|Other names||3-(2-(ethyl(methyl)amino)ethyl)-1H-indol-4-ol; 4-Hydroxy-N-methyl-N-ethyltryptamine; Colour|
|CompTox Dashboard (EPA)|
|Chemical and physical data|
|Molar mass||218.300 g·mol−1|
|3D model (JSmol)|
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 people have reported taking doses up to 150 mg,  more than an order of magnitude above the effective dose.  [ unreliable source? ]
This section needs more medical references for verification or relies too heavily on primary sources .(September 2017)
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,   and 3–4 hours after intranasal use. 
|Binding Sites||Binding Affinity Ki (μM) |
Sveriges 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 listed as 4-HO-MET 3-[2-[etyl(metyl)amino]etyl]-1H-indol-4-ol. 
4-HO-MET is a class A drug in the UK, as a result of the tryptamine catch-all clause.[ citation needed ]
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.[ citation needed ]
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 ]
α-Methyltryptamine is a psychedelic, stimulant, and entactogen drug of the tryptamine class. It was originally developed as an antidepressant by workers at Upjohn in the 1960s, and was used briefly as an antidepressant in Russia under the trade name Indopan before being discontinued.
2C-B (4-Bromo-2,5-dimethoxyphenethylamine) is a psychedelic drug of the 2C family. It was first synthesized by Alexander Shulgin in 1974. In Shulgin's book PiHKAL, the dosage range is listed as 12–24 mg. As a recreational drug, 2C-B is sold as a white powder sometimes pressed in tablets or gel caps. It is also referred to by a number of street names. The drug is usually taken orally, but can also be insufflated or vaporized. While being primarily a psychedelic it is also a mild entactogen.
5-MeO-aMT or 5-methoxy-α-methyltryptamine, α,O-Dimethylserotonin (Alpha-O) is a potent psychedelic tryptamine. It is soluble in ethanol.
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.
Diisopropyltryptamine is a psychedelic hallucinogenic drug of the tryptamine family that has a unique effect. While the majority of hallucinogens affect the visual sense, DiPT is primarily aural.
DET, also known under its chemical name N,N-diethyltryptamine and as T-9, is a psychedelic drug closely related to DMT and 4-HO-DET. However, despite its structural similarity to DMT, its activity is induced by an oral dose of around 50–100 mg, without the aid of MAO inhibitors, and the effects last for about 2–4 hours.
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.
4-Acetoxy-DET (4-Acetoxy-N,N-diethyltryptamine), also known as ethacetin, ethylacybin or 4-AcO-DET, is a psychedelic tryptamine. It was first synthesized in 1958 by Albert Hofmann in the Sandoz lab.
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.
5-MeO-DALT or N,N-di allyl-5-methoxy tryptamine is a psychedelic tryptamine first synthesized by Alexander Shulgin.
4-Acetoxy-DiPT is a synthetic psychedelic tryptamine. It is relatively uncommon and has only a short history of human use.
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.
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.
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.
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.
2,N,N-trimethyltryptamine, 2,N,N-TMT, or 2-Me-DMT is a tryptamine derivative that is a psychedelic drug. It was invented by Alexander Shulgin and reported in his book TiHKAL (#34). It is claimed to show psychoactive effects at a dosage of 50–100 mg orally, but these are relatively mild compared to other similar drugs, suggesting that while the 2-methyl group has blocked the binding of metabolic enzymes, it is also interfering with binding to the 5HT2A receptor target that mediates the hallucinogenic effects of these drugs.
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.
4-MeO-MiPT, or 4-methoxy-N-methyl-N-isopropyltryptamine, is a lesser-known psychedelic drug. It is the 4-methoxy analog of MiPT. 4-MeO-MiPT was first synthesized by Alexander Shulgin and is mentioned in his book TiHKAL. Subsequent testing by Shulgin on human test subjects showed the effective dose as 20-30 mg ; the onset time between ingestion and the first noticeable effects was 45-60 min, with sensations lasting between 2-2.5 hours. The sensation were significantly milder than those of 4-HO-MiPT, with 4-MeO-MiPT producing erotic-enhancing effects, and few of the visuals common with tryptamines. Very little data exists about the pharmacological properties, metabolism, and toxicity of 4-MeO-MiPT.
5,6-MDO-DMT, or 5,6-methylenedioxy-N,N-dimethyltryptamine, is a lesser-known psychedelic drug. It is the 5,6-methylenedioxy analog of DMT. 5,6-MDO-DMT was first synthesized by Alexander Shulgin. In his book TiHKAL, 5,6-MDO-DMT produces no noticeable psychoactive effects, although it was only tested up to a dose of 5 mg. Very little data exists about the pharmacological properties, metabolism, and toxicity of 5,6-MDO-DMT.
4-Hydroxy-α-methyltryptamine (4-HO-αMT) is a psychedelic drug of the tryptamine class. It is a close structural analogue of α-methyltryptamine (αMT) and produces similar effects to it, but with exacerbated side effects similarly to 5-MeO-αMT. Alexander Shulgin describes 4-HO-αMT briefly in his book TiHKAL:
The 4-hydroxy analogue of αMT has been looked at in human subjects. It is reported to be markedly visual in its effects, with some subjects reporting dizziness and a depressed feeling. There were, however, several toxic signs at doses of 15 to 20 milligrams orally, including abdominal pain, tachycardia, increased blood pressure and, with several people, headache and diarrhea.