Chemical compound
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 .[ 1]
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.[ 2]
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.[citation needed ] It was later explored by Alexander Shulgin in his 1997 book TiHKAL .[ 3]
TiHKAL reports moderate effects at 10–25 mg ingested orally.[ 4]
4-HO-DET produces psychedelic effects similar to LSD and psilocybin .[ 4]
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 .[ 5]
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.[ 6]
^ 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 .
^ 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 .
^ Shulgin, Alexander ; Shulgin, Ann (September 1997). TiHKAL: The Continuation . Berkeley, California : Transform Press. ISBN 0-9630096-9-9 . OCLC 38503252 .
^ a b Shulgin A, Shulgin A (September 1997). "#16 4-HO-DET" . Isomer Design . Transform Press. Retrieved 28 November 2023 .
^ "21 U.S. Code § 841 - Prohibited acts A" , LII / Legal Information Institute , retrieved 2016-08-02
^ "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 .
Psychedelics (5-HT2A agonists)
Benzofurans Lyserg‐ amides Phenethyl‐ amines
2C-x 25x -NBx
25x -NB 25x -NB3OMe
25B-NB3OMe
25C-NB3OMe
25D-NB3OMe
25E-NB3OMe
25H-NB3OMe
25I-NB3OMe
25N-NB3OMe
25P-NB3OMe
25T2-NB3OMe
25T4-NB3OMe
25T7-NB3OMe
25TFM-NB3OMe
25x -NB4OMe
25B-NB4OMe
25C-NB4OMe
25D-NB4OMe
25E-NB4OMe
25H-NB4OMe
25I-NB4OMe
25N-NB4OMe
25P-NB4OMe
25T2-NB4OMe
25T4-NB4OMe
25T7-NB4OMe
25TFM-NB4OMe
25x -NBF 25x -NBMD
25B-NBMD
25C-NBMD
25D-NBMD
25E-NBMD
25F-NBMD
25H-NBMD
25I-NBMD
25P-NBMD
25T2-NBMD
25T7-NBMD
25TFM-NBMD
25x -NBOH 25x -NBOMe Atypical structures
25x -NMx
25B-NMe7BF
25B-NMe7BT
25B-NMe7Bim
25B-NMe7Box
25B-NMe7DHBF
25B-NMe7Ind
25B-NMe7Indz
25B-NMePyr
25I-NMe7DHBF
25I-NMeFur
25I-NMeTHF
25I-NMeTh
N-(2C)-fentanyl
N-(2C-B) fentanyl
N-(2C-C) fentanyl
N-(2C-D) fentanyl
N-(2C-E) fentanyl
N-(2C-G) fentanyl
N-(2C-H) fentanyl
N-(2C-I) fentanyl
N-(2C-IP) fentanyl
N-(2C-N) fentanyl
N-(2C-P) fentanyl
N-(2C-T) fentanyl
N-(2C-T-2) fentanyl
N-(2C-T-4) fentanyl
N-(2C-T-7) fentanyl
N-(2C-TFM) fentanyl
3C-x 4C-x DOx HOT-x MDxx Mescaline (subst.) TMAs
TMA
TMA-2
TMA-3
TMA-4
TMA-5
TMA-6
Others
Piperazines Tryptamines
alpha -alkyltryptaminesx -DALT x -DET x -DiPT x -DMT
4,5-DHP-DMT
2,N,N-TMT
4-AcO-DMT
4-HO-5-MeO-DMT
4,N,N-TMT
4-Propionyloxy-DMT
5,6-diBr-DMT
5-AcO-DMT
5-Bromo-DMT
5-MeO-2,N ,N -TMT
5-MeO-4,N ,N -TMT
5-MeO-α,N,N-TMT
5-MeO-DMT
5-N ,N -TMT
7,N,N-TMT
α,N,N-TMT
(Bufotenin) 5-HO-DMT
DMT
Norbaeocystin
(Psilocin) 4-HO-DMT
(Psilocybin) 4-PO-DMT
