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{{Short description|Psychedelic drug}}
{{Drugbox
| Verifiedfields = verified
| Watchedfields = verified
| verifiedrevid = 477221917
| image = 4-HO-DET.svg
| image_class = skin-invert-image
| width = 225px
| image2 = 4-HO-DET-3d-sticks.png
| image_class2 = bg-transparent
| width2 = 225px


| tradename =
| pregnancy_AU =
| pregnancy_US =
| pregnancy_category =
| routes_of_administration = [[Oral administration|Oral]]<ref name="Shulgin_1997" />
| class = [[Serotonin receptor agonist]]; [[Serotonin]] [[5-HT2A receptor|5-HT2A receptor]] [[agonist]]; [[Serotonergic psychedelic]]; [[Hallucinogen]]
| ATC_prefix = None
| ATC_suffix =


| legal_AU =
| legal_CA =
| legal_UK = Class A
| legal_US =
| legal_DE = Anlage I


| bioavailability =
| protein_bound =
| metabolism =
| onset = 30–45 minutes<ref name="Shulgin_1997" />
| elimination_half-life =
| duration_of_action = 2–6 hours<ref name="Shulgin_1997" /><ref name="Shulgin1976" /><ref name="RossFrancoReiff2021" />
| excretion =


| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 22204-89-3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 7E0BR15575
| PubChem = 9991554
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 8167136
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 143202
| synonyms = 4-Hydroxy-DET; 4-OH-DET; 4-Hydroxy-''N'',''N''-diethyltryptamine; Ethocin; CZ-74; CZ74


| IUPAC_name = 3-(2-diethylaminoethyl)-1''H''-indol-4-ol
| C=14 | H=20 | N=2 | O=1
| SMILES = CCN(CC)CCc1c[nH]c2cccc(O)c12
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C14H20N2O/c1-3-16(4-2)9-8-11-10-15-12-6-5-7-13(17)14(11)12/h5-7,10,15,17H,3-4,8-9H2,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = OHHYMKDBKJPILO-UHFFFAOYSA-N


| melting_point = 104
| melting_high = 106
}}

'''4-HO-DET''', also known as '''4-hydroxy-''N'',''N''-diethyltryptamine''' as well as '''ethocin''' or '''CZ-74''', is a [[psychedelic drug]] of the [[substituted tryptamine|tryptamine]] and [[substituted 4-hydroxytryptamine|4-hydroxytryptamine]] families related to [[psilocin]] (4-HO-DMT).<ref name="Shulgin_1997" /> It is taken [[oral administration|orally]].<ref name="Shulgin_1997" />

The drug acts as a [[binding selectivity|non-selective]] [[serotonin receptor agonist]], including of the [[serotonin]] [[5-HT2A receptor|5-HT2A receptor]] among others.<ref name="KozellEshlemanSwanson2023" /><ref name="KleinChathaLaskowski2021" /><ref name="GlatfelterNaeemPham2023" /> It produces psychedelic-like effects in animals.<ref name="KleinChathaLaskowski2021" /> 4-HO-DET is closely [[structural analog|structurally related]] to other psychedelic tryptamines such as psilocin, [[diethyltryptamine]] (DET), and [[4-HO-MET]].<ref name="Shulgin_1997" /><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> [[Ethocybin]] (4-PO-DET; CEY-19) and [[4-AcO-DET]] are assumed to act as [[prodrug]]s of 4-HO-DET.<ref name="Shulgin_1997" /><ref name="KleinChathaLaskowski2021" />

4-HO-DET was first described in the literature by 1963.<ref name="US3075992" /><ref name="LeunerBaer1965" /><ref name="KleinChathaLaskowski2021" /> It was developed at [[Sandoz]] by [[Albert Hofmann]] and colleagues.<ref name="US3075992" /><ref name="KleinChathaLaskowski2021" /> The drug was studied in [[psychedelic-assisted psychotherapy]] by [[Hanscarl Leuner]] and colleagues in the 1960s.<ref name="Passie2022" /><ref name="Shulgin_1997" /><ref name="LeunerBaer1965" /> Later, it was described further by [[Alexander Shulgin]] in his 1997 book ''[[TiHKAL]]'' (''Tryptamines I Have Known and Loved'').<ref name="Shulgin_1997" /> 4-HO-DET was encountered as a novel [[designer drug]] in 2005.<ref name="EMCDDA2005" />

