Ephenidine

Source: Wikipedia, the free encyclopedia.
Ephenidine
Legal status
Legal status
Identifiers
  • N-Ethyl-1,2-diphenylethylamine
JSmol)
  • CCNC(CC1=CC=CC=C1)C2=CC=CC=C2

  • HCl: 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

  • HCl: 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]

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.

Final colors produced by reagent tests[12]
Reagent Reaction color
Marquis Orange > Brown
Mandelin Green
Liebermann Deep red > Brown (fast)
Froehde Light Yellow

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. PMID 24678061
    .
  2. PMID 23273999
    .
  3. ^
    PMID 24591097
    .
  4. PMID 26276083
    .
  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. PMID 19345586
    .
  7. PMID 25044512. Archived
    (PDF) from the original on 2020-03-07. Retrieved 2021-05-31.
  8. PMID 2561843. Archived from the original
    (PDF) on 2017-08-23. Retrieved 2016-08-11.
  9. PMID 21002222
    .
  10. PMID 27520396
    .
  11. S2CID 26014465
    .
  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. ^ "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. ^ 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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