3-Fluorophenmetrazine

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3-Fluorophenmetrazine
3-Fluorophenmetrazine.svg
Systematic (IUPAC) name
2-(3-Fluorophenyl)-3-methylmorpholine
Legal status
Legal status
Identifiers
CAS Number 1350768-28-3 YesY
HCl: 1803562-83-5
PubChem CID 54673723
HCl: CID 75481405
ChemSpider 37509994
HCl: 34212559
UNII BEV6RF569G YesY
Synonyms 3-FPM, 3-FPH, PAL-593
Chemical data
Formula C11H14FNO
Molar mass 195.24 g·mol−1
3D model (Jmol) Interactive image

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]

Pharmacology[edit]

3-FPM acts as a dopamine-norepinephrine releasing agent with EC50 values of 43 nM and 30 nM, respectively.[3] It shows only negligible efficacy as a releaser of serotonin, with an EC50 value of 2558 nM.[3]

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.[4]

Legality[edit]

Sweden's public health agency suggested to classify 3-Fluorophenmetrazine as illegal narcotic on June 1, 2015.[5] It was finally classified on October 15, 2015.[6]

3-Fluorophenmetrazine is illegal in Switzerland as of December 2015.[7]

See also[edit]

References[edit]

  1. ^ McLaughlin, Gavin; Morris, Noreen; Kavanagh, Pierce V.; Dowling, Geraldine; Power, John D.; Twamley, Brendan; O'Brien, John; Talbot, Brian; Sitte, Harald H.; Brandt, Simon D. (26 January 2016). "Test purchase, synthesis and characterization of 3-fluorophenmetrazine (3-FPM) and differentiation from its ortho- and para-substituted isomers". Drug Testing and Analysis. doi:10.1002/dta.1945. ISSN 1942-7611. PMID 26810957. 
  2. ^ Bäckberg, Matilda; Westerbergh, Jenny; Beck, Olof; Helander, Anders (5 August 2016). "Adverse events related to the new psychoactive substance 3-fluorophenmetrazine – results from the Swedish STRIDA project". Clinical Toxicology. doi:10.1080/15563650.2016.1211288. ISSN 1556-3650. PMID 27491700. 
  3. ^ a b Bruce E. Blough; Richard Rothman; Antonio Landavazo; Kevin M. Page; Ann Marie Decker (8 August 2013). "US Patent 20130203752 A1 - Phenylmorpholines and analogues thereof". 
  4. ^ Mardal, Marie; Miserez, Bram; Bade, Richard; Portolés, Tania; Bischoff, Markus; Hernández, Félix; Meyer, Markus R. (5 September 2016). "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. doi:10.1016/j.jpba.2016.06.011. PMID 27372653 – via ScienceDirect. 
  5. ^ "23 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. 1 June 2015. 
  6. ^ "Nya substanser klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. 18 August 2015. 
  7. ^ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Der Bundesrat.