Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 4-HO-DET: Difference between pages

{{short description|Chemical compound}}

{{more citations needed|date=June 2013}}

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477221917

| IUPAC_name = 3-(2-Diethylaminoethyl)-1''H''-indol-4-ol

| legal_UK = Class A

| legal_DE = Anlage I

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 22204-89-3

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 7E0BR15575

| C=14 | H=20 | N=2 | O=1

| smiles = CCN(CC)CCc1c[nH]c2cccc(O)c12

'''4-HO-DET''', also known as '''4-hydroxy-diethyl-tryptamine''', '''CZ-74''', is a [[Psychedelics, dissociatives and deliriants|hallucinogenic drug]] and [[Psychedelic drug|psychedelic compound]] of moderate duration. 4-HO-DET is a [[substitution reaction|substituted]] [[tryptamine]], structurally related to [[psilocin]], [[ethocybin]], and [[4-HO-DIPT]].<ref name = "Greene_2021">{{cite book | vauthors = Greene SL | chapter = Tryptamines |veditors = Dargan PI, Wood DM |title=Novel Psychoactive Substances: Classification, Pharmacology and Toxicology |date=2021 |publisher=Academic Press |location=London, United Kingdom |isbn=978-0-12-819030-2 |page=499 |edition=Second | chapter-url=https://books.google.com/books?id=8WIFEAAAQBAJ&dq=4-HO-DET&pg=PA499}}</ref>

==Analogs==

4-HO-DET is the N,N-diethyl analog of psilocin. The [[acetic acid]] [[ester]] of 4-HO-DET is known as [[4-AcO-DET]] and the [[phosphoric acid]] ester of 4-HO-DET is known as 4-phosphoryloxy-DET, CEY-19, or [[ethocybin]]. These compounds may likely be [[Prodrug|prodrugs]] of 4-HO-DET as has been shown with the acetate and phospate esters of other methylated tryptamines such as psilocin.<ref>{{Cite journal | vauthors = Nichols DE |title=Improvements to the Synthesis of Psilocybin and a Facile Method for Preparing the O-Acetyl Prodrug of Psilocin |date=February 11, 1999 |url=http://www.thieme-connect.de/DOI/DOI?10.1055/s-1999-3490 |journal=Synthesis |volume=1999 |issue=6 |pages=935–938 |doi=10.1055/s-1999-3490|s2cid=32044725 }}</ref>

==History==

4-HO-DET received the lab code CZ-74 in the late 1950s by the inventors of the substance, [[Albert Hofmann]] and [[Franz Troxler]]. The substance was used together with its phosphoryloxy-analog ethocybin in human clinical trials in the 1960s by the German researchers [[Hanscarl Leuner]] and G. Baer.{{citation needed|date=June 2017}} It was later explored by Alexander Shulgin in his 1997 book ''[[TiHKAL]]''.<ref>{{CiteTiHKAL}}</ref>

==Dosage==

''[[TiHKAL]]'' reports moderate effects at 10–25&nbsp;mg ingested orally.<ref name="Shulgin_1997">{{cite web |url=http://isomerdesign.com/PiHKAL/read.php?id=16&domain=tk |title=#16 4-HO-DET | vauthors = Shulgin A, Shulgin A |publisher=Transform Press |date=September 1997 |website=Isomer Design |access-date=28 November 2023}}</ref>

==Effects==

4-HO-DET produces [[Psychedelic drug|psychedelic]] effects similar to [[LSD]] and [[psilocybin]].<ref name="Shulgin_1997" />

==Legality==

===United States===

4-HO-DET is unscheduled in the United States, but purchase, sale, or possession for human consumption could be prosecuted under the [[Federal Analogue Act]].<ref>{{Cite web |title=21 U.S. Code § 841 - Prohibited acts A |url=https://www.law.cornell.edu/uscode/text/21/841 |access-date=2016-08-02 |website=LII / Legal Information Institute |mode=cs2}}</ref>

===Sweden===

[[Riksdag|''Sveriges riksdags'']] health ministry [[:sv:Statens folkhälsoinstitut|''Statens folkhälsoinstitut'']] classified 4-HO-DET as "health hazard" under the act [[:sv:Lagen om förbud mot vissa hälsofarliga varor|''Lagen om förbud mot vissa hälsofarliga varor'']] (translated ''Act on the Prohibition of Certain Goods Dangerous to Health'') as of Nov 1, 2005, in their regulation SFS 2005:733 listed as 4-hydroxi-N,N-diethyltryptamin (4-HO-DET), making it illegal to sell or possess.<ref>{{cite web | title = Förordning om ändring i förordningen (1999:58) om förbud mot vissa hälsofarliga varor; | trans-title = Ordinance amending the ordinance (1999: 58) on the prohibition of certain dangerous goods; | language = sv | url = http://www.notisum.se/rnp/sls/sfs/20050733.pdf | date = 6 October 2005 | work = Svensk författningssamling (Swedish Code of Statutes) | access-date = 6 September 2013 | archive-date = 26 June 2021 | archive-url = https://web.archive.org/web/20210626164247/http://www.notisum.se/rnp/sls/sfs/20050733.pdf | url-status = dead }}</ref>

==See also==

* [[TiHKAL]]

* [[Indole]]s

==References==

{{reflist}}

==External links==

* [http://www.erowid.org/library/books_online/tihkal/tihkal16.shtml TiHKAL 4-HO-DET] information at [[Erowid]]

* [http://tihkal.info/read.php?domain=tk&id=16 4-HO-DET entry in TiHKAL • info]

* [http://www.erowid.org/chemicals/4_acetoxy_det/4_acetoxy_det_article1.shtml Ethacetin degradation]

{{Hallucinogens}}

{{Tryptamines}}

[[Category:Phenols]]

[[Category:Psychedelic tryptamines]]

[[Category:Designer drugs]]

[[Category:Diethylamino compounds]]