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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 new research has shown very low serotonin reuptake inhibition.<ref name=":0"> | 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> | ||
Role of amino terminal substitutions in the pharmacological, rewarding and psychostimulant profiles of novel synthetic cathinones | |||
2021 | |||
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 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. | ||
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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== | ||
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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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*'''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> | *'''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> | *'''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> | ||
*'''United Kingdom''': NEP is a Class B drug in the United Kingdom as a result of the cathinone catch-all clause.<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>21 U.S. Code § 813 https://www.law.cornell.edu/uscode/text/21/813</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> | ||
==See also== | ==See also== | ||