theoretical Q: 4,5-OH-hydroxytryptamine

[Jabberwocky]

theoretical Q: 4-OH-5-hydroxytryptamine

I'm trying to understand fourth position substitution of tryptamines more clearly...I am searching for a molecule with a hydroxy on the fourth position with serotonin as the base...is this chemical impossible to synthesize? Am I searching for it wrong?

thanks

 

[nuke]

4,5-dione-tryptamine is a neurotoxin that causes damage to serotonergic neurons. Normally 4,5-D-T irreversibly inhibits NADH-CoQ1 and COX. In the presence of ascorbic acid, 4,5-D-T is converted into 4,5-dihydroxytryptamine which prevents damage to NADH-CoQ1 and exacerbates damage to COX (the redox cycle generates free radicals mediated by oxygen and iron). It's hypothesized that this molecule may have something to do with the damage to tryptophan hydroxylase and serotonin neurons when exposed to methamphetamine or MDMA.

Could you safely use 4,5-dihydroxytryptamine? Maybe, but the two hydroxy groups make it pretty polar and difficult to get across the blood brain barrier anyway.

 

[HeaT]

thats a dione, two keto groups, not a diol, with two hydroxies..

 

[nuke]

I know. I was saying, the in vitro metabolite is 4,5-dihydroxytryptamine, but 4,5-dihydroxytryptamine seems to cause COX destruction and may not be safe, either.

 

[vecktor]

it would appear that a few dihydroxy tryptamines get accross the BBB, 5.7 dihydroxy tryptamine is also a potent serotinergic neurotoxin used for lesioning test animals and unwary psychonauts.

 

[Xorkoth]

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