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Ephylone: Difference between revisions
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'''N-Ethylpentylone''' (also known as '''bk-EBDP''', '''βk-EBDP''', and '''ephylone''') is a novel [[Psychoactive class::stimulant]]-[[Psychoactive class::entactogen]] substance of the [[chemical class::cathinone]] class. Ephylone is chemically related to [[pentylone]] and belongs to a group of compounds known as the [[substituted cathinones]]. Little is known about its pharmacology, although it likely produces its effects by increasing levels of [[serotonin]], [[dopamine]], and [[norepinephrine]] in the brain.<ref name="Wood">Wood, M. R., Bernal, I., | '''N-Ethylpentylone''' (also known as '''bk-EBDP''', '''βk-EBDP''', and '''ephylone''') is a novel [[Psychoactive class::stimulant]]-[[Psychoactive class::entactogen]] substance of the [[chemical class::cathinone]] class. Ephylone is chemically related to [[pentylone]] and belongs to a group of compounds known as the [[substituted cathinones]]. Little is known about its pharmacology, although it likely produces its effects by increasing levels of [[serotonin]], [[dopamine]], and [[norepinephrine]] in the brain.<ref name="Wood">{{cite journal | vauthors=((Wood, M. R.)), ((Bernal, I.)), ((Lalancette, R. A.)) | journal=Structural Chemistry | title=The hydrochloride hydrates of pentylone and dibutylone and the hydrochloride salt of ephylone: the structures of three novel designer cathinones | volume=28 | issue=5 | pages=1369–1376 | date=1 October 2017 | url=https://doi.org/10.1007/s11224-017-0951-x | issn=1572-9001 | doi=10.1007/s11224-017-0951-x}}</ref> | ||
Ephylone was developed in the 1960s by Boehringer Ingelheim as a central nervous system stimulant,<ref name="Wood" /> although it never became marketed. Reports of recreational use first appeared in late 2015. Since then, its prevalence has steadily risen, particularly at dance music festivals where it appears as an adulterant or counterfeit for [[MDMA]].<ref name="Wood" /> Ephylone has been linked to numerous hospitalizations and overdose deaths.<ref>Krotulski, A. J., Papsun, D. M., De Martinis, B. S., Mohr, A. L., | Ephylone was developed in the 1960s by Boehringer Ingelheim as a central nervous system stimulant,<ref name="Wood" /> although it never became marketed. Reports of recreational use first appeared in late 2015. Since then, its prevalence has steadily risen, particularly at dance music festivals where it appears as an adulterant or counterfeit for [[MDMA]].<ref name="Wood" /> Ephylone has been linked to numerous hospitalizations and overdose deaths.<ref name="Krotulski2018">{{cite journal | vauthors=((Krotulski, A. J.)), ((Papsun, D. M.)), ((De Martinis, B. S.)), ((Mohr, A. L. A.)), ((Logan, B. K.)) | journal=Journal of Analytical Toxicology | title=N-Ethyl Pentylone (Ephylone) Intoxications: Quantitative Confirmation and Metabolite Identification in Authentic Human Biological Specimens | volume=42 | issue=7 | pages=467–475 | date=1 September 2018 | url=https://academic.oup.com/jat/article/42/7/467/4957061 | issn=0146-4760 | doi=10.1093/jat/bky025}}</ref> | ||
User reports indicate that ephylone produces a mixture of classic [[stimulant]] and [[entactogen|entactogenic]] effects resembling those of [[MDMA]], [[methylone]] and [[cocaine]]. Typical effects include [[stimulation]], [[disinhibition]], [[increased libido]], [[compulsive redosing]], and [[euphoria]]. Unlike similar substances, however, ephylone is reported to be very long lasting when taken in larger doses. The significance of this is not known, although it may indicate that it has a different toxicity profile compared to other stimulants. | User reports indicate that ephylone produces a mixture of classic [[stimulant]] and [[entactogen|entactogenic]] effects resembling those of [[MDMA]], [[methylone]] and [[cocaine]]. Typical effects include [[stimulation]], [[disinhibition]], [[increased libido]], [[compulsive redosing]], and [[euphoria]]. Unlike similar substances, however, ephylone is reported to be very long lasting when taken in larger doses. The significance of this is not known, although it may indicate that it has a different toxicity profile compared to other stimulants. | ||
