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{{distinguish2|[[Pentedrone]]}}
{{SummarySheet}}
{{SummarySheet}}
{{SubstanceBox/N-Ethyl-(nor)-pentedrone}}
{{SubstanceBox/NEP}}


'''N-Ethyl-(nor)-pentedrone''' (also known as '''N-Ethylpentedrone''', '''Ethyl-pentedrone''' or more commonly, '''NEP''') is a novel synthetic [[psychoactive class::stimulant]] substance of the [[psychoactive class::cathinone]] chemical class that produces [[cathinone]]-like [[stimulating]], [[disinhibition|disinhibiting]], [[thought acceleration|thought accelerating]], [[immersion enhancement|immersion enhancing]] and [[euphoria|euphoria|euphoric]] effects when [[Routes of administration|administered]]. The effects of stimulating effects of NEP is believed to be caused by its affinity as a [[norepinephrine]]-[[dopamine]] [[reuptake inhibitor]] (NDRI); however, there have been no scientific studies confirming this. It may also act as a serotonin reuptake inhibitor or releasing agent in moderate to high doses, although this also has yet to be scientifically validated.  
'''N-Ethyl-nor-pentedrone''' (also known as '''N-Ethylpentedrone''', '''Ethyl-pentedrone''' or more commonly, '''NEP''') is a lesser-known novel [[psychoactive class::stimulant]] substance of the [[chemical class::cathinone]] class that produces [[stimulating]], [[euphoric]], and mildly [[entactogenic]] effects when [[Routes of administration|administered]].  


NEP shares a close structural relationship to [[pentedrone]], differing by an addition ethyl group on the terminal nitrogen on the carbon chain. This addition reportedly makes it about three times as potent as pentedrone.{{citation needed}} NEP is also closely related to [[N-Ethylhexedrone]] (commonly known as ''Hexen''), and has been reported as producing largely-similar effects.  
The stimulating effects of NEP are believed to mainly be caused by its activity as a [[norepinephrine]]-[[dopamine]] [[reuptake inhibitor]] (NDRI). The reported entactogenic effects it displays may also be due to its activity as a [[serotonin]] [[reuptake inhibitor]] or [[releasing agent]] in moderate to high doses, although new research has shown very low serotonin reuptake inhibition.<ref name=":0">{{cite journal | vauthors=((Duart-Castells, L.)), ((Nadal-Gratacós, N.)), ((Muralter, M.)), ((Puster, B.)), ((Berzosa, X.)), ((Estrada-Tejedor, R.)), ((Niello, M.)), ((Bhat, S.)), ((Pubill, D.)), ((Camarasa, J.)), ((Sitte, H. H.)), ((Escubedo, E.)), ((López-Arnau, R.)) | journal=Neuropharmacology | title=Role of amino terminal substitutions in the pharmacological, rewarding and psychostimulant profiles of novel synthetic cathinones | volume=186 | pages=108475 | date= March 2021 | url=https://linkinghub.elsevier.com/retrieve/pii/S0028390821000290 | issn=00283908 | doi=10.1016/j.neuropharm.2021.108475}}</ref>NEP probably acts as unselective [[serotonin]]-[[norepinephrine]]-[[dopamine]] [[reuptake inhibitor]] (SNDRI).


NEP first became known in the [[research chemical]] market during 2016. It is an example of a contemporary [[designer drug]] specifically chosen to mimic/replace the functional and structural features of its popular potent and short-lived-type stimulant predecessors, which are sometimes imprecisely referred to as "bath salts".As with its parent compound [[pentedrone]], very little data exists about the pharmacological properties, metabolism, and toxicity of NEP. Due to its novelty and extremely short history of human usage, all information related to the use of this compound should be treated with extreme caution. It is highly advised that one use [[responsible drug use|harm reduction practices]] if choosing to use this substance.
NEP shares a close structural relationship to its parent compound [[pentedrone]], differing by an addition ethyl group on the terminal nitrogen on the carbon chain. This addition reportedly makes it about three times as potent as pentedrone.<ref name=":0" /> NEP is also closely related to [[N-Ethylhexedrone]] (commonly known as ''Hexen''), and has been reported as producing largely-similar effects.
 
