N-Ethylpentylone

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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
PubChem CID
ChemSpider
UNII
KEGG
E number{{#property:P628}}
CompTox Dashboard (EPA)
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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.[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

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N-Ethylpentylone has been reported to cause lethal heart palpitations and hallucinations.[10] It has been linked to a number of overdose deaths[11][7] and hospitalisations,[12][13] and has increasingly been mis-sold as MDMA.[14]

Pharmacology

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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

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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.[16][17]

Legality

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  • In the United States, N-ethylpentylone is a Schedule 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]
  • In the Netherlands it has been added to the Opium Law on July 1 2025.[20]

See also

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References

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  2. ^ GB 1085135, "Substituted phenyl-α-amino ketones", published Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value)., assigned to Boehringer Sohn Ingelheim 
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  8. ^ Pill testing at festivals has hidden benefits that could reduce drug taking, Claudia Long, ABC News Online, 2018-07-20
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