4-HO-MET

Last updated
4-HO-MET
4-HO-MET.svg
4-OH-MET 3D.png
Clinical data
Other names3-(2-(ethyl(methyl)amino)ethyl)-1H-indol-4-ol; 4-Hydroxy-N-methyl-N-ethyltryptamine
Legal status
Legal status
  • US:Unscheduled
Schedule I controlled substance in Virginia [1]
Identifiers
  • 3-{2-[Ethyl(methyl)amino]ethyl}-1H-indol-4-ol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C13H18N2O
Molar mass 218.300 g·mol−1
3D model (JSmol)
  • CCN(C)CCc2c[nH]c1cccc(O)c12
  • InChI=1S/C13H18N2O/c1-3-15(2)8-7-10-9-14-11-5-4-6-12(16)13(10)11/h4-6,9,14,16H,3,7-8H2,1-2H3
  • Key:ORWQBKPSGDRPPA-UHFFFAOYSA-N

4-HO-MET (4-hydroxy-N-methyl-N-ethyltryptamine, metocin, or methylcybin) 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.[ citation needed ] In his book TiHKAL (Tryptamines I Have Known and Loved), the dosage is listed as 10-20 mg. [2] 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,[ citation needed ] more than an order of magnitude above the effective dose. [2]

Contents

Effects

Users report similar effects to psilocin, including mydriasis, closed and open eye visuals, euphoria, time dilation and general change in thought processes. [2] [3] These effects occur in a wavelike pattern such as that of psilocybin with near-normal perception and high effect varying rapidly. The effects last for about 4–6 hours after oral administration. [2] [4]

Pharmacology

Pharmacodynamics

Binding sitesBinding affinity Ki (μM) [5]
5-HT1A0.228
5-HT2A0.057
5-HT2C0.141
D1>25
D24
D36.7
α1A9.7
α2A2.4
TAAR13.1
H10.82
SERT0.2
DAT>26
NET13

Drug prohibition laws

Sweden

The Swedish Riksdag added 4-HO-MET to Schedule I ("substances, plant materials and fungi which normally do not have medical use") as narcotics in Sweden as of May 1, 2012, published by Medical Products Agency in their regulation LVFS 2012:6. [6]

United Kingdom

4-HO-MET is a class A drug in the UK, as a result of the tryptamine catch-all clause.[ citation needed ]

United States

4-HO-MET is not scheduled at the federal level in the United States, but it is possible that it could be considered an analogue of psilocin, in which case purchase, sale, or possession could be prosecuted under the Federal Analogue Act. [7]

It is a schedule I substance in some states, such as South Dakota [8] and West Virginia. [9]

Germany

4-HO-MET is ruled under the Neue-psychoaktive-Stoffe-Gesetz (NpSG) since July 18, 2019. Production and Import with intent to distribute is punishable. Possession is forbidden but not punishable, although ordering it in small quantities can still be seen as an intent to distribute it and be punished.[ citation needed ]

See also

Related Research Articles

α-Methyltryptamine Chemical compound

α-Methyltryptamine is a psychedelic, stimulant, and entactogen drug of the tryptamine class. It was originally developed as an antidepressant by chemists at Upjohn in the 1960s, and was used briefly as an antidepressant in Russia under the trade name Indopan before being discontinued.

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

2C-I is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin and described in his 1991 book PiHKAL. The drug has been used recreationally as psychedelic and other reported effects and was sometimes confused with the more potent chemical cousin 25I-NBOMe, nicknamed "Smiles," in the media.

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

2C-B (4-bromo-2,5-dimethoxyphenethylamine) is a synthetic psychedelic drug of the 2C family, initially synthesized by Alexander Shulgin in 1974 and commonly used as a recreational drug. There is limited scientific information regarding the drug's pharmacokinetics and pharmacological effects in humans. The existing studies primarily classify 2C-B as a stimulant, and hallucinogen, and less commonly as an entactogen, and empathogen.

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

2C-T-2 is a psychedelic and entactogenic phenethylamine of the 2C family. It was first synthesized in 1981 by Alexander Shulgin, and rated by him as one of the "magical half-dozen" most important psychedelic phenethylamine compounds. The drug has structural and pharmacodynamic properties similar to those of 2C-T-7.

<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 is a substituted tryptamine alkaloid and a serotonergic psychedelic substance. 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 5-HT2A receptors, psilocin modulates the production and reuptake of serotonin. The mind-altering effects of psilocin are highly variable and subjective and resemble those of LSD and DMT.

<span class="mw-page-title-main">4-HO-DET</span> 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.

