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| NIAID_ChemDB =
| NIAID_ChemDB =
| PDB_ligand =
| PDB_ligand =
| synonyms = 3-(2-(ethyl(methyl)amino)ethyl)-1H-indol-4-ol; 4-Hydroxy-N-methyl-N-ethyltryptamine
| synonyms = 3-(2-(ethyl(methyl)amino)ethyl)-1H-indol-4-ol; 4-Hydroxy-''N''-methyl-''N''-ethyltryptamine


<!-- Chemical data -->
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Revision as of 05:07, 10 June 2024

4-HO-MET
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
FormulaC13H18N2O
Molar mass218.300 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]

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 sites Binding affinity Ki (μM)[5]
5-HT1A 0.228
5-HT2A 0.057
5-HT2C 0.141
D1 >25
D2 4
D3 6.7
α1A 9.7
α2A 2.4
TAAR1 3.1
H1 0.82
SERT 0.2
DAT >26
NET 13

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

References

  1. ^ "§ 54.1-3446. Schedule I." Virginia Law. Retrieved 29 October 2023.
  2. ^ a b c d 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. 43 (3). J Psychoactive Drugs: 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.
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