==Use and effects==
In his book ''[[TiHKAL]]'' (''Tryptamines I Have Known and Loved'') and other publications, [[Alexander Shulgin]] variably lists the dose range of 4-HO-DET as 10 to 25{{nbsp}}mg [[oral administration|orally]], either as 4-HO-DET itself or as presumed [[prodrug]]s like [[ethocybin]] (4-PO-DET) or [[4-AcO-DET]], and its [[duration of action|duration]] as 2 to 6{{nbsp}}hours.<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><ref name="HalberstadtChathaKlein2020">{{cite journal | vauthors = Halberstadt AL, Chatha M, Klein AK, Wallach J, Brandt SD | title = Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species | journal = Neuropharmacology | volume = 167 | issue = | article-number = 107933 | date = May 2020 | pmid = 31917152 | pmc = 9191653 | doi = 10.1016/j.neuropharm.2019.107933 | url = http://usdbiology.com/cliff/Courses/Advanced%20Seminars%20in%20Neuroendocrinology/Serotonergic%20Psychedelics%2020/Halberstadt%2020%20Neuropharm%20potency%20of%20hallucinogens%20%20head-twitch.pdf | quote = Table 4 Human potency data for selected hallucinogens. [...] }}</ref><ref name="Shulgin1976" /><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 | issue = | pages = 74–91 | date = 1994 | pmid = 8742795 | doi = | url = https://bitnest.netfirms.com/external/Books/NIDA146.74 }}</ref><ref name="Shulgin2003">{{cite book | vauthors = Shulgin AT | chapter=Basic Pharmacology and Effects | pages=67–137 | veditors = Laing RR | title=Hallucinogens: A Forensic Drug Handbook | publisher=Elsevier Science | series=Forensic Drug Handbook Series | year=2003 | isbn=978-0-12-433951-4 | url=https://books.google.com/books?id=l1DrqgobbcwC | chapter-url=https://web.archive.org/web/20250223164514/https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=6bb3a7499da8e9852b39cd4db16891147c83f5c6}}</ref><ref name="Passie2022" /><ref name="RossFrancoReiff2021" /> Threshold effects are said to occur at doses of 5 to 15{{nbsp}}mg, whereas loss of contact with reality is said to occur at doses over 30{{nbsp}}mg.<ref name="GlennonRosecrans1982">{{cite journal | vauthors = Glennon RA, Rosecrans JA | title = Indolealkylamine and phenalkylamine hallucinogens: a brief overview | journal = Neuroscience and Biobehavioral Reviews | volume = 6 | issue = 4 | pages = 489–497 | date = 1982 | pmid = 6757811 | doi = 10.1016/0149-7634(82)90030-6 }}</ref><ref name="Shulgin1976" /> However, strong effects have also been reported at a dose of 15{{nbsp}}mg of ethocybin.<ref name="Shulgin_1997" /> A typical dose estimate has been reported to be around 17.5{{nbsp}}mg.<ref name="HalberstadtChathaKlein2020" /> The [[onset of action|onset]] of 4-HO-DET is described as being around 30 to 45{{nbsp}}minutes.<ref name="Shulgin_1997" />