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

2,5-Dimethoxy-4-iodoamphetamine (DOI) is a psychedelic drug and a substituted amphetamine. Unlike many other substituted amphetamines, however, it is not primarily a stimulant. DOI has a stereocenter and R-(−)-DOI is the more active stereoisomer. In neuroscience research, [125I]-R-(−)-DOI is used as a radioligand and indicator of the presence of 5-HT2A serotonin receptors. DOI's effects have been compared to LSD, although there are differences that experienced users can distinguish. Besides the longer duration, the trip tends to be more energetic than an LSD trip, with more body load and a different subjective visual experience. The after effects include residual stimulation and difficulty sleeping, which, depending on the dose, may persist for days. While rare, it is sometimes sold as a substitute for LSD, or even sold falsely as LSD, which may be dangerous because DOI does not have the same established safety profile as LSD.

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

5-MeO-MiPT is a psychedelic and hallucinogenic drug, used by some as an entheogen. It has structural and pharmacodynamic properties similar to the drugs 5-MeO-DiPT, DiPT, and MiPT. It is commonly used as a "substitute" for 5-MeO-DiPT because of the very similar structure and effects.

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

5-MeO-DALT or N,N-di allyl-5-methoxy tryptamine is a psychedelic tryptamine first synthesized by Alexander Shulgin.

<span class="mw-page-title-main">ALD-52</span> Chemical compound

ALD-52, also known as 1-acetyl-LSD, has chemical structural features similar to lysergic acid diethylamide (LSD), a known psychedelic drug. Similarly, ALD-52 has been reported to produce psychoactive effects, but its pharmacological effects on humans are poorly understood. Given its psychoactive properties, it has been reported to be consumed as a recreational drug, and the purported first confirmed detection of the substance on the illicit market occurred in April 2016.

<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.

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

2C-T is a psychedelic and hallucinogenic drug of the 2C family. It is used by some as an entheogen. It has structural and pharmacodynamic properties similar to the drugs mescaline and 2C-T-2.

<span class="mw-page-title-main">AL-LAD</span> Chemical compound (psychedelic drug)

AL-LAD, also known as 6-allyl-6-nor-LSD, is a psychedelic drug and an analog of lysergic acid diethylamide (LSD). It is described by Alexander Shulgin in the book TiHKAL. It is synthesized starting from nor-LSD as a precursor, using allyl bromide as a reactant.

<i>O</i>-Acetylpsilocin Chemical compound

O-Acetylpsilocin is a semi-synthetic psychoactive 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-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-AcO-MET</span> Chemical compound

4-acetoxy-MET (4-acetoxy-N-methyl-N-ethyltryptamine), also known as 4-AcO-MET or metacetin, is a hallucinogenic tryptamine. It is the acetate ester of 4-HO-MET, and a homologue of 4-AcO-DMT. It is a novel compound with very little history of human use. It is sometimes sold as a research chemical by online retailers.

<span class="mw-page-title-main">4-PrO-DMT</span> Chemical compound

4-Propionoxy-N,N-dimethyltryptamine is a synthetic psychedelic drug from the tryptamine family with psychedelic effects, and is believed to act as a prodrug for psilocin. It produces a head-twitch response in mice. It has been sold online as a designer drug since May 2019. It was first identified as a new psychoactive substance in Sweden, in July 2019. A number of related derivatives have been synthesised as prodrugs of psilocin for medical applications.

References

  1. "§ 54.1-3446. Schedule I." Virginia Law. Retrieved 29 October 2023.
  2. 1 2 3 4 Shulgin A, Shulgin A (September 1997). "#47 MIPT". Isomer Design. Transform Press. Retrieved 28 November 2023.
  3. Palamar JJ, Acosta P (January 2020). "A qualitative descriptive analysis of effects of psychedelic phenethylamines and tryptamines". Human Psychopharmacology. 35 (1): e2719. doi:10.1002/hup.2719. PMC   6995261 . PMID   31909513.
  4. Kjellgren A, Soussan C (2011). "Heaven and hell--a phenomenological study of recreational use of 4-HO-MET in Sweden". Journal of Psychoactive Drugs. J Psychoactive Drugs. 43 (3): 211–219. doi:10.1080/02791072.2011.605699. PMID   22111404. S2CID   25483726.
  5. Rickli A, Moning OD, Hoener MC, Liechti ME (August 2016). "Receptor interaction profiles of novel psychoactive tryptamines compared with classic hallucinogens" (PDF). European Neuropsychopharmacology. 26 (8): 1327–1337. doi:10.1016/j.euroneuro.2016.05.001. PMID   27216487. S2CID   6685927.
  6. "Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 2011:10) om förteckningar över narkotika" [Regulations on changes in the Swedish Medicines Agency's regulations (LVFS 2011:10) on lists of narcotics](PDF) (in Swedish). Elanders Sverige AB. 2012-04-20. Archived from the original (PDF) on 2013-09-28. Retrieved 2014-02-25.
  7. "21 U.S. Code § 841 - Prohibited acts A", LII / Legal Information Institute, retrieved 2016-08-02
  8. "Chapter 34-20B Drugs and Substances Control". South Dakota Legislature. Retrieved 2023-10-09.
  9. "Chapter 60A. Uniform Controlled Substances Act". West Dakota Legislature. Retrieved 2023-10-09.