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4-HO-DET

Legal status
Legal status	DE: Anlage I (Authorized scientific use only) UK: Class A
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
3D model (JSmol)	Interactive image
Melting point	104 to 106 °C (219 to 223 °F)
SMILES CCN(CC)CCc1cc2cccc(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-diethyl-tryptamine, CZ-74, is a hallucinogenic drug and psychedelic compound of moderate duration. 4-HO-DET is a substituted tryptamine, structurally related to psilocin, ethocybin, and 4-HO-DIPT.

Analogs

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 phospate 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 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. It was later explored by Alexander Shulgin in his 1997 book TiHKAL.

Dosage

TiHKAL reports moderate effects at 10–25 mg ingested orally.

Effects

4-HO-DET produces psychedelic effects similar to LSD and psilocybin.

Legality

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.

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.

See also

• TiHKAL
• Indoles

References

1. Greene SL (2021). "Tryptamines". In Dargan PI, Wood DM (eds.). Novel Psychoactive Substances: Classification, Pharmacology and Toxicology (Second ed.). London, United Kingdom: Academic Press. p. 499. ISBN 978-0-12-819030-2.
2. Nichols DE (February 11, 1999). "Improvements to the Synthesis of Psilocybin and a Facile Method for Preparing the O-Acetyl Prodrug of Psilocin". Synthesis. 1999 (6): 935–938. doi:10.1055/s-1999-3490. S2CID 32044725.
3. Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252.
4. ^ Shulgin A, Shulgin A (September 1997). "#16 4-HO-DET". Isomer Design. Transform Press. Retrieved 28 November 2023.
5. "21 U.S. Code § 841 - Prohibited acts A", LII / Legal Information Institute, retrieved 2016-08-02
6. "Förordning om ändring i förordningen (1999:58) om förbud mot vissa hälsofarliga varor;" [Ordinance amending the ordinance (1999: 58) on the prohibition of certain dangerous goods;] (PDF). Svensk författningssamling (Swedish Code of Statutes) (in Swedish). 6 October 2005. Archived from the original (PDF) on 26 June 2021. Retrieved 6 September 2013.

External links

• TiHKAL 4-HO-DET information at Erowid
• 4-HO-DET entry in TiHKAL • info
• Ethacetin degradation

• Hydroxyarenes
• Psychedelic tryptamines
• Designer drugs
• Diethylamino compounds