View source for Chemistry:2C-E

{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477216166
| Name = 
| ImageFile = 
| ImageFile1 = 2C-E.svg
| ImageFileL2 = 2C-E-3d-sticks.png
| ImageFileR2 = 2C-E animation.gif
| PIN = 2-(4-Ethyl-2,5-dimethoxyphenyl)ethan-1-amine
| SystematicName = 
| OtherNames = 4-Ethyl-2,5-dimethoxyphenethylamine, Aquarust
| IUPACName = 
| Section1 = {{Chembox Identifiers
| InChI = 1/C12H19NO2/c1-4-9-7-12(15-3)10(5-6-13)8-11(9)14-2/h7-8H,4-6,13H2,1-3H3
| InChIKey = VDRGNAMREYBIHA-UHFFFAOYAI
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 124063
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = I190284UXX
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C12H19NO2/c1-4-9-7-12(15-3)10(5-6-13)8-11(9)14-2/h7-8H,4-6,13H2,1-3H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VDRGNAMREYBIHA-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|changed|??}}
| CASNo = 71539-34-9
| PubChem = 24729233
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 21106222
| SMILES = COc1cc(CC)c(cc1CCN)OC
}}
| Section2 = {{Chembox Properties
| C=12 | H=19 | N=1 | O=2 
| Appearance = White crystals
| Density =
| MeltingPt =
| BoilingPt =
| Solubility = >70 mg/ml (20°C)
}}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
| Section4 = {{Chembox Pharmacology
| Legal_status = 
| Legal_BR = F2
| Legal_CA = Schedule III
| Legal_DE = Anlage I
| Legal_NZ = Class C
| Legal_UK = Class A
| Legal_US = Schedule I
 }}
}}

'''2C-E''' is a [[Chemistry:Psychedelic drug|psychedelic]] phenethylamine of the [[Chemistry:2C (psychedelics)|2C family]]. It was first synthesized by Alexander Shulgin<ref name=PiHKAL>{{CitePiHKAL}} [https://www.erowid.org/library/books_online/pihkal/pihkal024.shtml 2C-E in ''PiHKAL'']</ref> and documented in his book ''[[Chemistry:PiHKAL|PiHKAL]]''. Like the other substances in its family, it produces sensory and cognitive effects in its physical reactions with living organisms.<ref>{{cite journal |last1=Papaseit |first1=Esther |last2=Olesti |first2=Eulalia |last3=Pérez-Mañá |first3=Clara |last4=Torrens |first4=Marta |last5=Grifell |first5=Marc |last6=Ventura |first6=Mireia |last7=Pozo |first7=Oscar J. |last8=de Sousa Fernandes Perna |first8=Elizabeth B. |last9=Ramaekers |first9=Johannes G. |last10=de la Torre |first10=Rafael |last11=Farré |first11=Magí |date=2020 |title=Acute Effects of 2C-E in Humans: An Observational Study |journal=Frontiers in Pharmacology |volume=11 |page=233 |doi= 10.3389/fphar.2020.00233|doi-access=free |pmid=32256350 |pmc=7093582 |issn=1663-9812}}</ref>

==Properties==
[[File:MSpectro2C-E.gif|thumb|right|Mass Spectrometer Analysis: 2C-E]]
2,5-Dimethoxy-4-ethylphenethylamine is a colorless oil.  Crystalline forms are obtained as the amine salt by reacting the free base with a mineral acid, typically [[Chemistry:Hydrochloric acid|hydrochloric acid]] (HCl).

Shulgin does not report an exact boiling point for the free base, stating only that during one synthesis the fraction boiling between 90 and 100&nbsp;°C at 0.25&nbsp;mmHg pressure was collected and converted to the hydrochloride salt. Shulgin reports the melting point of the hydrochloride salt as 208.5–210.5&nbsp;°C.<ref name="shulginIndex">{{cite book|last1=Shulgin|first1=Alexander T.|last2=Manning|first2=Tania|last3=Daley|first3=Paul F.|title=The Shulgin Index: Volume 1|date=2011|publisher=Transform Press|location=Berkeley, CA|isbn=978-0-9630096-3-0|edition=First}}</ref>

==Effects==
[[File:ethylphenethylamine.jpg|thumb|right|20&nbsp;mg Capsules of 2C-E]]
[[File:2,5-dimethoxy-4-ethyl.jpg|thumb|right|2C-E Pile]]
According to Shulgin, the duration of 2C-E's effects is generally between six and ten hours for an average dose, with the plateau lasting between three and six hours.<ref name=PiHKAL/>

