Chemistry:3-Fluorophenmetrazine

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Short description: Stimulant designer drug
3-Fluorophenmetrazine
3-Fluorophenmetrazine.svg
Clinical data
Other names3-FPM, 3-FPH, PAL-593
Legal status
Legal status
  • BR: F2
  • 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
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC11H14FNO
Molar mass195.237 g·mol−1
3D model (JSmol)
Boiling point280.6 °C (537.1 °F)

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.[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

  1. ↑ "Test purchase, synthesis and characterization of 3-fluorophenmetrazine (3-FPM) and differentiation from its ortho- and para-substituted isomers". Drug Testing and Analysis 9 (3): 369–377. March 2017. doi:10.1002/dta.1945. PMID 26810957. http://researchonline.ljmu.ac.uk/3143/1/DTA-15-0338.R1_accepted_uncorrected.pdf. 
  2. ↑ "Adverse events related to the new psychoactive substance 3-fluorophenmetrazine - results from the Swedish STRIDA project". Clinical Toxicology 54 (9): 819–825. November 2016. doi:10.1080/15563650.2016.1211288. PMID 27491700. 
  3. ↑ 3.0 3.1 Blough BE, Rothman R, Landavazo A, Page KM, Decker AM, "Phenylmorpholines and analogues thereof", US patent 20130203752, issued 8 August 2013
  4. ↑ 4.0 4.1 4.2 "Fluorinated phenmetrazine "legal highs" act as substrates for high-affinity monoamine transporters of the SLC6 family". Neuropharmacology 134 (Pt A): 149–157. May 2018. doi:10.1016/j.neuropharm.2017.10.006. PMID 28988906. 
  5. ↑ "3-Fluorophenmetrazine, a fluorinated analogue of phenmetrazine: Studies on in vivo metabolism in rat and human, in vitro metabolism in human CYP isoenzymes and microbial biotransformation in Pseudomonas Putida and wastewater using GC and LC coupled to (HR)-MS techniques". Journal of Pharmaceutical and Biomedical Analysis 128: 485–495. September 2016. doi:10.1016/j.jpba.2016.06.011. PMID 27372653. 
  6. ↑ "VA.R. Doc. No. R17-4746" (in en). 17 December 2018. http://register.dls.virginia.gov/details.aspx?id=6000. 
  7. ↑ "§ 54.1-3446. Schedule I.". https://law.lis.virginia.gov/vacode/title54.1/chapter34/section54.1-3446/#:~:text=any%20quantity%20of%20the%20following%20substances%20having%20a%20stimulant,2%2D(3%2Dfluorophenyl)%2D3%2Dmethylmorpholine%20(other%20name%3A%203%2Dfluorophenmetrazine)%3B. 
  8. ↑ "21 U.S. Code § 812 - Schedules of controlled substances" (in en). 8 September 2023. https://www.law.cornell.edu/uscode/text/21/812. 
  9. ↑ "23 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in sv). Folkhälsomyndigheten. 1 June 2015. https://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2015/juni/23-nya-amnen-kan-klassas-som-narkotika-eller-halsofarlig-vara/. 
  10. ↑ "Nya substanser klassas som narkotika eller hälsofarlig vara" (in sv). Folkhälsomyndigheten. 18 August 2015. https://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2015/augusti/nya-substanser-klassas-som-narkotika-eller-halsofarlig-vara/. 
  11. ↑ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in de). Der Bundesrat. https://www.admin.ch/opc/de/classified-compilation/20101220/index.html. 



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