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{{SummarySheet}}
{{SubstanceBox/4-HO-DET}}
{{SubstanceBox/4-HO-DET}}
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| ''[[4-HO-DET/Summary|Summary sheet: 4-HO-DET]]''
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'''N,N-Diethyl-4-hydroxytryptamine'''  (abbreviated '''4-HO-DET'''; also known as '''4-hydroxy-N,N-diethyltryptamine''', '''CZ-74''', or '''Ethocin''') is a synthetic [[psychoactive class::psychedelic]] [[chemical class::tryptamine]] that is a close structural and functional analog of [[psilocin]] (4-HO-DMT), the principal psychoactive substance in [[magic mushrooms]]. It is notable for sharing many but of its core features while retaining variations in style and effects.


This compound was first discovered in the late 1950s by [[Albert Hofmann]] (famed inventor/discoverer of [[LSD]]) and Franz Troxler.<ref>Therapeutic indoles for psychic stimulation and relief of mental depression | http://www.google.com/patents/US3072530</ref><ref>United States Patent Office | https://www.erowid.org/archive/rhodium/pdf/psilocin.esters.pdf</ref> The substance was used together with its phosphoryloxy-analog [[4-PO-DET]] in human clinical trials in the 1960s by the German researchers Hanscarl Leuner and G. Baer.
'''4-Hydroxy-N,N-diethyltryptamine'''  (also known as '''4-HO-DET''', '''CZ-74''', and '''Ethocin''') is a lesser-known synthetic [[psychoactive class::psychedelic]] of the [[chemical class::tryptamine]] chemical class that produces [[psilocin]]-like [[psychedelic]] effects when [[Routes of administration|adminstered]]. 4-HO-DET is a close structural and functional analog of [[psilocin]] (4-HO-DMT), the principal psychoactive component in [[magic mushrooms]]. It is notable for sharing many of its core features while retaining subtle variations in its duration, visual, cognitive and bodily effects.


As a psychedelic, 4-HO-DET remains relatively uncommon and has very little documentation of human usage. Today it is either used as a recreational substance or an [[entheogen]]. It is almost never available on the street and primarily acquired through the use of online [[research chemical]] vendors.
This compound was first discovered in the late 1950s by [[wikipedia:Albert Hofmann|Albert Hofmann]] and Franz Troxler<ref>{{cite web|title=US Patent 3072530 -  Therapeutic indoles for psychic stimulation and relief of mental depression|url=https://patents.google.com/patent/US3072530/en|access-date=July 18, 2020|website=Google Patents}}</ref><ref>{{cite web|url=https://www.erowid.org/archive/rhodium/pdf/psilocin.esters.pdf|publisher=United States Patent Office|title=Esters of Indoles|date=January 29, 1963|id=3,075,992}}</ref> in their investigation of various [[psychedelic]] compounds that were structurally and chemically related to the principle active components he isolated from [[magic mushrooms]], [[psilocybin]] ('''4-PO-DMT''') and [[psilocin]] ('''4-HO-DMT'''). The substance was used together with its phosphoryloxy-analog [[wikipedia:4-PO-DET|4-PO-DET]] in human clinical trials in the 1960s by the German researchers Hanscarl Leuner <ref>"Psycholytische Therapie nach Hanscarl Leuner – Grundlagen, Praxis, Perspektiven" (in German), Torsten Passie, Michael Schlichting, Ralf Bolle (published September, 2023).</ref> and G. Baer.
 
Since its inception, 4-HO-DET has remained relatively uncommon and has very little documentation of human usage, with the majority of [[psychedelic]] users preferring more traditional [[psychedelics]] like the [[psilocybin]] and [[psilocin]] in [[psilocybin mushrooms]], or more recently, [[4-AcO-DMT]]. Today, it is either used as a recreational substance or an [[entheogen]], has no documentation of being sold on the streets and is primarily acquired through the use of online [[research chemical]] vendors.


