N-Ethylpentylone

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]

N-Ethylpentylone
Clinical data
ATC code
  • none
Legal status
Legal status
  • CA: Schedule I
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class B
  • US: Schedule I
Identifiers
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC14H19NO3
Molar mass249.310 g·mol−1
3D model (JSmol)

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

A doctor, David Caldicott, has said N-ethylpentylone "can cause circulation problems, lethal heart palpitations and hallucinations".[8] It has been linked to a number of overdose deaths[9][10] and mass-casualty incidents,[11][12] and has increasingly been mis-sold as MDMA.[13]

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).[14]

Legality

In the United States, N-ethylpentylone is a Schedule I controlled substance.[15]

See also

References
  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.
  3. Umraw A, Pillay K (15 April 2016). "No antidote yet for killer drug's special ingredient". The Witness.
  4. "This summer's crap drug: N-ethylpentylone". KnowYourStuffNZ. 2018-02-07. Retrieved 2 April 2018.
  5. 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.
  6. Pill testing at festivals has hidden benefits that could reduce drug taking, Claudia Long, ABC News Online, 2018-07-20
  7. "Emerging Threat Report: Annual 2018" (PDF). Special Testing and Research Laboratory, Drug Enforcement Administration.
  8. "Arnica, metal paint and Polish toothpaste: Festival pill test comes back with all sorts". ABC News. 30 April 2018. Retrieved 2018-09-17.
  9. Stewart M (9 March 2018). "Deadly new Wellington drug ring busted as police seize cash, cars, and drugs". Stuff.co.nz.
  10. 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.
  11. "13 hospitalised in Christchurch after taking drugs they thought were MDMA". Newshub NZ. Retrieved 14 March 2018.
  12. 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.
  13. "Thousands have drugs tested at festivals". BBC News. 3 September 2018. Retrieved 3 September 2018.
  14. 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. doi:10.1002/dta.2502. ISSN 1942-7603. PMID 30207090.
  15. "Schedules of Controlled Substances: Temporary Placement of N-Ethylpentylone in Schedule I". Federal Register. June 13, 2018.
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