4-HO-DET

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4-HO-DET
4-HO-DET.svg
4-HO-DET-3d-sticks.png
Legal status
Legal status
Identifiers
  • 3-(2-Diethylaminoethyl)-1H-indol-4-ol
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C14H20N2O
Molar mass 232.327 g·mol−1
3D model (JSmol)
Melting point 104 to 106 °C (219 to 223 °F)
  • CCN(CC)CCc1c[nH]c2cccc(O)c12
  • 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 Yes check.svgY
  • Key:OHHYMKDBKJPILO-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (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]

Contents

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 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]

See also

Related Research Articles

α-Methyltryptamine Chemical compound

α-Methyltryptamine is a psychedelic, stimulant, and entactogen drug of the tryptamine family. It was originally developed as an antidepressant at Upjohn in the 1960s, and was used briefly as an antidepressant in the Soviet Union under the brand name Indopan or Indopane before being discontinued.

<span class="mw-page-title-main">2C-T-7</span> Psychedelic phenthylamine drug

2C-T-7 is a psychedelic phenethylamine of the 2C family. In his book PiHKAL: A Chemical Love Story, Alexander Shulgin lists the dosage range as 10–30 mg. 2C-T-7 is generally taken orally, and produces psychedelic and entactogenic effects that last 8 to 15 hours. Up until Operation Web Tryp and three deaths, two of which involved the use of other drugs in addition to 2C-T-7, and one which involved an excessive insufflated dose, 2C-T-7 was sold commercially in Dutch and Japanese smartshops and online. It is known on the streets as Blue Mystic or 7th Heaven. There has been little real research done on this chemical other than Shulgin's comments in PiHKAL and a few small animal studies mostly aimed at detecting metabolites.

<span class="mw-page-title-main">2C-E</span> Chemical compound

2C-E is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin and documented in his book PiHKAL. Like the other substances in its family, it produces sensory and cognitive effects in its physical reactions with living organisms.

<span class="mw-page-title-main">2C-C</span> Chemical compound

2C-C is a psychedelic drug of the 2C family. It was first synthesized by Alexander Shulgin, sometimes used as an entheogen. In his book PiHKAL , Shulgin lists the dosage range as 20–40 mg. 2C-C is usually taken orally, but may also be insufflated. 2C-C is schedule I of section 202(c) of the Controlled Substances Act in the United States, signed into law as of July, 2012 under the Food and Drug Administration Safety and Innovation Act.

<span class="mw-page-title-main">2C-D</span> Chemical compound

2C-D is a psychedelic drug of the 2C family that is sometimes used as an entheogen. It was first synthesized in 1970 by a team from the Texas Research Institute of Mental Sciences, and its activity was subsequently investigated in humans by Alexander Shulgin. In his book PiHKAL, Shulgin lists the dosage range as being from 20 to 60 mg. Lower doses of 10 mg or less have been explored for microdosing.

<span class="mw-page-title-main">5-MeO-AMT</span> Chemical compound

5-MeO-αMT, or 5-methoxy-α-methyltryptamine, also known as α,O-dimethylserotonin (Alpha-O), is a serotonergic psychedelic of the tryptamine family. It is a derivative of α-methyltryptamine (αMT) and an analogue of 5-MeO-DMT.

<span class="mw-page-title-main">4-HO-DiPT</span> Chemical compound

4-Hydroxy-N,N-diisopropyltryptamine is a synthetic psychedelic drug. It is a higher homologue of psilocin, 4-HO-DET, and is a positional isomer of 4-HO-DPT and has a tryptamine molecular sub-structure.

<span class="mw-page-title-main">Psilocin</span> Chemical compound

Psilocin, also known as 4-hydroxy-N,N-dimethyltryptamine (4-OH-DMT), is a substituted tryptamine alkaloid and a serotonergic psychedelic. It is present in most psychedelic mushrooms together with its phosphorylated counterpart psilocybin. Psilocin is a Schedule I drug under the Convention on Psychotropic Substances. Acting on the serotonin 5-HT2A receptors, psilocin's psychedelic effects are directly correlated with the drug's occupancy at these receptor sites. The subjective mind-altering effects of psilocin are highly variable and are said to resemble those of lysergic acid diethylamide (LSD) and N,N-dimethyltryptamine (DMT).

<span class="mw-page-title-main">Diethyltryptamine</span> Chemical compound

DET, also known under its chemical name N,N-diethyltryptamine and as T-9, is a psychedelic drug closely related to DMT and 4-HO-DET. However, despite its structural similarity to DMT, its activity is induced by an oral dose of around 50–100 mg, without the aid of MAO inhibitors, and the effects last for about 2–4 hours.

