N-Ethylpentylone

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N-Ethylpentylone
Ephylone structure.png
N-Ethylpentylone.png
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
  • 1-(1,3-Benzodioxol-5-yl)-2-(ethylamino)pentan-1-one
CAS Number
  • 727641-67-0 checkY
  • HCl: 17763-02-9 checkY
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC14H19NO3
Molar mass249.310 g·mol−1
3D model (JSmol)
  • CCNC(CCC)C(=O)c2ccc1OCOc1c2
  • InChI=1S/C14H19NO3/c1-3-5-11(15-4-2)14(16)10-6-7-12-13(8-10)18-9-17-12/h6-8,11,15H,3-5,9H2,1-2H3
  • Key:VERDHJIMZYXGIW-UHFFFAOYSA-N

N-Ethylpentylone (β-keto-ethylbenzodioxolylpentanamine, βk-ethyl-K, βk-EBDP, ephylone) is a substituted cathinone and stimulant drug which was developed in the 1960s.[1][2]

It has been reported as a novel designer drug in several countries including the United Kingdom,[3]South Africa,[4] New Zealand,[5] the United States,[6] and Australia.[7] In 2018, N-ethylpentylone was the most common drug of the cathinone class to be identified in Drug Enforcement Administration seizures.[8]

A doctor, David Caldicott, has said N-ethylpentylone "can cause circulation problems, lethal heart palpitations and hallucinations".[9] It has been linked to a number of overdose deaths[10][11] and mass-casualty incidents,[12][13] and has increasingly been mis-sold as MDMA.[14]

N-Ethylpentylone is primarily a mixed norepinephrine reuptake inhibitor and dopamine reuptake inhibitor. It binds to transporters with IC50 values of 37 nM (DAT), 105 nM (NET) and 383 nM (SERT).[15]

Legality[edit]

In the United States, N-ethylpentylone is a Schedule I controlled substance since June 2018.[16]

See also[edit]

References[edit]

  1. ^ GB 1085135, "Substituted phenyl-α-amino ketones", published 1969, assigned to Boehringer Sohn Ingelheim 
  2. ^ Wood MR, Bernal I, Lalancette RA (October 2017). "The hydrochloride hydrates of pentylone and dibutylone and the hydrochloride salt of ephylone: the structures of three novel designer cathinones". Structural Chemistry. 28 (5): 1369–1376. doi:10.1007/s11224-017-0951-x. ISSN 1040-0400. S2CID 102424824.
  3. ^ Blanco G, Vidler D, Roper C, Wood DM, Dargan PI, Keating L, Macfarlane R, Emmett S, Johnson G, Eddleston M, Hill SL, Thomas SHL. Acute toxicity from the synthetic cathinone N-ethylpentylone (ephylone) in the United Kingdom. Clin Toxicol (Phila). 2021 Apr 15:1-4. doi:10.1080/15563650.2021.1909730 PMID 33855924
  4. ^ Umraw A, Pillay K (15 April 2016). "No antidote yet for killer drug's special ingredient". The Witness.
  5. ^ "This summer's crap drug: N-ethylpentylone". KnowYourStuffNZ. 2018-02-07. Retrieved 2 April 2018.
  6. ^ Thirakul P, Hair LS, Bergen KL, Pearson JM (May 2017). "Clinical Presentation, Autopsy Results and Toxicology Findings in an Acute N-Ethylpentylone Fatality". Journal of Analytical Toxicology. 41 (4): 342–346. doi:10.1093/jat/bkx004. PMID 28137731.
  7. ^ Pill testing at festivals has hidden benefits that could reduce drug taking, Claudia Long, ABC News Online, 2018-07-20
  8. ^ "Emerging Threat Report: Annual 2018" (PDF). Special Testing and Research Laboratory, Drug Enforcement Administration.
  9. ^ "Arnica, metal paint and Polish toothpaste: Festival pill test comes back with all sorts". ABC News. 30 April 2018. Retrieved 2018-09-17.
  10. ^ Stewart M (9 March 2018). "Deadly new Wellington drug ring busted as police seize cash, cars, and drugs". Stuff.co.nz.
  11. ^ Thirakul, Phoutthasone; s. Hair, Laura; l. Bergen, Kirstin; m. Pearson, Julia (2017). "Clinical Presentation, Autopsy Results and Toxicology Findings in an AcuteN-Ethylpentylone Fatality". Journal of Analytical Toxicology. 41 (4): 342–346. doi:10.1093/jat/bkx004. PMID 28137731.
  12. ^ "13 hospitalised in Christchurch after taking drugs they thought were MDMA". Newshub NZ. Retrieved 14 March 2018.
  13. ^ Krotulski, Alex J.; Papsun, Donna M.; Martinis, De; S, Bruno; Mohr, Amanda L. A.; Logan, Barry K. (2018). "N-Ethyl Pentylone (Ephylone) Intoxications: Quantitative Confirmation and Metabolite Identification in Authentic Human Biological Specimens". Journal of Analytical Toxicology. 42 (7): 467–475. doi:10.1093/jat/bky025. PMID 29618077.
  14. ^ "Thousands have drugs tested at festivals". BBC News. 3 September 2018. Retrieved 3 September 2018.
  15. ^ Costa, Jose Luiz; Cunha, Kelly Francisco; Lanaro, Rafael; Cunha, Ricardo Leal; Walther, Donna; Baumann, Michael H. (2018-10-21). "Analytical quantification, intoxication case series, and pharmacological mechanism of action for N-ethylnorpentylone (N-ethylpentylone or ephylone)". Drug Testing and Analysis. 11 (3): 461–471. doi:10.1002/dta.2502. ISSN 1942-7603. PMC 7316160. PMID 30207090.
  16. ^ "Schedules of Controlled Substances: Temporary Placement of N-Ethylpentylone in Schedule I". Federal Register. June 13, 2018.