The drug has been reported to be very similar to [[psilocin]] and [[psilocybin]] in its qualitative effects but to be somewhat shorter in duration, for instance as short as 2 to 3{{nbsp}}hours.<ref name="Nichols2018">{{cite book | vauthors = Nichols DE | title = Chemistry and Structure-Activity Relationships of Psychedelics | series = Current Topics in Behavioral Neurosciences | volume = 36 | pages = 1–43 | date = 2018 | pmid = 28401524 | doi = 10.1007/7854_2017_475 | isbn = 978-3-662-55878-2 | url = https://bitnest.netfirms.com/external/10.1007/7854_2017_475 | quote = One of the earliest modifications of the tryptamines to be studied for psychoactive effects was the N,N-diethyl analogue of psilocin (CZ-74, 16). Both CZ-74 and its O-phosphoryl derivative CEY 19 (17) were studied in humans. Qualitatively, these compounds were very similar to psilocin and psilocybin, respectively, but had somewhat reduced durations of action (Leuner and Baer 1965).}}</ref><ref name="Shulgin1976">{{cite book | veditors=Gordon M | title=Psychopharmacological Agents: Use, Misuse and Abuse | series=Medicinal Chemistry: A Series of Monographs | volume=4 | vauthors = Shulgin AT | chapter=Psychotomimetic Agents | date=1976 | isbn=978-0-12-290559-9 | doi=10.1016/b978-0-12-290559-9.50011-9 | pages=59–146 | publisher=Academic Press | url=https://bitnest.netfirms.com/external/10.1016/B978-0-12-290559-9.50011-9 | quote= Although the N-dealkylated homologs are as yet untested clinically, the N,N-diethyl homologs of psilocybin and of psilocin have been studied in man (Leunder and Baer, 1965). These compounds [CEY-19, (XXXIII); CZ-74, (XXXIV)] in dosages of from 5 to 20 mg appear to resemble psilocybin in the qualitative nature of their action but to be of shorter duration. Maximum effects are obtained in an hour, and 2 hours later the subject is for the most part recovered, thus providing a valuable time course for psychiatric therapy.}}</ref><ref name="Passie2022" /><ref name="RossFrancoReiff2021" /> The effects of 4-HO-DET, either as 4-HO-DET itself or as presumed prodrugs, have been reported to include [[closed-eye visual]]s, [[open-eye visual]]s such as fire light turning into bursts of color, potential for intense [[psychedelic visual]]s, [[auditory hallucination]]s, [[time dilation]], temporal and [[spatial disorientation]], [[body image]] disturbance, [[music]]al immersion, [[derealization]], [[ego death]], feeling like one has ceased to exist, feelings of oneness with the universe or reality, [[ineffability]], "sparkly-ness", powerful emotions including feelings of intense love, peace, acceptance, awe, reverence, and joy, feelings of [[sadness]], uncomfortableness, and feeling overwhelmed.<ref name="Shulgin_1997" />

Other effects included feeling [[drug intoxication|intoxicated]], [[sedation]], [[psychomotor agitation|restlessness]], [[aphasia|loss of language ability]], [[impaired concentration]], compulsion to talk and interact with others, and lack of [[erotic]] feelings.<ref name="Shulgin_1997" /> At very high doses, effects including temporary [[psychosis]], [[depersonalization]], [[mystical experience]]s, [[delirium]], [[schizophrenia]]-like behavior, [[catatonia]], and [[paranoia]] have been found to occur.<ref name="Shulgin_1997" /> Physical effects have been reported to include [[stomach discomfort|stomach]] and [[abdominal discomfort]], [[appetite loss]], [[jaw tightening]], [[body tremor]]s, [[motor incoordination]], body disturbance, [[diuretic]] effects, and increased [[blood pressure]].<ref name="Shulgin_1997" />

