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Clinical data | |
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Other names | 4-OH-MET; 4-Hydroxy-N-methyl-N-ethyltryptamine; Metocin; Methylcybin |
Routes of administration | Oral [1] |
Drug class | Non-selective serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen |
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Pharmacokinetic data | |
Onset of action | ≤30 minutes [1] |
Duration of action | 4–6 hours [1] [3] |
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Chemical and physical data | |
Formula | C13H18N2O |
Molar mass | 218.300 g·mol−1 |
3D model (JSmol) | |
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4-HO-MET, also known as 4-hydroxy-N-methyl-N-ethyltryptamine, as well as metocin or methylcybin, is a psychedelic drug of the tryptamine and 4-hydroxytryptamine families related to psilocin (4-HO-DMT). [1] It is taken orally. [1]
The drug acts as a non-selective serotonin receptor agonist, including of the serotonin 5-HT2A receptor. [4] [5] [6] [7] It is a close structural analogue of psilocin (4-HO-DMT) and is the 4-hydroxyl analogue of methylethyltryptamine (MET). [1]
4-HO-MET was discovered by Alexander Shulgin in the 1970s. [8] [9] [1] It was first described in the literature by David Repke and colleagues in 1981. [10] The drug was encountered as a novel recreational and designer drug by 2008. [11]
In his book TiHKAL (Tryptamines I Have Known and Loved), Alexander Shulgin lists the dose range as 10 to 20 mg orally and its duration as 4 to 6 hours. [1] [12] [3] However, a wider recreational dosage range of 2 to 45 mg or more, with a dose estimate of 15 mg, has also been reported. [13] Its onset is within 30 minutes. [1]
The effects of 4-HO-MET have been reported to include pupil dilation, 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. [3] [8] [1]
4-HO-MET is said to produce qualitative effects very similar to those of psilocin. [1] [8] [3] Shulgin has stated that he doubts it could be distinguished from psilocin in any blinded clinical study. [1] However, the drug has also been described as being relatively or very light, more clear-headed and functional, and having less head space. [8] On the other hand, it is said to still produce strong psychedelic visuals. [8] This has been described as being analogous to the case of 2C-B. [8]
In addition to its use on its own, 4-HO-MET is employed as a component of the MDMA-mimicking Borax combo. [14] [15] [16]
Target | Affinity (Ki, nM) |
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5-HT1A | 135–950 (Ki) 1,390 (EC50 ) 90% (Emax ) |
5-HT1B | 331 |
5-HT1D | 197 |
5-HT1E | 161 |
5-HT1F | ND |
5-HT2A | 4.0–177 (Ki) 18–97 (EC50) 54–95% (Emax) |
5-HT2B | 12 (Ki) 2.64–>20,000 (EC50) 44–71% (Emax) |
5-HT2C | 141–164 (Ki) 30–113 (EC50) 87–101% (Emax) |
5-HT3 | ND |
5-HT4 | ND |
5-HT5A | 304 |
5-HT6 | 70 |
5-HT7 | 60 |
α1A | 9,700 |
α1B, α1D | ND |
α2A | 1,666–2,400 |
α2B, α2C | IA |
β1–β3 | ND |
β2 | ND |
D1 | 25,000 |
D2 | 4,000 |
D3 | 6,700 |
D4, D5 | IA |
H1 | 483–820 |
H2 | IA |
H3, H4 | ND |
M1–M3, M5 | ND |
M2 | IA |
I1 | ND |
σ1, σ2 | IA |
TAAR1 | 12,000 (Ki) (mouse) 3,100 (Ki) (rat) 2,500 (EC50) (mouse) 2,100 (EC50) (rat) >10,000 (EC50) (human) 78% (Emax) (mouse) 71% (Emax) (rat) |
SERT | 200–2,310 (Ki) 830–9,000 (IC50 ) IA (EC50) |
NET | 13,000 (Ki) 11,000 (IC50) IA (EC50) |
DAT | >26,000 (Ki) >100,000 (IC50) IA (EC50) |
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [4] [5] [6] [7] [17] |
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. [4] [5] [6] [7] It is thought that the hallucinogenic effects of serotonergic psychedelics like 4-HO-MET are mediated by serotonin 5-HT2A receptor activation. [18]
The metabolism of 4-HO-MET has been studied. [19]
4-HO-MET, also known as 4-hydroxy-N-methyl-N-ethyltryptamine, is a substituted tryptamine and 4-hydroxytryptamine. [1] It is the 4-hydroxy derivative of N-methyl-N-ethyltryptamine (MET) and is a close analogue of psilocin (4-hydroxy-N,N-dimethyltryptamine; 4-HO-DMT). [1]
The chemical synthesis of 4-HO-MET has been described.. [1] [10]
Analogues of 4-HO-MET include psilocin (4-HO-DMT), 4-HO-DET (ethocin), 4-HO-MiPT (miprocin), 4-HO-DPT (deprocin), 4-HO-MPT (meprocin), 4-HO-DALT (dalocin), and 4-HO-MALT (malocin), among others. [1] 4-AcO-MET (metacetin) is an ester prodrug of 4-HO-MET. [7]
4-HO-MET was first synthesized and discovered by Alexander Shulgin in the 1970s. [8] [9] [1] It was first described in the scientific literature by David Repke and colleagues by 1981. [10] Subsequently, 4-HO-MET was described by Shulgin in his book TiHKAL (Tryptamines I Have Known and Loved) in 1997. [1] It was encountered as a novel recreational and designer drug in Europe by 2008. [11]
Scheduled in the "government decree on psychoactive substances banned from the consumer market". [20]
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 ]
4-Propionoxy-N-methyl-N-ethyltryptamine (also referred to as 4-PrO-MET) is the ester prodrug of 4-HO-MET. Unlike many other tryptamine derivatives, it is currently not explicitly listed under the German Neue-psychoaktive-Stoffe-Gesetz (NpSG). This means that, while its use as a recreational substance is not legally permitted, the compound may be obtained and handled for legitimate research purposes, provided all other relevant legal requirements and safety regulations are observed. [21]
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. [22]
4-HO-MET is a class A drug in the United Kingdom, 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. [23]
It is a schedule I substance in some states, such as South Dakota [24] and West Virginia. [25]
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).