4-HO-DET

4-HO-DET
Clinical data
Other names	4-Hydroxy-DET; 4-OH-DET; 4-Hydroxy-N,N-diethyltryptamine; Ethocin; CZ-74; CZ74
Routes of; administration	Oral
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
Onset of action	30–45 minutes
Duration of action	2–6 hours
Identifiers
	IUPAC name 3-(2-diethylaminoethyl)-1H-indol-4-ol;
CAS Number	22204-89-3 ;
PubChem CID	9991554;
ChemSpider	8167136 ;
UNII	7E0BR15575;
ChEMBL	ChEMBL143202 ;
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 ; Key:OHHYMKDBKJPILO-UHFFFAOYSA-N ;
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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). It is taken orally.

The drug acts as a non-selective serotonin receptor agonist, including of the serotonin 5-HT_2A receptor among others. It produces psychedelic-like effects in animals. 4-HO-DET is closely structurally related to other psychedelic tryptamines such as psilocin, diethyltryptamine (DET), and 4-HO-MET. Ethocybin (4-PO-DET; CEY-19) and 4-AcO-DET are assumed to act as prodrugs of 4-HO-DET.

4-HO-DET was first described in the literature by 1963. It was developed at Sandoz by Albert Hofmann and colleagues. The drug was studied in psychedelic-assisted psychotherapy by Hanscarl Leuner and colleagues in the 1960s. Later, it was described further by Alexander Shulgin in his 1997 book TiHKAL (Tryptamines I Have Known and Loved). 4-HO-DET was encountered as a novel designer drug in 2005.