2C-E: Difference between revisions

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{{SubstanceBox/2C-E}}
{{SubstanceBox/2C-E}}


'''2,5-Dimethoxy-4-ethylphenethylamine''' (also known as '''2C-E''', or colloquially as '''"Aquarust"'''<ref name="pubchemSYN">https://pubchem.ncbi.nlm.nih.gov/compound/2C-E#section=Synonyms</ref> and '''"Eternity"'''<ref name="pubchemSYN" />) is a lesser-known [[psychoactive class::psychedelic]] substance of the [[chemical class::phenethylamine]] class. It is a member of the [[2C-x family]] of psychedelic phenethylamines, which are closely related to the classical psychedelic [[mescaline]]. Like other psychedelics, it is thought to produce its effects by binding to [[serotonin]] [[receptors]] in the brain, although the precise mechanism is poorly understood.  
'''2,5-Dimethoxy-4-ethylphenethylamine''' (also known as '''2C-E''', or colloquially as '''"Aquarust"'''<ref name="pubchemSYN">{{cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/2C-E#section=Synonyms|title=Compound Summary: 2,5-Dimethoxy-4-ethylphenethylamine: 2.4 Synonyms|publisher=PubChem|access-date=October 11, 2020}}</ref> and '''"Eternity"'''<ref name="pubchemSYN" />) is a lesser-known [[psychoactive class::psychedelic]] substance of the [[chemical class::phenethylamine]] class. It is a member of the [[2C-x family]] of psychedelic phenethylamines, which are closely related to the classical psychedelic [[mescaline]]. Like other psychedelics, it is thought to produce its effects by binding to [[serotonin]] [[receptors]] in the brain, although the precise mechanism is poorly understood.  


2C-E was first synthesized and tested for human activity by [[Alexander Shulgin]] in 1977,<ref>Shulgin, Alexander. "Pharmacology Lab Notes #2". Lafayette, CA. (1976-1980). p236 (Erowid.org) | https://erowid.org/library/books_online/shulgin_labbooks/shulgin_labbook2_searchable.pdf</ref> who documented his findings in the 1991 book [[PiHKAL]] ("Phenethylamines I Have Known and Loved").<ref name="pihkal2CE">Shulgin, A., & Shulgin, A. (1991).
2C-E was first synthesized and tested for human activity by [[Alexander Shulgin]] in 1977,<ref name="Shulgin1980">{{cite book|author=Alexander Shulgin|author-link=Alexander Shulgin|title=Pharmacology Notes II (The Shulgin Lab Books)|publisher=Erowid|url=https://erowid.org/library/books_online/shulgin_labbooks/shulgin_pharmacology_notebook9_searchable.pdf|page=236|place=Lafayette, CA, USA|year=1980}}</ref> who documented his findings in the 1991 book [[PiHKAL]] ("Phenethylamines I Have Known and Loved").<ref name="PiHKAL">{{cite book|title=PiHKAL: A Chemical Love Story|title-link=PiHKAL|author-link1=Alexander Shulgin|author1=Alexander Shulgin|author2=Ann Shulgin|year=1991|publisher=Transform Press|location=United States|isbn=0963009605|oclc=1166889264|chapter-url=https://erowid.org/library/books_online/pihkal/pihkal024.shtml|chapter=#24. 2C-E}}</ref> It began to appear in drug seizures around 2004.<ref>{{cite journal|title=2,5-Dimethoxy-4-Ethylphenethylamine (2C-E) encountered in Ft. Pierce, Florida and Royal Oak, Michigan|journal=Microgram Bulletin|publisher=Drug Enforcement Agency|date=November 2004|volume=37|issue=11|pages=193-194|url=https://erowid.org/library/periodicals/microgram/microgram_2004-11.pdf|oclc=54464390}}</ref> While primarily distributed online as a [[research chemical]], it is also sometimes distributed on the street as 'mescaline' or 'synthetic mescaline'.
[http://isomerdesign.com/PiHKAL/read.php?id=24 Read #24 2C-E | PiHKAL &thinsp;·&thinsp;info]. Retrieved Jan 22, 2018.</ref> It began to appear in drug seizures around 2004.<ref>"2,5-Dimethoxy-4-Ethylphenethylamine (2C-E) encountered in Ft. Pierce, Florida and Royal Oak, Michigan". Microgram Bulletin. Drug Enforcement Agency. Nov 2004. 37(11):p193-194 (Erowid.org) | https://erowid.org/library/periodicals/microgram/microgram_2004-11.pdf</ref> While primarily distributed online as a [[research chemical]], it is also sometimes distributed on the street as 'mescaline' or 'synthetic mescaline'.


