Sunday, August 10, 2014

PwKHAL Part III: Mescaline Part II

PwKHAL: Mescaline Part II
Psychedelics we Have Known And Loved - Reflections on Shulgins Death and the Magic Six.

Mescaline the Magic Molecule

The Magic Six
1. Mescaline (3,4,5 - trimethoxyphenethylamine)
2. DOM (2,5-dimethoxy-4-methlyamphetamine)
3. 2C-B (2,5-dimethoxy-4-bromophenethylamine)
4. 2C-E (2,5-dimethoxy-4-ethylphenethylamine)
5. 2C-T-2 (2,5-dimethoxy-4-ethylthiophenethylamine)
6. 2C-T-7 (2,5-dimethoxy-4-propylthiophenethylamine)

The benzene ring and what makes mescaline a molecule. 

3,4,5 trimethoxyphenethylamine
On the picture to the right
the ring is at an angle but
the clock anaolgy still holds just
move hour 1 to the top, instead
of the top right position.
 C equals Carbon
H equals Hydrogen.
- sign equals a single bond
= sign equals a double bond
The difference between a phenethylamine and mescaline is three simple molecules, that's it. The hexagon shaped benzene ring on the diagram to the right, represents 6 carbon atoms and is the centre of the mescaline molecule.
The diagramatic benzene ring shown on the left of the page is also a benzene ring - but not part of any larger molecule. The left diagram also labels the carbon and hydrogen atoms. This is not needed as wherever a line ends, or wherever a line meets another line in the diagram, it represents a carbon atom. This is true of the mescaline diagram and any 2D molecular diagram. Carbon is always bonded to the needy, exigent hydrogen atom. Hydrogen is always trying to partner up it's lonely, single electron with one of carbons four free electrons.

Each carbon atom is labelled positions 1-6. Think of the benzene ring as a clock with 6 hours. Each hour representing the 6 carbon atoms. Now using the mescaline diagram, hour 1 is where the ethyl chain or up-down-up line is bonded to the hexagon ring. An ethyl group/chain is just two carbon atoms bonded together, hydrogen again promiscuously filling the other free bonds. These ethyl carbons are called alpha and beta, but the benzene ring is where the mescaline molecule does it's psychedelic magic and is also the only place where the other 5 magic phenethylamines differ from eachother.

3,4,5 trimethoxyphenethylamine
Back to the benzene ring in the mescaline molecule to the right. Working anti-clockwise from hour/position 1 you get hours 2-6. Mescaline AKA 3,4,5, trimethoxyphenethylamine is potentially incomprehensible if we just read the chemical name. Nevertheless it can be understood using the picture to the right, and the clock analogy.

The 3,4,5 represent hours or carbon positions 3,4 and 5 on our clock. These numbers tell us exactly which carbon positions/atoms, on the benzene ring, a molecule has been added - positions 3,4 and 5 as the chemical name alludes to have something other than hydrogen attached. The molecule located at these positions is found in the chemical name too. The "trimethoxy" that follows the numbers in the chemical name is literally the molecule that is to be found at positions 3,4 and 5. Moreover it tells us how many of these molecules are to be found on the benzene ring.

 The "Tri" simply means 3. So there are 3 "methoxy" molecules at our clock/carbon positions. A methoxy molecule is very simple. It is an oxygen atom, bonded to a carbon atom - as usual hydrogen atoms fill the rest of the free electrons in the outer shells. On the diagram to the right oxygen is labelled as O. Carbon is not labelled but is represented as "points" or intersections or bonds on the diagram - and hydrogen being so ubiqitous, is not labelled, but is assumed to be there, unless specified otherwise. So there are three methoxy molecules at hours 3,4 and 5 - easy. This is the only difference between phenthylamine and what Shulgin might call a profoundly rich psychedelic drug - Mescaline.
Mescaline is in his magic 6. The 6 most important or valuable psychedelics he thought our species had at it's disposal. I tend to agree with him.

Now we have the basic chemistry down we can begin examining the interaction between the brain and the mescaline molecule or molecules - plural. This raises many intruiging questions, such as why or how mescaline produces a psychedelic effect. How is it "better" than other psychedelics that look almost the same? By what mechanism is this accomplished and how does it acheive this effect and not some other?

The brain did not evolve to be manipulated into the fascinating service of mescaline molecules, yet it can be and we are finally over the line between hypothesis and theory. We know many, but not all of mescalines secrets. Mescaline may always be a little enigmatic. We know the basics of why a molecule can do so much, it is not the molecule it is the molecule and it's connection with serotonin as we will see. We will eventually see why Shulgin and many others thought so highly of such a humble compound.


Thanks, Brady.