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4-HO-MET

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Description

Tryptamines. 4-HO-MET.

4-HO-MET is a novel substituted tryptamine that is a functional and structural analog of Psilocin. It was synthesized by the noted chemist Alexander Shulgin and described in his book, TiHKaL (Tryptamines I Have Known and Loved). 4-HO-MET is the ethyl homolog of psilocin and referred to as 4-Hydroxy-N-methyl-N–ethyltryptamine, Metocin or Methylcybin. Whilst there are no reported deaths attributed solely to 4-HO-MET, despite some experiences describing extremely large dosages consumed, it is nonetheless important to take note that very little data exists about the pharmacological properties and toxicity of 4-HO-MET.

4-HO-MET belongs in a category called 4-substituted tryptamines, the classics of which include Psilocybin and Psilocin. Many such substitutions in this pattern have been developed, some of which have been studied and tested in various degrees.

The synthesis and description of effects of 4-HO-MET was detailed in TiHKaL under the heading “#21 – 4-HO-MET”. It was noted by Shulgin to be “qualitatively a lot like psilocin”, with the same alteration of color and form with occasional synesthesia. It was noted to share the same wave-like experience as psilocin, with alteration of effects shifting from near-normal perception one minute, to a swirl of concept and color at the next.

PHARMACOLOGY

As noted before, there is little by way of research into the pharmacology of many of the 4-substituted tryptamines, although they have been proposed to act in a similar fashion to Psilocin, as a partial agonist of the oligomerized complex of Serotonin 5-HT2A – mGlu2 receptors, as opposed to monomeric 5-HT2A agonists like lisuride.

A study published in the journal of the European College of Neuropsychopharmacology in 2016, investigated the interactions between novel tryptamines at monoamine receptors and transporters, compared with the classical psychedelics Psilocybin, LSD and Mescaline. It was found that the binding affinities at the 5-HT2A receptor site for all of the tryptamines tested were lower in comparison to LSD. This correlated with the higher psychoactive dosages in humans commonly reported. It was noted that several tryptamines, including 4-HO-MET, interacted with both the serotonin and (partially) norepinephrine transporters [1].

[1] – Receptor interaction profiles of novel psychoactive tryptamines compared with classic hallucinogens.

The reported binding affinities for 4-HO-MET at the various sites are:

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

ADDITIONAL STUDIES:

A phenomenological study was done pertaining to recreational use of 4-HO-MET in Sweden and was published in the Journal of Psychoactive Drugs in 2011. The study was aimed at establishing an understanding of the characteristics of recreational use, due to the fact that very little was known about the substance at the time. This was done through collected reports from the Internet and analyzed using the Empirical Phenomenological Psychological Method
[2]. The studied noted drastic changes in cognitive, emotional and bodily functions. The various descriptions of experiences shifted between “heaven” and “hell” and exhibited great similarity with the classic psychedelic substances LSD and/or Psilocybin.

[2] Heaven and Hell – A Phenomenological Study of Recreational Use of 4-HO-MET in Sweden

RECOMMENDED READING:

TiHKaL Entry #21 – 4-HO-MET

Tryptamines i Have Known And Loved: The Chemistry Continues – Shulgin & Shulgin

 

 

Purity Analysis

4-ho-met-fumarate-hnmr-64-1