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Phthalimidopropiophenone

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Title: Phthalimidopropiophenone  
Author: World Heritage Encyclopedia
Language: English
Subject: Fencamine, Trazium, Cilobamine, 3,4-Dimethylmethcathinone, 4-Fluoromethamphetamine
Collection: Cathinones, Ketones, Phthalimides, Stimulants
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Phthalimidopropiophenone

Phthalimidopropiophenone
Identifiers
CAS number  YesY
PubChem
ChemSpider
Jmol-3D images Image 1
Properties
Molecular formula C17H13NO3
Molar mass 279.29 g mol−1
Density 1.304 g/cm3
Melting point 87-88 °C
Boiling point 447.2 °C
Hazards
Flash point 204.4 °C (399.9 °F; 477.5 K)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)

Phthalimidopropiophenone is a chemical intermediate used in the synthesis of cathinone. It has been found to be sold on the illicit market as a controlled substance analogue, but little is currently known about its pharmacology or toxicology.[1]

Phthalimidopropiophenone is not an active stimulant, but is believed to be potentially capable of acting as a prodrug for cathinone when ingested, as similar N-substituted cathinone derivatives have been encountered by law enforcement, and were found to form cathinone in vivo by initial hydroxylation of the pyrrolidine ring followed by subsequent dehydrogenation to the corresponding lactam, then by double dealkylation of the pyrrolidine ring to form the primary amine.[2] It is unclear how rapidly or to what extent this metabolic pathway is followed in humans however, and the phthalimido substituted cathinones encountered may have been produced merely as a more stable form for storage than the relatively unstable primary amine cathinone derivatives.

References

  1. ^ Camilleri A, Johnston MR, Brennan M, Davis S, Caldicott DG. Chemical analysis of four capsules containing the controlled substance analogues 4-methylmethcathinone, 2-fluoromethamphetamine, alpha-phthalimidopropiophenone and N-ethylcathinone. Forensic Science International. 2010 Jan 13. doi:10.1016/j.forsciint.2009.12.048 PMID 20074881
  2. ^ Springer D, Fritschi G, Maurer HH. Metabolism of the new designer drug alpha-pyrrolidinopropiophenone (PPP) and the toxicological detection of PPP and 4'-methyl-alpha-pyrrolidinopropiophenone (MPPP) studied in rat urine using gas chromatography-mass spectrometry. Journal of Chromatography B. Analytical Technologies in the Biomedical and Life Sciences. 2003 Nov 5;796(2):253-66. PMID 14581066


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