4-HO-DET, also known as 4-hydroxy-''N'',''N''-diethyltryptamine as well as ethocin or CZ-74, is a

psychedelic drug Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary mental states (known as psychedelic experiences or "trips") and a perceived "expansion of consciousness". Also referred to as classic halluc ...

of the

tryptamine Tryptamine is an indolamine metabolite of the essential amino acid tryptophan. The chemical structure is defined by an indole—a fused benzene and pyrrole ring, and a 2-aminoethyl group at the second carbon (third aromatic atom, with the firs ...

family. It is a

substituted Substitution may refer to: Arts and media *Substitution (poetry), a variation in poetic scansion *Substitution (theatre), an acting methodology Music *Chord substitution, swapping one chord for a related one within a chord progression *Tritone ...

, structurally related to

psilocin Psilocin, also known as 4-hydroxy-''N'',''N''-dimethyltryptamine (4-HO-DMT), is a substituted tryptamine alkaloid and a serotonergic psychedelic. It is present in most psychedelic mushrooms together with its phosphorylated counterpart psilocy ...

ethocybin Ethocybin (code name CEY-19), also known as 4-phosphoryloxy-''N'',''N''-diethyltryptamine (4-PO-DET), is a homologue of the mushroom alkaloid psilocybin, and a semi-synthetic psychedelic alkaloid of the tryptamine family. Pharmacology Ethocyb ...

, and

4-HO-DIPT 4-HO-DiPT, also known as 4-hydroxy-''N'',''N''-diisopropyltryptamine or as iprocin, is a synthetic compound, synthetic psychedelic drug of the substituted tryptamine, tryptamine family. It is a higher homologous series, homologue of psilocin and ...

Use

TiHKAL ''TiHKAL: The Continuation'' is a 1997 book written by Alexander Shulgin and Ann Shulgin about a family of psychoactive drugs known as tryptamines. A sequel to '' PiHKAL: A Chemical Love Story'', ''TiHKAL'' is an acronym that stands for "Trypt ...

'' reports moderate effects at 10 to 25mg ingested

orally The word oral may refer to: Relating to the mouth * Relating to the mouth, the first portion of the alimentary canal that primarily receives food and liquid **Oral administration of medicines ** Oral examination (also known as an oral exam or oral ...

Effects

4-HO-DET produces

psychedelic Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary mental states (known as psychedelic experiences or "trips") and a perceived "expansion of consciousness". Also referred to as classic halluci ...

effects similar to

psilocybin Psilocybin, also known as 4-phosphoryloxy-''N'',''N''-dimethyltryptamine (4-PO-DMT), is a natural product, naturally occurring tryptamine alkaloid and Investigational New Drug, investigational drug found in more than List of psilocybin mushroom ...

. Its duration is 4 to 6hours.

Interactions

Pharmacology

The

pharmacology Pharmacology is the science of drugs and medications, including a substance's origin, composition, pharmacokinetics, pharmacodynamics, therapeutic use, and toxicology. More specifically, it is the study of the interactions that occur betwee ...

of 4-HO-DET has been studied.

Chemistry

Analogues

4-HO-DET is the N,N-diethyl analog of psilocin. The

acetic acid Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main compone ...

ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...

of 4-HO-DET is known as

4-AcO-DET 4-AcO-DET, also known as 4-acetoxy-''N'',''N''-diethyltryptamine as well as ethacetin or ethylacybin, is a psychedelic tryptamine. It was first synthesized in 1958 by Albert Hofmann in the Sandoz lab.

and the

phosphoric acid Phosphoric acid (orthophosphoric acid, monophosphoric acid or phosphoric(V) acid) is a colorless, odorless phosphorus-containing solid, and inorganic compound with the chemical formula . It is commonly encountered as an 85% aqueous solution, ...

ester of 4-HO-DET is known as 4-phosphoryloxy-DET, CEY-19, or

. These compounds may likely be

prodrugs A prodrug is a pharmacologically inactive Pharmaceutical drug, medication or compound that, after Drug administration, intake, is Drug metabolism, metabolized (i.e., converted within the body) into a pharmacologically active drug. Instead of admin ...

of 4-HO-DET as has been shown with the acetate and phosphate esters of other methylated tryptamines such as psilocin.

History

4-HO-DET received the lab code CZ-74 in the late 1950s by the inventors of the substance,

Albert Hofmann Albert Hofmann (11 January 1906 – 29 April 2008) was a Swiss chemist known for being the first to synthesize, ingest, and learn of the psychedelic effects of lysergic acid diethylamide (LSD). Hofmann's team also isolated, named and synthesi ...

and

Franz Troxler Franz may refer to: People * Franz (given name) * Franz (surname) Places * Franz (crater), a lunar crater * Franz, Ontario, a railway junction and unorganized town in Canada * Franz Lake, in the state of Washington, United States – see Fran ...

. The substance was used together with its phosphoryloxy-analog ethocybin in human clinical trials in the 1960s by the German researchers

Hanscarl Leuner Hanscarl Leuner (born 8 January 1919 in Bautzen - d. 22 June 1996 in Göttingen) was a German psychiatrist, psychotherapist and researcher. He is the founder of "Psycholytic Therapy" also known as Guided Affective Imagery (":de:Katathym Imaginat ...

and G. Baer. It was later explored by

Alexander Shulgin Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an American biochemist, broad researcher of synthetic psychoactive compounds, and author of works regarding these, who independently explored the organic chemistry and ph ...

in his 1997 book ''

''.

Society and culture

Legal status

Finland

Scheduled in the "government decree on psychoactive substances banned from the consumer market".

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.

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 The Federal Analogue Act, , is a section of the United States Controlled Substances Act passed in 1986 which allows any chemical "substantially similar" to a controlled substance listed in Schedule I or II to be treated as if it were listed ...

References

External links

4-HO-DET - Isomer Design

TiHKAL 4-HO-DET
information at

Erowid Erowid, also called Erowid Center, is a non-profit educational organization that provides information about psychoactive plants and chemicals. Erowid documents legal and illegal substances, including their intended and adverse effects. Inform ...

4-HO-DET entry in TiHKAL • info

Ethacetin degradation
{{Tryptamines 5-HT1A agonists 5-HT2A agonists 5-HT2C agonists Designer drugs N,N-Dialkyltryptamines Diethylamino compounds 4-Hydroxytryptamines Psychedelic tryptamines