does tryptophan actually convert to tryptamine?

[(zonk)]

I was always under the impression that L-TP converted to Tryptamine through some decarboxylase type enzyme but I can't seem to find any info for this or any conversion rates. It seems that it is 1st converted to 5-HTP and then converted to the tryptamines:5-HT and melatonin...

This would also mean that the biosynth-huasca of L-TP+L-Me+B6,B9,B12 is impossible.

If I'm wrong can someone let me know, and if they could give conversion rates that would be awesome.

I also think the same thing may apply to L-Phenylalanine in that it converts to tyrosine then tyramine then dopamine...(but not PEA)

 

[Swerlz]

http://www.biochem.arizona.edu/clas...norsprojects/462bhonors2001/schmitz/auxin.htm

 

[(zonk)]

That doesn't seem very conclusive to me, that and i'm not a vegetable despite what some may say...
love yer avatar tho

 

[sekio]

Yes, tryptophan is decarboxylated in small amounts by the L-amino acid decarboxylase. It's not present in very large levels though - I think about the same levels as you'd expect from phenylalanine -> phenethylamine metabolism.

DMT is not active at the levels that it's present endogenously - and unless you inhibit MAO it will never build to appreciable levels through any sort of "natural" mechanism. Even if you did find a way to have it made enzymatically then you'd have a huge excess of tryptamine floating around (not to mention all the other monoamines )

 

[(zonk)]

Thanks, u came thru again... I was wondering this because alpha-Methyl and alpha-Ethyl Tryptophans r available and even if the conversion rate is slow, since AMT/AET are not subject to MAO I'm guessing eventually active levels will be reached. I know bufotonin is toxic but I dont think the alpha-alkylated serotonins are, atleast i see not mention of it and I dont see any studies of 5-HO-AET.

 

[(zonk)]

Perhaps taking a CYP450 inhibitor will block some of the conversion to 5-Hydroxy as the O-Hydrolase takes place in the liver if i remember right

 

[sekio]

AMT and AET are subject to MAO, just not nearly as rapidly as regular tryptamine.

It looks like most alpha-methyltryptophan gets converted to alpha-methylserotonin or 5-HO-AMT (not straight AMT - this would be expected copared to the levels of tryptamine vs serotonin present naturally) - which would be very unpleasant. Inhibiting tryptophan 5-hydroxylase (to stop this from happening) will also inhibit production of serotonin without auxillary 5-HTP supplementation and is not a smart idea. CYP450 is not really involved here.

I have a feeling alpha-alkyl tryptamines will mess with enzyme kinetics. I know certain phenylalanine "analogs" are good inhibitors of tyrosine (and therefore dopamine) synthesis.

 

[(zonk)]

Your right, 5-HO-AMT inhibits 5-HTP decarboxylase. Can you tell me why you think 5-HO-aMT would be unpleasant tho?

 

[sekio]

5-MeO-AMT is reported as being unpleasant by many (esp. body-load) and I would definitely expect the O-desmethyl counterpart to be an active serotonin agonist that doesn't cross into the brain. Think a stronger version of bufotenin.

 

[Thou]

I have a feeling alpha-alkyl tryptamines will mess with enzyme kietics. I know certain phenylalanine "analogs" are good inhibitors of tyrosine (and therefore dopamine) synthesis.

Did you mean to write kinetics?

I searched google for that word and couldn't find anything about. Is it a different form of the word kinetic?

I hope you're not offended as I'm genuinely curious because I wanted to understand more concretely what you were saying.

 

[sekio]

It's a typo of "kinetics".

 

[(zonk)]

Thanks for your input, I don't think alpha-alkylated or beta-alkylated tryptamines are the same rules as n,n-dialkylated ones. 5-HO-AMT is primarily a 5-HT2 agonist where Bufotenin is 5-HT3and the whole purpose of AMTP was to get 5-HO-AMT into the brain. I've always been aprehensive to take 5-meo-amt due to the reported nausea+bodyload however 5-meo-AET doesn't seem much different than aET which both seem pretty benign compared to aMTs so maybe AETP is better to start with...

 

[(zonk)]

Another thought has come to mind... I wonder if certain indole analogs would yeild psychedelic tryptamines biosynthetically, like 4-hydroxyindole or 5 and 7-Fluoroindoles..

 

[sekio]

I think trying to use humans as bioreactors to make psychedelics is a bad plan. None of the enzyme kinetics are favourable.

Mushrooms do accept certain indolic precursors and integrate them into the psilocin structure. (i.e. 5-MeO-DMT in the growth media will produce 4-HO-5-MeO-DMT) Humans won't because we do not synthesize our own tryptophan.

 

[(zonk)]

Thanks so much, I guess my research skills are lacking, damn wikipedia didn't mention Tryptophan synthase wasn't a mammalian enzyme in the tryptophan metabolism page. Perhaps I can find some plants or microorganisms todo the work for me, probly not worth it.