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3-Fluorophenmetrazine

Stimulant designer drug From Wikipedia, the free encyclopedia

3-Fluorophenmetrazine

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]

Quick Facts Clinical data, Other names ...
3-Fluorophenmetrazine
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Clinical data
Other names3-FPM, 3-FPH, PAL-593
Legal status
Legal status
  • BR: Class F2 (Prohibited psychotropics)
  • CA: Unscheduled
  • DE: NpSG (Industrial and scientific use only)
  • UK: Under Psychoactive Substances Act
  • US: Unscheduled;
    Not controlled at the federal level, but possibly illegal under Federal Analogue Act of 1986, Schedule I in the state of Virginia
  • Illegal in Sweden and Switzerland
Identifiers
  • 2-(3-Fluorophenyl)-3-methylmorpholine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H14FNO
Molar mass195.237 g·mol−1
3D model (JSmol)
Boiling point280.6 °C (537.1 °F)
  • CC1C(OCCN1)C2=CC(=CC=C2)F

  • HCl: CC1C(OCCN1)C2=CC(=CC=C2)F.Cl
  • InChI=1S/C11H14FNO/c1-8-11(14-6-5-13-8)9-3-2-4-10(12)7-9/h2-4,7-8,11,13H,5-6H2,1H3
  • Key:VHYVKJAQSJCYCK-UHFFFAOYSA-N

  • HCl: InChI=1S/C11H14FNO.ClH/c1-8-11(14-6-5-13-8)9-3-2-4-10(12)7-9;/h2-4,7-8,11,13H,5-6H2,1H3;1H
  • Key:MHJBXKFJWSBWRE-UHFFFAOYSA-N
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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 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]

Legality

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 the Schedule II drug Phenmetrazine, but only if intended for human consumption.

On November 16, 2016, it became an illegal substance in the state of Virginia.[6] As of 2019, it is also a schedule I substance in Virginia. The positional isomers of 3-fluorophenmetrazine such as 2-fluorophenmetrazine and 4-fluorophenmetrazine are also illegal under Virginia law,[7] but not federal law.[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]

See also

References

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