== Interactions ==

{{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}

==Pharmacology==
===Pharmacodynamics===
{| class="wikitable floatright" style="font-size:small;"
|+ {{Nowrap|4-HO-DET activities}}
|-
! Target !! Affinity (Ki, nM)
|-
| [[5-HT1A receptor|5-HT1A]] || 396–1,840 (Ki) 1,030 ({{Abbrlink|EC50|half-maximal effective concentration}}) 80% ({{Abbrlink|Emax|maximal efficacy}})
|-
| [[5-HT1B receptor|5-HT1B]] || 2,242
|-
| [[5-HT1D receptor|5-HT1D]] || 585
|-
| [[5-HT1E receptor|5-HT1E]] || 568
|-
| [[5-HT2A receptor|5-HT2A]] || 269–400 (Ki) 6.5–296a ({{Abbr|EC50|half-maximal effective concentration}}) 80a–100% ({{Abbr|Emax|maximal efficacy}})
|-
| [[5-HT2B receptor|5-HT2B]] || 73 (Ki) 6.3 ({{Abbr|EC50|half-maximal effective concentration}}) 71% ({{Abbr|Emax|maximal efficacy}})
|-
| [[5-HT2C receptor|5-HT2C]] || 388–436 (Ki) 151a–264 ({{Abbr|EC50|half-maximal effective concentration}}) 80–83%a ({{Abbr|Emax|maximal efficacy}})
|-
| [[5-HT5A receptor|5-HT5A]] || 1,429
|-
| [[5-HT6 receptor|5-HT6]] || 230
|-
| [[5-HT7 receptor|5-HT7A]] || 826
|-
| [[Alpha-2A adrenergic receptor|α2A]]–[[Alpha-2C adrenergic receptor|α2C]]|| {{Abbr|IA|Inactive}}
|-
| [[Dopamine_receptor_D2|D2]]–[[Dopamine_receptor_D5|D5]]|| {{Abbr|IA|Inactive}}
|-
| [[Histamine H1 receptor|H1]] || 1,079
|-
| [[Histamine H2 receptor|H2]] || 9,984
|-
| [[Muscarinic_acetylcholine_receptor_M4|M4]] || {{Abbr|IA|Inactive}}
|-
| [[Sigma-1_receptor|σ1]] || {{Abbr|IA|Inactive}}
|-
| [[Sigma-2_receptor|σ2]] || 3,026
|-
| [[GRIN2B|NR2B]] || 8,720
|-
| {{Abbrlink|SERT|Serotonin transporter}} || 1,411–1,800 (Ki) 383 ({{Abbr|[[IC50|IC50]]|half-maximal inhibitory concentration}})
|-
| {{Abbrlink|DAT|Dopamine transporter}} || {{Abbr|IA|Inactive}}
|- class="sortbottom"
| colspan="2" style="width: 1px; background-color:var(--background-color-notice-subtle,#eaecf0); color:inherit; text-align: center;" | '''Notes:''' The smaller the value, the more avidly drug interacts with the site. '''Footnotes:''' a = Stimulation of {{Abbrlink|IP1|inositol phosphate|}} formation. '''Sources:''' <ref name="KozellEshlemanSwanson2023">{{cite journal | vauthors = Kozell LB, Eshleman AJ, Swanson TL, Bloom SH, Wolfrum KM, Schmachtenberg JL, Olson RJ, Janowsky A, Abbas AI | display-authors = 6 | title = Pharmacologic Activity of Substituted Tryptamines at 5-Hydroxytryptamine (5-HT)2A Receptor (5-HT2AR), 5-HT2CR, 5-HT1AR, and Serotonin Transporter | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 385 | issue = 1 | pages = 62–75 | date = April 2023 | pmid = 36669875 | pmc = 10029822 | doi = 10.1124/jpet.122.001454 }}</ref><ref name="KleinChathaLaskowski2021">{{cite journal | vauthors = Klein AK, Chatha M, Laskowski LJ, Anderson EI, Brandt SD, Chapman SJ, McCorvy JD, Halberstadt AL | display-authors = 6 | title = Investigation of the Structure-Activity Relationships of Psilocybin Analogues | journal = ACS Pharmacology & Translational Science | volume = 4 | issue = 2 | pages = 533–542 | date = April 2021 | pmid = 33860183 | pmc = 8033608 | doi = 10.1021/acsptsci.0c00176 | quote = Following the isolation of psilocybin and psilocin by Hofmann and colleagues in 1957,34 various 4-substituted tryptamines were reported in the literature. For example, Hofmann synthesized 4-hydroxy-N,N-diethyltryptamine (CZ-74, 4-HO-DET) and 4-phosphoryloxy-N,N-diethyltryptamine (CEY-19).75 Similar to psilocybin and psilocin, CEY-19 and CZ-74 have equivalent molar potencies in humans.3,50 }}</ref><ref name="GlatfelterNaeemPham2023">{{cite journal | vauthors = Glatfelter GC, Naeem M, Pham DN, Golen JA, Chadeayne AR, Manke DR, Baumann MH | title = Receptor Binding Profiles for Tryptamine Psychedelics and Effects of 4-Propionoxy-N,N-dimethyltryptamine in Mice | journal = ACS Pharmacology & Translational Science | volume = 6 | issue = 4 | pages = 567–577 | date = April 2023 | pmid = 37082754 | pmc = 10111620 | doi = 10.1021/acsptsci.2c00222 }}</ref><ref name="McKennaRepkeLo1990">{{cite journal | vauthors = McKenna DJ, Repke DB, Lo L, Peroutka SJ | title = Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes | journal = Neuropharmacology | volume = 29 | issue = 3 | pages = 193–198 | date = March 1990 | pmid = 2139186 | doi = 10.1016/0028-3908(90)90001-8 }}</ref>
|}