==Chemistry==
==Chemistry==
4-HO-DET, or 4-hydroxy-N,N-diethyltryptamine, is a synthetic indole alkaloid molecule of the [[tryptamine]] class. Tryptamines share a core structure comprised of a bicylic indole heterocycle attached at R<sub>3</sub> to an amino group via an ethyl side chain. 4-HO-DET is substituted at R<sub>4</sub> of its indole heterocycle with a hydroxyl functional group OH−. It also contains two ethyl chains bound to the terminal amine R<sub>N</sub> of its tryptamine backbone ([[DET]]).  
4-HO-DET, or 4-hydroxy-N,N-diethyltryptamine, is a synthetic indole alkaloid molecule of the [[tryptamine]] chemical class. Tryptamines share a core structure comprised of a bicyclic indole heterocycle attached at R<sub>3</sub> to an amino group via an ethyl side chain. 4-HO-DET is substituted at R<sub>4</sub> of its indole heterocycle with a hydroxyl functional group OH−. It also contains two ethyl chains bound to the terminal amine R<sub>N</sub> of its tryptamine backbone ([[DET]]).  


4-HO-DET is a 4-hydroxy analogue of [[4-AcO-DET]] and the N-substituted diethyl homolog of [[4-HO-DMT]].
4-HO-DET is the lower homolog of [[4-AcO-DET]], the N-substituted diethyl homolog of [[4-HO-DMT]] ('''psilocin''') and the 4-hydroxy analog of [[DET]].


==Pharmacology==
==Pharmacology==
{{Further|Serotonergic psychedelic}}
{{Further|Serotonergic psychedelic}}
4-HO-DET acts as a [[Serotonin#The_5-HT_system|5-HT<sub>2A</sub>]] [[Agonist#Agonists|partial agonist]]. The [[psychedelic]] effects are believed to come from 4-HO-DET's efficacy at the 5-HT<sub>2A</sub> receptors. However, the role of these interactions and how they result in the psychedelic experience continues to remain elusive.
As with its structurally related tryptamines, 4-HO-DET principally acts as a [[Serotonin#The_5-HT_system|5-HT<sub>2A</sub>]] [[Agonist#Agonists|partial agonist]], through which it exerts its psychedelic effects.{{citation needed}}
 
However, the role of these interactions and how they result in the psychedelic experience continues to remain an object of scientific elucidation.


==Subjective effects==
==Subjective effects==
{{effectStub}}
{{effectStub}}
In comparison to other isolated synthetic [[tryptamine]] compounds such as [[4-AcO-DMT]] and [[4-HO-DMT]], [[4-HO-DET]] has been reported as being similar in terms of its visual, cognitive and physical effects, albeit with a slightly longer duration, less in the way of bodily effects, and more "synthetic" or "algorithmic"-style visuals.
{{Preamble/SubjectiveEffects}}
{{Preamble/SubjectiveEffects}}
 
{{effects/base
In comparison to other [[tryptamine]]s such as [[4-AcO-DMT]] and [[4-HO-DMT]] it is extremely similar in terms of its visual, cognitive and physical effects although it feels somewhat less natural and slightly more synthetic.
|{{effects/physical|
===Physical effects===
*'''[[Effect::Spontaneous physical sensations]]'''
*'''[[Effect::Spontaneous tactile sensations]]'''
*'''[[Effect::Tactile enhancement]]'''
*'''[[Effect::Stimulation]]'''
*'''[[Effect::Temperature regulation suppression]]'''
*'''[[Effect::Bodily control enhancement]]'''
*'''[[Effect::Bodily control enhancement]]'''
*'''[[Effect::Increased heart rate]]'''
*'''[[Effect::Increased heart rate]]'''
*'''[[Effect::Nausea]]'''
*'''[[Effect::Excessive yawning]]'''  - This effect seems to be uniquely pronounced among psilocin and related tryptamines. It can occur to a lesser degree on LSD and very rarely on psychedelic phenethylamines like mescaline. It typically occurs in combination with watery eyes. However, many anecdotal reports suggest that this component is not as noticeable compared to the aforementioned psychedelics
*'''[[Effect::Watery eyes]]'''
*'''[[Effect::Frequent urination]]'''
*'''[[Effect::Muscle contractions]]'''
*'''[[Effect::Olfactory hallucination]]'''
*'''[[Effect::Pupil dilation]]'''
*'''[[Effect::Pupil dilation]]'''
*'''[[Effect::Tactile enhancement]]'''
*'''[[Effect::Runny nose]]'''
*'''[[Effect::Salivation]]'''


