3-Fluorophenmetrazine (also known as 3-FPM, 3-FPH and PAL-593) is a phenylmorpholine-based

stimulant Stimulants (also often referred to as psychostimulants or colloquially as uppers) is an overarching term that covers many drugs including those that increase activity of the central nervous system and the body, drugs that are pleasurable and inv ...

and

fluorinated In chemistry, halogenation is a chemical reaction that entails the introduction of one or more halogens into a chemical compound, compound. Halide-containing compounds are pervasive, making this type of transformation important, e.g. in the prod ...

analogue of

phenmetrazine Phenmetrazine (INN, USAN, BAN) (brand name Preludin, and many others) is a stimulant drug first synthesized in 1952 and originally used as an appetite suppressant, but withdrawn from the market in the 1980s due to widespread abuse. It was initia ...

that has been sold online as a

designer drug A designer drug is a structural or functional analog of a controlled substance that has been designed to mimic the pharmacological effects of the original drug, while avoiding classification as illegal and/or detection in standard drug tests. Des ...

Chemistry

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.

Pharmacology

3-FPM acts as a

norepinephrine–dopamine releasing agent A norepinephrine–dopamine releasing agent (NDRA) is a type of drug which induces the release of norepinephrine (and epinephrine) and dopamine in the body and/or brain. Examples of NDRAs include phenethylamine, tyramine, amphetamine, methampheta ...

with EC₅₀ values of 30 nM and 43 nM, respectively. It shows only negligible efficacy as a releaser of serotonin, with an EC₅₀ value of 2558 nM. 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). 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. Evaluation of its

metabolic pathway In biochemistry, a metabolic pathway is a linked series of chemical reactions occurring within a cell. The reactants, products, and intermediates of an enzymatic reaction are known as metabolites, which are modified by a sequence of chemical reac ...

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.

Legality

In the United States, 3-fluorophenmetrazine is not explicitly illegal at the federal level. However, on November 16, 2016, it became an illegal substance in the state of Virginia. 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. 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. Sweden's public health agency suggested to classify 3-Fluorophenmetrazine as illegal narcotic on June 1, 2015. It was finally classified on October 15, 2015. 3-Fluorophenmetrazine is illegal in Switzerland as of December 2015.

References

{{DEFAULTSORT:Fluorophenmetrazine, 3- Substituted amphetamines Phenylmorpholines Norepinephrine-dopamine releasing agents Stimulants Designer drugs Fluoroarenes

Chemistry

Pharmacology

Legality

See also

References