Ephenidine

Ephenidine
Systematic (IUPAC) name
N-ethyl-1,2-diphenylethylamine
Identifiers
CAS Number 6272-97-5
PubChem CID 110821
ChemSpider 99470
Chemical data
Formula C16H19N
Molar mass 225.328 g/mol

Ephenidine (also known as NEDPA and EPE) is a dissociative anesthetic that has been sold online as a designer drug.[1][2] It is illegal in some countries as a structural isomer of the banned opioid drug lefetamine, but has been sold in countries where it is not yet banned.[3][4]

Ephenidine and related diarylethylamines have been studied in vitro as treatments for neurotoxic injuries, and are antagonists of the NMDA receptor.[5][6][7]

Metabolism

Ephenidine undergoes the following metabolic steps: N-oxidation, N-dealkylation, mono- and bis-hydroxylation of the benzene ring, and hydroxylation of the phenyl ring only after N-dealkylation. The dihydroxy metabolites were conjugated by methylation of one hydroxy group, and hydroxy metabolites by glucuronidation or sulfation.[3][8]

Chemistry

Ephenidine reacts with reagent tests to give a semi-unique array of colors which can be used to aid its identification.

Final colors produced by reagent tests[9]
Reagent Reaction color
Marquis Orange > Brown
Mandelin Green
Liebermann Deep red > Brown (fast)
Froehde Light Yellow

Legality

Sweden's public health agency suggested that Ephenidine be classified as a hazardous substance on the 1st of June, 2015. Due to that suggestion, Ephenidine became a scheduled substance, in Sweden, as of the 18th of August, 2015.[10]

See also

References

  1. ↑ Hamilton Morris, Jason Wallach (March 2014). "From PCP to MXE: a comprehensive review of the non-medical use of dissociative drugs". Drug Testing and Analysis 6: 614–632. doi:10.1002/dta.1620. PMID 24678061.
  2. ↑ Markus R. Meyer, Tina Orschiedt, Hans H. Maurer (February 2013). "Michaelis–Menten kinetic analysis of drugs of abuse to estimate their affinity to human P-glycoprotein". Toxicology Letters 217 (2): 137–142. doi:10.1016/j.toxlet.2012.12.012. PMID 23273999.
  3. 1 2 Carina S. D. Wink, Golo M. J. Meyer, Dirk K. Wissenbach, Andrea Jacobsen-Bauer, Markus R. Meyer, Hans H. Maurer (March 2014). "Lefetamine-derived designer drugs N-ethyl-1,2-diphenylethylamine (NEDPA) and N-iso-propyl-1,2-diphenylethylamine (NPDPA): Metabolism and detectability in rat urine using GC-MS, LC-MSn and LC-HR-MS/MS". Drug Testing and Analysis 6 (10): 1038–1048. doi:10.1002/dta.1621. PMID 24591097.
  4. ↑ Carina S.D. Wink, Golo M.J. Meyer, Markus R. Meyer, Hans H. Maurer (August 2015). "Toxicokinetics of lefetamine and derived diphenylethylamine designer drugs – Contribution of human cytochrome P450 isozymes to their main phase I metabolic steps". Toxicology Letters 238: 39–44. doi:10.1016/j.toxlet.2015.08.012. PMID 26276083.
  5. ↑ Nancy M. Gray, Brian K. Cheng. "Patent EP 0346791 B1 - 1,2-diarylethylamines for treatment of neurotoxic injury.". Retrieved 17 June 2015.
  6. ↑ Michael L. Berger, Anna Schweifer, Patrick Rebernik, Friedrich Hammerschmidt (May 2009). "NMDA receptor affinities of 1,2-diphenylethylamine and 1-(1,2-diphenylethyl)piperidine enantiomers and of related compounds". Bioorganic & Medicinal Chemistry 17 (1): 3456–3462. doi:10.1016/j.bmc.2009.03.025. PMID 19345586.
  7. ↑ Jason Wallach, Pierce V. Kavanagh, Gavin McLaughlin, Noreen Morris, John D. Power, Simon P. Elliott, Marion S. Mercier, David Lodge, Hamilton Morris, Nicola M. Dempster, Simon D. Brandt (May 2014). "Preparation and characterization of the ‘research chemical’ diphenidine, its pyrrolidine analogue, and their 2,2-diphenylethyl isomers". Drug Testing and Analysis 7 (5): 358–367. doi:10.1002/dta.1689.
  8. ↑ Carina S. D. Wink, Golo M. J. Meyer, Josef Zapp, Hans H. Maurer (February 2015). "Lefetamine, a controlled drug and pharmaceutical lead of new designer drugs: synthesis, metabolism, and detectability in urine and human liver preparations using GC-MS, LC-MSn , and LC-high resolution-MS/MS". Analytical and Bioanalytical Chemistry 407 (6): 1545–1557. doi:10.1007/s00216-014-8414-3. PMID 25577353.
  9. ↑ "Ephenidine reaction results with various reagent tests". Reagent Tests UK. 17 January 2016. Retrieved 23 January 2016.
  10. ↑ "23 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. Retrieved 16 June 2015.


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