Gramine

[endlessness]

Recently there has been a considerable amount of reports of people trying to extract dmt from Arundo, Phragmites and Phalaris species. However, there are several reports about several of these plants containing toxic alkaloid gramine.

So I thought it would be useful to get some of the sharp minds here thinking about how we can get rid of potential gramine for those extracting from these plants....

In this post 69ron mentiones that gramine is slightly more polar than dmt, so through something like a heptane recrystalization one could possibly get rid of gramine. Can anybody confirm this?

What about the pKa, and separating through the pH? Any information on that?

Can anything be deducted about the stability of gramine to different conditions by its molecular structure?

I've also heard about gramine decomposing when smoking, but no idea if thats true and neither if the decomposition product/s is really safe.. Or maybe very high pH in the base part of an extraction could destroy gramine and other possible toxic alkaloids?

 

[benzyme]

Gramine: a vasorelaxing alkaloid acting on 5-HT(2A) receptors - PubMed

The vascular effects of gramine on resistance vessels were evaluated, in particular as regards the 5-hydroxytryptamine (5-HT) system. We compared the action of gramine with that of ketanserin, a 5-HT (2A) antagonist; both compounds induced concentration-dependent relaxation in precontracted...

www.ncbi.nlm.nih.gov

some 5HT2A antagonists also antagonize dopamine, which could result in tardive dyskinesia...parkinsonian-like symptoms.
perhaps people just don't typically eat gramine

nonetheless, gramine isn't something you want in your extraction.
it can be separated from DMT with a column, silica, and EtOAc:MeOH.

 

[kemist]

We were discussing it the other night, on the chat.

Somebody wrote that gramine has significantly higher boiling point then DMT.

Vapouriser seted up on 80 C shouldn`t vapourise any gramine, only DMT.

Can anybody confirm it?

 

[endlessness]

Gramine: a vasorelaxing alkaloid acting on 5-HT(2A) receptors - PubMed

The vascular effects of gramine on resistance vessels were evaluated, in particular as regards the 5-hydroxytryptamine (5-HT) system. We compared the action of gramine with that of ketanserin, a 5-HT (2A) antagonist; both compounds induced concentration-dependent relaxation in precontracted...

www.ncbi.nlm.nih.gov

some 5HT2A antagonists also antagonize dopamine, which could result in tardive dyskinesia...parkinsonian-like symptoms.
perhaps people just don't typically eat gramine

nonetheless, gramine isn't something you want in your extraction.
it can be separated from DMT with a column, silica, and EtOAc:MeOH.

yeah and anyways I wouldnt want to be a test rabbit for a potentially toxic alkaloid and neither that some uninformed people here do it



as for the column, well, wonderful for those who have it but this is not the case for the average psychonaut amateur chemist... Is there any other way you can see? You and some others usually have access or know where to look in chemistry databases, can you find its pka or confirm the xlogP3 (whats the difference between the P3 and the normal one?) 69ron posted in the link I gave?

Or can you, by looking at the molecular structure, deduce ways of breaking it into something relatively harmless?

We were discussing it the other night, on the chat.

Somebody wrote that gramine has significantly higher boiling point then DMT.

Vapouriser seted up on 80 C shouldn`t vapourise any gramine, only DMT.

Can anybody confirm it?

Wikipedia does mention melting point being just under 140 celcius... but then only people with very controlled vaporizers could do this... Also I still wonder if its totally wrong the information I once read, god-knows-where, that heat from smoking would actually destroy gramine..

Would be nice if we found some information that could make it simple for everybody to get rid of this

 

[benzyme]

aha

yes, sublimation could easily separate the two.
so the question is, at what temp does gramine vaporize?


very odd how both tryptamine and gramine have higher m.p./b.p. than dmt :?

 

[burnt]

very odd how both tryptamine and gramine have higher m.p./b.p. than dmt Confused

mp and bp is not always correlated with mass. compounds that can form hydrogen bonds with each other have higher melting points etc.

when you derivitize compounds for GC analysis often people use silyating reagents (trimethyl silyating are most common) which make the molecule heavier. but by replacing OH groups with OSi(CH3)3 you reduce hydrogen bonding and thus decrease boiling point.

 

[Jorkest]

sublimation sounds like a great way to separate it...it would be nice though if the heat from smoking would destroy it

 

[benzyme]

sublimation sounds like a great way to separate it

hmm, maybe sublimation is a great way to separate it. :?