NEP first became known in the [[research chemical]] market during 2016. It is an example of a contemporary [[designer drug]] specifically chosen to mimic/replace the functional and structural features of its popular potent and short-lived-type stimulant predecessors, which are sometimes imprecisely referred to as "bath salts".  
 
As with its parent compound [[pentedrone]], very little data exists about the pharmacological properties, metabolism, and toxicity of NEP in humans. Due to its novelty and extremely short history of human usage, all information related to the use of this compound should be treated with extreme caution. It is highly advised that one use [[responsible drug use|harm reduction practices]] if choosing to use this substance.


==Chemistry==
==Chemistry==
NEP, or N-Ethyl-(nor)-pentedrone, belongs to the [[Substituted cathinone|cathinone]] chemical class. It features a [[phenethylamine]] core with an alkyl group attached to the alpha carbon and an oxygen group attached to the beta carbon. Cathinones are beta-ketone analogues of [[amphetamine]]s. Cathinones refer to a class of molecules which are principally constituted of a [[phenethylamine]] core with an alkyl group attached to the alpha carbon and an oxygen group attached to the beta carbon. They are also known as the beta-ketone (double-bonded oxygen to the β-carbon) analogs of [[amphetamine]]s. The cathinone backbone can be modified in three different places to create hundreds of possible compounds, which include substituents on the aromatic ring, the alpha carbon, and the amine group.<ref>Liu, C., Jia, W., Li, T., Hua, Z., & Qian, Z. (n.d.). Identification and analytical characterization of nine synthetic cathinone derivatives N-ethylhexedrone, 4-Cl-pentedrone, 4-Cl--EAPP, propylone, N-ethylnorpentylone, 6-MeO-bk-MDMA, -PiHP, 4-Cl--PHP, and 4-F--PHP. https://doi.org/10.1002/dta.2136</ref>
NEP, or N-Ethyl-(nor)-pentedrone, belongs to the [[Substituted cathinone|cathinone]] chemical class. It features a [[phenethylamine]] core with an alkyl group attached to the alpha carbon and an oxygen group attached to the beta carbon. Cathinones are beta-ketone analogues of [[amphetamine]]s. Cathinones refer to a class of molecules which are principally constituted of a [[phenethylamine]] core with an alkyl group attached to the alpha carbon and an oxygen group attached to the beta carbon. They are also known as the beta-ketone (double-bonded oxygen to the β-carbon) analogs of [[amphetamine]]s. The cathinone backbone can be modified in three different places to create hundreds of possible compounds, which include substituents on the aromatic ring, the alpha carbon, and the amine group.<ref>{{cite journal | vauthors=((Liu, C.)), ((Jia, W.)), ((Li, T.)), ((Hua, Z.)), ((Qian, Z.)) | journal=Drug Testing and Analysis | title=Identification and analytical characterization of nine synthetic cathinone derivatives N -ethylhexedrone, 4-Cl-pentedrone, 4-Cl- α -EAPP, propylone, N -ethylnorpentylone, 6-MeO-bk-MDMA, α -PiHP, 4-Cl- α -PHP, and 4-F- α -PHP: Identification of nine synthetic cathinones | volume=9 | issue=8 | pages=1162–1171 | date= August 2017 | url=https://onlinelibrary.wiley.com/doi/10.1002/dta.2136 | issn=19427603 | doi=10.1002/dta.2136}}</ref>


