3-Fluorophenmetrazine

Edit links
Source: Wikipedia, the free encyclopedia.
3-Fluorophenmetrazine
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, Schedule I in the state of Virginia
  • Illegal in Sweden and Switzerland
Identifiers
  • 2-(3-Fluorophenyl)-3-methylmorpholine
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

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]

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.

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

  1. S2CID 205762700
    .
  2. S2CID 26118285
    .
  3. ^ a b US 20130203752, Blough BE, Rothman R, Landavazo A, Page KM, Decker AM, "Phenylmorpholines and analogues thereof", issued 8 August 2013 
  4. ^
    PMID 28988906
    .
  5. PMID 27372653
    .
  6. ^ "VA.R. Doc. No. R17-4746". 17 December 2018.
  7. ^ "§ 54.1-3446. Schedule I." Retrieved 8 September 2023.
  8. ^ "21 U.S. Code § 812 - Schedules of controlled substances". 8 September 2023.
  9. ^ "23 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. 1 June 2015.
  10. ^ "Nya substanser klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. 18 August 2015.
  11. ^ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Der Bundesrat.
Retrieved from "https://en.wikipedia.org/w/index.php?title=3-Fluorophenmetrazine&oldid=1192951924"