4-HO-DET acts as a [[potency (pharmacology)|potent]] [[binding selectivity|non-selective]] [[serotonin receptor agonist]], including of the [[serotonin]] [[5-HT2A receptor|5-HT2A]], [[5-HT2B receptor|5-HT2B]], and [[5-HT2C receptor|5-HT2C receptor]]s.<ref name="KozellEshlemanSwanson2023" /><ref name="KleinChathaLaskowski2021" /><ref name="GlatfelterNaeemPham2023" /> It may also act as a [[serotonin reuptake inhibitor]], with low [[affinity (pharmacology)|affinity]] but moderate potency.<ref name="KozellEshlemanSwanson2023" /> The drug showed no significant activity at various other assessed [[biological target|target]]s, including [[adrenergic receptor]]s ([[alpha-2A adrenergic receptor|α2A-]], [[alpha-2B adrenergic receptor|α2B]], [[alpha-2C adrenergic receptor|α2C]]), [[dopamine receptor]]s ([[D2 receptor|D2]]–[[D5 receptor|D5]]), [[muscarinic acetylcholine receptor]]s ([[muscarinic acetylcholine receptor M4|M4]]), and the [[dopamine transporter]] (DAT).<ref name="GlatfelterNaeemPham2023" />

It induces the [[head-twitch response]], a behavioral proxy of [[psychedelic drug|psychedelic]] effects, in rodents.<ref name="KleinChathaLaskowski2021" /> Its potency for inducing the head-twitch response in mice is approximately 2-fold lower than that of [[psilocin]].<ref name="KleinChathaLaskowski2021" />

==Chemistry==
4-HO-DET, also known as 4-hydroxy-''N'',''N''-diethyltryptamine, is a [[substituted tryptamine]] and [[substituted 4-hydroxytryptamine|4-hydroxytryptamine]].<ref name="Shulgin_1997" /> It is the 4-[[hydroxyl group|hydroxy]] [[chemical derivative|derivative]] of [[diethyltryptamine|''N'',''N''-diethyltryptamine]] (DET) and is a close [[structural analog|analogue]] of [[psilocin]] (4-hydroxy-''N'',''N''-dimethyltryptamine; 4-HO-DMT).<ref name="Shulgin_1997" />

===Synthesis===
The [[chemical synthesis]] of 4-HO-DET has been described.<ref name="Shulgin_1997" />

===Analogues===
4-HO-DET is the ''N'',''N''-[[ethyl group|diethyl]] [[structural analog|analogue]] of [[psilocin]] (4-HO-DMT).<ref name="Shulgin_1997" /> Other analogues of 4-HO-DET include [[diethyltryptamine]] (DET), [[5-MeO-DET]], [[4-HO-DPT]], [[4-HO-MET]], [[4-HO-EPT]], and [[5-HO-DET]], among others.<ref name="Shulgin_1997" /> The [[acetate]] [[ester]] of 4-HO-DET is known as [[4-AcO-DET]] and the [[phosphate]] ester is known as [[ethocybin]] (4-PO-DET or CEY-19).<ref name="Shulgin_1997" /><ref name="KleinChathaLaskowski2021" /> These compounds are assumed to be [[prodrug]]s of 4-HO-DET, as has been shown with the acetate and phosphate esters of other methylated tryptamines such as psilocin (e.g., [[psilocybin]] (4-PO-DMT) and [[4-AcO-DMT]]).<ref name="Shulgin_1997" /><ref name="Nichols1999">{{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 |url-access=subscription }}</ref><ref name="KleinChathaLaskowski2021" />

