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Other names | 3-FPM, 3-FPH, PAL-593 |
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Chemical and physical data | |
Formula | C11H14FNO |
Molar mass | 195.237 g·mol−1 |
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Boiling point | 280.6 °C (537.1 °F) |
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3-Fluorophenmetrazine (also known as 3-FPM, 3-FPH and PAL-593) is a phenylmorpholine-based stimulant and fluorinated analogue of phenmetrazine that has been sold online as a designer drug.[1][2]
3-Fluorophenmetrazine is a fluorinated analogue of phenmetrazine, a stimulant of the morpholine class.
3-Fluorophenmetrazine is a regioisomer of both 2-fluorophenmetrazine and 4-fluorophenmetrazine.
3-FPM acts as a norepinephrine–dopamine releasing agent with EC50 values of 30 nM and 43 nM, respectively.[3][4] It shows only negligible efficacy as a releaser of serotonin, with an EC50 value of 2558 nM.[3]
3-FPM also inhibits uptake mediated by dopamine transporters and norepinephrine transporters in HEK293 cells with potencies comparable to cocaine (IC50 values < 2.5 μM), but with less potent effects at serotonin transporters (IC50 values >80 μM).[4]
At sufficient doses, 3-FPM is capable of reversing monoamine transporters, particularly transporters of the catecholamines dopamine and norepinephrine, and, to a much lesser degree, serotonin transporters, thereby releasing these neurotransmitters from the cytosol into the extracellular space, where they are active.[4]
Evaluation of its metabolic pathway revealed N‐oxidation, aryl hydroxylation and subsequent O‐methylation, alkyl hydroxylation, oxidation, and degradation of the ethyl‐bridge yielding the O/N‐bis‐dealkylated metabolite, combinations thereof and further glucuronidation or sulfations.[5]
In the United States, 3-fluorophenmetrazine is not explicitly illegal at the federal level, but may be considered under the federal analogue act if intended for consumption as a structural analog of Schedule II Phenmetrazine. On November 16, 2016, it became an illegal substance in the state of Virginia.[6] Pursuant to subsection D of § 54.1-3443 of the Code of Virginia, the state Board of Pharmacy designated it as a Schedule I controlled substance, effective through May 10, 2018.[7] Although the initial regulatory period has lapsed, during their 2019 legislative session, the Virginia state legislature is set to vote on a bill that would permanently schedule 3-fluorophenmetrazine as an illegal, Schedule I substance, and it is likely that the bill will succeed. [8]
Sweden's public health agency suggested to classify 3-Fluorophenmetrazine as illegal narcotic on June 1, 2015.[9] It was finally classified on October 15, 2015.[10]
3-Fluorophenmetrazine is illegal in Switzerland as of December 2015.[11]