4-HO-DET

Chemical compound

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^N

PubChem CID

9991554

ChemSpider

8167136^Y

UNII

7E0BR15575

ChEMBL

ChEMBL143202^Y

CompTox Dashboard (EPA)

DTXSID60176755

Chemical and physical dataFormulaC₁₄H₂₀N₂OMolar mass232.327 g·mol⁻¹3D model (JSmol)

Interactive image

Melting point104 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

^NY (what is this?) (verify)

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]

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.^[2]

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.^{[citation needed]} It was later explored by Alexander Shulgin in his 1997 book TiHKAL.^[3]

Dosage

TiHKAL reports moderate effects at 10–25 mg ingested orally.^[4]

Effects

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

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.^[5]

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.^[6]

References

^ 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.

External links

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

Hallucinogens

Psychedelics
(5-HT_2A
agonists)

Benzofurans

Lyserg‐
amides

Phenethyl‐
amines

2C-x

2C-B
2C-B-AN
2C-Bn
2C-Bu
2C-C
2C-CN
2C-CP
2C-D
2C-E
2C-EF
2C-F
2C-G
2C-G-1
2C-G-2
2C-G-3
2C-G-4
2C-G-5
2C-G-6
2C-G-N
2C-H
2C-I
2C-iP
2C-N
2C-NH2
2C-O
2C-O-4
2C-P
2C-Ph
2C-SE
2C-T
2C-T-2
2C-T-3
2C-T-4
2C-T-5
2C-T-6
2C-T-7
2C-T-8
2C-T-9
2C-T-10
2C-T-11
2C-T-12
2C-T-13
2C-T-14
2C-T-15
2C-T-16
2C-T-17
2C-T-18
2C-T-19
2C-T-20
2C-T-21
2C-T-22
2C-T-22.5
2C-T-23
2C-T-24
2C-T-25
2C-T-27
2C-T-28
2C-T-30
2C-T-31
2C-T-32
2C-T-33
2C-TFE
2C-TFM
2C-YN
2C-V

25x-NBx

25x-NB	25B-NB 25C-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	25B-NBF 25C-NBF 25D-NBF 25E-NBF 25H-NBF 25I-NBF 25P-NBF 25T2-NBF 25T7-NBF 25TFM-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	25B-NBOH 25C-NBOH 25CN-NBOH 25D-NBOH 25E-NBOH 25F-NBOH 25H-NBOH 25I-NBOH 25P-NBOH 25T2-NBOH 25T7-NBOH 25TFM-NBOH
25x-NBOMe	25B-NBOMe 25C-NBOMe 25CN-NBOMe 25D-NBOMe 25E-NBOMe 25F-NBOMe 25G-NBOMe 25H-NBOMe 25I-NBOMe 25iP-NBOMe 25N-NBOMe 25P-NBOMe 25T-NBOMe 25T2-NBOMe 25T4-NBOMe 25T7-NBOMe 25TFM-NBOMe
Atypical structures	25B-N1POMe 25B-NAcPip 25B-NB23DM 25B-NB25DM 25C-NBCl 25C-NBOEt 25C-NBOiPr 25I-N2Nap1OH 25I-N3MT2M 25I-N4MT3M 25I-NB34MD 25I-NBAm 25I-NBBr 25I-NBMeOH 25I-NBTFM 2CBCB-NBOMe 2CBFly-NBOMe 4-EA-NBOMe 5-APB-NBOMe 5MT-NBOMe C30-NBOMe DOB-NBOMe DOI-NBOMe FECIMBI-36 MDPEA-NBOMe N-Ethyl-2C-B NBOMe-escaline NBOMe-mescaline ZDCM-04

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

4C-B
4C-C
4C-D
4C-E
4C-I
4C-N
4C-P
4C-T-2

DOx

DOT
DOB
DOC
DOEF
DOET
DOF
DOI
DOiPR
DOM
DON
DOPR
DOTFM
MEM

HOT-x

MDxx

Mescaline (subst.)

TMAs

TMA
TMA-2
TMA-3
TMA-4
TMA-5
TMA-6

Others

2C-B-BUTTERFLY
2C-B-DragonFLY
2C-B-DragonFLY-NBOH
2C-B-FLY-NB2EtO5Cl
2CB-5-hemifly
2CB-Ind
2CD-5EtO
2-TOET
5-TOET
2-TOM
5-TOM
BOB
BOD
βk-2C-B
βk-2C-I
DESOXY
DMCPA
DMBMPP
DOB-FLY
Fenfluramine
Ganesha
Macromerine
MMA
TCB-2
TOMSO