2C-E's effects are often described as "neutral", in comparison with other psychedelic chemicals and even other [[Chemistry:2C (psychedelics)|2C-x]] related molecules. In ''PiHKAL'', Shulgin states:
:"Here is another of the magical half-dozen. The range is purposefully broad. At 10 milligrams there have been some pretty rich +++<ref group="nb">Shulgin's +/- rating scale, per ''PiHKAL''. See References below. Quoting: "Plus Three (+++) = Not only are the chronology and the nature of a drug's action quite clear, but ignoring its action is no longer an option. The subject is totally engaged in the experience, for better or worse."</ref> experiences, and yet I have had the report from one young lady of a 30 milligram trial that was very frightening. My first experience with 2C-E was really profound, and it is the substance of a chapter within the story. Several people have said, about 2C-E, "I don't think I like it, since it isn't that much fun. But I intend to explore it again." There is something here that will reward the experimenter. Someday, the full character of 2C-E will be understood, but for the moment, let it rest as being a difficult and worth-while material. A very much worth-while material."

===Adverse effects===
Adverse effects include [[Medicine:Tachycardia|tachycardia]], [[Medicine:Hypertension|hypertension]],  [[Medicine:Psychomotor agitation|agitation]], [[Medicine:Delirium|delirium]], and [[Unsolved:Hallucination|hallucination]]s.<ref name=Topeff>{{cite journal | author1 = Topeff JM | author2 = Ellsworth H | author3 = Willhite LA | author4 = Bangh SA | author5 = Edwards EM | author6 = Cole JB | title = A case series of symptomatic patients, including one fatality, following 2C-E exposure | journal = Clin. Toxicol. | date = 2011 | volume = 49 | page = 526}}</ref>  At least two deaths have been attributed to a 2C-E overdose.<ref name=Topeff/><ref>{{cite news|last1=Pham|first1=Sherisse|title=Man Arrested in Mass Drug Overdose That Killed 1 Teen and Left 10 People Hospitalized|url=https://abcnews.go.com/US/man-arrested-minnesota-deadly-mass-drug-overdose/story?id=13166375|access-date=29 June 2014|work=ABC World News|date=18 March 2011}}</ref><ref name=Sacks>{{cite journal | author1 = Sacks J | author2 = Ray MJ | author3 = Williams S | author4 = Opatowsky MJ | title = Fatal toxic leukoencephalopathy secondary to overdose of a new psychoactive designer drug 2C-E ("Europa") | journal = Baylor University Medical Center Proceedings | date = 2012 | volume = 25 | issue = 4| pages = 374–376 | doi = 10.1080/08998280.2012.11928883 | pmid = 23077393 | pmc = 3448584 }}</ref>

==Drug prohibition laws==

===Australia===
In Queensland, 2C-E was added to the 'Dangerous Drugs' list of the 'Drugs Misuse Act 1986'<ref>{{cite web|url=https://www.legislation.qld.gov.au/LEGISLTN/CURRENT/D/DrugsMisuseA86.pdf|title=In force legislation - Queensland Legislation - Queensland Government|website=legislation.qld.gov.au|url-status=live|archive-url=https://web.archive.org/web/20140911060554/https://www.legislation.qld.gov.au/LEGISLTN/CURRENT/D/DrugsMisuseA86.pdf|archive-date=2014-09-11}}</ref> by the 'Drugs Misuse Amendment Act 2008'.<ref>{{cite web|url=https://www.legislation.qld.gov.au/LEGISLTN/ACTS/2008/08AC004.pdf|title=Acts as passed - Queensland Legislation - Queensland Government|website=legislation.qld.gov.au|url-status=live|archive-url=https://web.archive.org/web/20150407024051/https://www.legislation.qld.gov.au/LEGISLTN/ACTS/2008/08AC004.pdf|archive-date=2015-04-07}}</ref>  Making it illegal to produce, supply or possess.

