| Width: | 200px |
| Width2: | 200px |
| Legal Us: | UnscheduledSchedule I controlled substance in Virginia[1] |
| Cas Number: | 77872-41-4 |
| Pubchem: | 21786582 |
| Chemspiderid: | 10513072 |
| Unii: | 6RN01B78NY |
| Synonyms: | 3-(2-(ethyl(methyl)amino)ethyl)-1H-indol-4-ol; 4-Hydroxy-N-methyl-N-ethyltryptamine |
| Iupac Name: | 3--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 (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. 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, more than an order of magnitude above the effective dose.
Users report similar effects to psilocin, including mydriasis, closed and open eye visuals, euphoria, time dilation and general change in thought processes.[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.[4]
| 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 |
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]
4-HO-MET is a class A drug in the UK, as a result of the tryptamine catch-all clause.
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]
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.