==Pharmacology==
==Pharmacology==
Due to the lack of research regarding the substance, all discussion regarding the pharmacology of it is purely based upon its structure and subjective effect similarities to other [[Substituted cathinone|cathinone]]s such as [[mephedrone]] and others. NEP most likely acts as both a [[dopamine]] and [[norepinephrine]] [[releasing agent]] or [[reuptake inhibitor]]. This allows dopamine and norepinephrine to accumulate within the brain, resulting in [[stimulation|stimulating]] and [[physical euphoria|euphoric]] effects. Additionally, it has been speculated that it may possess some serotonergic properties, as users have described experiencing mild [[entactogenic]] effects on common to strong doses of this compound.  
Due to the lack of research regarding the substance, a lot of the discussion regarding the pharmacology of it is purely based upon its structure and subjective effect similarities to other [[Substituted cathinone|cathinone]]s such as [[mephedrone]] and others. However, a recent study has shown that NEP acts as a potent [[Reuptake inhibitor|serotonin-norepinephrine-dopamine reuptake inhibitor]] (SNDRI) with very poor affinity for [[Serotonin|SERT]].<ref name=":0" /> This allows dopamine, serotonin and norepinephrine to accumulate within the brain, resulting in [[stimulation|stimulating]] and [[physical euphoria|euphoric]] effects. That being said, an interaction with other receptor sites cannot yet be fully ruled out.


==Subjective effects==
==Subjective effects==
{{Preamble/SubjectiveEffects}}                                                                             
{{Preamble/SubjectiveEffects}}                                                                             
===Physical effects===
 
{{effects/base
 
|{{effects/physical|
 
*'''[[Effect::Stimulation]]''' - In terms of its effects on the user's physical energy levels, NEP can be considered to be extremely stimulating and energetic.  
*'''[[Effect::Stimulation]]''' - In terms of its effects on the user's physical energy levels, NEP can be considered to be extremely stimulating and energetic.  
*'''[[Effect::Spontaneous tactile sensations]]''' - High doses of NEP result in a pleasurable body high characterized by pleasant tingling.   
*'''[[Effect::Spontaneous tactile sensations]]''' - High doses of NEP result in a pleasurable body high characterized by pleasant tingling.   
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*'''[[Effect::Dehydration]]''' - Dry mouth and increased sweating can occur after consuming NEP. Low doses of the substance in question cause minimal dehydration.
*'''[[Effect::Dehydration]]''' - Dry mouth and increased sweating can occur after consuming NEP. Low doses of the substance in question cause minimal dehydration.
*'''[[Effect::Vasoconstriction]]''' - NEP has been reported as being slightly vasoconstricting.
*'''[[Effect::Vasoconstriction]]''' - NEP has been reported as being slightly vasoconstricting.
*'''[[Effect::Abnormal heartbeat]]'''
*'''[[Effect::Abnormal heartbeat]]'''  
*'''[[Effect::Increased blood pressure]]'''
*'''[[Effect::Increased blood pressure]]'''
*'''[[Effect::Increased heart rate]]'''
*'''[[Effect::Increased heart rate]]''' - NEP increases heart rate significantly compared to other stimulants, even at low doses.
*'''[[Effect::Increased perspiration]]'''
*'''[[Effect::Increased perspiration]]'''
*'''[[Effect::Appetite suppression]]'''
*'''[[Effect::Appetite suppression]]'''
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*'''[[Effect::Teeth grinding]]''' - This component can be considered to be less intense when compared with that of [[MDMA]].
*'''[[Effect::Teeth grinding]]''' - This component can be considered to be less intense when compared with that of [[MDMA]].


===Cognitive effects===
}}
|{{effects/cognitive|
 
*'''[[Effect::Cognitive euphoria]]'''  
*'''[[Effect::Cognitive euphoria]]'''  
*'''[[Effect::Thought acceleration]]'''
*'''[[Effect::Thought acceleration]]'''
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*'''[[Effect::Ego inflation]]'''
*'''[[Effect::Ego inflation]]'''
*'''[[Effect::Disinhibition]]
*'''[[Effect::Disinhibition]]
*'''[[Effect::Increased libido]]'''
*'''[[Effect::Increased music appreciation]]'''
*'''[[Effect::Increased music appreciation]]'''
*'''[[Effect::Time distortion]]'''
*'''[[Effect::Time distortion]]'''
*'''[[Effect::Thought acceleration]]'''
*'''[[Effect::Motivation enhancement]]'''
*'''[[Effect::Motivation enhancement]]'''
*'''[[Effect::Compulsive redosing]]'''
*'''[[Effect::Compulsive redosing]]'''