===Canada===
As of October 31, 2016, 2C-E is a controlled substance (Schedule III) in Canada.<ref>{{cite periodical |url=http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php |periodical=Canada Gazette |volume=150 |issue=9 |title=Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines) |date=4 May 2016|url-status=live|archive-url=https://web.archive.org/web/20160831014117/http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php|archive-date=2016-08-31}}</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=China Food and Drug Administration | date=27 September 2015 | language=zh | access-date=1 October 2015 | archive-url=https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html | archive-date=1 October 2015 }}</ref>

===Denmark===
2C-E is added to the list of Schedule B controlled substances.<ref>{{cite web|url=https://www.retsinformation.dk/Forms/R0710.aspx?id=137169|title=Bekendtgørelse om euforiserende stoffer - retsinformation.dk<!-- Bot generated title -->|last=Sundheds- og Ældreministeriet|website=retsinformation.dk|url-status=live|archive-url=https://web.archive.org/web/20131004215445/https://www.retsinformation.dk/Forms/R0710.aspx?id=137169|archive-date=2013-10-04}}</ref>

===Germany===
2C-E is an [[Medicine:Drugs controlled by the German Betäubungsmittelgesetz|Anlage I]] controlled drug.

===New Zealand===
New Zealand has a catch-all Analogues section in Schedule 3 / Class C of their drug laws that would make [[Chemistry:2C-I|2C-I]], 2C-E, DOI, [[Chemistry:Ephedrine|ephedrine]], and [[Chemistry:Pseudoephedrine|pseudoephedrine]] Schedule 3 compounds in New Zealand.

=== Portugal ===
Portugal has decriminalized possession of all recreational drugs in quantities no more than a ten-day supply of that substance.{{CN|date=November 2023}} However production and distribution (buying/selling) are a criminal offense.

===Sweden===
''Sveriges riksdags'' health ministry {{ill|''Statens folkhälsoinstitut''|sv|Statens folkhälsoinstitut|vertical-align=sup}} classified 2C-E as "health hazard" under the act {{ill|''Lagen om förbud mot vissa hälsofarliga varor''|sv|Lagen om förbud mot vissa hälsofarliga varor|vertical-align=sup}} (translated ''Act on the Prohibition of Certain Goods Dangerous to Health'') as of Oct 1, 2004,  in their regulation '''SFS 2004:696''' listed as '''2,5-dimetoxi-4-etylfenetylamin (2C-E)''', making it illegal to sell or possess.<ref>{{cite web |url=http://www.notisum.se/rnp/sls/sfs/20040696.pdf |title=20040696 |access-date=2013-09-06 |url-status=live |archive-url=https://web.archive.org/web/20130929063316/http://www.notisum.se/rnp/sls/sfs/20040696.pdf |archive-date=2013-09-29 }}</ref>

===UK===
In the United Kingdom, 2C-E is a Class A controlled substance. The UK has the strictest laws in the EU on designer drugs. The Misuse Of Drugs Act was amended in 2002 to include a "catch most" clause outlawing every drug, and possible future drug, from the LSD ([[Chemistry:Ergoline|ergoline]]) and MDMA ([[Biology:Phenethylamine|phenethylamine]]) chemical families (including 2C-E). The amendment is a near verbatim quote from the books of the American biochemist Alexander Shulgin, who obtained a PhD from the University of California, Berkeley. Dr. Shulgin, a former research chemist at the Dow Chemical Company, re-discovered the synthesis for MDMA in 1976 and published the syntheses for more than 200 phenethylamine compounds of his own invention, and 55 tryptamine compounds many of which were also his own invention. The Shulgins were motivated to release the synthesis information as a way to protect the public's access to information about psychedelic compounds, a goal Alexander Shulgin has noted many times.

===United States===
As of July 9, 2012, in the {{wipe|United States}} 2C-E is a Schedule I substance under the Food and Drug Administration Safety and Innovation Act of 2012, making possession, distribution and manufacture illegal.<ref name="erowid-law">{{cite web|url=https://www.erowid.org/chemicals/2ce/2ce_law.shtml|title=Erowid 2C-E Vault: Legal Status|website=erowid.org|url-status=live|archive-url=https://web.archive.org/web/20151208043457/https://www.erowid.org/chemicals/2ce/2ce_law.shtml|archive-date=2015-12-08}}</ref>

==Notes==
<references group="nb" />

==References==
{{reflist}}

==External links==
* [https://www.mdma.net/uk/2005.html Project WebTryp, includes description of UK laws regarding Phenethylamines]
* [https://www.erowid.org/chemicals/2ce/ Erowid 2C–E vault]
* [https://web.archive.org/web/20140305212114/http://www.maps.org/t2e/c6.html Chapter in Myron J. Stolaroff's ''Thanatos To Eros, 35 Years of Psychedelic Exploration'' discussing author's experiments with 2C-E]

{{2C's}}
{{Hallucinogens}}
{{Serotonergics}}
{{Phenethylamines}}

[[Category:Designer drugs]]
[[Category:O-methylated phenols]]

{{Sourceattribution|2C-E}}