Home > Analytical characterization and pharmacological evaluation of the new psychoactive substance 4-fluoromethylphenidate (4F-MPH) and differentiation between the (±)-threo and (±)-erythro diastereomers.

McLaughlin, Gavin and Morris, Noreen and Kavanagh, Pierce V and Power, John D and Dowling, Geraldine and Twamley, Brendan and O'Brien, John and Hessman, Gary and Murphy, Brian and Walther, Donna and Partilla, John S and Baumann, Michael H and Brandt, Simon D (2017) Analytical characterization and pharmacological evaluation of the new psychoactive substance 4-fluoromethylphenidate (4F-MPH) and differentiation between the (±)-threo and (±)-erythro diastereomers. Drug Testing and Analysis , 9 , (3) , pp. 347-357.

URL: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC53786...

Misuse of (±)-threo-methylphenidate (methyl-2-phenyl-2-(piperidin-2-yl)acetate; Ritalin®; MPH) has long been acknowledged, but the appearance of MPH analogs in the form of 'research chemicals' has only emerged in more recent years. 4-Fluoromethylphenidate (4F-MPH) is one of these recent examples. This study presents the identification and analytical characterization of two powdered 4F-MPH products that were obtained from an online vendor in 2015. Interestingly, the products appeared to have originated from two distinct batches given that one product consisted of (±)-threo-4F-MPH isomers whereas the second sample consisted of a mixture of (±)-threo and (±)-erythro 4F-MPH. Monoamine transporter studies using rat brain synaptosomes revealed that the biological activity of the 4F-MPH mixture resided with the (±)-threo and not the (±)-erythro isomers based on higher potencies determined for blockage of dopamine uptake (IC 4F-MPH  = 66 nM vs. IC (±)-threo = 61 nM vs. IC (±)-erythro = 8,528 nM) and norepinephrine uptake (IC 4F-MPH  = 45 nM vs. (±)-threo = 31 nM vs. IC (±)-erythro = 3,779 nM). In comparison, MPH was three times less potent than (±)-threo-4F-MPH at the dopamine transporter (IC  = 131 nM) and around 2.5 times less potent at the norepinephrine transporter (IC  = 83 nM). Both substances were catecholamine selective with IC values of 8,805 nM and >10,000 nM for (±)-threo-4F-MPH and MPH at the serotonin transporter. These findings suggest that the psychostimulant properties of (±)-threo-4F-MPH might be more potent in humans than MPH. Copyright © 2017 John Wiley & Sons, Ltd.


Item Type:Article
Date:2017
Page Range:pp. 347-357
Publisher:John Wiley & Sons, Ltd
Volume:9
Number:3
EndNote:View
Accession Number:HRB (Electronic Only)
Subjects:B Substances > CNS stimulants
B Substances > New (novel) psychoactive substances
VA Geographic area > Europe > Ireland

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