Ephenidine

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Ephenidine
Legal status
Legal status
Identifiers
  • N-Ethyl-1,2-diphenylethylamine
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC16H19N
Molar mass225.328 g/mol g·mol−1
3D model (JSmol)
  • CCNC(CC1=CC=CC=C1)C2=CC=CC=C2

  • CCNC(CC1=CC=CC=C1)C2=CC=CC=C2.Cl
  • InChI=1S/C16H19N/c1-2-17-16(15-11-7-4-8-12-15)13-14-9-5-3-6-10-14/h3-12,16-17H,2,13H2,1H3
  • Key:IGFZMQXEKIZPDR-UHFFFAOYSA-N

  • InChI=1S/C16H19N.ClH/c1-2-17-16(15-11-7-4-8-12-15)13-14-9-5-3-6-10-14;/h3-12,16-17H,2,13H2,1H3;1H
  • Key:WOSDTAOMYCNNJE-UHFFFAOYSA-N

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][8][9] Ephenidine also possesses substantially weaker affinity for dopamine and norepinephrine transporters (379 nM and 841 nM, respectively) as well as σ1R (629 nM) and σ2R (722 nM) binding sites.[10]

Metabolism

Ephenidines metabolic pathway consists of 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][11]

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[12]
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.[13]

In Canada, MT-45 and its analogues were made Schedule I controlled substances.[14] Possession without legal authority can result in maximum 7 years imprisonment. Further, Health Canada amended the Food and Drug Regulations in May, 2016 to classify AH-7921 as a restricted drug. Only those with a law enforcement agency, person with an exemption permit or institutions with Minister's authorization may possess the drug.

See also

References

  1. ^ Hamilton Morris; Jason Wallach (July–August 2014). "From PCP to MXE: a comprehensive review of the non-medical use of dissociative drugs". Drug Testing and Analysis. 6 (7–8): 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. ^ a b Carina S. D. Wink; Golo M. J. Meyer; Dirk K. Wissenbach; Andrea Jacobsen-Bauer; Markus R. Meyer; Hans H. Maurer (October 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 (November 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 (3): 39–44. doi:10.1016/j.toxlet.2015.08.012. PMID 26276083.
  5. ^ Nancy M. Gray; Brian K. Cheng (6 April 1994). "Patent EP 0346791 - 1,2-diarylethylamines for treatment of neurotoxic injury". G.D. Searle, LLC – via SureChEMBL.
  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 2015). "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. PMID 25044512.
  8. ^ Thurkauf, Andrew; Monn, James; Mattson, Marienna V.; Jacobson, Arthur E.; Rice, Kenner C. (1989). "Structural and conformational aspects of the binding of aryl-alkyl amines to the phencyclidine binding site" (PDF). NIDA research monograph. 95: 51–56. ISSN 1046-9516. PMID 2561843.
  9. ^ Goodson, L. H.; Wiegand, C. J. W.; Splitter, Janet S. (November 1946). "Analgesics. I. N-Alkylated-1,2-diphenylethylamines Prepared by the Leuckart Reaction". Journal of the American Chemical Society. 68 (11): 2174–2175. doi:10.1021/ja01215a018. PMID 21002222.
  10. ^ Kang, Heather; Park, Pojeong; Bortolotto, Zuner A.; Brandt, Simon D.; Colestock, Tristan; Wallach, Jason; Collingridge, Graham L.; Lodge, David (2016). "Ephenidine: A new psychoactive agent with ketamine-like NMDA receptor antagonist properties". Neuropharmacology. doi:10.1016/j.neuropharm.2016.08.004.
  11. ^ 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.
  12. ^ "Ephenidine reaction results with various reagent tests". Reagent Tests UK. 17 January 2016. Retrieved 23 January 2016.
  13. ^ "23 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. 1 June 2015.
  14. ^ Denis Arsenault (1 June 2016). "Regulations Amending the Food and Drug Regulations (Parts G and J — Lefetamine, AH-7921, MT-45 and W-18)". Canada Gazette. 150 (11). Government of Canada.
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