''N''-Ethylpentylone (β-keto-ethylbenzodioxolylpentanamine, βk-ethyl-K, βk-EBDP, ephylone) is a
substituted cathinone
Substituted cathinones, which include some stimulants and entactogens, are derivatives of cathinone. They feature a phenethylamine core with an alkyl group attached to the alpha carbon, and a ketone group attached to the beta carbon, alon ...
and
stimulant
Stimulants (also often referred to as psychostimulants or colloquially as uppers) is an overarching term that covers many drugs including those that increase activity of the central nervous system and the body, drugs that are pleasurable and inv ...
drug which was developed in the 1960s.
It has been reported as a novel
designer drug
A designer drug is a structural or functional analog of a controlled substance that has been designed to mimic the pharmacological effects of the original drug, while avoiding classification as illegal and/or detection in standard drug tests. Des ...
in several countries including the United Kingdom,
South Africa, New Zealand, the United States,
and Australia.
[Pill testing at festivals has hidden benefits that could reduce drug taking](_blank)
Claudia Long, ABC News Online
ABC News, or ABC News and Current Affairs, is a public news service produced by the Australian Broadcasting Corporation. Broadcasting within Australia and the rest of the world, the service covers both local and world affairs.
The division of ...
, 2018-07-20
In 2018, ''N''-ethylpentylone was the most common drug of the cathinone class to be identified in
Drug Enforcement Administration
The Drug Enforcement Administration (DEA; ) is a Federal law enforcement in the United States, United States federal law enforcement agency under the U.S. Department of Justice tasked with combating drug trafficking and distribution within th ...
seizures.
Adverse effects
''N''-Ethylpentylone has been reported to cause lethal
heart palpitation
Palpitations are perceived abnormalities of the heartbeat characterized by awareness of cardiac muscle contractions in the chest, which is further characterized by the hard, fast and/or irregular beatings of the heart.
Symptoms include a rapid ...
s and
hallucination
A hallucination is a perception in the absence of an external stimulus that has the qualities of a real perception. Hallucinations are vivid, substantial, and are perceived to be located in external objective space. Hallucination is a combinati ...
s. It has been linked to a number of overdose deaths
and mass-casualty incidents, and has increasingly been mis-sold as
MDMA
3,4-Methylenedioxymethamphetamine (MDMA), commonly seen in tablet form (ecstasy) and crystal form (molly or mandy), is a potent empathogen–entactogen with stimulant properties primarily used for recreational purposes. The desired ...
.
Pharmacology
''N''-Ethylpentylone is primarily a mixed
norepinephrine reuptake inhibitor
A norepinephrine reuptake inhibitor (NRI, NERI) or noradrenaline reuptake inhibitor or adrenergic reuptake inhibitor (ARI), is a type of drug that acts as a reuptake inhibitor for the neurotransmitters norepinephrine (noradrenaline) and epine ...
and
dopamine reuptake inhibitor
A dopamine reuptake inhibitor (DRI) is a class of drug which acts as a reuptake inhibitor of the monoamine neurotransmitter dopamine by blocking the action of the dopamine transporter (DAT). Reuptake inhibition is achieved when extracellular do ...
. It binds to transporters with
IC50 values of 37 nM (
dopamine transporter
The dopamine transporter (also dopamine active transporter, DAT, SLC6A3) is a membrane-spanning protein that pumps the neurotransmitter dopamine out of the synaptic cleft back into cytosol. In the cytosol, other transporters sequester the dopam ...
), 105 nM (
norepinephrine transporter
The norepinephrine transporter (NET), also known as noradrenaline transporter (NAT), is a protein that in humans is encoded by the solute carrier family 6 member 2 (SLC6A2) gene.
NET is a monoamine transporter and is responsible for the sodium- ...
) and 383 nM (
serotonin transporter
The serotonin transporter (SERT or 5-HTT) also known as the sodium-dependent serotonin transporter and solute carrier family 6 member 4 is a protein that in humans is encoded by the SLC6A4 gene. SERT is a type of monoamine transporter protein th ...
).
The methylenedioxy ring-substitution provides a higher potency at inhibiting serotonin reuptake than its analogue
''N''-ethylpentedrone.
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.
Legality
* In the United States, ''N''-ethylpentylone is a
Schedule I controlled substance
This is the list of Schedule I drugs as defined by the United States Controlled Substances Act.21 CFRbr>1308.11(CSA Sched I) with changes through (Oct 18, 2012). Retrieved September 6, 2013. The following findings are required for drugs to be pla ...
since June 2018.
* In Taiwan, ''N''-ethylpentylone is a controlled substance under Taiwan's Controlled Drugs Act since Dec 2017.
See also
*
5-Methylethylone
5-Methylethylone (5-methyl-βk-MDEA, 5ME) is an empathogen, stimulant and psychedelic drug of the amphetamine, phenethylamine, and cathinone chemical classes. It is structurally related to ethylone, a novel designer drug. Relatively little data e ...
*
Dipentylone
*
Ethyl-K
*
Eutylone
Eutylone (also known as β-keto-1,3-benzodioxolyl-''N''-ethylbutanamine, bk-EBDB, and ''N''-ethylbutylone) is a stimulant and empathogenic compound developed in the 1960s, which is classified as a designer drug. It was first reported to the EMC ...
*
Methylenedioxypyrovalerone
Methylenedioxypyrovalerone (MDPV) is a stimulant of the cathinone class that acts as a norepinephrine–dopamine reuptake inhibitor (NDRI). It was first developed in the 1960s by a team at Boehringer Ingelheim. Its activity at the dopamine tra ...
(MDPV)
*
''N''-Ethylhexedrone
*
N-Ethylhexylone
*
N-Ethylheptylone
''N''-Ethylheptylone (HEP) is a recreational designer drug from the substituted cathinone family, with stimulant effects. It is a homologue of related drugs such as ethylone, eutylone, ephylone and ''N''-ethylhexylone but with a longer hept ...
*
Pentylone
Pentylone (β-Keto-Methylbenzodioxolylpentanamine, βk-Methyl-K, βk-MBDP, methylenedioxypentedrone, or 1‐(3,4‐methylenedioxyphenyl)‐2‐(methylamino)pentan‐1‐one) is a stimulant developed in the 1960s. It is a substituted cathinone ( ...
*
Isohexylone
Isohexylone is a recreational designer drug from the substituted cathinone family, with stimulant effects. It was first identified in the United Kingdom in June 2019.
See also
* Methylone
* 5-Methylethylone
* Butylone
* Desmethylsibutramine
...
References
{{DEFAULTSORT:Ethylpentylone, N-
Cathinones
Benzodioxoles
Designer drugs
Serotonin–norepinephrine–dopamine reuptake inhibitors