Ephenidine

Ephenidine

Ephenidine

Dissociative anesthetic designer drug

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]

Quick Facts Legal status, Identifiers ...

Pharmacology

Pharmacodynamics

Ephenidine and related diarylethylamines have been studied in vitro as treatments for neurotoxic injuries, and are antagonists of the NMDA receptor (Ki = 66.4 nM for ephenidine).[5][6][7][8][9] Ephenidine also possesses 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]

Pharmacokinetics

Metabolism

Ephenidine's metabolic pathway consists of N-oxidation, N-dealkylation, mono- and bis-hydroxylation of the benzyl 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 testing kits to give a semi-unique array of colors which can be used to aid its identification.

More information Reagent, Reaction color ...

Society and culture

Sweden's public health agency suggested that ephenidine be classified as a hazardous substance on 1 June, 2015. Due to that suggestion, ephenidine became a scheduled substance, in Sweden, as of 18 August, 2015.[13]

In 2016, Canada added MT-45 and "its salts, derivatives, isomers and analogues" to the Schedule I controlled substance list, and explicitly included ephenidine.[14] Possession without legal authority can result in maximum 7 years imprisonment.

See also

References

  1. [1]
    Morris H, Wallach J (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): 614–32. doi:10.1002/dta.1620. PMID 24678061.
  2. [2]
    Meyer MR, Orschiedt T, Maurer HH (February 2013). "Michaelis-Menten kinetic analysis of drugs of abuse to estimate their affinity to human P-glycoprotein". Toxicology Letters. 217 (2): 137–42. doi:10.1016/j.toxlet.2012.12.012. PMID 23273999.
  3. [3]
    Wink CS, Meyer GM, Wissenbach DK, Jacobsen-Bauer A, Meyer MR, Maurer HH (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): 1038–48. doi:10.1002/dta.1621. PMID 24591097.
  4. [4]
    Wink CS, Meyer GM, Meyer MR, Maurer HH (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. [5]
    Gray NM, Cheng BK (6 April 1994). "Patent EP 0346791 - 1,2-diarylethylamines for treatment of neurotoxic injury". G.D. Searle, LLC. Archived from the original on 20 September 2018. Retrieved 11 August 2016 – via SureChEMBL.
  6. [6]
    Berger ML, Schweifer A, Rebernik P, Hammerschmidt F (May 2009). "NMDA receptor affinities of 1,2-diphenylethylamine and 1-(1,2-diphenylethyl)piperidine enantiomers and of related compounds". Bioorganic & Medicinal Chemistry. 17 (9): 3456–62. doi:10.1016/j.bmc.2009.03.025. PMID 19345586.
  7. [7]
    Wallach J, Kavanagh PV, McLaughlin G, Morris N, Power JD, Elliott SP, et al. (May 2015). "Preparation and characterization of the 'research chemical' diphenidine, its pyrrolidine analogue, and their 2,2-diphenylethyl isomers" (PDF). Drug Testing and Analysis. 7 (5): 358–67. doi:10.1002/dta.1689. PMID 25044512. Archived (PDF) from the original on 2020-03-07. Retrieved 2021-05-31.
  8. [8]
    Thurkauf A, Monn J, Mattson MV, Jacobson AE, Rice KC (1989). "Structural and conformational aspects of the binding of aryl-alkyl amines to the phencyclidine binding site" (PDF). NIDA Research Monograph. 95: 51–6. PMID 2561843. Archived from the original (PDF) on 2017-08-23. Retrieved 2016-08-11.
  9. [9]
    Goodson LH, Wiegand CJ, Splitter JS (November 1946). "Analgesics; 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. [10]
    Kang H, Park P, Bortolotto ZA, Brandt SD, Colestock T, Wallach J, et al. (January 2017). "Ephenidine: A new psychoactive agent with ketamine-like NMDA receptor antagonist properties". Neuropharmacology. 112 (Pt A): 144–149. doi:10.1016/j.neuropharm.2016.08.004. PMC 5084681. PMID 27520396.
  11. [11]
    Wink CS, Meyer GM, Zapp J, Maurer HH (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-MS(n), and LC-high resolution-MS/MS". Analytical and Bioanalytical Chemistry. 407 (6): 1545–57. doi:10.1007/s00216-014-8414-3. PMID 25577353. S2CID 26014465.
  12. [12]
    "Ephenidine reaction results with various reagent tests". Reagent Tests UK. 17 January 2016. Archived from the original on 20 September 2018. Retrieved 23 January 2016.
  13. [13]
    "23 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. 1 June 2015. Archived from the original on 17 June 2019. Retrieved 15 August 2016.
  14. [14]
    Arsenault D (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). Archived from the original on 2017-12-02. Retrieved 2016-11-17.
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