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NEP: Difference between revisions
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'''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]]. | '''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]]. | ||
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 | 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 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. | 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". | 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". | ||
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==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., | 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, | 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}} | ||
{{effects/base | {{effects/base | ||
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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::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::Motivation enhancement]]''' | *'''[[Effect::Motivation enhancement]]''' | ||
*'''[[Effect::Compulsive redosing]]''' | *'''[[Effect::Compulsive redosing]]''' | ||
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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 | | 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" /> | ||
===Dangerous interactions=== | ===Dangerous interactions=== | ||
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==Legal status== | ==Legal status== | ||
*'''Brazil | *'''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> | ||
*'''Germany | *'''China''': NEP is a controlled substance.{{citation needed}} | ||
*'''United Kingdom | *'''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> | ||
*'''United States | *'''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== | ||
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==References== | ==References== | ||
<references /> | <references /> | ||
[[Category:Psychoactive substance]] | [[Category:Psychoactive substance]] | ||
[[Category:Stimulant]] | |||
[[Category:Cathinone]] | |||
[[Category:Research chemical]] | [[Category:Research chemical]] | ||
{{#set:Featured=true}} | |||