===After effects===
}}
{{effects/aftereffects|
 
The effects which occur during the [[offset]] of a [[stimulant]] experience generally feel negative and uncomfortable in comparison to the effects which occurred during its [[peak]]. This is often referred to as a "comedown" and occurs because of [[neurotransmitter]] depletion. Its effects commonly include:
The effects which occur during the [[offset]] of a [[stimulant]] experience generally feel negative and uncomfortable in comparison to the effects which occurred during its [[peak]]. This is often referred to as a "comedown" and occurs because of [[neurotransmitter]] depletion. Its effects commonly include:


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It should be noted that many users of this substance report it has relatively smooth [[Durations#Coming down|"come down"]] compared to similar cathinone stimulants, so these effects may not be present to as great of a degree.
It should be noted that many users of this substance report it has relatively smooth [[Durations#Coming down|"come down"]] compared to similar cathinone stimulants, so these effects may not be present to as great of a degree.


==Dangerous interactions==
 
{{DangerousInteractions/Intro}}
}}
*'''[[Stimulants]]''' - NEP can be potentially dangerous in combination with other [[stimulants]] as it can [[increased heart rate|increase one's heart rate]] and [[increased blood pressure|blood pressure]] to dangerous levels.
}}
{{DangerousInteractions/Stimulants}}
===Experience reports===
*'''[[MDMA]]''' - The neurotoxic effects of MDMA may be increased when combined with [[amphetamine]] and other stimulants.
There are currently no anecdotal reports which describe the effects of this compound within our [[experience index]]. Additional experience reports can be found here:
{{DangerousInteractions/MAOI|nt=dopamine}}
 
*'''[[Cocaine]]''' - This combination may increase strain on the heart to dangerous, potentially fatal levels.
*[https://www.erowid.org/experiences/subs/exp_NEthylpentedrone.shtml Erowid Experience Vaults: N-Ethylpentedrone]


==Toxicity and harm potential==
==Toxicity and harm potential==
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===Psychosis===
===Psychosis===
{{Main|Stimulant psychosis}}
{{Main|Stimulant psychosis}}
Abuse of compounds within the stimulant class at high dosages for prolonged periods of time can potentially result in a stimulant psychosis that may present with a variety of symptoms (e.g., [[Paranoia|paranoia]], [[External hallucinations|hallucinations]], or [[Delusions|delusions]]).<ref>Treatment for amphetamine psychosis | [http://onlinelibrary.wiley.com/doi/10.1002/14651858.CD003026.pub3/abstract?systemMessage=Wiley+Online+Library+will+be+disrupted+Saturday%2C+15+March+from+10%3A00-12%3A00+GMT+%2806%3A00-08%3A00+EDT%29+for+essential+maintenance]</ref> A review on treatment for amphetamine, [[dextroamphetamine]], and [[methamphetamine]] abuse-induced psychosis states that about 5–15% of users fail to recover completely.<ref>Treatment for amphetamine psychosis | [http://onlinelibrary.wiley.com/doi/10.1002/14651858.CD003026.pub3/abstract?systemMessage=Wiley+Online+Library+will+be+disrupted+Saturday%2C+15+March+from+10%3A00-12%3A00+GMT+%2806%3A00-08%3A00+EDT%29+for+essential+maintenance]</ref><ref>Hofmann FG (1983). A Handbook on Drug and Alcohol Abuse: The Biomedical Aspects (2nd ed.). New York: Oxford University Press. p. 329. ISBN 9780195030570.</ref> The same review asserts that, based upon at least one trial, [[antipsychotic]] medications effectively resolve the symptoms of acute amphetamine psychosis.<ref>Treatment for amphetamine psychosis | [http://onlinelibrary.wiley.com/doi/10.1002/14651858.CD003026.pub3/abstract?systemMessage=Wiley+Online+Library+will+be+disrupted+Saturday%2C+15+March+from+10%3A00-12%3A00+GMT+%2806%3A00-08%3A00+EDT%29+for+essential+maintenance]</ref>
Abuse of compounds within the stimulant class at high dosages for prolonged periods of time can potentially result in a stimulant psychosis that may present with a variety of symptoms (e.g., [[Paranoia|paranoia]], [[External hallucinations|hallucinations]], or [[Delusions|delusions]]).<ref name="Shoptaw2009">{{cite journal | vauthors=((Shoptaw, S. J.)), ((Kao, U.)), ((Ling, W.)) | veditors=((Cochrane Drugs and Alcohol Group)) | journal=Cochrane Database of Systematic Reviews | title=Treatment for amphetamine psychosis | date=21 January 2009 | url=https://doi.wiley.com/10.1002/14651858.CD003026.pub3 | issn=14651858 | doi=10.1002/14651858.CD003026.pub3}}</ref> A review on treatment for amphetamine, [[dextroamphetamine]], and [[methamphetamine]] abuse-induced psychosis states that about 5–15% of users fail to recover completely.<ref name="Shoptaw2009" /><ref>{{cite book | vauthors=((Hofmann, F. G.)) | date= 1983 | title=A handbook on drug and alcohol abuse: the biomedical aspects | publisher=Oxford University Press | edition=2nd ed | isbn=9780195030563}}</ref> The same review asserts that, based upon at least one trial, [[antipsychotic]] medications effectively resolve the symptoms of acute amphetamine psychosis.<ref name="Shoptaw2009" />