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==History and culture== | ==History and culture== | ||
{{Further|Research chemicals#History and culture}} | {{Further|Research chemicals#History and culture}} | ||
Synthetic cathinones were first synthesized in the late 1920s, starting with [[methcathinone]] and [[mephedrone]]. However, they did not find medical use due to their side effects. In the early 2000s, synthetic cathinones began to be sold in "head" shops and online as [[designer drugs]], also known as [[research chemicals]] and "legal highs".<ref>Coppola, M., | Synthetic cathinones were first synthesized in the late 1920s, starting with [[methcathinone]] and [[mephedrone]]. However, they did not find medical use due to their side effects. In the early 2000s, synthetic cathinones began to be sold in "head" shops and online as [[designer drugs]], also known as [[research chemicals]] and "legal highs".<ref>{{cite journal | vauthors=((Coppola, M.)), ((Mondola, R.)) | journal=Toxicology Letters | title=Synthetic cathinones: Chemistry, pharmacology and toxicology of a new class of designer drugs of abuse marketed as “bath salts” or “plant food” | volume=211 | issue=2 | pages=144–149 | date= June 2012 | url=https://linkinghub.elsevier.com/retrieve/pii/S0378427412001117 | issn=03784274 | doi=10.1016/j.toxlet.2012.03.009}}</ref> Their quasi-legality and ability to substitute for traditional stimulants like [[cocaine]] or [[amphetamine]] made them popular in certain demographics. Due to a history of being falsely marketed as bath salt products, they are referred in the media as "bath salts." | ||
The synthesis of ephylone was first described in a patent filed by Boehringer Ingelheim in 1969. It was described alongside the synthesis of other novel central nervous system stimulants including [[pentylone]], [[butylone]] and [[dibutylone]]. However, its pharmacological properties were not tested and it was never marketed. | The synthesis of ephylone was first described in a patent filed by Boehringer Ingelheim in 1969. It was described alongside the synthesis of other novel central nervous system stimulants including [[pentylone]], [[butylone]] and [[dibutylone]]. However, its pharmacological properties were not tested and it was never marketed. | ||
The emergence of ephylone on the recreational drug market was reported in drug seizures for the first time in 2016. According to 2017 DEA reports, ephylone was the number one reported synthetic cathinone accounting for 55%, 50% and 38% of cases reported for the first three quarters of 2017, respectively.<ref | The emergence of ephylone on the recreational drug market was reported in drug seizures for the first time in 2016. According to 2017 DEA reports, ephylone was the number one reported synthetic cathinone accounting for 55%, 50% and 38% of cases reported for the first three quarters of 2017, respectively.<ref name="Krotulski2018"/> | ||
Reports about the availability and effects of ephylone began to appear in forums such as bluelight.org or drugs-forum.com by mid-2015. A 2018 report issued by the drug testing organization Energy Control found evidence indicating increasing use of ephylone as a counterfeit or adulterant for [[MDMA]].<ref> | Reports about the availability and effects of ephylone began to appear in forums such as bluelight.org or drugs-forum.com by mid-2015. A 2018 report issued by the drug testing organization Energy Control found evidence indicating increasing use of ephylone as a counterfeit or adulterant for [[MDMA]].<ref>{{Citation | vauthors=DoctorX | title=Ecstasy and MDMA aldulterated with N-Ethyl-Pentylone. A brief report |publisher=International Energy Control | url=https://energycontrol-international.org/ecstasy-mdma-aldulterated-with-n-ethyl-pentylone-report/}}</ref> | ||
==Chemistry== | ==Chemistry== | ||
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==Pharmacology== | ==Pharmacology== | ||