==History==
4-HO-DET was first described in the literature by 1963.<ref name="US3075992">{{US patent reference | number = 3075992 | y = 1963 | m = 1 | d = 29 | inventor = Hofmann, Albert; Troxler, Franz. | title = Esters of indoles }}</ref><ref name="LeunerBaer1965" /> It was developed by [[Albert Hofmann]] and Franz Troxler at [[Sandoz]] in the 1950s and went by the developmental code name ''CZ-74''.<ref name="US3075992" /><ref name="KleinChathaLaskowski2021" /><ref name="RossFrancoReiff2021">{{cite book | vauthors=Ross S, Franco S, Reiff C, Agin-Liebes G | chapter=Psilocybin | pages=181–214 | veditors = Grob CS, Grigsby J | title=Handbook of Medical Hallucinogens | publisher=Guilford Publications | date=9 March 2021 | isbn=978-1-4625-4544-5 | url=https://books.google.com/books?id=ebb2DwAAQBAJ&pg=PA181 | quote=Sandoz began manufacturing and distributing pure synthetic psilocybin pills (under the name Indocybin) to curious physicians and researchers around the world and would do so until recalling the drug in 1965 due to a growing political backlash in the United States (Hofmann, 2005). Sandoz also produced two synthetic drugs derived from mushroom-extracted psilocybin, CZ-74 (4-hydroxy-N,N-diethyltryptamine) and CEY-19 (4-phosphoryloxy-N,N-diethyltryptamine), both of which are shorter (approximately 3 hours in duration) acting than psilocybin (Baer, 1967). [...]}}</ref> Along with its presumed [[prodrug]] [[ethocybin]] (4-PO-DET; CEY-19), 4-HO-DET was one of the earliest [[structural modification|structurally modified]] or [[synthetic compound|synthetic]] psychedelic tryptamines to be developed.<ref name="Nichols2018" /><ref name="RossFrancoReiff2021" /> It was used along with ethocybin in [[clinical study|clinical studies]] of [[psychedelic-assisted psychotherapy]] by the [[German people|German]] researchers [[Hanscarl Leuner]] and Gerhard Baer in the 1960s.<ref name="Passie2022">{{cite book | vauthors = Passie T | chapter=History of the Use of Hallucinogens in Psychiatric Treatment | pages = 95–118 | veditors = Grob CS, Grigsby J | title=Handbook of Medical Hallucinogens | publisher=Guilford Publications | date=7 November 2022 | isbn=978-1-4625-5189-7 | url=https://books.google.com/books?id=r46ZEAAAQBAJ&pg=PA95 | quote=Psycholytic therapy underwent a number of modifications during its active years. Some European therapists experimented with shorter-acting psilocybin derivatives such as CZ-74 (4-hydroxy-N,N-diethyltryptamine, also known as 4-HO-DET; Baer, 1967; Shulgin & Shulgin, 2014), which has a duration of 4—6 hours and is phenomenologically similar to LSD; CEY-19 (phosphoryloxy-N,N-diethyltryptamine, also known as 4-PO-DET or ethocybin), which has a duration of 2—4 hours and is also similar to LSD, and the mescaline derivative 2-CD (2,5-dimethoxy-4-methylphenethylamine; Schlichting, 1989). Therapists in the United States experimented with the short-acting dipropyltrytamine (DP T) in psycholytic therapy (Soskin, 1975; Soskin, Grof, & Richards, 1973), as well as in psychedelic therapy (Richards, Rhead, DiLeo, Yensen, & Kurland, 1977).}}</ref><ref name="Shulgin_1997" /><ref name="LeunerBaer1965">{{cite journal | vauthors = Leuner H, Baer G | title = Two new short-acting hallucinogens of the psilocybin group | date = 1965 | journal = Neuropsychopharmacology | volume = 4 | issue = | pages = 471–474 | url = https://bibliography.maps.org/resources/download/19910 | archive-url = https://web.archive.org/web/20250422014123/https://bibliography.maps.org/resources/download/19910 | url-status = dead | archive-date = 2025-04-22 }}</ref> The drug was [[chemical synthesis|synthesized]] and studied, along with many other [[substituted 4-hydroxytryptamine|4-hydroxytryptamine]]s, by [[David Repke]] and colleagues in the 1970s and 1980s.<ref name="Repke_1977">{{cite journal | vauthors = Repke DB, Ferguson WJ, Bates DK | title = Psilocin analogs. 1. Synthesis of 3‐[2‐(dialkylamino)ethyl] ‐and 3‐[2‐(cycloalkylamino)ethyl] indol‐4‐ols | journal = Journal of Heterocyclic Chemistry | volume = 14 | issue = 1 | pages = 71–74 | date = 1977 | doi = 10.1002/jhet.5570140113 | issn = 0022-152X | doi-access = free | url = https://onlinelibrary.wiley.com/doi/pdfdirect/10.1002/jhet.5570140113 | access-date = 16 October 2025 }}</ref><ref name="Repke_1982">{{cite journal | vauthors = Repke DB, Ferguson WJ | title = Psilocin analogs. III. Synthesis of 5‐methoxy‐ and 5‐hydroxy‐1,2,3,4‐tetrahydro‐9 H ‐pyrido[3,4‐ b ]indoles | journal = Journal of Heterocyclic Chemistry | volume = 19 | issue = 4 | pages = 845–848 | date = 1982 | doi = 10.1002/jhet.5570190428 | issn = 0022-152X | url = https://onlinelibrary.wiley.com/doi/10.1002/jhet.5570190428 | access-date = 16 October 2025 | url-access = subscription }}</ref> It was later additionally described by [[Alexander Shulgin]] in his 1997 book ''[[TiHKAL]]'' (''Tryptamines I Have Known and Loved'').<ref name="Shulgin_1997" /> 4-HO-DET was encountered as a novel [[designer drug]] in [[Europe]] in 2005.<ref name="EMCDDA2005">{{cite web | title = EMCDDA–Europol Annual Report on the implementation of Council Decision 2005/387/JHA | url = https://isomerdesign.com/bitnest/external/EMCDDA/New-Drugs-In-Europe-2005 | work = European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) }}</ref>