===Cognitive effects===
}}
The cognitive effects of 4-HO-DET can be described as relaxing and stoning in style when compared to other commonly used psychedelics such as [[LSD]] or [[2C-B]] which tend to be energetic and stimulating.
 
The most prominent of these typical effects generally include:
*'''[[Effect::Analysis enhancement]]'''
*'''[[Effect::Conceptual thinking]]'''
*'''[[Effect::Delusions]]'''
*'''[[Effect::Emotion enhancement]]'''
*'''[[Effect::Immersion enhancement]]'''
*'''[[Effect::Increased music appreciation]]'''
*'''[[Effect::Memory suppression]]'''
**'''[[Effect::Ego death]]'''
*'''[[Effect::Novelty enhancement]]'''
*'''[[Effect::Personal bias suppression]]'''
*'''[[Effect::Thought acceleration]]'''
*'''[[Effect::Thought loops]]'''
*'''[[Effect::Time distortion]]'''
*'''[[Effect::Unity and interconnectedness]]'''
*'''[[Effect::Wakefulness]]'''


===Visual effects===
{{effects/visual|
====Enhancements====
====Enhancements====
*'''[[Effect::Colour enhancement]]'''
*'''[[Effect::Colour enhancement]]'''
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====Distortions====
====Distortions====
*'''[[Effect::Drifting]]''' ''([[Drifting#Melting|melting]], [[Drifting#Breathing|breathing]], [[Drifting#Morphing|morphing]] and [[Drifting#Flowing|flowing]])''
*'''[[Effect::Drifting]]''' ''([[Drifting#Melting|melting]], [[Drifting#Breathing|breathing]], [[Drifting#Morphing|morphing]] and [[Drifting#Flowing|flowing]])''
*'''[[Effect::Tracers]]'''
*'''[[Effect::Colour tinting]]'''
*'''[[Effect::Colour shifting]]'''
*'''[[Effect::Colour shifting]]'''
*'''[[Effect::Depth perception distortions]]'''
*'''[[Effect::Depth perception distortions]]'''
*'''[[Effect::Perspective distortions]]'''
*'''[[Effect::Perspective distortions]]'''
*'''[[Effect::Symmetrical texture repetition]]'''
*'''[[Effect::Symmetrical texture repetition]]'''
*'''[[Effect::Tracers]]'''


====[[Effect::Geometry]]====
====[[Effect::Geometry]]====
The visual geometry that is present throughout this trip can be described as more similar in appearance to that of [[Psilocin]], [[ayahuasca]] and [[2C-E]] than [[LSD]] or [[2C-B]]. It can be comprehensively described through its [[Visual_effects:_Geometry#Variations|variations]] as intricate in complexity, abstract in form, mostly synthetic in style, unstructured in organization, brightly lit and multicolored in scheme, glossy in shading, sharp in edges, large in size, slow in speed, smooth in motion, equally rounded and angular in corners, non-immersive in depth and consistent in intensity. They have a very "natural" feel to them and at higher dosages are significantly more likely to result in states of [[Effect::Level 8B]] visual geometry over [[Level 8A]].
The visual geometry that is present throughout this trip can be described as more similar in appearance to that of [[psilocin]], [[ayahuasca]] and [[2C-T-7]] than [[LSD]] or [[2C-B]]. It can be comprehensively described through its [[Visual_effects:_Geometry#Variations|variations]] as intricate in complexity, abstract in form, mostly synthetic in style, unstructured in organization, dimly lit and monotone in scheme, glossy in shading, sharp in edges, large in size, slow in speed, smooth in motion, equally rounded and angular in corners, non-immersive in-depth and consistent in intensity. They have a notably "synthetic" feel to them and at higher dosages are significantly more likely to result in states of [[Effect::Level 8B]] visual geometry over [[Level 8A]].


