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Synthesis, analytical characterization and monoamine transporter activity of the new psychoactive substance 4-methylphenmetrazine (4-MPM), with differentiation from its ortho- and meta- positional isomers.

McLaughlin, G, Baumann, MH, Kavanagh, PV, Morris, N, Power, JD, Dowling, G, Twamley, B, O’Brien, J, Hessman, G, Westphal, F, Walther, D and Brandt, SD (2018) Synthesis, analytical characterization and monoamine transporter activity of the new psychoactive substance 4-methylphenmetrazine (4-MPM), with differentiation from its ortho- and meta- positional isomers. Drug Testing and Analysis. ISSN 1942-7611

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Abstract

The availability of new psychoactive substances on the recreational drug market continues to create challenges for scientists in the forensic, clinical and toxicology fields. Phenmetrazine (3-methyl-2-phenylmorpholine) 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 drug market following the introduction of 3-fluorophenmetrazine (3-FPM), namely 4-methylphenmetrazine (4-MPM) and 3-methylphenmetrazine (3-MPM). 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 in order to assess whether MPM isomers might display stimulant-like 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-MPM in two of the samples and 3-MPM in the third sample, which agreed with the product label. The pharmacological findings suggest that 2-MPM and 3-MPM will exhibit stimulant properties similar to the parent compound phenmetrazine, whereas 4-MPM may display entactogen properties more similar to 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.

Item Type: Article
Additional Information: This is the accepted version of the following article:McLaughlin, G, Baumann, MH, Kavanagh, PV, Morris, N, Power, JD, Dowling, G, Twamley, B, O’Brien, J, Hessman, G, Westphal, F, Walther, D and Brandt, SD (2018) Synthesis, analytical characterization and monoamine transporter activity of the new psychoactive substance 4-methylphenmetrazine (4-MPM), with differentiation from its ortho- and meta- positional isomers. Drug Testing and Analysis, which has been published in final form at https://doi.org/10.1002/dta.2396
Uncontrolled Keywords: 0301 Analytical Chemistry, 1115 Pharmacology And Pharmaceutical Sciences
Subjects: Q Science > QD Chemistry
R Medicine > RM Therapeutics. Pharmacology
Divisions: Pharmacy & Biomolecular Sciences
Publisher: Wiley
Date Deposited: 16 Apr 2018 11:07
Last Modified: 23 Apr 2018 09:13
URI: http://researchonline.ljmu.ac.uk/id/eprint/8490

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