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N-Ethylpentylone

From Wikipedia, the free encyclopedia
(Redirected fromEphylone)
Substituted cathinone stimulant drug
Pharmaceutical compound
N-Ethylpentylone
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
  • 1-(1,3-Benzodioxol-5-yl)-2-(ethylamino)pentan-1-one
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
CompTox Dashboard(EPA)
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 asubstituted cathinone andstimulant drug which was developed in the 1960s.[2][3]

It has been reported as a noveldesigner drug in several countries including the United Kingdom,[4] South Africa,[5] New Zealand,[6] the United States,[7] and Australia.[8] In 2018,N-ethylpentylone was the most common drug of the cathinone class to be identified inDrug Enforcement Administration seizures.[9]

Adverse effects

[edit]

N-Ethylpentylone has been reported to cause lethalheart palpitations andhallucinations.[10] It has been linked to a number of overdose deaths[11][7] and mass-casualty incidents,[12][13] and has increasingly been mis-sold asMDMA.[14]

Pharmacology

[edit]

N-Ethylpentylone is primarily a mixednorepinephrine reuptake inhibitor anddopamine reuptake inhibitor. It binds to transporters withIC50 values of 37 nM (dopamine transporter), 105 nM (norepinephrine transporter) and 383 nM (serotonin transporter).[15] The methylenedioxy ring-substitution provides a higher potency at inhibiting serotonin reuptake than its analogueN-ethylpentedrone.[16]

Animal studies

[edit]

In vivo studies in mice demonstrated that acute intraperitoneal administration of N-ethylpentylone induced anincrease in locomotor activity,anxiolytic effects but also anaggressive 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.[16][17]

Legality

[edit]
  • In the United States,N-ethylpentylone is aSchedule I controlled substance since June 2018.[18]
  • In Taiwan,N-ethylpentylone is a controlled substance under Taiwan's Controlled Drugs Act since Dec 2017.[19]

See also

[edit]

References

[edit]
  1. ^Anvisa (2023-07-24)."RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).Diário Oficial da União (published 2023-07-25).Archived from the original on 2023-08-27. Retrieved2023-08-27.
  2. ^GB 1085135, "Substituted phenyl-α-amino ketones", published 1969, assigned to Boehringer Sohn Ingelheim 
  3. ^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.
  4. ^Blanco G, Vidler D, Roper C, Wood DM, Dargan PI, Keating L, et al. (December 2021). "Acute toxicity from the synthetic cathinoneN-ethylpentylone (ephylone) in the United Kingdom".Clinical Toxicology.59 (12):1270–1273.doi:10.1080/15563650.2021.1909730.PMID 33855924.S2CID 233242607.
  5. ^Umraw A, Pillay K (15 April 2016)."No antidote yet for killer drug's special ingredient".The Witness.
  6. ^"This summer's crap drug: N-ethylpentylone".KnowYourStuffNZ. 2018-02-07. Retrieved2 April 2018.
  7. ^abThirakul 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.
  8. ^Pill testing at festivals has hidden benefits that could reduce drug taking, Claudia Long,ABC News Online, 2018-07-20
  9. ^"Emerging Threat Report: Annual 2018"(PDF). Special Testing and Research Laboratory, Drug Enforcement Administration.
  10. ^"Arnica, metal paint and Polish toothpaste: Festival pill test comes back with all sorts".ABC News. 30 April 2018. Retrieved2018-09-17.
  11. ^Stewart M (9 March 2018)."Deadly new Wellington drug ring busted as police seize cash, cars, and drugs".Stuff.co.nz.
  12. ^"13 hospitalised in Christchurch after taking drugs they thought were MDMA". Newshub NZ. Archived fromthe original on March 18, 2018. Retrieved14 March 2018.
  13. ^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.
  14. ^"Thousands have drugs tested at festivals".BBC News. 3 September 2018. Retrieved3 September 2018.
  15. ^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.
  16. ^abNadal-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.
  17. ^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.
  18. ^"Schedules of Controlled Substances: Temporary Placement of N-Ethylpentylone in Schedule I".Federal Register. June 13, 2018.
  19. ^"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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