{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T02:06:04Z","timestamp":1760148364625,"version":"build-2065373602"},"reference-count":25,"publisher":"MDPI AG","issue":"2","license":[{"start":{"date-parts":[[2023,4,23]],"date-time":"2023-04-23T00:00:00Z","timestamp":1682208000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Associate Laboratory for Green Chemistry\u2014LAQV","award":["UIDB\/50006\/2020","UIDP\/50006\/2020"],"award-info":[{"award-number":["UIDB\/50006\/2020","UIDP\/50006\/2020"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molbank"],"abstract":"<jats:p>5-(2-Aminopropyl)benzofuran (5-APB), also known as \u201cBenzo Fury,\u201d is a novel psychoactive substance (NPS) belonging to a new class of synthetic phenethylamines. It acts by disrupting serotonergic circuits as a serotonin\u2013norepinephrine\u2013dopamine reuptake inhibitor and is classified as an entactogen, similar to MDMA and MDA. Despite its popularity among users, recent toxicity events have been associated with the consumption of 5-APB and other benzofurans, highlighting the need for a better understanding of their pharmacodynamics and toxicity. One way to achieve this is by developing the synthesis of 5-APB metabolites as biomarkers of exposure. In this study, we present a six-step synthesis for one of the 5-APB metabolites, 2-(5-(2-aminopropyl)-2-hydroxyphenyl)acetic acid (1), involving methylation, formylation, Aldol-type condensation, reduction, and hydrolysis reactions. The compound was obtained in an overall yield of 11%.<\/jats:p>","DOI":"10.3390\/m1629","type":"journal-article","created":{"date-parts":[[2023,4,24]],"date-time":"2023-04-24T06:20:42Z","timestamp":1682317242000},"page":"M1629","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Synthesis of 2-(5-(2-Aminopropyl)-2-hydroxyphenyl)acetic Acid, a Metabolite of the Drug 5-APB"],"prefix":"10.3390","volume":"2023","author":[{"given":"Andr\u00e9 L.","family":"Silva","sequence":"first","affiliation":[{"name":"Department of Chemistry, NOVA School of Science & Technolgy, Universidade NOVA Lisboa, LAQV REQUIMTE, 2829-516 Caparica, Portugal"}]},{"given":"In\u00eas","family":"Fino","sequence":"additional","affiliation":[{"name":"Department of Chemistry, NOVA School of Science & Technolgy, Universidade NOVA Lisboa, LAQV REQUIMTE, 2829-516 Caparica, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8474-3925","authenticated-orcid":false,"given":"Lu\u00edsa M.","family":"Ferreira","sequence":"additional","affiliation":[{"name":"Department of Chemistry, NOVA School of Science & Technolgy, Universidade NOVA Lisboa, LAQV REQUIMTE, 2829-516 Caparica, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7312-8596","authenticated-orcid":false,"given":"Paula S.","family":"Branco","sequence":"additional","affiliation":[{"name":"Department of Chemistry, NOVA School of Science & Technolgy, Universidade NOVA Lisboa, LAQV REQUIMTE, 2829-516 Caparica, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2023,4,23]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.drugalcdep.2015.09.030","article-title":"Next Generation of Novel Psychoactive Substances on the Horizon\u2014A Complex Problem to Face","volume":"157","author":"Zawilska","year":"2015","journal-title":"Drug Alcohol Depend."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"3700","DOI":"10.1021\/jm00075a027","article-title":"Synthesis and Pharmacological Examination of Benzofuran, Indan, and Tetralin Analogs of 3,4-(Methylenedioxy)Amphetamine","volume":"36","author":"Monte","year":"1993","journal-title":"J. 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