Very little data exists on the human pharmacokinetics and pharmacodynamics of ethylone and other substituted cathinones. Like amphetamines, synthetic cathinones exert their stimulating and sympathomimetic effects via increasing synaptic concentration of [[catecholamines]] such as [[dopamine]], [[serotonin]] and [[norepinephrine]]. These molecules are able to inhibit [[monoamine]] [[reuptake transporters]] producing a decreased clearance of the [[neurotransmitters]] from the synapse. Furthermore, they may cause release of biogenic amines from intracellular stores.<ref>Cozzi, N.V., Sievert, M.K., Shulgin, A.T., | Very little data exists on the human pharmacokinetics and pharmacodynamics of ethylone and other substituted cathinones. Like amphetamines, synthetic cathinones exert their stimulating and sympathomimetic effects via increasing synaptic concentration of [[catecholamines]] such as [[dopamine]], [[serotonin]] and [[norepinephrine]]. These molecules are able to inhibit [[monoamine]] [[reuptake transporters]] producing a decreased clearance of the [[neurotransmitters]] from the synapse. Furthermore, they may cause release of biogenic amines from intracellular stores.<ref>{{cite journal | vauthors=((Cozzi, N. V.)), ((Sievert, M. K.)), ((Shulgin, A. T.)), ((Jacob, P.)), ((Ruoho, A. E.)) | journal=European Journal of Pharmacology | title=Inhibition of plasma membrane monoamine transporters by β-ketoamphetamines | volume=381 | issue=1 | pages=63–69 | date= September 1999 | url=https://linkinghub.elsevier.com/retrieve/pii/S0014299999005385 | issn=00142999 | doi=10.1016/S0014-2999(99)00538-5}}</ref> | ||
Synthetic cathinones are generally less able than amphetamines to cross the blood–brain barrier because the beta-keto group causes an increase in polarity. Unlike other synthetic cathinones, pyrrolidine derivatives have a higher ability to cross the blood–brain barrier because the pyrrolidine ring confers a low polarity to these molecules. The studies on the metabolism of synthetic cathinones have shown that they are N-demethylated, the keto group is reduced to hydroxyl and ring alkyl groups are oxidised.<ref>Meyer, M.R., Maurer, H.H. | Synthetic cathinones are generally less able than amphetamines to cross the blood–brain barrier because the beta-keto group causes an increase in polarity. Unlike other synthetic cathinones, pyrrolidine derivatives have a higher ability to cross the blood–brain barrier because the pyrrolidine ring confers a low polarity to these molecules. The studies on the metabolism of synthetic cathinones have shown that they are N-demethylated, the keto group is reduced to hydroxyl and ring alkyl groups are oxidised.<ref>{{cite journal | vauthors=((Meyer, M. R.)), ((Maurer, H. H.)) | journal=Current Drug Metabolism | title=Metabolism of Designer Drugs of Abuse: An Updated Review | volume=11 | issue=5 | pages=468–482 | url=https://www.eurekaselect.com/article/16867}}</ref> | ||
==Subjective effects== | ==Subjective effects== | ||
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Ephylone is a [[research chemical]] with a very short history of human usage. Very little is known about its long-term health effects and the [[Toxicity::exact toxic dosage is unknown]]. | Ephylone is a [[research chemical]] with a very short history of human usage. Very little is known about its long-term health effects and the [[Toxicity::exact toxic dosage is unknown]]. | ||
Numerous reports of hospitalizations and overdose deaths indicate that ephylone is extremely toxic at very high dosages.<ref>Clinical Presentation, Autopsy Results and Toxicology Findings in an Acute | Numerous reports of hospitalizations and overdose deaths indicate that ephylone is extremely toxic at very high dosages.<ref>{{cite journal | vauthors=((Thirakul, P.)), ((S Hair, L.)), ((L Bergen, K.)), ((M Pearson, J.)) | journal=Journal of Analytical Toxicology | title=Clinical Presentation, Autopsy Results and Toxicology Findings in an Acute N-Ethylpentylone Fatality | volume=41 | issue=4 | pages=342–346 | date=1 May 2017 | issn=1945-2403 | doi=10.1093/jat/bkx004}}</ref> The DEA claimed approximately 151 ephylone-related deaths occurred in the U.S. between 2014 and 2018.<ref name="2018SchedulesofControlledSubstances">{{Citation | year=2018 | title=Schedules of Controlled Substances: Temporary Placement of N-Ethylpentylone in Schedule I | url=https://www.federalregister.gov/documents/2018/06/13/2018-12669/schedules-of-controlled-substances-temporary-placement-of-n-ethylpentylone-in-schedule-i}}</ref> Higher dosages of ephylone have been linked to [[serotonin syndrome]], rhabdomyolysis, kidney injury, acidemia and other life-threatening symptoms.<ref name="Krotulski2018"/> | ||