==Society and culture==
===Legal status===
====Finland====
Scheduled in the "government decree on psychoactive substances banned from the consumer market".<ref>{{cite web | title = Valtioneuvoston asetus kuluttajamarkkinoilta kielletyistä psykoaktiivisista aineista | trans-title = Government Decree on psychoactive substances banned from the consumer market | language = fi | date = 19 December 2014 | url = https://finlex.fi/fi/lainsaadanto/2014/1130 | work = Finlex | publisher = Finnish Ministry of Justice }}</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>

====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>

==Research==
4-HO-DET, under the code name CZ-74 and along with [[ethocybin]] (CEY-19), has been studied in [[psychedelic-assisted psychotherapy]].<ref name="Passie2022" /><ref name="Shulgin_1997" /><ref name="LeunerBaer1965" />

== See also ==
* [[Substituted tryptamine]]

== References ==
{{Reflist}}

== External links ==
* [https://isomerdesign.com/pihkal/explore/5016 4-HO-DET - Isomer Design]
* [https://psychonautwiki.org/wiki/4-HO-DET 4-HO-DET - PsychonautWiki]
* [https://erowid.org/experiences/subs/exp_4HODET.shtml 4-HO-DET - Erowid Experience Vaults - Erowid]
* [https://www.bluelight.org/xf/threads/480200 The Big & Dandy 4-HO-DET Thread - Bluelight]
* [http://www.erowid.org/library/books_online/tihkal/tihkal16.shtml 4-HO-DET - TiHKAL - Erowid]
* [http://tihkal.info/read.php?domain=tk&id=16 4-HO-DET - TiHKAL - Isomer Design]
* [http://www.erowid.org/chemicals/4_acetoxy_det/4_acetoxy_det_article1.shtml 4-Acetoxy-DET / Ethacetin Degradation Investigation - Murple - Erowid]

{{Psychedelics}}
{{Serotonin receptor modulators}}
{{Monoamine reuptake inhibitors}}
{{Tryptamines}}

[[Category:5-HT1A agonists]]
[[Category:5-HT2A agonists]]
[[Category:5-HT2B agonists]]
[[Category:5-HT2C agonists]]
[[Category:Designer drugs]]
[[Category:N,N-Dialkyltryptamines]]
[[Category:Diethylamino compounds]]
[[Category:4-Hydroxytryptamines]]
[[Category:Psychedelic-assisted therapy]]
[[Category:Psychedelic tryptamines]]
[[Category:Serotonin receptor modulators]]
[[Category:Serotonin reuptake inhibitors]]

4-HO-DET - Revision history

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