Chemistry:4-HO-MET

Short description: Chemical compound

4-HO-MET

Clinical data
Other names	3-(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
Identifiers
IUPAC name 3-{2-[Ethyl(methyl)amino]ethyl}-1H-indol-4-ol
CAS Number	77872-41-4
PubChem CID	21786582
ChemSpider	10513072
UNII	6RN01B78NY
Chemical and physical data
Formula	C13H18N2O
Molar mass	218.300 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCN(C)CCc2c[nH]c1cccc(O)c12
InChI 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. In his book TiHKAL (Tryptamines I Have Known and Loved), 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.

Effects

Users report similar effects to psilocin, including mydriasis, closed and open eye visuals, euphoria, time dilation and general change in thought processes. 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.

Pharmacology

Pharmacodynamics

Binding sites	Binding affinity Ki (μM)
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.

United Kingdom

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

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.

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

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.

See also

• Psychedelics, dissociatives and deliriants
• 4-HO-DET