4-HO-DET

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Template:Short description Template:Drugbox

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

The drug acts as a non-selective serotonin receptor agonist, including of the serotonin 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 structurally related to other psychedelic tryptamines such as psilocin, diethyltryptamine (DET), and 4-HO-MET.<ref name="Shulgin_1997" /><ref name="Greene_2021">Template:Cite book</ref> Ethocybin (4-PO-DET; CEY-19) and 4-AcO-DET are assumed to act as prodrugs 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 25Template:Nbspmg orally, either as 4-HO-DET itself or as presumed prodrugs like ethocybin (4-PO-DET) or 4-AcO-DET, and its duration as 2 to 6Template:Nbsphours.<ref name="Shulgin_1997">Template:Cite web</ref><ref name="HalberstadtChathaKlein2020">Template:Cite journal</ref><ref name="Shulgin1976" /><ref name="JacobShulgin1994">Template:Cite journal</ref><ref name="Shulgin2003">Template:Cite book</ref><ref name="Passie2022" /><ref name="RossFrancoReiff2021" /> Threshold effects are said to occur at doses of 5 to 15Template:Nbspmg, whereas loss of contact with reality is said to occur at doses over 30Template:Nbspmg.<ref name="GlennonRosecrans1982">Template:Cite journal</ref><ref name="Shulgin1976" /> However, strong effects have also been reported at a dose of 15Template:Nbspmg of ethocybin.<ref name="Shulgin_1997" /> A typical dose estimate has been reported to be around 17.5Template:Nbspmg.<ref name="HalberstadtChathaKlein2020" /> The onset of 4-HO-DET is described as being around 30 to 45Template:Nbspminutes.<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 3Template:Nbsphours.<ref name="Nichols2018">Template:Cite book</ref><ref name="Shulgin1976">Template:Cite book</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 visuals, open-eye visuals such as fire light turning into bursts of color, potential for intense psychedelic visuals, auditory hallucinations, time dilation, temporal and spatial disorientation, body image disturbance, musical 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 intoxicated, sedation, restlessness, 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 experiences, delirium, schizophrenia-like behavior, catatonia, and paranoia have been found to occur.<ref name="Shulgin_1997" /> Physical effects have been reported to include stomach and abdominal discomfort, appetite loss, jaw tightening, body tremors, motor incoordination, body disturbance, diuretic effects, and increased blood pressure.<ref name="Shulgin_1997" />

Interactions

Template:See also

Pharmacology

Pharmacodynamics

Template:Nowrap
Target Affinity (Ki, nM)
5-HT1A 396–1,840 (Ki)
1,030 (Template:Abbrlink)
80% (Template:Abbrlink)
5-HT1B 2,242
5-HT1D 585
5-HT1E 568
5-HT2A 269–400 (Ki)
6.5–296a (Template:Abbr)
80a–100% (Template:Abbr)
5-HT2B 73 (Ki)
6.3 (Template:Abbr)
71% (Template:Abbr)
5-HT2C 388–436 (Ki)
151a–264 (Template:Abbr)
80–83%a (Template:Abbr)
5-HT5A 1,429
5-HT6 230
5-HT7A 826
α2A–α2C Template:Abbr
D2–D5 Template:Abbr
H1 1,079
H2 9,984
M4 Template:Abbr
σ1 Template:Abbr
σ2 3,026
NR2B 8,720
Template:Abbrlink 1,411–1,800 (Ki)
383 (Template:Abbr)
Template:Abbrlink Template:Abbr
Notes: The smaller the value, the more avidly drug interacts with the site. Footnotes: a = Stimulation of Template:Abbrlink formation. Sources: <ref name="KozellEshlemanSwanson2023">Template:Cite journal</ref><ref name="KleinChathaLaskowski2021">Template:Cite journal</ref><ref name="GlatfelterNaeemPham2023">Template:Cite journal</ref><ref name="McKennaRepkeLo1990">Template:Cite journal</ref>

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

It induces the head-twitch response, a behavioral proxy of 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 4-hydroxytryptamine.<ref name="Shulgin_1997" /> It is the 4-hydroxy derivative of N,N-diethyltryptamine (DET) and is a close 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-diethyl 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 prodrugs 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">Template:Cite journal</ref><ref name="KleinChathaLaskowski2021" />

History

4-HO-DET was first described in the literature by 1963.<ref name="US3075992">Template:US patent reference</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">Template:Cite book</ref> Along with its presumed prodrug ethocybin (4-PO-DET; CEY-19), 4-HO-DET was one of the earliest structurally modified or synthetic psychedelic tryptamines to be developed.<ref name="Nichols2018" /><ref name="RossFrancoReiff2021" /> It was used along with ethocybin in clinical studies of psychedelic-assisted psychotherapy by the German researchers Hanscarl Leuner and Gerhard Baer in the 1960s.<ref name="Passie2022">Template:Cite book</ref><ref name="Shulgin_1997" /><ref name="LeunerBaer1965">Template:Cite journal</ref> The drug was synthesized and studied, along with many other 4-hydroxytryptamines, by David Repke and colleagues in the 1970s and 1980s.<ref name="Repke_1977">Template:Cite journal</ref><ref name="Repke_1982">Template:Cite journal</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">Template:Cite web</ref>

Society and culture

Finland

Scheduled in the "government decree on psychoactive substances banned from the consumer market".<ref>Template:Cite web</ref>

Sweden

Sveriges riksdags health ministry Statens folkhälsoinstitut classified 4-HO-DET as "health hazard" under the act 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>Template:Cite web</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>Template:Cite web</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

References

Template:Reflist

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