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2C-E: Difference between revisions
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'''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 | 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'. | ||
[[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 | 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]]. | ||
==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 | 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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*'''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).{{citation needed}} | ||
*'''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> | *'''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§ion=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 | *'''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) | *'''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> | *'''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}} | *'''Sweden''': 2C-E is a Schedule I drug.{{citation needed}} | ||
*'''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> | *'''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 Kingdom''': 2C-E is a Class A drug in the United Kingdom as a result of the phenethylamine catch-all clause.<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>http://www.justice.gov/ola/views-letters/112/093011-ltr-re-hr1254-synthetic-drug-control-act-2011.pdf</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== | ||