==Legal issues==
===Dangerous interactions===
{{LegalStub}}
{{DangerousInteractions/Intro}}
*'''United Kingdom''' - It is illegal to produce, supply, or import this drug under the Psychoactive Substance Act, which came into effect on May 26th, 2016.<ref>Psychoactive Substances Act 2016 (Legislation.gov.uk) | http://www.legislation.gov.uk/ukpga/2016/2/contents/enacted</ref>
 
*'''[[Stimulants]]''' - NEP can be potentially dangerous in combination with other [[stimulants]] as it can [[increased heart rate|increase one's heart rate]] and [[increased blood pressure|blood pressure]] to dangerous levels.
{{DangerousInteractions/Stimulants}}
*'''[[MDMA]]''' - The neurotoxic effects of MDMA may be increased when combined with [[amphetamine]] and other stimulants.
 
{{DangerousInteractions/MAOI|nt=dopamine}}
*'''[[Cocaine]]''' - This combination may increase strain on the heart to dangerous, potentially fatal levels.
 
====[[Serotonin syndrome]] risk====
{{DangerousInteractions/SerotoninSyndrome}}
 
==Legal status==
 
*'''Brazil''': On September 7, 2018, all cathinone analogues are controlled substances considered illegal to possess, use and distribute. This was made possible due to a blanket ban law appended to Portaria SVS/MS nº 344.<ref>New blanket ban on synthetic illegal drugs is approved (Portuguese) | http://portal.anvisa.gov.br/noticias/-/asset_publisher/FXrpx9qY7FbU/content/combate-a-drogas-ilicitas-sinteticas-fica-mais-facil</ref>
*'''China''': NEP is a controlled substance.{{citation needed}}
*'''France''': As a derivative of cathinone with alkyl substitutions on the nitrogen and R2 position, NEP is scheduled as a "stupéfiant", i.e. a recognized drug of abuse. It is illegal to possess, buy, sell or manufacture.<ref>{{Citation | title=Arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants  | url=https://www.legifrance.gouv.fr/loda/id/JORFTEXT000000533085/2020-11-20/}}</ref>
*'''Germany''': NEP is controlled under the NpSG (''New Psychoactive Substances Act'')<ref>{{cite web|url=https://www.gesetze-im-internet.de/npsg/anlage.html|title=Anlage NpSG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 11, 2019|language=de}}</ref> as of November 26, 2016.<ref>{{cite web|url=https://www.bgbl.de/xaver/bgbl/start.xav?startbk=Bundesanzeiger_BGBl&jumpTo=bgbl116s2615.pdf#__bgbl__%2F%2F*%5B%40attr_id%3D%27bgbl116s2615.pdf%27%5D__1576017393518|title=Gesetz zur Bekämpfung der Verbreitung neuer psychoaktiver Stoffe|publisher=Bundesanzeiger Verlag|access-date=December 11, 2019|language=de}}</ref> Production and import with the aim to place it on the market, administration to another person and trading is punishable. Possession is illegal but not penalized.<ref>{{cite web|url=https://www.gesetze-im-internet.de/npsg/__4.html|title=§ 4 NpSG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 11, 2019|language=de}}</ref>
*'''Japan''': NEP is a controlled substance.<ref>{{cite web|url=https://www.mhlw.go.jp/seisakunitsuite/bunya/kenkou_iryou/iyakuhin/yakubuturanyou/dl/meisho.pdf|title=指定薬物一覧|publisher=Ministry of Health, Labour and Welfare|access-date=December 27, 2019|language=ja}}</ref>