[[Subjective effects]] include [[geometry|open and closed-eye visuals]], [[time distortion]], [[introspection|enhanced introspection]], [[ego loss]], and [[euphoria]]. User reports characterize 2C-E as a highly unpredictable, dose-sensitive psychedelic that is capable of producing strong visual distortions along with a significant "body load", which includes nausea and bodily discomfort.  
[[Subjective effects]] include [[geometry|open and closed-eye visuals]], [[time distortion]], [[introspection|enhanced introspection]], [[ego loss]], and [[euphoria]]. User reports characterize 2C-E as a highly unpredictable, dose-sensitive psychedelic that is capable of producing strong visual distortions along with a significant "body load", which includes nausea and bodily discomfort.  
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==History and culture==
==History and culture==
{{historyStub}}
{{historyStub}}
2C-E was first synthesized and tested for human activity by [[Alexander Shulgin]] in 1977,<ref>Shulgin, Alexander. "Pharmacology Lab Notes #2". Lafayette, CA. (1976-1980). p236 (Erowid.org) | https://erowid.org/library/books_online/shulgin_labbooks/shulgin_labbook2_searchable.pdf</ref> who documented his findings in the 1991 book [[PiHKAL]] ("Phenethylamines I Have Known and Loved").<ref name="pihkal2CE">Shulgin, A., & Shulgin, A. (1991).
2C-E was first synthesized and tested for human activity by [[Alexander Shulgin]] in 1977,<ref name="Shulgin1980" /> who documented his findings in the 1991 book [[PiHKAL]] ("Phenethylamines I Have Known and Loved").<ref name="PiHKAL" /> It is a member of the so-called "magical half-dozen" which refers to Shulgin's self-rated most important [[phenethylamines|phenethylamine]]-derived compounds, all of which except [[mescaline]] he developed and synthesized himself. They are found within the first book of [[PiHKAL]], and are as follows: [[Mescaline]], [[DOM]], [[2C-B]], 2C-E, [[2C-T-2]] and [[2C-T-7]].
[http://isomerdesign.com/PiHKAL/read.php?id=24 Read #24 2C-E | PiHKAL &thinsp;·&thinsp;info]. Retrieved Jan 22, 2018.</ref> It is a member of the so-called "magical half-dozen" which refers to Shulgin's self-rated most important [[phenethylamines|phenethylamine]]-derived compounds, all of which except [[mescaline]] he developed and synthesized himself. They are found within the first book of [[PiHKAL]], and are as follows: [[Mescaline]], [[DOM]], [[2C-B]], 2C-E, [[2C-T-2]] and [[2C-T-7]].


==Chemistry==
==Chemistry==
2C-E or 2,5-dimethoxy-4-ethylphenethylamine is a [[substituted phenethylamines|phenethylamine]] featuring a phenyl ring bound to an amino (NH<sub>2</sub>) group through an ethyl chain. 2C-E contains methoxy functional groups CH<sub>3</sub>O- attached to carbons R<sub>2</sub> and R<sub>5</sub> and an ethyl chain bound to carbon R<sub>4</sub> of the phenyl ring. 2C-E belongs to the 2C family of phenethylamines which contain methoxy groups on the 2 and 5 positions of the benzene ring.<ref>http://isomerdesign.com/PiHKAL/read.php?id=24</ref>
2C-E or 2,5-dimethoxy-4-ethylphenethylamine is a [[substituted phenethylamines|phenethylamine]] featuring a phenyl ring bound to an amino (NH<sub>2</sub>) group through an ethyl chain. 2C-E contains methoxy functional groups CH<sub>3</sub>O- attached to carbons R<sub>2</sub> and R<sub>5</sub> and an ethyl chain bound to carbon R<sub>4</sub> of the phenyl ring. 2C-E belongs to the 2C family of phenethylamines which contain methoxy groups on the 2 and 5 positions of the benzene ring.<ref name="PiHKAL" />


