4-HO-MET
{{Short description|Chemical compound}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Infobox drug
| drug_name =
| image = 4-HO-MET.svg
| width = 200px
| caption =
| image2 = 4-OH-MET 3D.png
| width2 = 200px
| caption2 =
| pronounce =
| tradename =
| Drugs.com =
| MedlinePlus =
| licence_CA =
| licence_EU =
| DailyMedID =
| licence_US =
| pregnancy_AU =
| pregnancy_category =
| dependency_liability =
| addiction_liability =
| routes_of_administration = Oral
| class = Serotonin receptor agonist; Serotonergic psychedelic; Hallucinogen
| ATC_prefix = None
| ATC_suffix =
| legal_US = Unscheduled
Schedule I controlled substance in Virginia{{cite web |title=§ 54.1-3446. Schedule I. |url=https://law.lis.virginia.gov/vacode/title54.1/chapter34/section54.1-3446/ |website=Virginia Law |access-date=29 October 2023}}
| bioavailability =
| protein_bound =
| metabolism =
| metabolites =
| onset =
| elimination_half-life =
| duration_of_action = 4–6 hours
| excretion =
| CAS_number = 77872-41-4
| CAS_supplemental =
| PubChem = 21786582
| IUPHAR_ligand =
| DrugBank =
| ChemSpiderID = 10513072
| UNII = 6RN01B78NY
| KEGG =
| ChEBI =
| ChEMBL =
| NIAID_ChemDB =
| PDB_ligand =
| synonyms = 4-Hydroxy-N-methyl-N-ethyltryptamine; 4-OH-MET; Metocin; Methylcybin
| IUPAC_name = 3-{2-[Ethyl(methyl)amino]ethyl}-1H-indol-4-ol
| C=13 | H=18 | N=2 | O=1
| SMILES = CCN(C)CCc2c[nH]c1cccc(O)c12
| StdInChI = 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
| StdInChIKey = ORWQBKPSGDRPPA-UHFFFAOYSA-N
}}
4-HO-MET, also known as 4-hydroxy-N-methyl-N-ethyltryptamine or as metocin, is a lesser-known psychedelic drug of the tryptamine family related to psilocin. It is a close structural and functional analogue of psilocin (4-HO-DMT) and is the 4-hydroxyl analogue of methylethyltryptamine (MET). The drug has been encountered as a novel recreational and designer drug.{{cite web | title=2015 Annual Reports on the implementation of Council Decision 2005/387/JHA | website=Europol | date=2008 | url=https://www.europol.europa.eu/publications-events/publications/emcdda%E2%80%93europol-2005-2015-annual-reports-implementation-of-council-decision-2005/387/jha | access-date=30 March 2025}}
Effects
4-HO-MET was first synthesized by Alexander Shulgin.{{cite journal | vauthors = Zamberlan F, Sanz C, Martínez Vivot R, Pallavicini C, Erowid F, Erowid E, Tagliazucchi E | title = The Varieties of the Psychedelic Experience: A Preliminary Study of the Association Between the Reported Subjective Effects and the Binding Affinity Profiles of Substituted Phenethylamines and Tryptamines | journal = Front Integr Neurosci | volume = 12 | issue = | pages = 54 | date = 2018 | pmid = 30467466 | pmc = 6235949 | doi = 10.3389/fnint.2018.00054 | doi-access = free | url = | quote = 4-OH-MET (4-Hydroxy-N-methyl-N-ethyltryptamine): substituted tryptamine and close analog of psilocin, first synthesized by A. Shulgin (Shulgin and Shulgin, 1997).}} In his book TiHKAL (Tryptamines I Have Known and Loved), the dosage is listed as 10 to 20{{nbsp}}mg orally and its duration as 4 to 6{{nbsp}}hours.{{cite web |url=http://isomerdesign.com/PiHKAL/read.php?domain=tk&id=47 |title=#47 MIPT | vauthors = Shulgin A, Shulgin A |publisher=Transform Press |date=September 1997 |website=Isomer Design |access-date=28 November 2023}}{{cite book | vauthors = Shulgin AT | chapter=Basic Pharmacology and Effects | pages=67–137 | veditors = Laing RR | title=Hallucinogens: A Forensic Drug Handbook | publisher=Elsevier Science | series=Forensic Drug Handbook Series | year=2003 | isbn=978-0-12-433951-4 | url=https://books.google.com/books?id=l1DrqgobbcwC | chapter-url=https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=6bb3a7499da8e9852b39cd4db16891147c83f5c6}} However, a wider recreational dosage range of 2 to 45{{nbsp}}mg or more, with a dose estimate of 15{{nbsp}}mg, has also been reported.{{cite journal | vauthors = Luethi D, Liechti ME | title = Monoamine Transporter and Receptor Interaction Profiles in Vitro Predict Reported Human Doses of Novel Psychoactive Stimulants and Psychedelics | journal = Int J Neuropsychopharmacol | volume = 21 | issue = 10 | pages = 926–931 | date = October 2018 | pmid = 29850881 | pmc = 6165951 | doi = 10.1093/ijnp/pyy047 }}
The effects of 4-HO-MET have been reported to include mydriasis, euphoria, tingling sensations, perceptual changes, closed- and open-eye visuals, synesthesia, time dilation, intensified perceptions, thoughts, and feelings, and a general change in thought processes.{{cite journal | vauthors = Kjellgren A, Soussan C | title = Heaven and hell--a phenomenological study of recreational use of 4-HO-MET in Sweden | journal = J Psychoactive Drugs | volume = 43 | issue = 3 | pages = 211–219 | date = 2011 | pmid = 22111404 | doi = 10.1080/02791072.2011.605699 | url = }}
4-HO-MET is said to produce qualitative effects very similar to those of psilocin.{{cite journal | vauthors = Palamar JJ, Acosta P | title = A qualitative descriptive analysis of effects of psychedelic phenethylamines and tryptamines | journal = Human Psychopharmacology | volume = 35 | issue = 1 | pages = e2719 | date = January 2020 | pmid = 31909513 | pmc = 6995261 | doi = 10.1002/hup.2719 }} However, it has also been described as being a relatively or very light and more clear-headed and functional psychedelic with less head space. On the other hand, it is said to still produce strong visuals. This has been described as being analogous to the case of 2C-B.