<span class="mw-page-title-main">2C-T-4</span> Chemical compound

2C-T-4 (2,5-dimethoxy-4-isopropylthiophenethylamine) is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin and is used as entheogenic recreational drug.

<span class="mw-page-title-main">4-AcO-DET</span> Chemical compound

4-Acetoxy-DET (4-Acetoxy-N,N-diethyltryptamine), also known as ethacetin, ethylacybin or 4-AcO-DET, is a psychedelic tryptamine. It was first synthesized in 1958 by Albert Hofmann in the Sandoz lab.

<span class="mw-page-title-main">4-Acetoxy-DiPT</span> Chemical compound

4-Acetoxy-DiPT is a synthetic psychedelic tryptamine. It is relatively uncommon and has only a short history of human use.

<span class="mw-page-title-main">4-HO-MiPT</span> Chemical compound

4-HO-MiPT is a synthetic substituted aromatic compound and a lesser-known psychedelic tryptamine. It is thought to be a serotonergic psychedelic, similar to magic mushrooms, LSD and mescaline. Its molecular structure and pharmacological effects somewhat resemble those of the tryptamine psilocin, which is the primary psychoactive chemical in magic mushrooms.

<span class="mw-page-title-main">MiPT</span> Chemical compound

N-methyl-N-isopropyltryptamine (MiPT) is a psychedelic tryptamine, closely related to DMT, DiPT and miprocin. It was first synthesized by David Repke in 1984 and was subsequently evaluated and described in Alexander Shulgin's 1997 book TiHKAL.

<span class="mw-page-title-main">2,5-Dimethoxy-4-chloroamphetamine</span> Chemical compound

2,5-Dimethoxy-4-chloroamphetamine (DOC) is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was presumably first synthesized by Alexander Shulgin, and was described in his book PiHKAL.

<i>O</i>-Acetylpsilocin Semi-synthetic psychoactive drug

Psilacetin, also known as O-acetylpsilocin or as 4-acetoxy-N,N-dimethyltryptamine, is a semi-synthetic serotonergic psychedelic drug that has been suggested by David Nichols to be a potentially useful alternative to psilocybin for pharmacological studies, as they are both believed to be prodrugs of psilocin. However, some users report that O-acetylpsilocin's subjective effects differ from those of psilocybin and psilocin. Additionally, some users prefer 4-AcO-DMT to natural psilocybin mushrooms due to feeling fewer adverse side effects such as nausea and heavy body load, which are more frequently reported in experiences involving natural mushrooms. It is the acetylated form of the psilocybin mushroom alkaloid psilocin and is a lower homolog of 4-AcO-MET, 4-AcO-DET, 4-AcO-MiPT and 4-AcO-DiPT.

<span class="mw-page-title-main">4-HO-MET</span> Chemical compound

4-HO-MET is a lesser-known psychedelic drug. It is a structural and functional analog of psilocin as well as the 4-hydroxyl analog of methylethyltryptamine (MET). 4-HO-MET was first synthesized by Alexander Shulgin. In his book TiHKAL, the dosage is listed as 10-20 mg. 4-HO-MET produces psilocin-like distortion of color, sound, and form. Very little data exists about the pharmacological properties, metabolism, and toxicity of 4-HO-MET. There have been no reports of deaths from 4-HO-MET, even though there exist anecdotal reports of the ingestion of up to 150 mg, more than an order of magnitude above the effective dose.

<span class="mw-page-title-main">4-HO-MPT</span> Chemical compound

4-Hydroxy-N-methyl-N-propyltryptamine, commonly known as 4-HO-MPT or meprocin, is a psychedelic drug in the tryptamine class of chemical compounds and is a higher homologue of the naturally occurring substituted tryptamine psilocin as well as being the 4-hydroxyl analog of MPT.

<span class="mw-page-title-main">4-HO-αMT</span> Chemical compound

4-Hydroxy-α-methyltryptamine (4-HO-αMT) is a psychedelic drug of the tryptamine class. It is a close structural analogue of α-methyltryptamine (αMT) and produces similar effects to it, but with exacerbated side effects similarly to 5-MeO-αMT. Alexander Shulgin describes 4-HO-αMT briefly in his book TiHKAL:

The 4-hydroxy analogue of αMT has been looked at in human subjects. It is reported to be markedly visual in its effects, with some subjects reporting dizziness and a depressed feeling. There were, however, several toxic signs at doses of 15 to 20 milligrams orally, including abdominal pain, tachycardia, increased blood pressure and, with several people, headache and diarrhea.

<span class="mw-page-title-main">4-AcO-MiPT</span> Chemical compound

4-AcO-MiPT is a psychedelic tryptamine. It is closely related to O-acetylpsilocin and MiPT.

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. 1 2 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.