Chemistry:N-Ethylpentylone

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Short description: Substituted cathinone stimulant drug


N-Ethylpentylone
N-Ethylpentylone.svg
N-Ethylpentylone.png
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
Chemical and physical data
FormulaC14H19NO3
Molar mass249.310 g·mol−1
3D model (JSmol)

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]

Adverse effects

N-Ethylpentylone has been reported to cause lethal heart palpitations and hallucinations.[9] It has been linked to a number of overdose deaths[10][6] and mass-casualty incidents,[11][12] and has increasingly been mis-sold as MDMA.[13]

Pharmacology

N-Ethylpentylone is primarily a mixed norepinephrine reuptake inhibitor and dopamine reuptake inhibitor. It binds to transporters with IC50 values of 37 nM (dopamine transporter), 105 nM (norepinephrine transporter) and 383 nM (serotonin transporter).[14] The methylenedioxy ring-substitution provides a higher potency at inhibiting serotonin reuptake than its analogue N-ethylpentedrone.[15]

Animal studies

In vivo studies in mice demonstrated that acute intraperitoneal administration of N-ethylpentylone induced an increase in locomotor activity, anxiolytic effects but also an aggressive behaviour as well as social exploration deficits. Repeated exposure to N-ethylpentylone induced hyperthermia, anorexia and rewarding effects. During withdrawal after repeated administration, depression-like symptoms, hyperlocomotion, and a decrease of social exploration were observed.[15][16]

Legality

  • In the United States, N-ethylpentylone is a Schedule I controlled substance since June 2018.[17]
  • In Taiwan, N-ethylpentylone is a controlled substance under Taiwan's Controlled Drugs Act since Dec 2017.[18]

See also

References

  1. ↑ "Substituted phenyl-α-amino ketones" GB patent 1085135, published 1969, assigned to Boehringer Sohn Ingelheim
  2. ↑ "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. October 2017. doi:10.1007/s11224-017-0951-x. ISSN 1040-0400. 
  3. ↑ "Acute toxicity from the synthetic cathinone N-ethylpentylone (ephylone) in the United Kingdom". Clinical Toxicology 59 (12): 1270–1273. December 2021. doi:10.1080/15563650.2021.1909730. PMID 33855924. 
  4. ↑ "No antidote yet for killer drug's special ingredient". 15 April 2016. https://www.news24.com/SouthAfrica/News/no-antidote-yet-for-killer-drugs-special-ingredient-20160414. 
  5. ↑ "This summer's crap drug: N-ethylpentylone". 2018-02-07. https://knowyourstuff.nz/2018/02/07/this-summers-crap-drug-n-ethylpentylone/. 
  6. ↑ 6.0 6.1 "Clinical Presentation, Autopsy Results and Toxicology Findings in an Acute N-Ethylpentylone Fatality". Journal of Analytical Toxicology 41 (4): 342–346. May 2017. 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". Special Testing and Research Laboratory, Drug Enforcement Administration. https://ndews.umd.edu/sites/ndews.umd.edu/files/Emerging-Threat-Report-2018-Annual.pdf. 
  9. ↑ "Arnica, metal paint and Polish toothpaste: Festival pill test comes back with all sorts". ABC News. 30 April 2018. http://www.abc.net.au/news/2018-04-30/groovin-the-moo-pill-testing-finds-lethal-product/9710112. 
  10. ↑ "Deadly new Wellington drug ring busted as police seize cash, cars, and drugs". 9 March 2018. https://www.stuff.co.nz/national/crime/102124143/deadly-new-nethylpentylone-drug-ring-busted-as-police-seize-405k-luxury-cars-and-6kg-of-drugs-in-wellington-sting. 
  11. ↑ "13 hospitalised in Christchurch after taking drugs they thought were MDMA". Newshub NZ. http://www.newshub.co.nz/home/new-zealand/2018/03/13-hospitalised-in-christchurch-after-taking-drugs-they-thought-were-mdma.html. 
  12. ↑ "N-Ethyl Pentylone (Ephylone) Intoxications: Quantitative Confirmation and Metabolite Identification in Authentic Human Biological Specimens". Journal of Analytical Toxicology 42 (7): 467–475. September 2018. doi:10.1093/jat/bky025. PMID 29618077. 
  13. ↑ "Thousands have drugs tested at festivals". 3 September 2018. https://www.bbc.com/news/uk-england-45367810?SThisFB. 
  14. ↑ "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. March 2019. doi:10.1002/dta.2502. PMID 30207090. 
  15. ↑ 15.0 15.1 "Structure-Activity Relationship of Novel Second-Generation Synthetic Cathinones: Mechanism of Action, Locomotion, Reward, and Immediate-Early Genes". Frontiers in Pharmacology 12: 749429. 2021. doi:10.3389/fphar.2021.749429. PMID 34764870. 
  16. ↑ "Behavioural and neurochemical effects after repeated administration of N-ethylpentylone (ephylone) in mice". Journal of Neurochemistry 160 (2): 218–233. January 2022. doi:10.1111/jnc.15542. PMID 34816436. 
  17. ↑ "Schedules of Controlled Substances: Temporary Placement of N-Ethylpentylone in Schedule I". June 13, 2018. https://www.deadiversion.usdoj.gov/fed_regs/rules/2018/fr0613_8.htm. 
  18. ↑ "公告增列MPHP、MPD、Ephylone及CEC為管制藥品" (in zh-TW). 管制藥品簡訊 74: 7. January 2018. ISSN 0255-6162. http://lawdata.com.tw/File/PDF/J996/A05020074_007.pdf. 



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