==Pharmacology==
==Pharmacology==
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==Subjective effects==
==Subjective effects==
{{Preamble/SubjectiveEffects}}
{{Preamble/SubjectiveEffects}}
{{effects/base
{{effects/base


|{{effects/physical|
|{{effects/physical|
*'''[[Effect::Stimulation]]''' - 2C-E is usually considered to be very energetic and stimulating in a fashion that is comparable to that of [[MDMA]], although it is 'encouraged' instead of 'forced'.
*'''[[Effect::Stimulation]]''' - 2C-E is usually considered to be very energetic and stimulating in a fashion that is comparable to that of [[MDMA]], although it is 'encouraged' instead of 'forced' according to many users.
*'''[[Effect::Spontaneous bodily sensations]]''' - The "body high" of 2C-E is manifested as one of the most proportionally intense in comparison to almost all of the classical psychedelics. The sensation itself can be described as an intense and slightly uncomfortable energetic pins and needles sensation that constantly encompasses a person's entire body. It is usually felt over the surface of the skin but occasionally manifests itself in the form of a continuously shifting, tingling sensation that travels up and down the body in intermittent waves. Alongside this, many users report uncomfortable body feelings characterized by dysphoric aches and urges to shift the position of one's body and prolonged tensing of unusual combinations of muscle groups.
*'''[[Effect::Spontaneous bodily sensations]]''' - The "body high" of 2C-E is manifested as one of the most proportionally intense in comparison to almost all of the classical psychedelics. The sensation itself can be described as an intense and slightly uncomfortable energetic pins and needles sensation that constantly encompasses a person's entire body. It is usually felt over the surface of the skin but occasionally manifests itself in the form of a continuously shifting, tingling sensation that travels up and down the body in intermittent waves. This skin tingling is much more pronounced than with other psychedelics.  Alongside this, many users report uncomfortable body feelings characterized by dysphoric aches and urges to shift the position of one's body and prolonged tensing of unusual combinations of muscle groups.
**'''[[Effect::Physical euphoria]]''' - Feelings of frequent but unpredictable rushes of warm physical euphoria are extremely common and very pleasurable. These move from the top of the head downwards before enveloping one's whole body.
**'''[[Effect::Physical euphoria]]''' - Feelings of frequent but unpredictable rushes of warm physical euphoria are extremely common and very pleasurable. These move from the top of the head downwards before enveloping one's whole body.
*'''[[Effect::Tactile enhancement]]'''
*'''[[Effect::Tactile enhancement]]'''
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}}
}}
{{effects/multisensory|
{{effects/multisensory|
*'''[[Effect::Synaesthesia]]''' - In its fullest manifestation, this is a very rare and non-reproducible effect. Increasing the dosage can increase the likelihood of this occurring, but seems to only be a prominent part of the experience among those who are already predisposed to synaesthetic states. However, many reports indicate that this substance is relatively reliable at inducing synaesthetic states in those who are predisposed to them.{{citation needed}}
*'''[[Effect::Synaesthesia]]''' - In its fullest manifestation, this is a very rare and non-reproducible effect. Increasing the dosage can increase the likelihood of this occurring, but seems to only be a prominent part of the experience among those who are already predisposed to synaesthetic states. However, many reports indicate that this substance is relatively reliable at inducing synaesthetic states.{citation needed}}


}}
}}
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*'''[[Effect::Unity and interconnectedness]]'''
*'''[[Effect::Unity and interconnectedness]]'''


}}
}}
}}
===Combination effects===
===Combination effects===
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Although no formal studies have been conducted, it is not unreasonable to assume that like psychedelics in general, 2C-E is [[Addiction potential::not habit-forming]] and that the desire to use it can actually decrease with use.  
Although no formal studies have been conducted, it is not unreasonable to assume that like psychedelics in general, 2C-E is [[Addiction potential::not habit-forming]] and that the desire to use it can actually decrease with use.  


Tolerance to the effects of 2C-E are built almost immediately after ingestion. After that, it takes about 1-2 days for the tolerance to be reduced to half and 2-4 days to be back at baseline (in the absence of further consumption). 2C-E presents cross-tolerance with [[Cross-tolerance::all [[psychedelic]]s]] but not evenly, meaning that after the consumption of 2C-E, some psychedelics will have significant reduced effects while some others will only be slighly affected.
Tolerance to the effects of 2C-E is built almost immediately after ingestion. After that, it takes about 1-2 days for the tolerance to be reduced to half and 2-4 days to be back at baseline (in the absence of further consumption). 2C-E presents cross-tolerance with [[Cross-tolerance::all [[psychedelic]]s]] but not evenly, meaning that after the consumption of 2C-E, some psychedelics will have significant reduced effects while some others will only be slighly affected.