x -DPT Ibogaine-related x -MET x -MiPT Others
Others
Dissociatives (NMDAR antagonists )
Deliriants (mAChR antagonists ) Others
Tryptamines
1-Methylpsilocin
2-HO-NMT
2-Me-DET
2-Methyl-5-HT
2,N ,N -TMT
4,5-DHP-DMT
4-AcO-DALT
4-AcO-DET
4-AcO-DiPT
4-AcO-EPT
4-AcO-NMT
4-AcO-MALT
4-AcO-MET
4-AcO-DPT
4-AcO-MiPT
4-F-5-MeO-DMT
4-HO-5-MeO-DMT
4-HO-DALT
4-HO-DBT
4-HO-DET
4-HO-DiPT
4-HO-DPT
4-HO-DSBT
4-HO-EPT
4-HO-MALT
4-HO-MET
4-HO-McPT
4-HO-McPeT
4-HO-MiPT
4-HO-MPT
4-HO-MsBT
4-HO-NALT
4-HO-NMT
4-HO-PiPT
4-HO-pyr-T
4-MeO-DiPT
4-MeO-DMT
4-MeO-MiPT
4-PrO-DMT
4,5-MDO-DMT
4,5-MDO-DiPT
5-BT
5-Bromo-DMT
5-CT
5-Chloro-DMT
5-Ethoxy-DMT
5-Ethyl-DMT
5-Fluoro-DET
5-Fluoro-DMT
5-Fluoro-EPT
5-Fluoro-MET
5-HO-DiPT
5-HTP (oxitriptan)
5-MeO-2-TMT
5-MeO-34MPEMT
5-MeO-7,N ,N -TMT
5-MeO-DALT
5-MeO-DBT
5-MeO-DET
5-MeO-DiPT
5-MeO-DMT
5-MeO-DPT
5-MeO-EiPT
5-MeO-EPT
5-MeO-MALT
5-MeO-MET
5-MeO-MiPT
5-MeO-NMT
5-MeO-pyr-T
5-MeO-NBpBrT
5-MeO-T-NBOMe
5-MeS-DMT
5-Methoxytryptamine (5-MT; mexamine)
5-Methyl-DMT
5-Methyltryptamine
5-MT-NB3OMe
5-(Nonyloxy)tryptamine
5,6-MeO-MiPT
5,6-MDO-DiPT
5,6-MDO-DMT
5,6-MDO-MiPT
5,6-DHT
5,7-DHT
6-Fluoro-DMT
7-Methyl-DMT
Acetryptine (5-AT)
Aeruginascin (4-PO-TMT)
AGH-107
AGH-192
AH-494
ALiPT
Baeocystin (4-PO-NMT)
Benzotript (4-chlorobenzoyl-L -tryptophan)
Bufotenidine (5-HTQ)
Bufotenin (5-HO-DMT)
Convolutindole A
CP-132,484
DALT
DBT
Desformylflustrabromine
DET
DiPT
DMT
DPT
E-6801
E-6837
EiPT
EMDT
EPT
Ethocybin (4-PO-DET)
FGIN-127
FGIN-143
FT-104
HIOC
Idalopirdine
Indolylethylfentanyl
Indorenate
Iprocin (4-HO-DiPT)
Lespedamine
MET
Methylbutyltryptamine
Miprocin (4-HO-MiPT)
MiPT
MPT
Milipertine
MS-245
MSBT
N -Feruloylserotonin (moschamine)
NET
NMT
Norbaeocystin (4-PO-T)
NTBT
O-4310
Oxypertine
PiPT
Psilacetin (O -acetylpsilocin; 4-AcO-DMT)
Psilocin (4-HO-DMT)
Psilocybin (4-PO-DMT)
Pyr-T
RS134-49
Serotonin (5-HT)
Solypertine
ST-1936
Tryptamine
Tryptophan
Yuremamine
Z2876442907
N -Acetyltryptaminesα-Alkyltryptamines Triptans Cyclized tryptamines
Bay R 1531
Ciclindole
Cyclic 3-OHM
Ergolines and lysergamides (e.g., LSD )
Flucindole
Harmala alkaloids and β-carbolines (e.g., 6-MeO-THH , 9-Me-BC , β-carboline (norharman) , harmaline , harmalol , harmane , harmine , pinoline , tetrahydroharmine , tryptoline )
Iboga alkaloids and related (e.g., DM-506 (ibogaminalog) , ibogaine , ibogamine , noribogaine , tabernanthalog , tabernanthine )
Metralindole
NDTDI
PHA-57378
PNU-22394
PNU-181731
RU-28306
Yohimbans (e.g., yohimbine , rauwolscine , spegatrine , corynanthine , ajmalicine , reserpine , deserpidine , rescinnamine )
Related compounds