====Hallucinatory states====
====Hallucinatory states====
*'''[[Effect::Machinescapes]]'''
*'''[[Effect::Transformations]]'''
*'''[[Effect::Transformations]]'''
*'''[[Effect::Internal hallucinations]]''' (''[[effect::autonomous entities]]''; ''[[effect::settings, sceneries, and landscapes]]''; ''[[effect::alterations in perspective]]'' and ''[[effect::scenarios and plots]]'')
*'''[[Effect::Internal hallucination]]''' (''[[effect::autonomous entities]]''; ''[[effect::settings, sceneries, and landscapes]]''; ''[[effect::perspective hallucinations]]'' and ''[[effect::scenarios and plots]]'')
*'''[[Effect::External hallucination]]''' (''[[effect::autonomous entities]]''; ''[[effect::settings, sceneries, and landscapes]]''; ''[[effect::perspective hallucinations]]'' and ''[[effect::scenarios and plots]]'')
 
}}
 
|{{effects/cognitive|
The cognitive effects of 4-HO-DET can be described as mildly more stimulating and lucid in style when compared to other similar psychedelics such as [[psilocybin]] or [[2C-C]] which tend to be more sedating. It has also been characterized as possessing a more "neutral", "analytical" headspace with minimal memory disruptions or emotional confusion compared to [[psilocybin mushrooms]].
 
The most prominent of these typical effects generally include:
*'''[[Effect::Analysis enhancement]]'''
*'''[[Effect::Conceptual thinking]]'''
*'''[[Effect::Immersion enhancement]]'''
*'''[[Effect::Increased music appreciation]]'''
*'''[[Effect::Increased sense of humor]]'''
**'''[[Effect::Laughter fits]]'''
*'''[[Effect::Memory suppression]]'''
**'''[[Effect::Ego death]]'''
*'''[[Effect::Novelty enhancement]]'''
*'''[[Effect::Personal bias suppression]]'''
*'''[[Effect::Thought acceleration]]'''
*'''[[Effect::Thought connectivity]]'''
*'''[[Effect::Thought loops]]'''
*'''[[Effect::Time distortion]]'''
*'''[[Effect::Wakefulness]]'''
 
}}


===Auditory effects===
{{effects/auditory|
*'''[[Effect::Auditory enhancement|Enhancements]]'''
*'''[[Effect::Auditory enhancement|Enhancements]]'''
*'''[[Effect::Auditory distortion|Distortions]]'''
*'''[[Effect::Auditory distortion|Distortions]]'''
*'''[[Effect::Auditory hallucinations|Hallucinations]]'''
*'''[[Effect::Auditory hallucinations|Hallucinations]]'''
}}
}}


===Experience reports===
===Experience reports===
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{{#ask: [[Category:4-HO-DET]][[Category:Experience]]|format=ul|Columns=1}}
{{#ask: [[Category:4-HO-DET]][[Category:Experience]]|format=ul|Columns=1}}
Additional experience reports can be found here:
Additional experience reports can be found here:
* [https://www.erowid.org/experiences/subs/exp_4HODET.shtml Erowid Experience Vaults: 4-HO-DET]
 
*[https://www.erowid.org/experiences/subs/exp_4HODET.shtml Erowid Experience Vaults: 4-HO-DET]


