N-Ethylpentylone

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N-Ethylpentylone
N-Ethylpentylone.svg
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
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]

Adverse effects[edit]

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[edit]

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[edit]

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[edit]

  • 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[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, 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. ^ a b 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. ^ a b 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.