CCould N-dimethyltryptophan have similar effects with DMT?

[/navarone/]

Well, th tiele tells everythng already.

Could N-dimethyltryptophan have similar effects with DMT.
Does the carboxylic group inhibit the substance affinity and potency?

BTW, between all the N alkylations of tryptamine, wich one is the more potent in terms of effects?

 

[fastandbulbous]

Well a COOH group is a fuck-off polar group so without an active transport/facilitated diffusion mechanism it can use to cross the blood-brain barrier, it's not getting anywhere near the receptors that make DMT fun

 

[(zonk)]

to answer yer 2nd Q, methyl is by far the winner, perhaps it's less orally active then some other alkys but it has the best effects by far, DPT is liked alot and is a lil more potent but it can also be VERY uncomfortable for some and not as visual IMO. MPT might be good, I'd like to check that out one of these days.

BTW. I sure u already know this but DMTryptophan will not decarboxylate to DMT in the body. I've always wonderd if n-FluoroTryptophan has any potential in terms of effects/passage into BBB

 

[Hammilton]

Although if you had DMTryptophan, it'd be a snap to convert to DMT proper.

 

[/navarone/]

Well a COOH group is a fuck-off polar group so without an active transport/facilitated diffusion mechanism it can use to cross the blood-brain barrier, it's not getting anywhere near the receptors that make DMT fun

Then what if that COOH group is substituted by an amine or by a halogen?

 

[/navarone/]

BTW wouldn't the tryptophan decarboxylase in our body remove the carboxylic group turning the molecule into DMT?

 

[MattPsy]

Yes, but this will happen in the general circulation, not in the brain (unless it does somehow make it past the BBB), and be destroyed by MAO.
I'm not sure how 5-HTP gets into the brain, but I expect it will be through a specialised transport protein across the BBB for tryptophan. These transporter proteins are pretty selective - I doubt it would tolerate the amine being dialkylated. Still, that's just my opinion.

 

[EN21]

don't try this!!

It is really possible, that ti will cross BBB,

but

the similarity to abrine (N-methyl tryptophane) tells me, that it could be very dangerous!

Here's a citation from the "Ask Dr. Shulgin"
N-Methyltryptophan (L-(+)-Abrine, or simply Abrine) is widely distributed throughout the plant world. It is a major component of the Rosary Pea (the Jequirity Bean) which has the botanical name Abrus precatorius and which has enjoyed some popular use as an insecticide. The toxicity of this rather poisonous plant is apparently not in its alkaloid composition but in its protein fraction. Abrine itself has shown some tumor inhibition properties in rats, but the search for possible pharmacology was disappointing. But be careful. The name "Abrin" is quite a different item. It is an extremely toxic protein from this same plant. The seeds of this plant have been used for poisoning people, and are very nasty.

N,N-Dimethyltryptophan has also been found in the Jequirity Bean seeds and several other plants, but other than having being described as a plant growth inhibitor, it is unknown pharmacologically.

 

[vecktor]

It is really possible, that ti will cross BBB,

but

the similarity to abrine (N-methyl tryptophane) tells me, that it could be very dangerous!

Here's a citation from the "Ask Dr. Shulgin"
N-Methyltryptophan (L-(+)-Abrine, or simply Abrine) is widely distributed throughout the plant world. It is a major component of the Rosary Pea (the Jequirity Bean) which has the botanical name Abrus precatorius and which has enjoyed some popular use as an insecticide. The toxicity of this rather poisonous plant is apparently not in its alkaloid composition but in its protein fraction. Abrine itself has shown some tumor inhibition properties in rats, but the search for possible pharmacology was disappointing. But be careful. The name "Abrin" is quite a different item. It is an extremely toxic protein from this same plant. The seeds of this plant have been used for poisoning people, and are very nasty.

N,N-Dimethyltryptophan has also been found in the Jequirity Bean seeds and several other plants, but other than having being described as a plant growth inhibitor, it is unknown pharmacologically.

abrine ie N-methyl tryptophan is not especially toxic.
abrin the protein lectin is.
they are not the same thing at all.

 

[indelibleface]

Yeah, it's easy to get confused between the two terms abrin and abrine. Both are components of the Rosary Pea. Abrin is a very poisonous protein quite similar to ricin in structure and effect, but abrine is completely different. I know, some taxonomists need to be hung.

 

[hugo24]

N-Fluorotryptophan is going to fluorinate you badly ...

 

[Limpet_Chicken]

I seem to recall alkylated tryptophans were toxic, but off the top of my head I can't recall where, might be wrong, might be right, I'd check first

 

[fastandbulbous]

Then what if that COOH group is substituted by an amine or by a halogen?

You'd have unstable compounds that would degrade to indoleacetaldehyde pretty quickly

 

[(zonk)]

5fl-tryptophan is a safe and active compound would the N-position make such an unhealthy difference? If one were really able to decarboxylate dm-tryptophan to dmt(in the body) and have it circulate, then in the presence of an maoi you'd have something great on yer hands, this just isn't the case unfortunately

 

[Limpet_Chicken]

It would probably be easier just to decarboxylate the lil fucker, and methylate the amines with any classically known methylating agent that will stick a methyl group on an amine.


Decarboxylating tryptophan doesn't require dangerous or hard to get reagents, although methylating agents re nice, if you like cancer
(thats not too close to synth discussion is it?, I'm not going to go any further with that one, at least, not here)

 

[vecktor]

5fl-tryptophan is a safe and active compound would the N-position make such an unhealthy difference?

yes.
and Hugo24 told you why.

the N-F bond is fairly labile, C-F bond particularly where the C is part of an aryl ring is very stable. which means that many N-fluoroamines act as electrophllic fluorinating agents producing F+ whereas aryl fluorides like the 5 fluoro compound are almost inert.

look on the positive side though N-fluorotryptophan might make you non stick.

 

[monotome]

Won't the tryptophan undergo thermal decarboxylation? I seem to remember some Australian species that have N,N dimethyl tryptophan esters in their composition. It would by no means be a clean route, but I guess you would end up with some DMT....

 

[MattPsy]

Some Australian species also have good ol' plain DMT in them. Save yourself the hassle.

 

[/navarone/]

I seem to recall alkylated tryptophans were toxic, but off the top of my head I can't recall where, might be wrong, might be right, I'd check first

Maybe because it could interfere with protein synthesis, the body could easily confuse DMTryptophan with tryptophan. However that doesn't alarm me since serotonin itself is made from tryptophan.

The big question here is, would tryptophan decarboxylase decarboxylate DMTryptophan. It's all a matter of enzyme affinity.
If it does, the DMTryptophan would become a DMT prodrug.

You know, tryptophan and methanol (plus something else) aren't not so hard to find afterall..hehe

 

[/navarone/]

BTW, short question, are bufotenin or 5-MeO-DMT stronger than DMT in terms of effect?