Piperazines

Tryptamines

alpha-alkyltryptamines	4,5-DHP-α-MT 5-MeO-α-ET 5-MeO-α-MT α-ET α-MT
x-DALT	(Daltocin) 4-HO-DALT (Daltacetin) 4-AcO-DALT 5-MeO-DALT DALT
x-DET	(Ethacetin) 4-AcO-DET (Ethocin) 4-HO-DET 5-MeO-DET (T-9) DET (Ethocybin) 4-PO-DET
x-DiPT	(Ipracetin) 4-AcO-DiPT (Iprocin) 4-HO-DiPT 5-MeO-DiPT 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	(Depracetin) 4-AcO-DPT (Deprocin) 4-HO-DPT 5-MeO-DPT (The Light) DPT
Ibogaine-related	18-MAC 18-MC Coronaridine Ibogaine Ibogamine ME-18-MC Noribogaine Tabernanthine Voacangine
x-MET	(Metocin) 4-HO-MET (Metocetin) 4-AcO-MET 5-MeO-MET MET
x-MiPT	(Mipracetin) 4-AcO-MiPT (Miprocin) 4-HO-MiPT 5-Me-MiPT (Moxy) 5-MeO-MiPT MiPT
Others	4-HO-DBT 4-HO-EPT 4-HO-McPT (Lucigenol) 4-HO-MPMI (Meprocin) 4-HO-MPT 5-MeO-EiPT 5-MeO-MALT 5-MeO-MPMI Aeruginascin Baeocystin DBT DCPT EiPT EPT MPT PiPT

Others

AL-38022A
ALPHA
Dimemebfe
Efavirenz
Glaucine
Lorcaserin
M-ALPHA
RH-34
Also empathogens in general (e. g.: 5-APB, 5-MAPB, 6-APB and other substituted benzofurans).

Dissociatives
(NMDAR
antagonists)

Arylcyclo‐
hexylamines

Ketamine-related	2-Fluorodeschloroketamine Arketamine ((R)-ketamine) Deschloroketamine Ethketamine (N-Ethylnorketamine) Esketamine ((S)-ketamine) Ketamine Methoxetamine Methoxmetamine Methoxyketamine MXiPr Norketamine Tiletamine
PCP-related	2'-Oxo-PCE 3-HO-PCP 3-MeO-PCE 3-MeO-PCMo 3-MeO-PCP 4-MeO-PCP BDPC Dieticyclidine (PCDE) Eticyclidine (PCE) PCPr Phencyclidine (PCP) Rolicyclidine (PCPy) Tenocyclidine (TCP)
Others	BTCP Gacyclidine PRE-084

Adamantanes

Diarylethylamines

Morphinans

Others

Deliriants
(mAChR
antagonists)

Others

Cannabinoids
(CB₁ agonists)

Natural

Synthetic

AM-x	AM-087 AM-251 AM-279 AM-281 AM-356 AM-374 AM-381 AM-404 AM-411 AM-630 AM-661 AM-678 AM-679 AM-694 AM-735 AM-855 AM-881 AM-883 AM-905 AM-906 AM-919 AM-926 AM-938 AM-1116 AM-1172 AM-1220 AM-1221 AM-1235 AM-1241 AM-1248 AM-1710 AM-1714 AM-1902 AM-2201 AM-2212 AM-2213 AM-2232 AM-2233 AM-2389 AM-3102 AM-4030 AM-4054 AM-4056 AM-4113 AM-6545
CP x	CP 47,497 CP 55,244 CP 55,940 (±)-CP 55,940 (+)-CP 55,940 (-)-CP 55,940
HU-x	HU-210 HU-211 HU-239 HU-243 HU-308 HU-320 HU-331 HU-336 HU-345
JWH-x	JWH-007 JWH-015 JWH-018 JWH-019 JWH-030 JWH-047 JWH-048 JWH-051 JWH-057 JWH-073 JWH-081 JWH-098 JWH-116 JWH-120 JWH-122 JWH-133 JWH-139 JWH-147 JWH-148 JWH-149 JWH-149 JWH-161 JWH-164 JWH-166 JWH-167 JWH-171 JWH-175 JWH-176 JWH-181 JWH-182 JWH-184 JWH-185 JWH-192 JWH-193 JWH-194 JWH-195 JWH-196 JWH-197 JWH-198 JWH-199 JWH-200 JWH-203 JWH-205 JWH-210 JWH-210 JWH-213 JWH-220 JWH-229 JWH-234 JWH-249 JWH-250 JWH-251 JWH-253 JWH-258 JWH-300 JWH-302 JWH-307 JWH-336 JWH-350 JWH-359 JWH-387 JWH-398 JWH-424
Misc. designer cannabinoids	4-HTMPIPO 5F-AB-FUPPYCA 5F-AB-PINACA 5F-ADB 5F-ADB-PINACA 5F-ADBICA 5F-AMB 5F-APINACA 5F-CUMYL-PINACA 5F-NNE1 5F-PB-22 5F-SDB-006 A-796,260 A-836,339 AB-001 AB-005 AB-CHFUPYCA AB-CHMINACA AB-FUBINACA AB-PINACA ADAMANTYL-THPINACA ADB-CHMINACA ADB-FUBINACA ADB-PINACA ADBICA ADSB-FUB-187 AMB-FUBINACA APICA APINACA APP-FUBINACA CB-13 CUMYL-PICA CUMYL-PINACA CUMYL-THPINACA DMHP EAM-2201 FAB-144 FDU-PB-22 FUB-144 FUB-APINACA FUB-JWH-018 FUB-PB-22 FUBIMINA JTE 7-31 JTE-907 Levonantradol MDMB-CHMICA MDMB-CHMINACA MDMB-FUBINACA MEPIRAPIM MAM-2201 MDA-19 MN-18 MN-25 NESS-0327 NESS-040C5 Nabilone Nabitan NM-2201 NNE1 Org 28611 Parahexyl PTI-1 PTI-2 PX-1 PX-2 PX-3 QUCHIC QUPIC RCS-4 RCS-8 SDB-005 SDB-006 STS-135 THC-O-acetate THC-O-phosphate THJ-018 THJ-2201 UR-144 WIN 55,212-2 XLR-11

