4-HO-DET

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 family.^[1] It is a substituted tryptamine, structurally related to psilocin, ethocybin, and 4-HO-DIPT.^[1][2]

4-HO-DET

Clinical data
Other names	4-OH-DET; 4-Hydroxy-N,N-diethyltryptamine; Ethocin; CZ-74; CZ74
Routes of administration	Oral[1]
Drug class	Serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code	None
Legal status
Legal status	DE: Anlage I (Authorized scientific use only) UK: Class A
Pharmacokinetic data
Duration of action	4–6 hours[1]
Identifiers
IUPAC name 3-(2-Diethylaminoethyl)-1H-indol-4-ol
CAS Number	22204-89-3 Y
PubChem CID	9991554
ChemSpider	8167136 Y
UNII	7E0BR15575
ChEMBL	ChEMBL143202 Y
CompTox Dashboard (EPA)	DTXSID60176755
Chemical and physical data
Formula	C14H20N2O
Molar mass	232.327 g·mol−1
3D model (JSmol)	Interactive image
Melting point	104 to 106 °C (219 to 223 °F)
SMILES CCN(CC)CCc1c[nH]c2cccc(O)c12
InChI InChI=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 Y Key:OHHYMKDBKJPILO-UHFFFAOYSA-N Y
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Use

TiHKAL reports moderate effects at 10 to 25 mg ingested orally.^[1][3]

Effects

4-HO-DET produces psychedelic effects similar to psilocybin.^[1] Its duration is 4 to 6 hours.^[1]

Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

The pharmacology of 4-HO-DET has been studied.^[4]

Chemistry

Analogues

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 prodrugs of 4-HO-DET as has been shown with the acetate and phosphate esters of other methylated tryptamines such as psilocin.^[5]

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.^[6] It was later explored by Alexander Shulgin in his 1997 book TiHKAL.^[7]

Society and culture

Legal status

Finland

Scheduled in the "government decree on psychoactive substances banned from the consumer market".^[8]

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.^[9]

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.^[10]