==Toxicity and harm potential==
==Toxicity and harm potential==
{|  
{{further|Research chemicals#Toxicity and harm potential|Responsible use #Hallucinogens}}
|-
The toxicity and long-term health effects of recreational 4-HO-DET use do not seem to have been studied in any scientific context and the exact [[Toxicity::toxic dose is unknown]]. This is because 4-HO-DET is a [[research chemical]] with very little history of human usage. Anecdotal evidence from people within the psychonaut community who have tried 4-HO-DET suggests that there are no negative health effects attributed to simply trying the substance by itself at low to moderate doses and using it sparingly (but nothing can be completely guaranteed). [https://www.google.com/ Independent research] should always be done to ensure that a combination of two or more substances is safe before consumption.
| [[File:Lolol.png|17px]]''Main articles: [[Research chemicals#Toxicity and harm potential|Research chemicals § Toxicity and harm potential]]'' ''&'' ''[[Responsible use #Hallucinogens|Responsible use § Hallucinogens]]''
 
|}
It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this substance.
The toxicity and long-term health effects of recreational 4-HO-DET use do not seem to have been studied in any scientific context and the exact [[Toxicity::toxic dose is unknown]]. This is because 4-HO-DET is a [[research chemical]] with very little history of human usage. Anecdotal evidence from people within the psychonaut community who have tried 4-HO-DET suggests that there are no negative health effects attributed to simply trying the drug by itself at low to moderate doses and using it very sparingly (but nothing can be completely guaranteed). [https://www.google.com/ Independent research] should always be done to ensure that a combination of two or more substances is safe before consumption.  


It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this drug.
===Tolerance and addiction potential===
===Tolerance and addiction potential===
4-HO-DET is [[Addiction potential::not habit-forming]] and the desire to use it can actually decrease with use. It is most often self-regulating.  
4-HO-DET is [[Addiction potential::not habit-forming]] and the desire to use it can actually decrease with use. It is most often self-regulating.  


Tolerance to the effects of 4-HO-DET are built [[Time to full tolerance::almost immediately after ingestion]]. After that, it takes about [[Time to half tolerance::3 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::7 days]] to be back at baseline (in the absence of further consumption). 4-HO-DET presents cross-tolerance with [[Cross-tolerance::all [[psychedelic]]s]], meaning that after the consumption of 4-HO-DET all psychedelics will have a reduced effect.
Tolerance to the effects of 4-HO-DET is built [[Time to full tolerance::almost immediately after ingestion]]. After that, it takes about [[Time to half tolerance::3 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::7 days]] to be back at baseline (in the absence of further consumption). 4-HO-DET presents cross-tolerance with [[Cross-tolerance::all [[psychedelic]]s]], meaning that after the consumption of 4-HO-DET all psychedelics will have a reduced effect.


==Legal issues==
===Dangerous interactions===
{{DangerousInteractions/Intro}}
{{DangerousInteractions/Psychedelics}}
 
==Legal status==
{{legalStub}}
{{legalStub}}
*'''United Kingdom''' - It is illegal to produce, supply, or import this drug under the Psychoactive Substance Act, which came into effect on May 26th, 2016.<ref>Psychoactive Substances Act 2016 (Legislation.gov.uk) | http://www.legislation.gov.uk/ukpga/2016/2/contents/enacted</ref>
 