 

[endlessness]

and what is the minimum necessary equipment for this? Again I just want to bring this more to the level of the average amateur psychonaut chemist, if possible.. If its not possible, then so be it, but I think it would be interesting if we did find out more simple ways of making these experiments safer

 

[benzyme]

ohh it's advanced. that's the point of this forum 8)

here's a simple lab-rigged setup

the vacuum source can be an aspirator you could attach to a faucet. would help to have a manometer in the line, so you can gauge the pressure. swim uses an IR therm with laser to get
the low part of the glass (microscale sublimator)

here are proper lab-grade subs.
the atmos. press. sub (the bottom one) needs no vacuum, but you need to regulate the heat.

 

[T]

Might be a silly idea, but you can buy gramine and test the solubility, then you'll definitely know how you can separate from DMT.

 

[MagikVenom]

Might be a silly idea, but you can buy gramine and test the solubility, then you'll definitely know how you can separate from DMT.

Not sure about buying it. I once ran across a Gramine extraction tek that used Maple tree leaves as a source of gramine.

Gramine is usually found in leaves. Now I do not know for sure but the roots of reeds should be pretty gramine free. I seem to remember this from some source I read but could be wrong.

Even if no effects on humans have been noted personnely I would not want to smoke this stuff.


PEACE
MV

 

[endlessness]

Might be a silly idea, but you can buy gramine and test the solubility, then you'll definitely know how you can separate from DMT.

well yeah T might not be a silly idea, if anybody has equipment/time/money for making this favour, it would be wonderful .. I personally dont, unfortunately, not for the moment at least...

 

[T]

Might be a silly idea, but you can buy gramine and test the solubility, then you'll definitely know how you can separate from DMT.

well yeah T might not be a silly idea, if anybody has equipment/time/money for making this favour, it would be wonderful .. I personally dont, unfortunately, not for the moment at least...

That's understandable, as long as SWIM has gramine free source available he wouldn't do it either. So hopefuly never.
If for legal reasons phalaris would be the only source for him, that's how he would try to find out, as he doesn't have the skills/equipment to test the end results otherwise.

 

[benzyme]

if gramine is more polar than dmt, it might even be cleaned out with a sodium carb wash. 8)

 

[sauroman1]

But there is no evidence that gramine is toxic to humans. Gramine was found to toxic to sheep and rodents. But sheep are also staggered by other alkaloids such as DMT. So maybe humans body can defend against gramine too?

 

[entheogenic-gnosis]

Gramine is DMT, only with a 1 carbon bridge connecting the amine nitrogen to the benzene ring ( ch2-Nh2 ) rather than a two carbon bridge ( ch2-ch2-Nh2 ), right?

Strange how removal of a single ch2 group in a side chain would change a compound from a benign psychedelic into something toxic...
( h20 is water and h202 is hydrogen peroxide, so I understand how very small changes to a molecule can drastically alter its properties, it just seemed strange to me in this situation...


GRAMINE SOLUBILITY IN WATER: Insoluble

SOLUBLE IN: alcohol, ether, toluene and chloroform, slightly soluble in acetone

GRAMINE [3-(N,N-DIMETHYLAMINOMETHYL) INDOLE]

Seems like DMT has a lower boiling point than gramine...so why not fractional distillation?

( sorry if this was suggested, I skimmed through most the posts but may have missed it)

-eg

 

[Leithen]

Is there any easy way of testing our product for gramine to see if it may be toxic? Does it change any colorimetric reagents?

 

[steppa]

Gramine is DMT, only with a 1 carbon bridge connecting the amine nitrogen to the benzene ring ( ch2-Nh2 ) rather than a two carbon bridge ( ch2-ch2-Nh2 ), right?

We should figure out how to add another carbon thingy to said bridge then.

 

[downwardsfromzero]

We should figure out how to add another carbon thingy to said bridge then.

It's called methylene insertion. This would be the reverse of part of the biosynthesis of gramine from tryptophan where a methylene bridge is removed - curiously, labelling studies show that the same nitrogen atom is retained in the molecule during this process even though it is attached to the carbon atom that gets removed.

What would be really great is if it could be possible to reverse the enzymatic process of methylene removal, although that occurs on the non-methylated substrate - primary amine/amino acid.

The tertiary amine would in principle make homologation of gramine to DMT 'relatively simple' but it would not be a trivial matter for the kitchen chemist as is generally the case with things involving addition of hydrogen. Also it would appear to fall into the category of synthesis so I won't go into any more detail here.