===Dangerous interactions===
===Dangerous interactions===
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==Legal status==
==Legal status==


*'''Austria''': 2C-E is illegal to possess, produce and sell under the NPSG (Neue-Psychoaktive-Substanzen-Gesetz Österreich).{{citation needed}}
*'''Austria''': 2C-E is illegal to possess, produce and sell under the NPSG (Neue-Psychoaktive-Substanzen-Gesetz Österreich). In its Schedule II, the further specifying NPSV (Neue-Psychoaktive-Substanzen-Verordnung Österreich) explicitly bans all substituted phenetylamines.<ref>{{cite web|url=https://www.ris.bka.gv.at/GeltendeFassung.wxe?Abfrage=Bundesnormen&Gesetzesnummer=20007642|title=Bundesrecht konsolidiert: Gesamte Rechtsvorschrift für Neue-Psychoaktive-Substanzen-Verordnung|date=June 26, 2019|language=de|access-date=January 10, 2021}}</ref>
*'''Brazil''': Possession, production and sale is illegal as it is listed on Portaria SVS/MS nº 344.<ref>http://portal.anvisa.gov.br/documents/10181/3115436/%281%29RDC_130_2016_.pdf/fc7ea407-3ff5-4fc1-bcfe-2f37504d28b7</ref>
*'''Brazil''': Possession, production and sale is illegal as it is listed on Portaria SVS/MS nº 344.<ref>{{cite web|url=http://portal.anvisa.gov.br/documents/10181/3115436/%281%29RDC_130_2016_.pdf/fc7ea407-3ff5-4fc1-bcfe-2f37504d28b7|title=RESOLUÇÃO DA DIRETORIA COLEGIADA - RDC N° 130, DE 2 DE DEZEMBRO DE 2016|publication-date=December 5, 2016|publisher=Agência Nacional de Vigilância Sanitária (ANVISA) [Brazilian Health Regulatory Agency (ANVISA)]|language=pt}}</ref>
*'''Canada''': 2C-E would be considered Schedule III as it is a derivative of 2,5-dimethoxyphenethylamine.<ref>Controlled Drugs and Substances Act (S.C. 1996, c. 19) |http://laws-lois.justice.gc.ca/eng/acts/C-38.8/page-12.html#h-28</ref>
*'''Canada''': 2C-E would be considered Schedule III as it is a derivative of 2,5-dimethoxyphenethylamine.<ref>{{cite web|url=http://isomerdesign.com/Cdsa/schedule.php?schedule=3&section=ALL&structure=C|title=Schedule III|work=Controlled Drugs and Substances Act (CDSA)|publisher=Isomer Design|access-date=October 10, 2020}}</ref>
*'''China''': As of October 2015 2C-E is a controlled substance in China.<ref>China Food and Drug Administration. (2017, April 10). 关于印发《非药用类麻醉药品和精神药品列管办法. Retrieved from http://www.buzzle.com</ref>
*'''China''': As of October 2015 2C-E is a controlled substance in China.<ref>{{cite web|url=http://www.sfda.gov.cn/WS01/CL0056/130753.html|title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知|publisher=国家食品药品监督管理总局 [China Food and Drug Administration (CFDA)]|date=September 27, 2015|language=zh|archive-url=https://web.archive.org/web/20170906191704/http://www.sfda.gov.cn/WS01/CL0056/130753.html|archive-date=September 6, 2017}}</ref>
*'''Denmark''': 2C-E is a Schedule I drug. {{citation needed}}
*'''Denmark''': 2C-E is a Schedule I drug. {{citation needed}}
*'''Finland''': The possession, production and sale is illegal.{{citation needed}}
*'''Finland''': The possession, production and sale is illegal.{{citation needed}}
*'''Germany''': 2C-E is controlled under Anlage I BtMG (Narcotics Act, Schedule I) as of December 13, 2014.<ref>{{cite web|url=https://www.bgbl.de/xaver/bgbl/start.xav?startbk=Bundesanzeiger_BGBl&jumpTo=bgbl114s1999.pdf#__bgbl__%2F%2F*%5B%40attr_id%3D%27bgbl114s1999.pdf%27%5D__1576023093735|title=Achtundzwanzigste Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften|publisher=Bundesanzeiger Verlag|access-date=December 10, 2019|language=de}}</ref><ref>{{cite web|url=https://www.gesetze-im-internet.de/btmg_1981/anlage_i.html|title=Anlage I BtMG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 10, 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 10, 2019|language=de}}</ref>