*'''United States''' - 4-HO-DET is unscheduled in the United States. It may be considered an analog of [[psilocin]] (''4-HO-DMT'') which is a Schedule I drug under the Controlled Substances Act. As such, the sale for human consumption or the use for illicit non-medical or industrial intents and purposes could be prosecuted as crimes under the Federal Analog Act.
*'''Germany''': 4-HO-DET is controlled under Anlage I BtMG<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> (''Narcotics Act, Schedule I''), former: Opiumgesetz (''Opium Act'') as of February 25, 1967.<ref>{{cite web|url=http://www.bgbl.de/xaver/bgbl/start.xav?startbk=Bundesanzeiger_BGBl&jumpTo=bgbl167s0197.pdf|title=Vierte Verordnung über die den Betäubungsmitteln gleichgestellten Stoffe|publisher=Bundesanzeiger Verlag|work=Bundesgesetzblatt Teil I: 1967 Nr. 10|publication-date=February 24, 1967|language=de|issn=0341-1095|page=197|}}</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>
*'''Sweden''' - 4-HO-DET is classified as a health hazard under the Act on the Prohibition of Certain Goods Dangerous to Health as of November 1, 2005 in the regulation SFS 2005:733, making it illegal to sell or possess.<ref>Svensk författningssamling | http://www.notisum.se/rnp/sls/sfs/20050733.pdf</ref>
*'''Sweden:''' 4-HO-DET is classified as a health hazard under the Act on the Prohibition of Certain Goods Dangerous to Health as of November 1, 2005 in the regulation SFS 2005:733, making it illegal to sell or possess.<ref>{{cite web|title=Svensk författningssamling Förordning om ändring i förordningen (1999:58) om förbud mot vissa hälsofarliga varor|url=http://www.notisum.se/rnp/sls/sfs/20050733.pdf|id=SFS 2005:733|language=sv|date=October 6, 2005|publication-date=October 18, 2005|}}</ref>
*'''Switzerland''': 4-HO-DET 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''': 4-HO-DET is a Class A drug in the United Kingdom as a result of the tryptamine 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''': 4-HO-DET is unscheduled in the United States. It may be considered an analogue of [[psilocin]] (''4-HO-DMT'') which is a Schedule I drug under the Controlled Substances Act. As such, the sale for human consumption or the use for illicit non-medical or industrial intents and purposes could be prosecuted as crimes under the Federal Analogue Act.{{citation needed}}


==See also==
==See also==
*[[Responsible use]]
*[[Responsible use]]
*[[Research chemical]]
*[[Research chemical]]
*[[Psychedelic]]
*[[Psychedelic]]
*[[Tryptamine]]
*[[Tryptamine]]
*[[DET]]
*[[4-AcO-DET]]
*[[4-AcO-DET]]
*[[4-HO-DMT]]
*[[4-HO-DMT]]
*[[4-HO-MET]]
*[[4-HO-MET]]
*[[DET]]


==External links==
==External links==
*[https://en.wikipedia.org/wiki/4-HO-DET 4-HO-DET (Wikipedia)]
*[https://en.wikipedia.org/wiki/4-HO-DET 4-HO-DET (Wikipedia)]
*[https://www.erowid.org/library/books_online/tihkal/tihkal16.shtml 4-HO-DET (TiHKAL)]
*[https://isomerdesign.com/PiHKAL/read.php?domain=tk&id=16 4-HO-DET  (TiHKAL / Isomer Design)]
*[https://isomerdesign.com/PiHKAL/explore.php?id=5057 4-HO-DET phosphate ester (Isomer Design)]
*[http://www.bluelight.org/vb/threads/480200-The-Big-amp-Dandy-4-HO-DET-Thread 4-HO-DET (Bluelight)]
*[http://www.bluelight.org/vb/threads/480200-The-Big-amp-Dandy-4-HO-DET-Thread 4-HO-DET (Bluelight)]
*[http://www.erowid.org/chemicals/4_acetoxy_det/4_acetoxy_det_article1.shtml 4-AcO-DET degradation (Erowid)]


==References==
==References==
<references/>
<references />
 
[[Category:Substance]]
[[Category:Psychoactive substance]]
[[Category:Psychoactive substance]]
[[Category:Research chemical]]
[[Category:Hallucinogen]]
[[Category:Psychedelic]]
[[Category:Psychedelic]]
[[Category:Tryptamine]]
[[Category:Tryptamine]]
[[Category:Research chemical]]
{{#set:Featured=true}}
{{#set:Featured=true}}
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