N-Ethylpentylone Explained

Drug Name:N-Ethylpentylone
Iupac Name:1-(1,3-Benzodioxol-5-yl)-2-(ethylamino)pentan-1-one
Legal Br:F2
Legal Br Comment:[1]
Legal Ca:Schedule I
Legal De:Anlage II
Legal Uk:Class B
Legal Us:Schedule I
Legal Un:P II
Cas Number:727641-67-0
Cas Number2:17763-02-9
Unii:D3H9D57JV9
Index2 Label:HCl
Atc Prefix:none
Pubchem:57359308
Chemspiderid:26949655
Kegg:C22710
Unii2:S3G8XZW25I
C:14
H:19
N:1
O:3
Smiles:CCNC(CCC)C(=O)c2ccc1OCOc1c2
Stdinchi: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
Stdinchikey: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.[2] [3]

It has been reported as a novel designer 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 in Drug Enforcement Administration seizures.[9]

Adverse effects

N-Ethylpentylone has been reported to cause lethal heart palpitations and hallucinations.[10] It has been linked to a number of overdose deaths[11] and mass-casualty incidents,[12] [13] and has increasingly been mis-sold as MDMA.[14]

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).[15] The methylenedioxy ring-substitution provides a higher potency at inhibiting serotonin reuptake than its analogue N-ethylpentedrone.[16]

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.[17]

Legality

See also

Notes and References

  1. Web site: Anvisa . Brazilian Health Regulatory Agency . 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. live . https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 . 2023-08-27 . 2023-08-27 . . pt-BR . 2023-07-25.
  2. Substituted phenyl-α-amino ketones . GB . 1085135 . 1969 . Boehringer Sohn Ingelheim .
  3. Wood MR, Bernal I, Lalancette RA . The hydrochloride hydrates of pentylone and dibutylone and the hydrochloride salt of ephylone: the structures of three novel designer cathinones. Structural Chemistry. October 2017. 1040-0400. 1369–1376. 28. 5. 10.1007/s11224-017-0951-x. 102424824.
  4. Blanco G, Vidler D, Roper C, Wood DM, Dargan PI, Keating L, Macfarlane R, Emmett S, Johnson G, Eddleston M, Hill SL, Thomas SH . 6 . Acute toxicity from the synthetic cathinone N-ethylpentylone (ephylone) in the United Kingdom . Clinical Toxicology . 59 . 12 . 1270–1273 . December 2021 . 33855924 . 10.1080/15563650.2021.1909730 . 233242607 .
  5. Web site: No antidote yet for killer drug's special ingredient . Umraw A, Pillay K . The Witness . 15 April 2016 .
  6. Web site: This summer's crap drug: N-ethylpentylone. KnowYourStuffNZ. 2 April 2018. 2018-02-07.
  7. Thirakul P, S Hair L, L Bergen K, M Pearson J . Clinical Presentation, Autopsy Results and Toxicology Findings in an Acute N-Ethylpentylone Fatality . Journal of Analytical Toxicology . 41 . 4 . 342–346 . May 2017 . 28137731 . 10.1093/jat/bkx004 . free .
  8. http://www.abc.net.au/news/2018-07-20/pill-testing-splendour-in-the-grass/10008522 Pill testing at festivals has hidden benefits that could reduce drug taking
  9. Web site: Emerging Threat Report: Annual 2018 . Special Testing and Research Laboratory, Drug Enforcement Administration .
  10. News: 2018-09-17. Arnica, metal paint and Polish toothpaste: Festival pill test comes back with all sorts. ABC News. 30 April 2018.
  11. Web site: Deadly new Wellington drug ring busted as police seize cash, cars, and drugs . Stewart M . Stuff.co.nz . 9 March 2018 .
  12. News: 13 hospitalised in Christchurch after taking drugs they thought were MDMA. 14 March 2018. Newshub NZ.
  13. Krotulski AJ, Papsun DM, De Martinis BS, Mohr AL, Logan BK . 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 . 29618077 . 10.1093/jat/bky025 .
  14. Web site: Thousands have drugs tested at festivals . BBC News . 3 September 2018 . 3 September 2018.
  15. Costa JL, Cunha KF, Lanaro R, Cunha RL, Walther D, Baumann MH . 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 . 30207090 . 7316160 . 10.1002/dta.2502 .
  16. Nadal-Gratacós N, Alberto-Silva AS, Rodríguez-Soler M, Urquizu E, Espinosa-Velasco M, Jäntsch K, Holy M, Batllori X, Berzosa X, Pubill D, Camarasa J, Sitte HH, Escubedo E, López-Arnau R . 6 . Structure-Activity Relationship of Novel Second-Generation Synthetic Cathinones: Mechanism of Action, Locomotion, Reward, and Immediate-Early Genes . Frontiers in Pharmacology . 12 . 749429 . 2021 . 34764870 . 8576102 . 10.3389/fphar.2021.749429 . free .
  17. Espinosa-Velasco M, Reguilón MD, Bellot M, Nadal-Gratacós N, Berzosa X, Puigseslloses P, Gómez-Canela C, Rodríguez-Arias M, Pubill D, Camarasa J, Escubedo E, López-Arnau R . 6 . Behavioural and neurochemical effects after repeated administration of N-ethylpentylone (ephylone) in mice . Journal of Neurochemistry . 160 . 2 . 218–233 . January 2022 . 34816436 . 10.1111/jnc.15542 . 2445/183029 . 244528106 . free .
  18. Web site: Schedules of Controlled Substances: Temporary Placement of N-Ethylpentylone in Schedule I . Federal Register . 83 . 114 . June 13, 2018.
  19. January 2018. 公告增列MPHP、MPD、Ephylone及CEC為管制藥品. 管制藥品簡訊. zh-TW. 74. 7. 0255-6162.

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