*'''Sweden''': NEP is a controlled substance as of November 12, 2019.<ref>{{cite web|url=https://svenskforfattningssamling.se/sites/default/files/sfs/2019-10/SFS2019-612.pdf|title=Svensk författningssamling: Förordningom ändring i förordningen (1999:58) om förbud mot vissa hälsofarliga varor|language=sv|access-date=December 27, 2019|publisher=Thomson Förlag}}</ref>
*'''Switzerland''': NEP can be considered a controlled substance as a defined derivative of Cathinone under Verzeichnis E point 1. It is legal when used for scientific or industrial use.<ref>{{cite web|url=https://www.admin.ch/opc/de/classified-compilation/20101220/index.html|title=Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien|publisher=Bundeskanzlei [Federal Chancellery of Switzerland]|access-date=January 1, 2020|language=de}}</ref>
*'''The Netherlands:''' NEP is a controlled substance as of July 1, 2025. <ref>{{Citation|title= Bepaalde groepen designerdrugs (ook wel nieuwe psychoactieve stoffen) zijn sinds 1 juli 2025 verboden. Deze stoffen zijn schadelijk. Gebruikers kunnen er gezondheidsproblemen van krijgen en er zelfs door overlijden. | year=2025|url=https://www.rijksoverheid.nl/onderwerpen/drugs/verbod-op-designerdrugs}}</ref>
*'''United Kingdom''': NEP is a Class B drug in the United Kingdom as a result of the cathinone catch-all clause.<ref>{{Citation | title=The Misuse of Drugs Act 1971 (Amendment) Order 2010 | url=https://www.legislation.gov.uk/uksi/2010/1207/made}}</ref>
*'''United States''': NEP is not a controlled substance in the United States but possession or distribution for human use could potentially be prosecuted under the Federal Analogue Act due to its structural and pharmacological similarities to [[pentedrone]].<ref>{{Citation | title=21 U.S. Code § 813 - Treatment of controlled substance analogues | url=https://www.law.cornell.edu/uscode/text/21/813}}</ref>
*'''Italy:''' NEP is a controlled substance in Italy. It was inserted in "Table 1 of psychotropic substances"<ref>[https://www.salute.gov.it/portale/medicinaliStupefacenti/dettaglioContenutiMedicinaliStupefacenti.jsp?lingua=italiano&id=3729&area=sostanzeStupefacenti&menu=vuoto&tab=1]</ref> in December 29, 2020.


==See also==
==See also==
*[[Responsible use]]
*[[Responsible use]]
*[[Designer drug]]
*[[Designer drug]]
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==External links==
==External links==
*[http://drugs.tripsit.me/ethyl-pentedrone Ethyl-Pentedrone (TripSit)]
 
*[https://en.wikipedia.org/wiki/N-Ethylpentedrone N-Ethylpentedrone (Wikipedia)]
*[https://isomerdesign.com/PiHKAL/explore.php?id=638 NEP (Isomer Design)]


==References==
==References==
<references />
<references />
[[Category:Psychoactive substance]]
[[Category:Psychoactive substance]]
[[Category:Stimulant]]
[[Category:Cathinone]]
[[Category:Research chemical]]
[[Category:Research chemical]]
[[Category:Cathinone]]
 
[[Category:Stimulant]]
{{#set:Featured=true}}
Retrieved from "http://psy.st/wiki/NEP"