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

stimulant Stimulants (also known as central nervous system stimulants, or psychostimulants, or colloquially as uppers) are a class of drugs that increase alertness. They are used for various purposes, such as enhancing attention, motivation, cognition, ...

and

fluorinated In chemistry, halogenation is a chemical reaction which introduces one or more halogens into a chemical compound. Halide-containing compounds are pervasive, making this type of transformation important, e.g. in the production of polymers, drugs. ...

analogue of

phenmetrazine Phenmetrazine, sold under the brand name Preludin among others, is a stimulant drug first chemical synthesis, synthesized in 1952 and originally used as an appetite suppressant, but withdrawn drug, withdrawn from the market in the 1980s due to ...

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. ...

Chemistry

3-Fluorophenmetrazine is a fluorinated analogue of phenmetrazine, a stimulant of the morpholine class. 3-Fluorophenmetrazine is a

regioisomer In chemistry, a structural isomer (or constitutional isomer in the IUPAC nomenclature) of a compound is a compound that contains the same number and type of atoms, but with a different connectivity (i.e. arrangement of bonds) between them. The ...

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 synapse, release of norepinephrine (and epinephrine) and dopamine in the body and/or brain. Many of these are amphetamine type stimulants. Examples Examples ...

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 (biology), cell. The reactants, products, and Metabolic intermediate, intermediates of an enzymatic reaction are known as metabolites, which are ...

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, but may be considered under the

federal analogue act The Federal Analogue Act, , is a section of the United States Controlled Substances Act passed in 1986 which allows any chemical "substantially similar" to a controlled substance listed in Schedule I or II to be treated as if it were listed ...

if intended for consumption as a structural analog of the Schedule II drug

Phenmetrazine Phenmetrazine, sold under the brand name Preludin among others, is a stimulant drug first chemical synthesis, synthesized in 1952 and originally used as an appetite suppressant, but withdrawn drug, withdrawn from the market in the 1980s due to ...

, but only if intended for human consumption. On November 16, 2016, it became an illegal substance in the state of Virginia. As of 2019, it is also a schedule I substance in Virginia. The

positional isomer In chemistry, a structural isomer (or constitutional isomer in the IUPAC nomenclature) of a compound is a compound that contains the same number and type of atoms, but with a different connectivity (i.e. arrangement of bonds) between them. The ...

s of 3-fluorophenmetrazine such as 2-fluorophenmetrazine and 4-fluorophenmetrazine are also illegal under Virginia law, but not federal law. 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- Beta-Hydroxyamphetamines Designer drugs 3-Fluorophenyl compounds Norepinephrine-dopamine releasing agents Phenylmorpholines Stimulants

Chemistry

Pharmacology

Legality

See also

References