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: Anlage II (Authorized trade only, not prescriptible)
  • UK: Class B
  • US: Schedule I
  • UN: Psychotropic Schedule II
Identifiers
IUPAC name
  • 1-(1,3-Benzodioxol-5-yl)-2-(ethylamino)pentan-1-one
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC14H19NO3
Molar mass249.310 g·mol−1
3D model (JSmol)
SMILES
  • CCNC(CCC)C(=O)c2ccc1OCOc1c2
InChI
  • 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

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. 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, et al. (December 2021). "Acute toxicity from the synthetic cathinone N-ethylpentylone (ephylone) in the United Kingdom". Clinical Toxicology. 59 (12): 1270–1273. doi:10.1080/15563650.2021.1909730. PMID 33855924. S2CID 233242607.
  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, S Hair L, L Bergen K, M Pearson J (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. "13 hospitalised in Christchurch after taking drugs they thought were MDMA". Newshub NZ. Retrieved 14 March 2018.
  12. Krotulski AJ, Papsun DM, De Martinis BS, Mohr AL, Logan BK (September 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 JL, Cunha KF, Lanaro R, Cunha RL, Walther D, Baumann MH (March 2019). "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. PMC 7316160. PMID 30207090.
  15. Nadal-Gratacós N, Alberto-Silva AS, Rodríguez-Soler M, Urquizu E, Espinosa-Velasco M, Jäntsch K, et al. (2021). "Structure-Activity Relationship of Novel Second-Generation Synthetic Cathinones: Mechanism of Action, Locomotion, Reward, and Immediate-Early Genes". Frontiers in Pharmacology. 12: 749429. doi:10.3389/fphar.2021.749429. PMC 8576102. PMID 34764870.
  16. Espinosa-Velasco M, Reguilón MD, Bellot M, Nadal-Gratacós N, Berzosa X, Puigseslloses P, et al. (January 2022). "Behavioural and neurochemical effects after repeated administration of N-ethylpentylone (ephylone) in mice". Journal of Neurochemistry. 160 (2): 218–233. doi:10.1111/jnc.15542. hdl:2445/183029. PMID 34816436. S2CID 244528106.
  17. "Schedules of Controlled Substances: Temporary Placement of N-Ethylpentylone in Schedule I". Federal Register. June 13, 2018.
  18. "公告增列MPHP、MPD、Ephylone及CEC為管制藥品" (PDF). 管制藥品簡訊 (in Chinese (Taiwan)). 74: 7. January 2018. ISSN 0255-6162.
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