulatory approval of both psilocybin and 5\u2010MeO\u2010DMT for treating mental health disorders such as depression, anxiety and post\u2010traumatic stress disorder.<\/jats:p>","DOI":"10.1002\/jlcr.4155","type":"journal-article","created":{"date-parts":[[2025,7,31]],"date-time":"2025-07-31T17:29:18Z","timestamp":1753982958000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Synthesis of Psilocin, Psilocybin and 5\u2010MeO\u2010DMT Succinate, All Labelled With Carbon\u201014 at the Indole 2\u2010Position"],"prefix":"10.1002","volume":"68","author":[{"given":"Rodney","family":"Brown","sequence":"first","affiliation":[{"name":"Isotope Chemistry Laboratories, Almac Sciences Ltd., Almac House Seagoe Industrial Estate  Craigavon UK"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0009-0007-8329-513X","authenticated-orcid":false,"given":"Niall\u00a0M.","family":"Hamilton","sequence":"additional","affiliation":[{"name":"Isotope Chemistry Laboratories, Almac Sciences Ltd., Almac House Seagoe Industrial Estate  Craigavon UK"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Connor","family":"Mallon","sequence":"additional","affiliation":[{"name":"Isotope Chemistry Laboratories, Almac Sciences Ltd., Almac House Seagoe Industrial Estate  Craigavon UK"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"James","family":"Stevenson","sequence":"additional","affiliation":[{"name":"Isotope Chemistry Laboratories, Almac Sciences Ltd., Almac House Seagoe Industrial Estate  Craigavon UK"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Michael\u00a0T.","family":"Faley","sequence":"additional","affiliation":[{"name":"Usona Institute  Madison Wisconsin USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Robert\u00a0B.","family":"Kargbo","sequence":"additional","affiliation":[{"name":"Usona Institute  Madison Wisconsin USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Alexander\u00a0M.","family":"Sherwood","sequence":"additional","affiliation":[{"name":"Usona Institute  Madison Wisconsin USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Balasubramaniam","family":"Upeandran","sequence":"additional","affiliation":[{"name":"Isotope Chemistry Laboratories, Almac Sciences Ltd., Almac House Seagoe Industrial Estate  Craigavon UK"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2025,7,31]]},"reference":[{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF02166696"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.19590420518"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.11.221"},{"key":"e_1_2_7_5_1","first-page":"149","volume-title":"Emerging Neurobiology of Antidepressant Treatments","author":"Nutt D. 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