D₂ agonists

Apomorphine
Aporphine
Bromocriptine
Cabergoline
Lisuride
LSD
Memantine
Nuciferine
Pergolide
Phenethylamine
Piribedil
Pramipexole
Ropinirole
Rotigotine
Salvinorin A
Also indirect D₂ agonists, such as dopamine reuptake inhibitors (cocaine, methylphenidate), releasing agents (amphetamine, methamphetamine), and precursors (levodopa).

GABA_A
enhancers

Inhalants
(Mixed MOA)

κOR agonists

Oneirogens

Others

v t e Tryptamines
1-Methylpsilocin 2,alpha-DMT 2-Me-DET 2-Methyl-5-HT 2,N,N-TMT 4,5-DHP-DMT 4,5-MDO-DMT 4,5-MDO-DiPT 4-AcO-DALT 4-AcO-DET 4-AcO-DMT 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-MPMI 4-HO-MPT 4-HO-MsBT 4-HO-NMT 4-HO-PiPT 4-HO-pyr-T 4-HO-αMT 4-Me-αET 4-Me-αMT 4-MeO-DiPT 4-MeO-DMT 4-MeO-MiPT 4-PrO-DMT 5,6-MeO-MiPT 5,6-MDO-DiPT 5,6-MDO-DMT 5,6-MDO-MiPT 5,7-Dihydroxytryptamine 5-BT 5-Bromo-DMT 5-CT 5-Chloro-αMT 5-Chloro-DMT 5-Ethoxy-αMT 5-Ethoxy-DMT 5-Ethyl-DMT 5-Fluoro-AET 5-Fluoro-αMT 5-Fluoro-DET 5-Fluoro-DMT 5-Fluoro-EPT 5-Fluoro-MET 5-HO-αMT 5-HO-DiPT 5-HTP 5-iPrO-AMT 5-MeS-DMT 5-Methoxytryptamine 5-MeO-7,N,N-TMT 5-Methyl-αET 5-MeO-2-TMT 5-MeO-αET 5-MeO-αMT 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-MPMI 5-MeO-NMT 5-MeO-pyr-T 5-MeO-NBpBrT 5-Methyl-DMT 5-(Nonyloxy)tryptamine 6-Fluoro-αMT 6-Fluoro-DMT 6-Hydroxymelatonin 6-MeO-THH 7-Chloro-AMT 7-Methyl-α-ethyltryptamine 7-Methyl-DMT Acetryptine Aeruginascin αET Alpha,N-DMT α,N,N-Trimethyltryptamine Alpha,N,O-TMS AL-37350A αMT Baeocystin BNC-210 Bufotenidine Bufotenin (5-HO-DMT) BW-723C86 Convolutindole A CP-132,484 DALT DBT Desformylflustrabromine DET DiPT DPT E-6801 E-6837 Ethocybin EiPT EMDT EPT FGIN-127 FGIN-143 Harmaline HIOC Ibogaine Idalopirdine Indorenate Iprocin Lespedamine Luzindole MET Methylbutyltryptamine MiPT MPT Miprocin Melatonin MPMI MS-245 NAS N-Ethyltryptamine N-Feruloylserotonin NMT DMT Norbaeocystin Normelatonin N-t-Butyltryptamine O-4310 Oxypertine Plakohypaphorine PiPT Psilocin (4-HO-DMT) Psilocybin (4-PO-DMT) Pyr-T Rizatriptan RU-28306 Serotonin ST-1936 Sumatriptan Tryptamine Tryptophan Yohimbine Yuremamine Zolmitriptan

Tryptamines