{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,4]],"date-time":"2026-08-04T21:33:40Z","timestamp":1785879220511,"version":"3.56.0"},"reference-count":37,"publisher":"Wiley","issue":"9","license":[{"start":{"date-parts":[[2018,5,23]],"date-time":"2018-05-23T00:00:00Z","timestamp":1527033600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["analyticalsciencejournals.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Drug Testing and Analysis"],"published-print":{"date-parts":[[2018,9]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The availability of new psychoactive substances (NPS) on the recreational drug market continues to create challenges for scientists in the forensic, clinical and toxicology fields. Phenmetrazine (3\u2010methyl\u20102\u2010phenylmorpholine) and an array of its analogs form a class of psychostimulants that are well documented in the patent and scientific literature. The present study reports on two phenmetrazine analogs that have been encountered on the NPS market following the introduction of 3\u2010fluorophenmetrazine (3\u2010FPM), namely 4\u2010methylphenmetrazine (4\u2010MPM), and 3\u2010methylphenmetrazine (3\u2010MPM). This study describes the syntheses, analytical characterization, and pharmacological evaluation of the positional isomers of MPM. Analytical characterizations employed various chromatographic, spectroscopic, and mass spectrometric platforms. Pharmacological studies were conducted to assess whether MPM isomers might display stimulant\u2010like effects similar to the parent compound phenmetrazine. The isomers were tested for their ability to inhibit uptake or stimulate release of tritiated substrates at dopamine, norepinephrine and serotonin transporters using in vitro transporter assays in rat brain synaptosomes. The analytical characterization of three vendor samples revealed the presence of 4\u2010MPM in two of the samples and 3\u2010MPM in the third sample, which agreed with the product label. The pharmacological findings suggest that 2\u2010MPM and 3\u2010MPM will exhibit stimulant properties similar to the parent compound phenmetrazine, whereas 4\u2010MPM may display entactogen properties more similar to 3,4\u2010methylenedioxymethamphetamine (MDMA). The combination of test purchases, analytical characterization, targeted organic synthesis, and pharmacological evaluation of NPS and their isomers is an effective approach for the provision of data on these substances as they emerge in the marketplace.<\/jats:p>","DOI":"10.1002\/dta.2396","type":"journal-article","created":{"date-parts":[[2018,4,19]],"date-time":"2018-04-19T13:06:14Z","timestamp":1524143174000},"page":"1404-1416","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Synthesis, analytical characterization, and monoamine transporter activity of the new psychoactive substance 4\u2010methylphenmetrazine (4\u2010MPM), with differentiation from its <i>ortho<\/i>\u2010 and <i>meta<\/i>\u2010 positional isomers"],"prefix":"10.1002","volume":"10","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-2496-8396","authenticated-orcid":false,"given":"Gavin","family":"McLaughlin","sequence":"first","affiliation":[{"name":"Department of Pharmacology and Therapeutics, School of Medicine, Trinity Centre for Health Sciences St James's Hospital  Dublin Ireland"},{"name":"Forensic Science Ireland Garda Headquarters  Dublin Ireland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Michael H.","family":"Baumann","sequence":"additional","affiliation":[{"name":"Designer Drug Research Unit, Intramural Research Program National Institute on Drug Abuse, National Institutes of Health  Baltimore Maryland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pierce V.","family":"Kavanagh","sequence":"additional","affiliation":[{"name":"Department of Pharmacology and Therapeutics, School of Medicine, Trinity Centre for Health Sciences St James's Hospital  Dublin Ireland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Noreen","family":"Morris","sequence":"additional","affiliation":[{"name":"Department of Life &amp; Physical Sciences Faculty of Science and Health, Athlone Institute of Technology, Co.  Westmeath Ireland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0926-1621","authenticated-orcid":false,"given":"John D.","family":"Power","sequence":"additional","affiliation":[{"name":"Department of Pharmacology and Therapeutics, School of Medicine, Trinity Centre for Health Sciences St James's Hospital  Dublin Ireland"},{"name":"Forensic Science Ireland Garda Headquarters  Dublin Ireland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Geraldine","family":"Dowling","sequence":"additional","affiliation":[{"name":"Department of Pharmacology and Therapeutics, School of Medicine, Trinity Centre for Health Sciences St James's Hospital  Dublin Ireland"},{"name":"Department of Life Sciences, School of Science Sligo Institute of Technology  Ireland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Brendan","family":"Twamley","sequence":"additional","affiliation":[{"name":"School of Chemistry Trinity College Dublin  Ireland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"John","family":"O'Brien","sequence":"additional","affiliation":[{"name":"School of Chemistry Trinity College Dublin  Ireland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1527-7056","authenticated-orcid":false,"given":"Gary","family":"Hessman","sequence":"additional","affiliation":[{"name":"School of Chemistry Trinity College Dublin  Ireland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Folker","family":"Westphal","sequence":"additional","affiliation":[{"name":"State Bureau of Criminal Investigation Schleswig\u2010Holstein Section Narcotics\/Toxicology  Kiel Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Donna","family":"Walther","sequence":"additional","affiliation":[{"name":"Designer Drug Research Unit, Intramural Research Program National Institute on Drug Abuse, National Institutes of Health  Baltimore Maryland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8632-5372","authenticated-orcid":false,"given":"Simon D.","family":"Brandt","sequence":"additional","affiliation":[{"name":"School of Pharmacy and Biomolecular Sciences Liverpool John Moores University  UK"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2018,5,23]]},"reference":[{"key":"e_1_2_5_2_1","unstructured":"BloughBE RothmanR LandavazoA PageKM DeckerAM.Preparation of phenylmorpholines and analogs thereof. 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