It is strongly advised to use [[responsible use|harm reduction practices]] if using this substance. | It is strongly advised to use [[responsible use|harm reduction practices]] if using this substance. | ||
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Ephylone is currently unscheduled in most parts of the world. | Ephylone is currently unscheduled in most parts of the world. | ||
*''' | *'''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/219201/pop_up?_101_INSTANCE_FXrpx9qY7FbU_viewMode=print&_101_INSTANCE_FXrpx9qY7FbU_languageId=pt_BR</ref> | ||
*'''Germany''': Ephylone is controlled under Anlage II BtMG (''Narcotics Act, Schedule II'')<ref>{{cite web|url=https://www.gesetze-im-internet.de/btmg_1981/anlage_ii.html|title=Anlage II BtMG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 25, 2019|language=de}}</ref> as of December 21, 2019.<ref>{{cite web|url=http://www.bgbl.de/xaver/bgbl/start.xav?startbk=Bundesanzeiger_BGBl&jumpTo=bgbl119s2850.pdf|title=Neunzehnte Verordnung zur Änderung von Anlagen des Betäubungsmittelgesetzes|publisher=Bundesanzeiger Verlag|access-date=December 25, 2019|language=de}}</ref> It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.<ref>{{cite web|url=https://www.gesetze-im-internet.de/btmg_1981/__29.html|title=§ 29 BtMG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 25, 2019|language=de}}</ref> | |||
*'''Switzerland''': Ephylone 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 States''': On July 13, 2018, the DEA issued a temporary scheduling order to place ephylone in schedule I of the Controlled Substances Act (CSA).<ref name="2018SchedulesofControlledSubstances"/> This makes the production, sale, and possession of ephylone illegal. | |||
==See also== | ==See also== | ||
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* Prosser, J. M., & Nelson, L. S. (2012). The toxicology of bath salts: a review of synthetic cathinones. Journal of Medical Toxicology, 8(1), 33-42. https://doi.org/0.1007/s13181-011-0193-z. | * Prosser, J. M., & Nelson, L. S. (2012). The toxicology of bath salts: a review of synthetic cathinones. Journal of Medical Toxicology, 8(1), 33-42. https://doi.org/0.1007/s13181-011-0193-z. | ||
* Wood, M. R., Bernal, I., & Lalancette, R. A. (2017). The hydrochloride hydrates of pentylone and dibutylone and the hydrochloride salt of ephylone: the structures of three novel designer cathinones. Structural Chemistry, 28(5), 1369-1376. http://dx.doi.org/10.1007/s11224-017-0951-x | * Wood, M. R., Bernal, I., & Lalancette, R. A. (2017). The hydrochloride hydrates of pentylone and dibutylone and the hydrochloride salt of ephylone: the structures of three novel designer cathinones. Structural Chemistry, 28(5), 1369-1376. http://dx.doi.org/10.1007/s11224-017-0951-x | ||
*Krotulski, A. J., Papsun, D. M., De Martinis, B. S., Mohr, A. L., & Logan, B. K. (2018). N-Ethyl Pentylone (Ephylone) Intoxications: Quantitative Confirmation and Metabolite Identification in Authentic Human Biological Specimens. Journal of Analytical Toxicology. https:// | *Krotulski, A. J., Papsun, D. M., De Martinis, B. S., Mohr, A. L., & Logan, B. K. (2018). N-Ethyl Pentylone (Ephylone) Intoxications: Quantitative Confirmation and Metabolite Identification in Authentic Human Biological Specimens. Journal of Analytical Toxicology. https://doi.org/10.1093/jat/bky025 | ||
==References== | ==References== | ||
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[[Category:Psychoactive substance]] | [[Category:Psychoactive substance]] | ||
[[Category:Stimulant]] | |||
[[Category:Entactogen]] | |||
[[Category:MDxx]] | |||
[[Category:Cathinone]] | [[Category:Cathinone]] | ||
[[Category: | [[Category:Research chemical]] | ||