*'''Germany''': 2C-E is controlled under Anlage I BtMG (''Narcotics Act, Schedule I'')<ref>{{cite web|url=https://www.gesetze-im-internet.de/btmg_1981/anlage_i.html|title=Gesetz über den Verkehr mit Betäubungsmitteln: Anlage I|publisher=Bundesamt für Justiz [Federal Office of Justice]|access-date=December 10, 2019|language=de}}</ref> as of December 13, 2014.<ref>{{cite web|url=http://www.bgbl.de/xaver/bgbl/start.xav?startbk=Bundesanzeiger_BGBl&jumpTo=bgbl114s1999.pdf|title=Achtundzwanzigste Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften|publisher=Bundesanzeiger Verlag|work=Bundesgesetzblatt Jahrgang 2014 Teil I Nr. 57|page=1999-2002|publication-date=December 12, 2014|language=de|oclc=231871244|issn=0341-1095|date=December 5, 2014}}</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=Gesetz über den Verkehr mit Betäubungsmitteln: § 29|publisher=Bundesamt für Justiz [Federal Office of Justice]|access-date=December 10, 2019|language=de}}</ref>
*'''Israel''': Possession, production and sale is illegal. {{citation needed}}
*'''Israel''': Possession, production and sale is illegal. {{citation needed}}
*'''Latvia''': 2C-E is a Schedule I controlled substance.<ref>Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem (2,5-Dimetoksifeniletānamīni) | http://likumi.lv/doc.php?id=121086</ref>
*'''Latvia''': 2C-E is a Schedule I controlled substance.<ref>{{cite web|url=http://likumi.lv/doc.php?id=121086|title=Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem|publisher=VSIA Latvijas Vēstnesis|access-date=January 1, 2020|publication-date=November 10, 2005|language=lv}}</ref>
*'''New Zealand''': 2C-E is a Class C drug. {{citation needed}}
*'''New Zealand''': 2C-E is a Class C drug. {{citation needed}}
*'''Sweden''': 2C-E is a Schedule I drug.{{citation needed}}
*'''Poland''': 2C-E is a controlled substance belonging to the IV-P psychotropic group. <ref>https://isap.sejm.gov.pl/isap.nsf/download.xsp/WDU20220001665/O/D20221665.pdf</ref>
*'''Switzerland''': Possession, production and sale is illegal.<ref>http://web.archive.org/web/20170329020935/https://www.admin.ch/opc/de/classified-compilation/20101220/index.html</ref>
*'''Sweden''': 2C-E is classified as a hazardous substance.{{citation needed}}
*'''United Kingdom''': 2C-E is a Class A drug in the United Kingdom as a result of the phenethylamine catch-all clause.<ref>United Kingdom. (1977). Misuse of Drugs Act 1971 (S.I. 1977/1243). London: The Stationery Office Limited. Retrieved July 5, 2017, from http://www.legislation.gov.uk/uksi/1977/1243/made</ref>
*'''Switzerland''': 2C-E is a controlled substance specifically named under Verzeichnis E.<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''': 2C-E is a Schedule I drug.<ref>http://www.justice.gov/ola/views-letters/112/093011-ltr-re-hr1254-synthetic-drug-control-act-2011.pdf</ref>
*'''United Kingdom''': 2C-E is a Class A drug in the United Kingdom as a result of the phenethylamine catch-all clause.<ref>{{cite web|title=Schedule 2: Part I: Class A Drugs|url=http://www.legislation.gov.uk/ukpga/1971/38/schedule/2/part/I|work="Misuse of Drugs Act 1971"|access-date=August 20, 2020|publisher=UK Government}}</ref>
*'''United States''': 2C-E is a Schedule I drug.<ref>{{cite letter|url=http://www.justice.gov/ola/views-letters/112/093011-ltr-re-hr1254-synthetic-drug-control-act-2011.pdf|publisher=Office of Legislative Affairs|author=Ronald Weich (Assistant Attorney General)|recipient=F. James Sensenbrenner Jr. (Subcommittee on Crime, Terrorism, and Homeland Security)|date=September 30, 2011|subject=Additional Synthetic Drugs for Inclusion in section 202(c) of the Controlled Substances Act}}</ref>


==See also==
==See also==
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*[https://erowid.org/chemicals/2ce/2ce.shtml 2C-E (Erowid Vault)]
*[https://erowid.org/chemicals/2ce/2ce.shtml 2C-E (Erowid Vault)]
*[https://isomerdesign.com/PiHKAL/read.php?domain=pk&id=24 2C-E (PiHKAL / Isomer Design)]
*[https://isomerdesign.com/PiHKAL/read.php?domain=pk&id=24 2C-E (PiHKAL / Isomer Design)]
*[https://drugs-forum.com/wiki/2C-E 2C-E (Drugs-Forum)]


===Discussion===
===Discussion===
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<references />
<references />


[[Category:Substance]]
[[Category:Psychoactive substance]]
[[Category:Psychoactive substance]]
[[Category:Hallucinogen]]
[[Category:Psychedelic]]
[[Category:Psychedelic]]
[[Category:Phenethylamine]]
[[Category:2C-x]]
[[Category:2C-x]]
[[Category:Research chemical]]
[[Category:Research chemical]]
Retrieved from "http://psy.st/wiki/2C-E"