{{Short description|Chemical compound}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 452174790 | image = 2CD-5EtO structure.svg | image_class = skin-invert-image | width = 200px | image2 = 2CD-5EtO ball-and-stick structure.png | image_class2 = bg-transparent | width2 = 175px
<!-- Clinical data --> | tradename = | routes_of_administration = Oral<ref name="PiHKAL" /> | class = Psychoactive drug
<!-- Pharmacokinetic data --> | bioavailability = | protein_bound = | metabolism = | metabolites = | onset = ~2 hours (peak)<ref name="PiHKAL" /> | elimination_half-life = | duration_of_action = 12 hours<ref name="PiHKAL" /><ref name="Shulgin2003" /><ref name="JacobShulgin1994" /> | excretion =
<!-- Identifiers --> | CAS_number_Ref = {{cascite|changed|??}} | CAS_number = 1354634-32-4 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 8HT47SKY9C | PubChem = 57458864 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 26234937 | synonyms = 2C-D-5-EtO; 2CD-5-EtO; 5-Ethoxy-2-methoxy-4-methylphenethylamine; 2-Methoxy-5-ethoxy-4-methylphenethylamine; 4-Methyl-2-methoxy-5-ethoxyphenethylamine; 2-Methoxy-4-methyl-5-ethoxyphenethylamine
<!-- Chemical data --> | IUPAC_name = 1-(5-ethoxy-2-methoxy-4-methylphenyl)-ethan-1-amine | C=12 | H=19 | N=1 | O=2 | SMILES = CCOC1=CC(=C(C=C1C)OC)CCN | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C12H19NO2/c1-4-15-11-8-10(5-6-13)12(14-3)7-9(11)2/h7-8H,4-6,13H2,1-3H3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = ZMQDQUPRBYFPSO-UHFFFAOYSA-N }}
'''2CD-5EtO''', also known as '''5-ethoxy-2-methoxy-4-methylphenethylamine''', is a psychoactive drug of the phenethylamine, 2C, and TWEETIO families related to 2C-D.<ref name="PiHKAL">{{CitePiHKAL}} https://www.erowid.org/library/books_online/pihkal/pihkal023.shtml#:~:text=2CD%2D5ETO</ref><ref name="Shulgin2003">{{cite book | vauthors = Shulgin AT | veditors = Laing RR | chapter = Basic Pharmacology and Effects | title = Hallucinogens: A Forensic Drug Handbook | pages = 67–137 | year = 2003 | publisher = Elsevier Science | series = Forensic Drug Handbook Series | isbn = 978-0-12-433951-4 | url = https://books.google.com/books?id=l1DrqgobbcwC | chapter-url = https://bibliography.maps.org/resources/download/12634 | archive-url = https://web.archive.org/web/20250713013624/https://bibliography.maps.org/resources/download/12634 | archive-date = 13 July 2025 }}</ref><ref name="JacobShulgin1994">{{cite journal | vauthors = Jacob P, Shulgin AT | title = Structure-activity relationships of the classic hallucinogens and their analogs | journal = NIDA Research Monograph | volume = 146 | pages = 74–91 | date = 1994 | pmid = 8742795 | url = http://www.erowid.org/psychoactives/journals/psychoactives_journal8.shtml }}</ref> It is the analogue of 2C-D in which the methoxy group at the 5 position has been extended to an ethoxy group.<ref name="PiHKAL" /><ref name="Shulgin2003" /><ref name="JacobShulgin1994" />
In his book ''PiHKAL'' (''Phenethylamines I Have Known and Loved'') and other publications, Alexander Shulgin lists 2CD-5EtO's dose as 40 to 50{{nbsp}}mg orally, its onset as slow and gradual, its time to peak or full effects as about 2{{nbsp}}hours, and its duration as 12{{nbsp}}hours.<ref name="PiHKAL" /><ref name="Shulgin2003" /><ref name="JacobShulgin1994" /> The effects of 2CD-5EtO were said to include being "largely free from excitement", having "a friendly openness and outgoingness that allowed easy talk, interaction, humor", and allowing for healthy appetite.<ref name="PiHKAL" />
The chemical synthesis of 2CD-5EtO has been described.<ref name="PiHKAL" />
2CD-5EtO was first described in the literature by Alexander Shulgin in his book ''PiHKAL'' (''Phenethylamines I Have Known and Loved'') in 1991.<ref name="PiHKAL" /> It was developed and tested by Darrell Lemaire, with publication via personal communication with Shulgin.<ref name="Shulgin2003" /><ref name="Erowid-Lemaire">{{cite web | title = Erowid Darrell Lemaire Vault | website = erowid.org | url = https://erowid.org/culture/characters/lemaire_darrell/lemaire_darrell.shtml | access-date = 14 November 2025 }}</ref><ref name="Morris2016-S01E06">{{cite episode | title = The Lazy Lizard School of Hedonism | issue = 6 | date = 7 December 2016 | credits = Morris H | series = Hamilton's Pharmacopeia | season = 1 | url = https://vimeo.com/546752807 | publisher = Vice Media | network = Viceland }}</ref><ref name="LemaireNez2010">{{cite book | vauthors = Nez H, Lemaire D | chapter = Notes About Psychoactive Compounds | title = Radiant Minds: Scientists Explore the Dimensions of Consciousness | pages = 201–207 | date = 2010 | veditors = Targ R, Radin D | publisher = Millay | isbn = 978-0-615-29633-3 | url = https://books.google.com/books?id=bF-jcQAACAAJ | chapter-url = https://erowid.org/culture/characters/lemaire_darrell/lemaire_darrell_article1.pdf }}</ref><ref name="LazarNez1990">{{cite book | author1 = Lazar (Darrell Lemaire) | author2 = Hosteen Nez | title = Certain Exotic Transmitters as Smart Pills or Compounds that Increase the Capacity for Mental Work in Humans: A Story About LAZAR as Told by Hosteen Nez | edition = 2nd | date = 1990 | url = https://erowid.org/chemicals/2cd/2cd_smartpills1.pdf | archive-url = https://web.archive.org/web/20010709231503/http://www.erowid.org/chemicals/2cd/2cd_smartpills1.shtml | archive-date = 9 July 2001}}</ref> 2CD-5EtO is a controlled substance in Canada under phenethylamine blanket-ban language.<ref name="CDSA">{{cite web | title=Controlled Drugs and Substances Act | website=Department of Justice Canada | url=https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html | access-date=19 January 2026}}</ref>
==See also== * TWEETIO (psychedelics) * Iris (DOM-5ETO)
==References== {{Reflist}}
==External links== * [https://isomerdesign.com/pihkal/explore/205 2CD-5ETO - Isomer Design] * [https://www.erowid.org/library/books_online/pihkal/pihkal023.shtml#:~:text=2CD%2D5ETO 2C-D (also discusses 2CD-5-ETO) - PiHKAL - Erowid] * [https://isomerdesign.com/pihkal/read/pk/23#205 2C-D (also discusses 2CD-5-ETO) - PiHKAL - Isomer Design]
{{Phenethylamines}}
Category:2C (psychedelics) Category:Ethoxy compounds Category:Methoxy compounds Category:Methyl compounds Category:Psychoactive drugs Category:TWEETIO (psychedelics)