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Acacia King

Interactive Metabolic Pathways Map

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I was bumbling around Sigma Aldrich's website this morning after reading a thread on here about p-coumaric acid.

While I was having a look around I came across this:

http://www.sigmaaldrich.com/technical-documents/articles/biology/interactive-metabolic-pathways-map.html?cm_sp=Insite-_-Academic-_-MetabolomicPathways

It maps the entire human metabolic process. Thought a lot of you would dig it.

Peace

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damn yeah. i had to post it on facebook when i found it.

meant to post it here too as its fascinating, but yesterday got a bit crazy.

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I don't think I understand 95% of it but goddamn that gets me hot.

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I have a huge printed version of this on my wall - I got it printed for one of my biochem subjects, but I often still look at it and find interesting bits i missed. Pretty amazing how complex basic metabolism is (not to mention the all the other pathways that arent on here)

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I have a question for anyone who understands this more than I do (which is sadly still very little lol). 
 

I’m curious at what point and WHY is the hydroxyl group on the 4 position for psilocin 4-HO-DMT, compared to why it’s on the 5 position for Bufotenine 5-HO-DMT?

 

Also, are there hydroxyls Off 1/4/6? I’m guessing they can’t be off 2/3 position due to the Nitrogen and Carbon atoms respectively? Is it because a hydrogen atom is shunted off more easily? In as minimalistic way I can get my query across lol. 


I see that according to the map and notes it mentions phosphorylation which IIRC relates also to the Difference between psilocybin and psilocin? But what in the great crippled fuck does that even mean? 
 

the reason I’ve been curious is the massive difference in effects between for example 5ho, 5meo, and nn; or baecystein(sp?) and aeruginacin to psilocin. 
 

I don’t even have my copy of TIKHAL atm but I probably wouldn’t understand anyway. 
 

 

5E29A2FB-F9CE-4F29-8180-26E7B9E99A46.jpeg

14855D7B-24C8-47EE-A05C-A51F0DE74116.jpeg

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Posted (edited)
On 01/06/2022 at 11:00 PM, FancyPants said:

 

I’m curious at what point and WHY is the hydroxyl group on the 4 position for psilocin 4-HO-DMT, compared to why it’s on the 5 position for Bufotenine 5-HO-DMT?
 

New Discoveries in Magic Mushroom Enzymes - Psychedelic Science Review (psychedelicreview.com)

 

Fungi seem to have different enzymes that hydroxylate the indoleamines at the 4 position (tryptamine-4-monooxygenase), whereas other metabolic pathways lead to 5-OH (eg enzymes like tryptophan-5-hydroxylase)

 

Quote

 are there hydroxyls Off 1/4/6? I’m guessing they can’t be off 2/3 position due to the Nitrogen and Carbon atoms respectively? 



If you consider the numbering on the indole nucleus that might help you get an idea of the way it's numbered

Skeletal formula with numbering scheme
 

Quote

massive difference in effects between for example 5ho, 5meo, and nn; or baecystein(sp?) and aeruginacin to psilocin. 


Consider changing the hydroxyl position from 4-OH to 5-OH changes a major part of the molecular structure that allows different binding characteristics to different receptors

 

Take for example serotonin (5-OH-tryptamine) binds something like this to 5-HT2ARs
2135491379_5-ht2a5-ht.thumb.jpg.636918182ecb58e4cd7545b9dd1e4e66.jpg

 

Psilocybin binds more like this

 


683431972_psilocin5-ht2a.thumb.png.2550f8e929e66c0a3598169dc7e48cdb.png



Consider how it changes the location of the hydroxyl group to allow different strength intermolecular forces with receptor proteins causing different binding profiles

See the source image


An important determinant of the neurobehavioral responses induced by a drug is its relative receptor selectivity.

These different molecular structures allow different receptor binding profiles eg

Psilocin: 4.00 5ht2b, 3.40 5ht1d, 3.37 D1, 3.03 5ht1e, 2.88 5ht1a, 2.83 5ht5a, 2.82 5ht7, 2.82 5ht6, 2.67 D3, 2.52 5ht2c, 2.19 5ht1b, 2.14 5ht2a, 1.77 Imidazoline1, 1.74 SERT, 1.57 Alpha2B, 1.36 Alpha2A, 1.03 Alpha2C where higher numbers mean higher binding. 

A 5-OH vs a 4-OH will change the profile of receptor binding


 

Edited by Alchemica
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Alchemica you are an absolute LEGEND. 

 

thank you so much for taking the time to explain all that!! It hadn’t occurred to me that the positions were inclusive of the entire indole lol. I had assumed all this time it was just in reference to the left side (the benzene?) not sure why tho. 
 

very fascinating about fungi having different enzymes compared to animals and plants in that part of the process!

 

i had a rudimentary understanding of how a molecule binds to a receptor, and how a seeming,y minor difference can have big practical differences (for example how one isomer can be far more potent than the other), but I hadn’t really clicked about the difference in the receptor subtypes either…

 

ah man I feel satisfied with that answer like you wouldn’t believe lol. 
 

thank you again :D 

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