Interactions
{{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}
Pharmacology
=Pharmacodynamics=
4-HO-MET binds to various serotonin receptors and is known to act as an agonist of the serotonin 5-HT2A, 5-HT2B, 5-HT2C, and 5-HT1A receptors. It is thought that the hallucinogenic effects of serotonergic psychedelics like 4-HO-MET are mediated by serotonin 5-HT2A receptor activation.{{cite journal | vauthors = Nichols DE | title = Psychedelics | journal = Pharmacol Rev | volume = 68 | issue = 2 | pages = 264–355 | date = April 2016 | pmid = 26841800 | pmc = 4813425 | doi = 10.1124/pr.115.011478 | url = https://psilosybiini.info/paperit/Psychedelics%20(Nichols,%202016).pdf}}
=Pharmacokinetics=
The metabolism of 4-HO-MET has been studied.{{cite journal | vauthors = Bruni PS, Grafinger KE, Nussbaumer S, König S, Schürch S, Weinmann W | title = Study of the in vitro and in vivo metabolism of 4-HO-MET | journal = Forensic Sci Int | volume = 290 | issue = | pages = 103–110 | date = September 2018 | pmid = 30015274 | doi = 10.1016/j.forsciint.2018.06.037 | url = }}
History
4-HO-MET was first synthesized and discovered by Alexander Shulgin in the 1970s. It was first described in the scientific literature by David Repke and colleagues by 1981.{{cite journal | vauthors = Repke DB, Ferguson WJ, Bates DK | title=Psilocin analogs II. Synthesis of 3-[2-(dialkylamino)ethyl]-, 3-[2-( N -methyl- N -alkylamino)ethyl]-, and 3-[2-(cycloalkylamino)ethyl]indol-4-ols | journal=Journal of Heterocyclic Chemistry | volume=18 | issue=1 | date=1981 | issn=0022-152X | doi=10.1002/jhet.5570180131 | pages=175–179}} Subsequently, 4-HO-MET was described by Shulgin in his book TiHKAL (Tryptamines I Have Known and Loved) in 1997. It was encountered as a novel recreational and designer drug in Europe by 2008.
Legal status
=Finland=
Scheduled in the "government decree on psychoactive substances banned from the consumer market".{{cite web | title = Valtioneuvoston asetus kuluttajamarkkinoilta kielletyistä psykoaktiivisista aineista | trans-title = Government Decree on psychoactive substances banned from the consumer market | language = Finnish | work = Finlex | publisher = Finish Ministry of Justice | url = https://finlex.fi/fi/lainsaadanto/2014/1130}}
=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.{{Fact|date=December 2022}}
=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.{{cite web | url = http://www.lakemedelsverket.se/upload/lvfs/LVFS_2012_6.pdf | title = Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 2011:10) om förteckningar över narkotika | trans-title = Regulations on changes in the Swedish Medicines Agency's regulations (LVFS 2011:10) on lists of narcotics | access-date = 2014-02-25 | date = 2012-04-20 | publisher = Elanders Sverige AB | language = sv | archive-url = https://web.archive.org/web/20130928024107/http://www.lakemedelsverket.se/upload/lvfs/LVFS_2012_6.pdf | archive-date = 2013-09-28 | url-status = dead }}
=United Kingdom=
4-HO-MET is a class A drug in the UK, as a result of the tryptamine catch-all clause.{{Fact|date=December 2022}}
=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.{{cite web |title=21 U.S. Code § 841 - Prohibited acts A |url=https://www.law.cornell.edu/uscode/text/21/841 |access-date=2016-08-02 |website=LII / Legal Information Institute |mode=cs2}}
It is a schedule I substance in some states, such as South Dakota{{cite web |title=Chapter 34-20B Drugs and Substances Control |url=https://sdlegislature.gov/Statutes/34-20B |access-date=2023-10-09 |website=South Dakota Legislature |language=en}} and West Virginia.{{cite web |title=Chapter 60A. Uniform Controlled Substances Act |url=https://code.wvlegislature.gov/60A-2-204/ |access-date=2023-10-09 |website=West Dakota Legislature}}
See also
References
{{Reflist}}
External links
- [https://isomerdesign.com/pihkal/explore/5021 4-HO-MET - Isomer Design]
- [https://psychonautwiki.org/wiki/4-HO-MET 4-HO-MET - PsychonautWiki]
- [https://erowid.org/chemicals/4_ho_met/4_ho_met.shtml 4-HO-MET - Erowid]
- [https://erowid.org/library/books_online/tihkal/tihkal21.shtml 4-HO-MET - TiHKAL - Erowid]
- [https://isomerdesign.com/pihkal/read/tk/21 4-HO-MET - TiHKAL - Isomer Design]
{{Psychedelics}}
{{Serotonin receptor modulators}}
{{Tryptamines}}